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    <title>Jason Yoong — Articles</title>
    <link>https://jasonyoong.com/</link>
    <description>Helping high performers make no BS career breakthroughs.</description>
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    <language>en-US</language>
    <lastBuildDate>Thu, 04 Jun 2026 16:32:18 GMT</lastBuildDate>
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      <title>How To Escape The Benchwarmer Bucket</title>
      <link>https://jasonyoong.com/benchwarmer-bucket/</link>
      <guid isPermaLink="true">https://jasonyoong.com/benchwarmer-bucket/</guid>
      <pubDate>Wed, 06 Aug 2025 17:29:34 GMT</pubDate>
      <description>Your manager already has you in a mental bucket: rockstar, reliable role player, or benchwarmer. The truth is, these impressions are sticky. If you fall…</description>
      <content:encoded><![CDATA[<p>Your manager already has you in a mental bucket: rockstar, reliable role player, or benchwarmer. The truth is, these impressions are sticky. </p>
<p>If you fall in the bottom buckets, you need to act fast to shift their perception before it becomes permanent.</p>
<p>Here are the two critical adjustments that can move you up the ladder.</p>
<h2>Weekly Updates</h2>
<p>Send a short weekly update every Thursday afternoon (giving yourself a Friday buffer) with exactly 4 bullet points:</p>
<ul><li>What you accomplished this week</li><li>What’s coming next</li><li>Risks/blockers you are managing</li><li>End with an ask: “What’s one thing I can help you with?”</li></ul>
<p>This simple framework keeps you visible and demonstrates proactive thinking. It shows you’re not just executing tasks—you’re managing outcomes and looking ahead.</p>
<p>But visibility without reliability is worthless. That’s where the second adjustment becomes crucial:</p>
<h2>No Surprises</h2>
<p>Avoid nasty surprises at all costs. No manager likes surprises, particularly bad news. This ties directly to the point above: raise risks early and always come with a proposed solution.</p>
<p>You’ll get one of two responses: “Yes, go ahead” or “Thanks for surfacing, here’s what to consider and look into.” Either way, you get a helpful response that moves things forward.</p>
<p>The combination of these two strategies—proactive communication and early risk management—creates a powerful perception shift. But timing matters:</p>
<h2>Conclusion</h2>
<p>Impressions are sticky, so work hard early to get on a positive note. </p>
<p>The mental bucket your manager puts you in during your first few months will likely stick for your entire tenure.</p>
<p>Don’t wait for your next performance review to make these changes. Make these two adjustments immediately if you want to climb out of the benchwarmer category and into rockstar territory.</p>
<p><em>Follow me on </em><a href="https://www.linkedin.com/in/jasonyoong?miniProfileUrn=urn%3Ali%3Afsd_profile%3AACoAAAJSXrIBSUgcR72YupYgoseFWNNHnvoVkq4&amp;lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_recent_activity_content_view%3BsEfDz20CSsKxb%2B5bNIJyHg%3D%3D"><em>LinkedIn</em></a><em>, </em><a href="https://x.com/JasonYoong"><em>X</em></a><em>, or </em><a href="https://patronview.com/patrons/"><em>Patron View</em></a><em> for more content like this</em>.</p>]]></content:encoded>
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      <title>Tips to Maximize Your Networking</title>
      <link>https://jasonyoong.com/networking/</link>
      <guid isPermaLink="true">https://jasonyoong.com/networking/</guid>
      <pubDate>Wed, 06 Aug 2025 15:25:18 GMT</pubDate>
      <description>Accept the fact that networking is transactional. It can be a transaction of information, skills, energy, connections, etc. Once you realize this, you…</description>
      <content:encoded><![CDATA[<p>Accept the fact that networking is transactional. </p>
<p>It can be a transaction of information, skills, energy, connections, etc. </p>
<p>Once you realize this, you gain clarity, respect for time, and adopt a value-added first approach.</p>
<p>Here are tactical tips to maximize your networking and turn it into a win/win.</p>
<h2>Build First</h2>
<p>Build goodwill BEFORE you ask for something. </p>
<p>This foundation creates trust and establishes you as someone who gives before they take.</p>
<h2>Ask Smart</h2>
<p>When meeting someone, ask “What is on your roadmap for the next 6 months?” Pinpoint how you can help them. </p>
<p>Pro tip: closing the loop makes you stand out from 99% of people.</p>
<h2>Rule of 3</h2>
<p>Use “The Rule of 3” when networking:</p>
<ul><li>Speak with 3 people</li><li>Share 3 things about yourself (focus on what is important to you for the next 6 months)</li><li>And learn 3 things about each person</li></ul>
<p>Remember that each time you connect with someone or ask for their time, you are competing with everything else in their lives (aka family time). So make it count and bring value.</p>
<h2>Conclusion</h2>
<p>Think about it. When both parties have this mindset and bring value, that’s where collaboration and partnership take form.</p>
<p>To recap, master networking with these three strategies:</p>
<ul><li>Build goodwill before asking for anything</li><li>Ask about their 6-month roadmap and find ways to help</li><li>Follow the Rule of 3: speak with 3 people, share 3 things, learn 3 things</li></ul>
<p><em>Follow me on </em><a href="https://www.linkedin.com/in/jasonyoong?miniProfileUrn=urn%3Ali%3Afsd_profile%3AACoAAAJSXrIBSUgcR72YupYgoseFWNNHnvoVkq4&amp;lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_recent_activity_content_view%3BsEfDz20CSsKxb%2B5bNIJyHg%3D%3D"><em>LinkedIn</em></a><em>, </em><a href="https://x.com/JasonYoong"><em>X</em></a><em>, or </em><a href="https://patronview.com/patrons/"><em>Patron View</em></a><em> for more content like this</em>.</p>]]></content:encoded>
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      <title>Tobi Lütke: 4 Ways to Make Your Team Truly Care About Your Product</title>
      <link>https://jasonyoong.com/tobi-lutke/</link>
      <guid isPermaLink="true">https://jasonyoong.com/tobi-lutke/</guid>
      <pubDate>Mon, 21 Jul 2025 23:03:19 GMT</pubDate>
      <description>In a terrific interview with Lenny, Shopify CEO Tobi Lütke said something that cuts right to the core of building great products. “It is not possible to…</description>
      <content:encoded><![CDATA[<p>In a terrific interview with Lenny, Shopify CEO Tobi Lütke said something that cuts right to the core of building great products. </p>
<blockquote>“It is not possible to make great products if the people who work on it do not give a shit about the product.”  Tobi Lütke </blockquote>
<p>Lütke continues that a critical role for any product leader is “to make sure that the team gives a shit.” This isn’t about motivational posters or shallow pep talks; it’s about creating an environment where genuine passion and ownership can thrive. If your team is just going through the motions, you’ll get mediocre results every time.</p>
<p>This got me thinking about the practical ways leaders can instill that deep sense of belief and energy into their teams. Here are four strategies that actually work.</p>
<h2>Anchor Your Team </h2>
<p>Your mission must be anchored to something bigger than the company and any single person on the team. When people feel their work contributes to a larger, meaningful purpose, their motivation shifts from completing tasks to achieving a shared vision. This provides a resilient “why” that fuels them through the inevitable challenges and setbacks.</p>
<h2>Leading From the Front</h2>
<p>As a leader, you must be the one to raise the heat first. You set the standard for energy, bias for action, and operational tempo. This also means driving the team to seek out the truth, even when it’s uncomfortable. Fostering a culture where challenging ideas is encouraged, not punished, is the only way to avoid complacency and unlock real innovation.</p>
<h2>Daily Customer Interaction</h2>
<p>You have to talk to your customers every single day. This is where you learn the good, the bad, and the creative use cases that never show up in a report. Data and spreadsheets tell you <em>what</em> is happening, but direct conversations tell you <em>why</em>. By building this feedback loop into your team’s regular cadence, and even into performance reviews, you cultivate a level of empathy that quantitative metrics can never replicate.</p>
<h2>Align Incentives</h2>
<p>Structuring an ownership compensation model with salary, bonus, and Restricted Stock Units (RSUs) or stock options is fundamental. It ensures that employees do well when the company does well. While building a great culture is essential, those efforts can feel hollow if they aren’t backed by financial alignment. When personal success is directly tied to the company’s success, the team’s focus sharpens dramatically.</p>
<p>As the great Charlie Munger said, “Show me the incentives and I will tell you the outcome.”</p>
<h2>Conclusion</h2>
<p>Getting your team to truly care about your product isn’t about fancy speeches—it’s about creating the right conditions where passion naturally develops.</p>
<ul><li><strong>Anchor Your Team</strong> – Connect their work to a bigger purpose beyond just the company</li><li><strong>Leading From the Front</strong> – Set the energy and encourage tough conversations about what’s really working</li><li><strong>Daily Customer Interaction</strong> – Talk to customers every day to understand the real problems you’re solving</li><li><strong>Align Incentives</strong> – Make sure your team wins financially when the product wins</li></ul>
<p>When you get these fundamentals right, you’ll have a team that fights for the product because they genuinely believe in it.</p>
<p><em>Huge thanks to Lenny for the terrific interview.</em></p>
<p><em>Follow me on </em><a href="https://www.linkedin.com/in/jasonyoong?miniProfileUrn=urn%3Ali%3Afsd_profile%3AACoAAAJSXrIBSUgcR72YupYgoseFWNNHnvoVkq4&amp;lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_recent_activity_content_view%3BsEfDz20CSsKxb%2B5bNIJyHg%3D%3D"><em>LinkedIn</em></a><em>, </em><a href="https://x.com/JasonYoong"><em>X</em></a><em>, or </em><a href="https://patronview.com/patrons/"><em>Patron View</em></a><em> for more content like this</em>.</p>]]></content:encoded>
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      <title>Maven: Top Course in Leadership</title>
      <link>https://jasonyoong.com/maven/</link>
      <guid isPermaLink="true">https://jasonyoong.com/maven/</guid>
      <pubDate>Tue, 01 Jul 2025 16:30:07 GMT</pubDate>
      <description>I&apos;m honored to see my course featured as a top course in Leadership &amp; Career on Maven ! About The Course This course is designed for ambitious individual…</description>
      <content:encoded><![CDATA[<p>I&#39;m honored to see my course featured as a top course in Leadership &amp; Career on <a href="https://maven.com/">Maven</a>!</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/TheMaven100-819x1024.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/TheMaven100-819x1024.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/TheMaven100-819x1024.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/TheMaven100-819x1024.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="TheMaven100-819x1024.jpeg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /></figure>
<h2>About The Course</h2>
<p>This course is designed for ambitious individual contributors or first / second time managers with more than 10 years of experience (applicable to all domains) who want the tactical &quot;how to&quot; insights for standing out, accelerating your growth, and using AI as your career copilot.</p>
<h2>Join Us</h2>
<p>Join me and special guest instructor <a href="https://www.linkedin.com/in/ethanevansvp/">https://www.linkedin.com/in/ethanevansvp/</a><a href="https://www.linkedin.com/in/ACoAAAAAnbYBPRCTKd7ra6QMDuyDlrNFM5EvaH0">Ethan Evans</a> (former Amazon VP). </p>
<p>We will go deep on the following topics:</p>
<h3>Learn what it takes to own your career and promote yourself.</h3>
<ul><li>How to use The Magic Loop: 5-step framework for rapid career growth</li><li>How to use advanced forms of The Magic Loop</li><li>How to build the skills required for the next level</li><li>How to establish trust with your manager, manager peers, and skip.</li><li>How to better manage your time &amp; energy to get more done</li><li>How to be a Change Agent, driving new initiatives</li><li>How to be more visible, getting full credit for you hardwork</li><li>How to be a magnet for executive sponsorship and build a network</li><li>How to start building the critical skill of EQ now</li></ul>
<blockquote></blockquote>
<h3>Learn how to lead your promotion conversation:</h3>
<blockquote></blockquote>
<ul><li>How to prepare and position your promotion review</li><li>Understanding the promotion process</li><li>Nailing your promotion document draft</li><li>How to effectively line up advocates</li><li>What to do in the final stretch (1.5 months out)</li><li>The final task</li></ul>
<p>With 8+ hours of live learning, you will also have dedicated time to small group discussions, lesson sharing, peer networking (to build your network of like-minded ambitious professionals now) and Q&amp;A.<br /><br />Be ready for many actionable &quot;How Tos&quot; to apply immediately (including specific AI prompts and templates).</p>
<h2>Amazing Offer</h2>
<p>For a limited time, Maven is offering a 20% discount (valid one week).<br /><em>Note: the promotion price of $396 will be the lowest offered for this course</em><br /><br />Course starts on July 12th (Saturday).</p>
<p><a href="https://maven.com/ethan-evans/early-career-promotion-fast-track">Click here to enroll</a>. Use the promo code &quot;MAVEN100&quot;.</p>]]></content:encoded>
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      <title>How We Kick Off Our In-Person Workweek</title>
      <link>https://jasonyoong.com/kick-off/</link>
      <guid isPermaLink="true">https://jasonyoong.com/kick-off/</guid>
      <pubDate>Fri, 27 Jun 2025 17:47:16 GMT</pubDate>
      <description>One way Ethan Evans and I kicked off our in-person workweek was a waterfall swim! Our Journey Our first workweek (Nov 2024) I visited Ethan in Seattle.…</description>
      <content:encoded><![CDATA[<p>One way <a href="https://www.ethanevans.com/">Ethan Evans</a> and I kicked off our in-person workweek was a waterfall swim!</p>
<h2>Our Journey</h2>
<p>Our first workweek (Nov 2024) I visited Ethan in Seattle. </p>
<p>This time, Ethan is visiting me in Honolulu.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/JasonWaterfall-1024x768.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/JasonWaterfall-1024x768.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/JasonWaterfall-1024x768.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/JasonWaterfall-1024x768.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="JasonWaterfall-1024x768.jpeg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /></figure>
<p><em>Swimming with Ethan</em></p>
<h2>Three Benefits</h2>
<p>We get a lot accomplished remotely and we drive deep benefits from our select in-person time:</p>
<ol><li>Forge a deeper bond and understanding through shared adventure and experiencing how the other person lives</li><li>Reconnect with the &quot;Why&quot; and the deeper purpose of our work (beyond the tasks and metrics)</li><li>Spontaneous creativity from in the moment conversation</li></ol>
<h2>Conclusion</h2>
<p>There are different ways to enter a &quot;flow&quot; state or slow down time — sometimes passing by a new art gallery with awe inspiring visuals spark an idea or memory.</p>
<p>The point is…you don&#39;t know when lighting strikes. </p>
<p>Be intentional on how you spend time and energy.</p>
<p><a href="https://www.linkedin.com/posts/jasonyoong_one-way-ethan-evans-and-i-kicked-off-our-activity-7339664166544134145-RM4W?utm_source=share&amp;utm_medium=member_desktop&amp;rcm=ACoAAAAG-MsBpRQwLJWANngKE4WOfcvMaQa859Y"><em>Follow me on LinkedIn for more content like this</em></a><em>. </em></p>]]></content:encoded>
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      <title>3 Career Mistakes Early Professionals Make</title>
      <link>https://jasonyoong.com/3-career-mistakes/</link>
      <guid isPermaLink="true">https://jasonyoong.com/3-career-mistakes/</guid>
      <pubDate>Fri, 20 Jun 2025 03:55:06 GMT</pubDate>
      <description>Starting your career can feel like navigating a maze blindfolded. Every decision seems monumental, every move permanent. But here&apos;s the thing — most of…</description>
      <content:encoded><![CDATA[<p>Starting your career can feel like navigating a maze blindfolded. Every decision seems monumental, every move permanent. </p>
<p>But here&#39;s the thing — most of us are making the same predictable mistakes. I know because I made them too.</p>
<p>After years of watching early professionals stumble through the same pitfalls, I&#39;ve identified the three most common missteps that derail promising careers. </p>
<p>The good news? They&#39;re all fixable.</p>
<h2>Title Chasing</h2>
<p>It&#39;s not just about the promotion. I get it — seeing that shiny new title on LinkedIn feels incredible. But focusing solely on climbing the corporate ladder without building the skills to back it up is a recipe for long-term stagnation.</p>
<p>Focus on developing valuable skills in growing industries for long-term upside. The professionals who thrive aren&#39;t the ones with the fanciest titles; they&#39;re the ones with the most valuable skill sets.</p>
<h2>Network Neglect</h2>
<p>Growing a network but not nurturing it is like planting a garden and never watering it. Do not just collect contacts — that&#39;s amateur hour.</p>
<p>Double down on rocket ship managers, mentors, and peers, and stay in touch consistently. Even simple text check-ins work. The relationships you build early in your career will become your most valuable assets later.</p>
<h2>Path Paralysis</h2>
<p>Thinking your first job defines your whole path is the biggest career myth out there. My first 7 years were linear, then came the fun roller coaster of Amazon, pre-seed startup, and entrepreneurship.</p>
<p>You don&#39;t need the perfect first step. Your career will zigzag, pivot, and surprise you in ways you can&#39;t imagine right now. That&#39;s not a bug — it&#39;s a feature.</p>
<h2>Conclusion</h2>
<p>If you&#39;ve made any of these missteps, don&#39;t worry. I did too. That&#39;s how you learn (and have good stories to tell).</p>
<p>Here&#39;s your quick recap of the three career mistakes to avoid:</p>
<ul><li><strong>Title Chasing</strong>: Focus on building valuable skills in growing industries instead of just climbing the ladder </li><li><strong>Network Neglect</strong>: Nurture relationships consistently rather than just collecting contacts</li><li><strong>Path Paralysis</strong>: Remember that your first job doesn&#39;t define your entire career trajectory</li></ul>
<p>Ready to fast-track your career? <a href="https://maven.com/ethan-evans/early-career-promotion-fast-track?promoCode=MAVEN100">Get in-depth tactical &quot;how to&quot; insights to stand out and accelerate your career flywheel in our course by clicking here</a>. </p>]]></content:encoded>
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      <title>How to Ace Interviews and Land the Job: Advice for USC Students and Recent Graduates</title>
      <link>https://jasonyoong.com/career-advice-for-usc-students-and-graduates/</link>
      <guid isPermaLink="true">https://jasonyoong.com/career-advice-for-usc-students-and-graduates/</guid>
      <pubDate>Sat, 07 Jun 2025 13:43:00 GMT</pubDate>
      <description>Next week, I&apos;m speaking with USC students and recent grads about how to ace interviews and land the job. Here are the four most common questions, with my…</description>
      <content:encoded><![CDATA[<p>Next week, I&#39;m speaking with USC students and recent grads about how to ace interviews and land the job.</p>
<p>Here are the four most common questions, with my lightning one-liners as answers below.</p>
<h2>Show Your Future Impact</h2>
<p>How do I best answer: &quot;Why are you interested in this position and our company?&quot;</p>
<p><strong>Make it about the impact you will have on the business.</strong></p>
<p>This shows you&#39;ve done your homework and that you&#39;re a problem-solver, not just a job-seeker. You&#39;re telling them you&#39;re ready to add value from day one.</p>
<h2>Connect Achievements to The Role</h2>
<p>How do I effectively answer: &quot;Can you tell me about yourself and your background?&quot;</p>
<p><strong>Focus on your key past achievements and how it ties with the role you are applying for.</strong></p>
<p>They don&#39;t need your whole life story, just the highlights that prove you can do this job. It makes their decision to hire you a no-brainer.</p>
<h2>Focus On Business Impact</h2>
<p>What&#39;s the most common mistake candidates make?</p>
<p><strong>The most common mistake that candidates make is that they talk about the tasks they did instead of the business impact they delivered.</strong></p>
<p>Companies hire people to solve problems and create value. Show them how your work moved the needle, not just how you checked off a to-do list.</p>
<h2>Ask About Team Dynamics</h2>
<p>How important is it to ask questions at the end — and what should I ask?</p>
<p><strong>It&#39;s critical. You are interviewing them just as much as they are interviewing you.</strong></p>
<p><strong>Ask thoughtful questions such as &quot;How does accountability work on your team?&quot; and &quot;How do you keep your stars challenged?&quot;</strong></p>
<p>Smart questions signal that you&#39;re a serious candidate who is also evaluating them. It shows you&#39;re thinking about your future success, not just trying to get an offer.</p>
<h2>Conclusion</h2>
<p>To land the job, just remember these key points:</p>
<ol><li>Show the impact you will make.</li><li>Tie your past wins to the job.</li><li>Share your results, not your tasks.</li><li>Ask smart questions at the end.</li></ol>
<p>I&#39;d love to hear your suggestions.</p>
<p>What interview advice do you have for college students today?</p>]]></content:encoded>
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      <title>Turn Your Out-of-Office Message Into a Career-Boosting Billboard</title>
      <link>https://jasonyoong.com/out-of-office-messages/</link>
      <guid isPermaLink="true">https://jasonyoong.com/out-of-office-messages/</guid>
      <pubDate>Mon, 02 Jun 2025 17:41:38 GMT</pubDate>
      <description>Most professionals treat their out-of-office messages as a simple notification tool. But what if this overlooked touchpoint could actually accelerate…</description>
      <content:encoded><![CDATA[<p>Most professionals treat their out-of-office messages as a simple notification tool. </p>
<p>But what if this overlooked touchpoint could actually accelerate your career growth and build meaningful connections with senior leadership? </p>
<p>Here&#39;s how a strategic approach to your OOO message can become your secret weapon for professional advancement.</p>
<h2>OOO Framework</h2>
<p>Early in my career, I used my OOO message to stand out to senior executives. The approach worked remarkably well, and here are the three key elements I included.</p>
<h3>Showcase Your Growth</h3>
<p>I included two to three interesting projects I was working on (e.g., co-chairing a non-profit industry event, launching XYZ marketing campaign).</p>
<p>This signaled my growth and demonstrated that I was taking on meaningful initiatives beyond my day-to-day responsibilities.</p>
<h3>Recent Wins and Achievements</h3>
<p>I made sure to mention recent work wins (e.g., press article, industry award). </p>
<p>This signaled my results and credibility, showing senior leaders that I was consistently delivering impact and gaining external recognition.</p>
<h3>Learnings and Curiosities</h3>
<p>I included one to two insightful things I learned (e.g., TED Talk, article). </p>
<p>This gave a peek into my curiosities and created natural conversation starters that sparked meaningful dialogue.</p>
<h2>The Surprising Results</h2>
<p>The people who replied most? </p>
<p>SVPs and above. They loved it.</p>
<p>One EVP asked for more TED Talk recommendations. Every time we met (e.g., hallway, meeting), we would briefly chat about the latest talk.</p>
<p>This built rapport, trust, and made me more confident (and comfortable) presenting in front of her and her leadership team — THIS was a big boost to my presence.</p>
<h2>OOO Message as a Billboard</h2>
<p>Your OOO message is a mini billboard. Do not waste it.</p>
<p>By strategically sharing your projects, wins, and learning journey, you transform a routine notification into a powerful networking tool. </p>
<p>The next time you set up your OOO, remember: you&#39;re not just informing people of your absence—you&#39;re creating an opportunity to showcase your value and spark conversations that could shape your career trajectory.</p>
<p><strong>Bonus:</strong> I did this on both personal and work emails. It&#39;s a great way to reconnect with people (and makes it easy for them to reply).</p>]]></content:encoded>
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      <title>3 Skills AI Can&apos;t Replace</title>
      <link>https://jasonyoong.com/3-skills-ai-cant-replace/</link>
      <guid isPermaLink="true">https://jasonyoong.com/3-skills-ai-cant-replace/</guid>
      <pubDate>Fri, 30 May 2025 01:58:18 GMT</pubDate>
      <description>Worried about AI? Don&apos;t be. Instead, focus on developing the skills it can&apos;t replicate. Here are three that will give you a standout edge in any…</description>
      <content:encoded><![CDATA[<p>Worried about AI? Don&#39;t be. </p>
<p>Instead, focus on developing the skills it can&#39;t replicate. </p>
<p>Here are three that will give you a standout edge in any industry.</p>
<h2>Judgment</h2>
<p>Artificial intelligence is an exceptional thought-partner, capable of processing vast amounts of information in seconds. </p>
<p>It provides the data and the dots, but you must be the one to connect them with strategic insight and business acumen. </p>
<p>Ultimately, you are the one who decides what truly matters and which direction to pursue.</p>
<h2>Executive Presence &amp; Influence</h2>
<p>AI can polish your message, refine your presentations, and draft compelling communications. </p>
<p>However, it cannot earn trust or build genuine credibility on your behalf. Your ability to embody the mission and inspire belief in others is built through authentic human interaction and leadership, getting people to join you, not just agree with your slides.</p>
<h2>Emotional Quotient</h2>
<p>AI will undoubtedly help you move faster and think bigger, handling complex tasks with ease. </p>
<p>Yet, in the Age of AI, the ability to &quot;be human&quot; becomes a powerful competitive advantage. As automation handles more of the analytical work, your capacity for empathy, collaboration, and personal connection becomes the scarce resource that drives team cohesion and innovation.</p>
<h2>Conclusion</h2>
<p>The strategy is clear: let artificial intelligence do 90% of the work for you, then focus your energy on the critical 10% that it cannot replace. </p>
<p>Here&#39;s a quick rundown of everything I mentioned above.</p>
<ul><li><strong>Judgment:</strong> Use AI as a tool, but own the strategic decision-making. Your insight is required to determine what is truly important.</li><li><strong>Influence:</strong> Credibility and trust are earned through human-to-human connection and leadership, not automated messages.</li><li><strong>Emotional Quotient (EQ):</strong> As AI makes work more efficient, genuine human connection becomes a scarce and valuable asset for building strong, innovative teams.</li></ul>
<p><a href="https://www.linkedin.com/in/jasonyoong?miniProfileUrn=urn%3Ali%3Afsd_profile%3AACoAAAJSXrIBSUgcR72YupYgoseFWNNHnvoVkq4&amp;lipi=urn%3Ali%3Apage%3Ad_flagship3_detail_base%3Bj0yikE7rQp6VgT2NbJ8XKg%3D%3D"><em>Follow me on LinkedIn for more content like this</em></a><em>.</em></p>]]></content:encoded>
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      <title>5 Underrated Ways to Stand Out Early in Your Career</title>
      <link>https://jasonyoong.com/5-underrated-ways-to-stand-out/</link>
      <guid isPermaLink="true">https://jasonyoong.com/5-underrated-ways-to-stand-out/</guid>
      <pubDate>Mon, 26 May 2025 12:03:00 GMT</pubDate>
      <description>Starting your career can feel overwhelming, with countless advice columns telling you to &quot;network more&quot; or &quot;work harder.&quot; While these suggestions aren&apos;t…</description>
      <content:encoded><![CDATA[<p>Starting your career can feel overwhelming, with countless advice columns telling you to &quot;network more&quot; or &quot;work harder.&quot; </p>
<p>While these suggestions aren&#39;t wrong, they often miss the subtle, practical strategies that truly set you apart. </p>
<p>The difference between blending in and standing out often lies in mastering the fundamentals that others overlook—the small but powerful habits that build your reputation one interaction at a time.</p>
<h2>The Five Strategies</h2>
<h3>Close the Loop</h3>
<p>Most people forget to follow up and tie loose ends, but you&#39;ll be remembered when you do. </p>
<p>Whether it&#39;s confirming next steps after a meeting, updating stakeholders on project progress, or simply acknowledging receipt of important information, closing the loop demonstrates reliability and professionalism that stands out in today&#39;s fast-paced work environment.</p>
<h3>Write Clearly and Concisely</h3>
<p>This skill enhances your clarity of thought and ensures senior people will take you more seriously.</p>
<p>In an age of information overload, the ability to communicate complex ideas simply and directly is invaluable. Your emails, reports, and proposals become a reflection of your thinking—make them count.</p>
<h3>Be Ready to Ask Thoughtful Questions</h3>
<p>Keep a handy list of &#39;general&#39; questions and a &#39;personalized&#39; list for key stakeholders for serendipitous chance encounters like elevator conversations. </p>
<p>Thoughtful questions show you&#39;re engaged, curious, and strategic in your thinking. They also create memorable interactions that can open unexpected doors.</p>
<h3>Nail the Boring Work Well</h3>
<p>You will quickly raise your credibility by excelling at mundane tasks. </p>
<p>While others rush through or avoid unglamorous assignments, treating every task—no matter how small—with care and attention to detail builds a reputation for excellence that precedes you.</p>
<h3>Keep a &quot;Brag File&quot;</h3>
<p>Track your wins, lessons, feedback, and metrics. You will wrongly believe you can remember everything, but future you will be grateful. </p>
<p>This isn&#39;t about ego—it&#39;s about having concrete examples ready for performance reviews, job interviews, and moments when you need to advocate for yourself.</p>
<h2>Conclusion</h2>
<p>These strategies work because they address the gap between good intentions and consistent execution. While everyone knows they should follow up or write well, few people actually do it consistently. By mastering these overlooked fundamentals, you create a competitive advantage that compounds over time.</p>
<p>The question remains: What is one thing you underestimated early in your career? Often, it&#39;s these seemingly simple practices that we wish we had prioritized from day one.<br /><br /><a href="https://www.linkedin.com/in/jasonyoong/"><em>Follow me on LinkedIn</em></a><em> for more content like this!</em></p>]]></content:encoded>
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      <title>5 Career Advice For My 21 Year-Old Self</title>
      <link>https://jasonyoong.com/5-career-advice/</link>
      <guid isPermaLink="true">https://jasonyoong.com/5-career-advice/</guid>
      <pubDate>Fri, 23 May 2025 01:45:34 GMT</pubDate>
      <description>Navigating the start of your career can feel overwhelming, with conflicting advice at every turn. While it’s easy to focus on traditional metrics, the…</description>
      <content:encoded><![CDATA[<p>Navigating the start of your career can feel overwhelming, with conflicting advice at every turn.</p>
<p>While it’s easy to focus on traditional metrics, the real drivers of long-term success are often less obvious. </p>
<p>This article covers five career tips (and one bonus mindset) that matter more than what you learn in a classroom.</p>
<h2>Build Your Network</h2>
<p>Your network is more important than your Grade Point Average. </p>
<p>While good grades can open the first door, a strong professional network keeps doors opening for your entire career. </p>
<p>Start building it early by focusing on adding value to others first, without expecting anything in return. </p>
<p>Genuine relationships built on mutual respect and helpfulness will always outperform a transactional approach.</p>
<h2>Leverage Internships</h2>
<p>Internships are a cheat code for figuring out what you want to do. </p>
<p>They provide a low-risk environment to test-drive different industries, roles, and company cultures. </p>
<p>Use these opportunities to learn what you enjoy and, just as importantly, what you don’t, before committing to a long-term path.</p>
<h2>Chasing Growth</h2>
<p>Don&#39;t chase job titles; chase learning and rocket ship mentors. </p>
<p>A fancy title at a slow-moving company is an empty prize compared to the skills you’ll gain working under a brilliant leader on a high-growth project. </p>
<p>Focus on environments that challenge you and people who invest in you. The earning potential will naturally follow that growth.</p>
<h2>Earn Your Passion</h2>
<p>You don&#39;t &quot;find&quot; your passion in a single moment of discovery. You earn it over time by trying, doing, and leaning into what energizes you. </p>
<p>Pay attention to the tasks and projects that make you feel engaged and alive. </p>
<p>Passion is the result of investing your effort into work that truly resonates with you.</p>
<h2>Learn How to Think</h2>
<p>It&#39;s more critical to learn <em>how</em> to think than <em>what</em> to think. </p>
<p>In the age of AI, information is a commodity, but the ability to apply judgment, creativity, and a bold point of view is irreplaceable. </p>
<p>Leaders don&#39;t need memorized copycats; they need people who can analyze complex situations and form unique insights.</p>
<h2>BONUS: Be a Time Billionaire</h2>
<p>As a young professional, you are a time billionaire. This means you have an abundance of one of the most valuable resources: time. </p>
<p>Embrace a mindset of being macro-patient and micro-impatient. Be patient with your overall career arc, but act with urgency every day to learn, contribute, and grow. </p>
<p>Most importantly, don&#39;t forget to enjoy the ride.</p>
<h2>Conclusion</h2>
<p>Building a meaningful career is a marathon, not a sprint, and these core principles will help you navigate the journey. </p>
<p>Here is a quick rundown of my best career advice.</p>
<ul><li><strong>Network Over GPA:</strong> Build genuine professional relationships by offering value first.</li><li><strong>Use Internships:</strong> Test different career paths to discover what you truly enjoy.</li><li><strong>Prioritize Learning:</strong> Seek out rapid growth and great mentors instead of just job titles.</li><li><strong>Develop Passion:</strong> Actively cultivate passion by investing in work that energizes you.</li><li><strong>Think Independently:</strong> Your unique judgment and creativity are your greatest assets.</li><li><strong>Value Your Time:</strong> Be patient with your long-term goals but impatient with your daily actions.</li></ul>
<p><a href="https://www.linkedin.com/in/jasonyoong"><em>For more content like this, follow me on LinkedIn</em></a><em>.</em></p>]]></content:encoded>
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      <title>Mark Zuckerberg on AI in Tech</title>
      <link>https://jasonyoong.com/mark-zuckerberg/</link>
      <guid isPermaLink="true">https://jasonyoong.com/mark-zuckerberg/</guid>
      <pubDate>Fri, 09 May 2025 03:34:31 GMT</pubDate>
      <description>In the rapidly evolving landscape of artificial intelligence and software development, Mark Zuckerberg has made a bold prediction that&apos;s sending ripples…</description>
      <content:encoded><![CDATA[<p>In the rapidly evolving landscape of artificial intelligence and software development, Mark Zuckerberg has made a bold prediction that&#39;s sending ripples through the tech industry. </p>
<p>Within just 12-18 months, he estimates that most code will be written by AI systems - and not in the limited way we might imagine.</p>
<h2>Zuckerberg&#39;s Vision</h2>
<p>Watch the clip below: </p>
<p>This statement represents a fundamental shift in how we conceptualize AI&#39;s role in software development. </p>
<p>He also reiterates: </p>
<blockquote>&quot;And I don&#39;t mean autocomplete...I am talking about you give it a goal, it can run tests, it can improve things, it can find issues. It writes higher quality code than the average very good person on the team already.&quot; </blockquote>
<p>It&#39;s not just about assistance with simple tasks - it&#39;s about AI systems that can function with significant autonomy.</p>
<h2>The Evolution of AI in Tech</h2>
<p>This prediction highlights two critical transitions occurring in the AI landscape:</p>
<ol><li>We&#39;ve moved beyond AI as merely a microtasker (completing quick, simple, contained tasks with clear guidelines) to AI functioning as a true copilot (handling complex tasks requiring collaborative iteration). The next phase, as Zuckerberg describes, is AI as a standalone teammate - you provide a goal with context, and the AI works autonomously to achieve it.</li><li>Progressive companies like Shopify and Duolingo have already publicly shifted to &quot;AI-first&quot; or &quot;AI-native&quot; approaches, integrating AI into their hiring processes and performance/promotion reviews.</li></ol>
<h2>Tech Companies on AI</h2>
<p>Given these advancements and the clear direction of the industry, it&#39;s puzzling that more tech companies haven&#39;t publicly declared their AI strategies. </p>
<p>Despite the proven capabilities and potential competitive advantages, many organizations remain hesitant to fully commit to an AI-first approach.</p>
<p>This reluctance raises important questions: </p>
<ol><li>Are companies concerned about workforce reactions? </li><li>Are there implementation challenges that aren&#39;t being publicly discussed? </li><li>Or is it simply a matter of waiting to see which way the wind blows before making definitive statements?</li></ol>
<h2>Is The Timeline Realistic?</h2>
<p>The 12-18 month timeline offered by Zuckerberg is ambitious but not necessarily unrealistic given the exponential pace of AI development. </p>
<p>We&#39;ve witnessed remarkable leaps in AI capabilities over just the past year, particularly in areas like code generation and problem-solving.</p>
<h2>Conclusion</h2>
<p>Whether Zuckerberg&#39;s timeline proves accurate or not, the direction is clear - AI is rapidly becoming a fundamental force in software development and tech operations. </p>
<p>Companies that hesitate too long may find themselves playing catch-up in a transformed landscape.</p>
<p>What are your thoughts on this transition? Is your organization preparing for an AI-first future? </p>
<p>The companies that thoughtfully integrate these technologies now will likely gain significant advantages in efficiency, innovation, and talent retention in the coming years.</p>]]></content:encoded>
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      <title>Unforgettable Presence by Lorraine K. Lee</title>
      <link>https://jasonyoong.com/unforgettable-presence/</link>
      <guid isPermaLink="true">https://jasonyoong.com/unforgettable-presence/</guid>
      <pubDate>Fri, 25 Apr 2025 03:34:30 GMT</pubDate>
      <description>It&apos;s a good day to read https://www.linkedin.com/in/ACoAAAKd-fgBGmhGXZNFWxd-9PoefBJT05imaNs Lorraine K. Lee &apos;s new bestselling book &apos;Unforgettable…</description>
      <content:encoded><![CDATA[<p>It&#39;s a good day to read <a href="https://www.linkedin.com/in/ACoAAAKd-fgBGmhGXZNFWxd-9PoefBJT05imaNs">https://www.linkedin.com/in/ACoAAAKd-fgBGmhGXZNFWxd-9PoefBJT05imaNs</a><a href="https://www.linkedin.com/in/lorraineklee/">Lorraine K. Lee</a>&#39;s new bestselling book &#39;Unforgettable Presence: Get Seen, Gain Influence, and Catapult Your Career&#39; — this is the book you wish you read earlier.</p>
<h2>Personal Notes</h2>
<ol><li>Big congrats to Lorraine for writing, publishing, and getting her book to bestselling rarified air (it&#39;s not easy).</li><li>Lorraine considers herself a sky overlooked introvert who then transformed into a sought-after keynote speaker and helps people be intentional about their professional presence. She&#39;s a great example of — if you want it, you can do it.</li><li>Lorraine is a terrific collaborator. She is positive-sum, high energy, acts fast, is win/win minded, and gets things done.</li><li>Her advice is clear, thoughtful, pragmatic, and actionable.</li></ol>
<h2>Full Conversation</h2>
<p>Watch our full conversation below. <a href="http://v">Or click here to watch it on YouTube</a>.</p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/t385bkCv7hk" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>Conclusion</h2>
<p>Developing Executive Presence is one of the most common topics/questions we get and Lorraine has written an excellent book on the topic with new ideas on how to up-level your VIRTUAL communication and LinkedIn presence.<br /><br /><a href="https://levelupwithethanevans.substack.com/p/the-new-rules-of-presence-how-to">Read Lorraine&#39;s article on &#39;The New Rules of Presence: How to Stand Out and Get Ahead&#39; by clicking here</a>. <br /><br /><a href="https://www.amazon.com/dp/1394281722?ref=cm_sw_r_ffobk_cp_ud_dp_AC6BP3GAMZK2ZY43976E&amp;ref_=cm_sw_r_ffobk_cp_ud_dp_AC6BP3GAMZK2ZY43976E&amp;social_share=cm_sw_r_ffobk_cp_ud_dp_AC6BP3GAMZK2ZY43976E&amp;bestFormat=true&amp;previewDoh=1">Buy Lorraine&#39;s book on Amazon by clicking here</a>. </p>]]></content:encoded>
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      <title>Tobias Lütke&apos;s Shopify AI Memo: A Leadership Masterclass</title>
      <link>https://jasonyoong.com/shopify-ai-masterclass/</link>
      <guid isPermaLink="true">https://jasonyoong.com/shopify-ai-masterclass/</guid>
      <pubDate>Wed, 09 Apr 2025 15:44:16 GMT</pubDate>
      <description>I came across Tobias Lütke&apos;s internal Shopify AI memo recently, and it&apos;s truly a must-read. The document offers a masterclass on how founders usher in…</description>
      <content:encoded><![CDATA[<p>I came across Tobias Lütke&#39;s internal Shopify AI memo recently, and it&#39;s truly a must-read. </p>
<p>The document offers a masterclass on how founders usher in immediate change with boldness and clarity. </p>
<p>These are the 8 points that caught my attention because they raise the industry bar and highlight what makes Tobi bold.</p>
<h2><strong>8 Key Points From Lutke&#39;s AI Memo</strong></h2>
<p>Here are the key points:</p>
<h2><strong>Reflexive AI Usage as Baseline</strong></h2>
<p>Reflexive AI usage is now a baseline expectation at Shopify.</p>
<ul><li>Crisp and clear at all levels. There is no other way around this.</li></ul>
<h2><strong>Learning AI Through Practice</strong></h2>
<p>What we have learned so far is that using AI well is a skill that needs to be carefully learned by… using it a lot.</p>
<ul><li>Learn via osmosis.</li></ul>
<h2><strong>The Red Queen Race</strong></h2>
<p>In my On Leadership memo years ago, I described Shopify as a red queen race based on the Alice in Wonderland story—you have to keep running just to stay still.</p>
<ul><li>Tobi raises the heat where room temperature is the norm.</li></ul>
<h2><strong>Stagnation Equals Failure</strong></h2>
<p>Stagnation is slow-motion failure. If you&#39;re not climbing, you&#39;re sliding.</p>
<h2><strong>AI in Performance Reviews</strong></h2>
<p>We will add AI usage questions to our performance and peer review questionnaire.</p>
<ul><li>&quot;Show me the incentives and I will tell you the results.&quot; — Charlie Munger</li></ul>
<h2><strong>AI Integration in Business Reviews</strong></h2>
<p>We&#39;ll dedicate time to AI integration in our monthly business reviews and product development cycles.</p>
<h2><strong>AI Before Additional Headcount</strong></h2>
<p>Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI.</p>
<ul><li>AI is no longer a tool, it&#39;s a headcount gatekeeper.</li></ul>
<h2><strong>Clear Mission Alignment</strong></h2>
<p>I already laid out a lot of the AI projects in the themes this year. Our roadmap is clear, and our product will better match our mission. </p>
<ul><li>Clarity in mission, vision, expectations, and communication is what sets the best leaders apart.</li></ul>
<p><em>You can </em><a href="https://lnkd.in/g-XzmFsS"><em>read the full memo here</em></a><em>.</em></p>]]></content:encoded>
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      <title>AI and Content Businesses: How We&apos;re Adapting at Level Up</title>
      <link>https://jasonyoong.com/ai-how-level-up-is-adapting/</link>
      <guid isPermaLink="true">https://jasonyoong.com/ai-how-level-up-is-adapting/</guid>
      <pubDate>Wed, 02 Apr 2025 01:35:19 GMT</pubDate>
      <description>For us at Level Up, the big word for 2025 is AI. We&apos;re going through this transformation right now, and the choice is pretty clear. Artificial…</description>
      <content:encoded><![CDATA[<p>For us at Level Up, the big word for 2025 is AI. </p>
<p>We&#39;re going through this transformation right now, and the choice is pretty clear. </p>
<p>Artificial intelligence will take us down one of two paths: either it&#39;s going to kill our business, or it&#39;s going to 10x our business. </p>
<p>We&#39;re obviously working hard to ensure it&#39;s the latter.</p>
<h2><strong>Our Adaptation Strategy</strong></h2>
<p>We believe adaptation is essential. We&#39;ve created an Ethan GPT that&#39;s free on ChatGPT. </p>
<p>It draws from a couple of hundred thousand texts and hundreds of hours of video content (including some never-released material), and it communicates with the same candid, straight-talking style as Ethan. </p>
<p>I&#39;d estimate it&#39;s about 70% there in capturing his authentic voice.</p>
<h2><strong>Reimagining Our Business</strong></h2>
<p>We&#39;re rethinking what our business would look like if we launched today as an AI-first company. </p>
<p>The core components that I believe will drive our growth are our commitment to providing free content consistently—blogs, podcasts, and YouTube videos. </p>
<p>Our YouTube channel now features over 320 videos, most running about an hour long.</p>
<h2><strong>Our Mission: Paying It Forward</strong></h2>
<p>The mission behind everything we do is, simply put, to pay it forward. </p>
<p>Ethan has enjoyed success in his career, as have I in mine, and we&#39;ve learned that companies typically fail at training people to become effective leaders or people managers. </p>
<p>When you become a first-time leader, your team essentially becomes your guinea pig—for better or worse.</p>
<h2><strong>The Give-First Mentality</strong></h2>
<p>We operate with a give-first philosophy. Virtually everything we offer has a free version. </p>
<p>Our thinking is that if you want a condensed six-hour course with peer networking and live Q&amp;A sessions with Ethan, then our paid courses are available. </p>
<p>But in the age of artificial intelligence, we believe human community will become the most valuable asset. Your network and warm referrals will increasingly determine your next career opportunity.</p>
<h2><strong>Building Connections in a Competitive Landscape</strong></h2>
<p>Think about it—thousands of AIs will compete for the next job. Many people will build in public, which gives you one filtering method. </p>
<p>But then what? </p>
<p>When you have 100 qualified candidates all building in public and showing results, who actually lands the job? It&#39;s probably the one with some sort of referral or warm connection. </p>
<p>That&#39;s the real value of community.</p>
<p>Fortune reports that 80% of all executive jobs are never posted publicly—they&#39;re filled through recruiting firms and warm referrals. </p>
<p>We want to help people excel at making these connections, and we believe community is the key to making this happen.</p>
<h2><strong>Free Content in an AI World</strong></h2>
<p>With AI, we&#39;re comfortable freely sharing our content. Many of our courses cost over a thousand dollars, and I frequently receive emails from people saying they can&#39;t afford that. </p>
<p>I simply direct them to these 10 YouTube videos and suggest they read our free newsletters—you&#39;ll find most of the same information there; you just need to invest more time.</p>
<h2><strong>Conclusion</strong></h2>
<p>The short answer is that we don&#39;t know exactly how AI will impact us yet. </p>
<p>We&#39;re actively trying to figure it out right now.</p>]]></content:encoded>
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      <title>My Career Jigsaw: Professional Growth and Personal Priorities</title>
      <link>https://jasonyoong.com/my-career-jigsaw/</link>
      <guid isPermaLink="true">https://jasonyoong.com/my-career-jigsaw/</guid>
      <pubDate>Fri, 28 Mar 2025 01:26:25 GMT</pubDate>
      <description>My career resembles a jigsaw puzzle, scattered and diverse rather than following a straight line. It defies the traditional linear progression most…</description>
      <content:encoded><![CDATA[<p>My career resembles a jigsaw puzzle, scattered and diverse rather than following a straight line. </p>
<p>It defies the traditional linear progression most people expect in professional journeys.</p>
<h2><strong>Finding the Right People</strong></h2>
<p>I love working on exciting projects with inspiring people. That&#39;s my fundamental approach. </p>
<p>While some advise, &quot;Follow your career to growing companies,&quot; I believe the opposite—follow exceptional leaders who champion you.</p>
<p>When you surround yourself with excellent people, you naturally engage in exciting, adventurous work, and everything else falls into place.</p>
<h2><strong>Prioritizing Flexibility</strong></h2>
<p>I deeply value life flexibility—particularly time flexibility (working on my own schedule), location flexibility (working wherever I choose), and content flexibility (doing what truly interests me).</p>
<h2><strong>My Core Interests</strong></h2>
<p>In conversations, I&#39;m drawn to discussing: travel, wealth and finance (especially the FIRE movement), business (revenue streams, business models, emerging trends), and parenting and time management. </p>
<p>These passions explain why my career path has zigzagged across different fields.</p>
<h2><strong>Life in Seasons</strong></h2>
<p>I view life through the lens of distinct seasons. </p>
<p>As the parent of a three-year-old daughter, three key insights have transformed my perspective:</p>
<p><strong>First</strong>, from ages zero to five, you have greater flexibility because your child isn&#39;t in school yet. This is the prime time to travel or live in different locations—exactly why we deliberately moved to Honolulu last December.</p>
<p><strong>Second</strong>, ages zero to ten represent the magic years when you remain your child&#39;s favorite person. They haven&#39;t reached the teenage phase yet.</p>
<p><strong>Third</strong>, by the time your child turns 18, you&#39;ve already spent approximately 93% of your total lifetime together. As a parent who adores my child, I&#39;m determined to maximize our time together now.</p>
<h2><strong>Paying It Forward</strong></h2>
<p>My greatest passion, which I&#39;ll always offer freely, is providing career and life guidance to high school and college students. </p>
<p>I speak at USC, NYU, and various high schools—whenever any educational institution reaches out, I accept them regardless of who they are. </p>
<p>If I can participate virtually, I&#39;ll always say yes because students often ask remarkably thoughtful questions.</p>]]></content:encoded>
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      <title>How to Manage Up and Down Effectively</title>
      <link>https://jasonyoong.com/manage-up-and-down/</link>
      <guid isPermaLink="true">https://jasonyoong.com/manage-up-and-down/</guid>
      <pubDate>Sat, 22 Mar 2025 01:16:11 GMT</pubDate>
      <description>My business partner, Ethan Evans (retired Amazon VP, LinkedIn Top Voice) developed a popular concept called “The Magic Loop” that works at any level of…</description>
      <content:encoded><![CDATA[<p>My business partner, <a href="https://www.ethanevans.com">Ethan Evans</a> (retired Amazon VP, LinkedIn Top Voice) developed a popular concept called “The Magic Loop” that works at any level of your job – from junior to manager to IC to director to VP.</p>
<p>It&#39;s about managing relationships effectively in both directions of the organizational hierarchy.</p>
<h2><strong>Starting with Observation</strong></h2>
<p>The Magic Loop begins with the power of observation—carefully watch your manager, understand their work style, and note the types of questions they regularly ask. </p>
<p>Then follow these five steps.</p>
<h2><strong>The Five Basic Steps</strong></h2>
<p><strong>Step 1:</strong> </p>
<p>Excel at your assigned work first.</p>
<p><strong>Step 2:</strong> </p>
<p>Ask your manager, &quot;How can I help you?&quot; Surprisingly, 90% of managers never hear this question from their direct reports. </p>
<p>By simply asking, you&#39;ll immediately stand out.</p>
<p><strong>Step 3:</strong> </p>
<p>Whatever task they assign, complete it excellently. Remember, you build credibility and trust by delivering consistent results. </p>
<p>No one will hand you a $10 billion product to lead immediately because you haven&#39;t established trust, credibility, or a track record yet. </p>
<p>You must earn these over time.</p>
<p><strong>Step 4:</strong> </p>
<p>After cycling through steps 1-3 several times, the magic happens in step 4. </p>
<p>Now when you ask, &quot;How can I help you?&quot; request a task or goal that aligns with your personal career objectives. </p>
<p>Perhaps you want a promotion, increased visibility with key stakeholders, expanded scope, or management experience. </p>
<p>For example: &quot;One of my goals is to learn how to manage people. With summer interns arriving soon, could I lead and mentor two of them? Would that help you?&quot;</p>
<p><strong>Step 5:</strong> </p>
<p>Rinse and repeat.</p>
<h2><strong>Advanced Magic Loop Techniques</strong></h2>
<p>Once you&#39;ve built sufficient trust, you can implement two advanced forms of the Magic Loop. </p>
<p>First, proactively present solutions: &quot;Hey manager, I noticed this problem. Here&#39;s my recommendation to fix it. Are you comfortable with me implementing it?&quot;</p>
<p>The ultimate form is taking initiative: &quot;Hey manager, I noticed we had this problem. I&#39;ve already fixed it. Here&#39;s what I did.&quot;</p>
<h2><strong>Conclusion</strong></h2>
<p>The best performers skillfully blend all three approaches, exercising good judgment about when each is most appropriate. </p>
<p>While taking initiative is valuable, constantly defaulting to &quot;just do it&quot; isn&#39;t ideal—your manager often possesses more information and context than you do, making their input essential in certain situations.</p>]]></content:encoded>
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      <title>How to Break Through to Executive Level</title>
      <link>https://jasonyoong.com/executive-level/</link>
      <guid isPermaLink="true">https://jasonyoong.com/executive-level/</guid>
      <pubDate>Tue, 18 Mar 2025 01:09:43 GMT</pubDate>
      <description>Here are my 5 tips needed to break through to the executive level. Tip 1: Become a Scaled Leader To break through to the executive level, you need to…</description>
      <content:encoded><![CDATA[<p>Here are my 5 tips needed to break through to the executive level.</p>
<h2><strong>Tip 1: Become a Scaled Leader</strong></h2>
<p>To break through to the executive level, you need to learn how to be a scaled deep leader—how do you truly scale your business and team? </p>
<p>This comes down to delegation and creating effective mechanism checkpoints. </p>
<p>Tell your team, &quot;I am not a micromanager, but part of my job is to regularly audit your performance so I can stay updated and help you when needed.&quot;</p>
<p>Implement these mechanisms through weekly and monthly business reviews that keep operations on schedule. </p>
<p>The most crucial aspect of leadership is setting clear expectations upfront, so your lieutenants understand exactly what you expect and the timeline they need to follow.</p>
<h2><strong>Tip 2: Be a Change Agent</strong></h2>
<p>You must become a change agent for the business. </p>
<p>If you want to scale into executive roles and become an influential leader, you need to drive measurable business results. </p>
<p>In for-profit companies, this means cultivating a team culture that embraces innovation and continuous improvement.</p>
<h2><strong>Tip 3: Master the Magic Loop</strong></h2>
<p>This is about effectively managing both up and down. </p>
<p>Start by carefully observing your manager—notice how they prefer to work and the specific questions they consistently ask. </p>
<p>Then follow these steps:</p>
<ol><li>Do your assigned work well first.</li><li>Ask your manager how you can help (90% of managers never get asked this).</li><li>Whatever they give you, execute it excellently.</li><li>Once you build trust, request tasks that align with your career goals.</li><li>Rinse and repeat.</li></ol>
<p>As you build credibility, begin proactively showcasing solutions: &quot;I noticed this problem; here&#39;s my recommendation on how we fix it.&quot; </p>
<p>Eventually, advance to taking more initiative: &quot;I noticed we had this problem; I fixed it; here&#39;s what I did.&quot;</p>
<h2><strong>Tip 4: Build Trust and Executive Presence</strong></h2>
<p>The senior level in companies can be intensely competitive. </p>
<p>Often there&#39;s only one spot for promotion, and it typically goes to whoever has established the highest trust, strongest industry reputation, compelling executive presence, solid relationships, and a consistent track record of delivering business results.</p>
<h2><strong>Tip 5: Demonstrate Bold Leadership</strong></h2>
<p>I&#39;ve witnessed bold leadership in action—executives who build innovative products that directly confront the innovator&#39;s dilemma, creating their company&#39;s future even when it might threaten current cash flows. </p>
<p>This willingness to potentially disrupt their own &quot;golden goose&quot; isn&#39;t easy, but it distinguishes truly visionary leaders from the rest.</p>]]></content:encoded>
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      <title>Working for Tech Giants vs. Startups</title>
      <link>https://jasonyoong.com/tech-giants-vs-startups/</link>
      <guid isPermaLink="true">https://jasonyoong.com/tech-giants-vs-startups/</guid>
      <pubDate>Sat, 15 Mar 2025 00:53:20 GMT</pubDate>
      <description>What&apos;s the difference between working for a startup and working for a huge corporation? Everything is different. The Startup Mentality At a startup, the…</description>
      <content:encoded><![CDATA[<p>What&#39;s the difference between working for a startup and working for a huge corporation? Everything is different.</p>
<h2><strong>The Startup Mentality</strong></h2>
<p>At a startup, the only thing that matters is product-market fit. There&#39;s no time for process. You don&#39;t have time for performance reviews. </p>
<p>None of that matters if your startup isn&#39;t making money and growing. It&#39;s all about speed, talking to customers, and &quot;build, build, build, sell, sell, sell.&quot; </p>
<p>You have to roll up your sleeves and get your hands dirty.</p>
<h2><strong>Traits of Successful Founders</strong></h2>
<p>The best founders I&#39;ve worked with share these traits.</p>
<p>They&#39;re relentless builders, they love talking to customers firsthand, and they can sell—they can &quot;sell sand to Hawaii.&quot;</p>
<h2><strong>The Corporate Advantage</strong></h2>
<p>In contrast, at a big-name company, the name itself is leverage. </p>
<p>At Amazon, almost everyone will take your call. At a startup, it&#39;s more like, &quot;Who are you and why do I need to waste 15 minutes?&quot;</p>
<p>At a big company, you&#39;re working with extremely talented people, so the internal network is incredibly powerful. </p>
<p>Especially at a company like Amazon with so many different business units, you can find a team, business, and product that you truly connect with.</p>
<h2><strong>Operational Excellence at Scale</strong></h2>
<p>The operational process at Amazon was A+. The way they conduct interviews, the bar-raising program, the writing culture, and how they run meetings—it was all exceptional. </p>
<p>What I particularly appreciated at Amazon is that there&#39;s no room for false harmony. Your job in meetings is to truth-seek and to find what&#39;s best for customers and the business. </p>
<p>That means there&#39;s a lot of heated discussion and hotly debated topics, but I love that because what I hate is sweeping things under the rug where nothing ever gets done. Builders hate that.</p>
<h2><strong>Leadership Lessons from Giants</strong></h2>
<p>At Amazon and other big corporations, I witnessed what strong leadership looks like from a people&#39;s inspiration and motivation standpoint—how to inspire large groups of people to move big mountains together.</p>]]></content:encoded>
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      <title>The Profitable Path of Being Unprofitable</title>
      <link>https://jasonyoong.com/jeff-bezos/</link>
      <guid isPermaLink="true">https://jasonyoong.com/jeff-bezos/</guid>
      <pubDate>Wed, 12 Mar 2025 21:09:00 GMT</pubDate>
      <description>Jeff Bezos&apos; candid acknowledgment of Amazon&apos;s unprofitability demonstrates the power of transparent leadership and unwavering conviction. His ability to…</description>
      <content:encoded><![CDATA[<p>Jeff Bezos&#39; candid acknowledgment of Amazon&#39;s unprofitability demonstrates the power of transparent leadership and unwavering conviction. </p>
<p>His ability to laugh at Amazon&#39;s financial situation disarmed critics while his commitment to &quot;investing in the future&quot; signaled his extraordinary vision.</p>
<p>Here&#39;s more about what he said.</p>
<h2>The Conversation</h2>
<p>In 1999, Jeff Bezos was asked this:</p>
<blockquote>&quot;The company&#39;s never made a profit?&quot;  </blockquote>
<p>This was his response, and it was great:</p>
<blockquote>&quot;That&#39;s right. Seems like a new math, doesn&#39;t it?   There are a whole series of Doonesbury cartoons about this.<br /><br />This is not a new phenomenon.<br /><br />We are a famously unprofitable company.<br /><br />And we are investing in the future. Which isn&#39;t unusual. Companies have done this before.<br /><br />What&#39;s a little surprising about <a href="http://amazon.com/">Amazon.com</a> is the scale which we&#39;re doing it, we&#39;re doing it in a big way.&quot; </blockquote>
<p><a href="https://www.youtube.com/watch?v=Pj8CthSn2tI">Watch the clip of his interview here</a>. </p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/Pj8CthSn2tI" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>A Reminder</h2>
<p>This reminded me of 2 things:</p>
<ol><li>Jeff&#39;s response is great because he laughs and makes jokes about it (the phrase &quot;We are a famously unprofitable company&quot; is gold), states that it&#39;s not uncommon practice BUT differentiates Amazon by the long-term thinking and outsized bets. No one can laugh at you when you laugh at yourself first.</li><li>Jeff says that inventing and pioneering requires a willingness to be misunderstood for long periods of time. That&#39;s where long-term thinking and &quot;Be stubborn on the vision but flexible on the details&quot; comes into play.</li></ol>
<h2>Conclusion</h2>
<p>The lesson for today&#39;s builders is clear: short-term profitability and immediate validation often stand at odds with transformative innovation. </p>
<p>By embracing self-awareness, maintaining conviction in your vision while adapting your approach, and having the courage to be misunderstood, you create space for the kind of long-term thinking that changes industries and builds lasting value.</p>]]></content:encoded>
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      <title>The Art of the 1-2 Page Document</title>
      <link>https://jasonyoong.com/1-2-page-document/</link>
      <guid isPermaLink="true">https://jasonyoong.com/1-2-page-document/</guid>
      <pubDate>Mon, 10 Mar 2025 00:39:21 GMT</pubDate>
      <description>The purpose of a 1-2 page document is to create a crisp summary that conveys the main points and sparks deeper discussion. It cuts through complexity and…</description>
      <content:encoded><![CDATA[<p>The purpose of a 1-2 page document is to create a crisp summary that conveys the main points and sparks deeper discussion. </p>
<p>It cuts through complexity and focuses attention on what matters most.</p>
<h2><strong>Document</strong> <strong>Structure</strong></h2>
<p>I structure these documents into distinct sections:</p>
<p><strong>Section 1: Clear Purpose</strong> </p>
<p>State the document&#39;s purpose in two to three sentences. </p>
<p>For example: The purpose of this document is to align our team, get approval, or discuss x, y, z. </p>
<p>Keep it straightforward.</p>
<p><strong>Section 2: Upfront Recommendation</strong> </p>
<p>Present your recommendation clearly: I recommend x, y, z. </p>
<p>Use a couple of bullets with a concise one-sentence rationale for each point.</p>
<p><strong>Section 3: Supporting Data</strong> </p>
<p>Include compelling data that backs up your rationale and reveals more of your thinking process.</p>
<p><strong>Section 4: FAQs</strong> </p>
<p>Anticipate questions from both the end customer&#39;s perspective and internal business stakeholders. Address concerns like: How will we make money? What happens if we do X? What would customer onboarding look like?</p>
<h2><strong>The Power of &quot;Rude FAQs&quot;</strong></h2>
<p>Add challenging questions like &quot;Have you considered this?&quot; We sometimes include what we call &quot;rude FAQs&quot; - tough questions such as &quot;What happens if this doesn&#39;t work?&quot; or &quot;Do we really have the skills to do this?&quot; </p>
<p>It&#39;s like having a pessimist or harsh QA person in the room, asking the difficult questions everyone&#39;s thinking but might not say.</p>
<h2><strong>Putting It Into Practice</strong></h2>
<p>I used this approach when pitching my vision to Ethan for what would become <a href="https://www.ethanevans.com/">Level Up</a>. </p>
<p>I wrote a business vision plan using this format. </p>
<p>I told him, &quot;Hey, look, I think there could be a big business here—very low lift, but it could be grounded in online courses, LinkedIn writing, potentially a newsletter, potentially community.&quot;</p>
<p>The document was clear and concise, sparking a productive conversation that eventually led to our partnership.</p>
<h2>Conclusion</h2>
<p>This approach to documentation has served me well throughout my career. It cuts through the noise and focuses on what truly matters. </p>
<p>It respects people&#39;s time while providing all the information they need to make informed decisions. </p>
<p>Most importantly, it creates a foundation for meaningful, productive discussions—where the real value ultimately emerges.</p>]]></content:encoded>
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      <title>What It Means to Be an Amazonian: My Time at Amazon</title>
      <link>https://jasonyoong.com/amazonian/</link>
      <guid isPermaLink="true">https://jasonyoong.com/amazonian/</guid>
      <pubDate>Fri, 07 Mar 2025 00:31:43 GMT</pubDate>
      <description>What does it mean to be an Amazonian? It means embracing a Day 1 mentality. It means being vocally self-critical while remaining open to evolving the…</description>
      <content:encoded><![CDATA[<p>What does it mean to be an Amazonian? </p>
<p>It means embracing a Day 1 mentality. It means being vocally self-critical while remaining open to evolving the leadership principles. </p>
<p>It means obsessively raising the bar for customers and preferring narrative documents to PowerPoint decks.</p>
<h2><strong>Thinking Long-Term</strong></h2>
<p>Perhaps most importantly, being an Amazonian means thinking long-term and being willing to be misunderstood. </p>
<p>This last part proves particularly challenging. People will tell you that you&#39;re crazy. </p>
<p>Critics will emerge from everywhere. But if you truly believe in your vision, if you believe it&#39;s the right thing for customers, it will ultimately pay off.</p>
<h2><strong>Operational Excellence</strong></h2>
<p>At Amazon, I witnessed what genuine operational excellence looks like. </p>
<p>The mechanisms Amazon establishes through its narrative culture effectively scale information dissemination. </p>
<p>This becomes a true force multiplier when managing large teams and creates valuable artifacts as your company continuously grows with new people.</p>
<h2><strong>Conclusion</strong></h2>
<p>I once believed I would be an Amazonian for life. I imagined retiring at Amazon. </p>
<p>I thrived in the culture and particularly enjoyed the writing-focused environment. </p>
<p>Yet, after four and a half years, I took one of the biggest leaps in my career—leaving Amazon to join a pre-seed, pre-product startup with nothing but a PowerPoint deck to its name.</p>]]></content:encoded>
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      <title>Brian Chesky: The Truth About The 1:1 Model</title>
      <link>https://jasonyoong.com/brian-chesky/</link>
      <guid isPermaLink="true">https://jasonyoong.com/brian-chesky/</guid>
      <pubDate>Fri, 21 Feb 2025 11:33:20 GMT</pubDate>
      <description>Brian Chesky, CEO of Airbnb has come out against the traditional CEO 1:1 model, claiming most great CEOs eventually realize it&apos;s flawed. According to…</description>
      <content:encoded><![CDATA[<p>Brian Chesky, CEO of Airbnb has come out against the traditional CEO 1:1 model, claiming most great CEOs eventually realize it&#39;s flawed. </p>
<p>According to Chesky, these meetings often devolve into therapy sessions where employees control the agenda, discussing issues that should really involve others. </p>
<p>While he still does impromptu 1:1 calls when he needs something specific, he&#39;s abandoned the recurring meeting format where direct reports own the conversation. </p>
<p>Here&#39;s the full transcript. </p>
<h2>The Interview</h2>
<p>Brian Chesky was interviewed on the Fortune Magazine.</p>
<p><a href="https://www.youtube.com/watch?v=-JnqbfeaXXA">You can watch the full interview here</a>. But this is what he said about the 1:1 model: </p>
<blockquote>&quot;Almost every CEO did 1:1s and realized that the 1:1 model was flawed.<br /><br />It&#39;s a recurring 1 hour 1-on-1 meeting where the employee owns the agenda and what happens is they often don&#39;t talk about things you want to talk about.<br /><br />You become their therapist...<br /><br />Often time they are bringing you problems that you want other people in the room to hear and there are very few times that employees should come to you 1:1 without their people...<br /><br />Now there is a caveat. I do a lot of 1:1 calls and emails.<br /><br />I&#39;ll call someone and say &#39;Hey, what&#39;s the status of this...’ but it&#39;s not a recurring meeting with them owning the agenda. It&#39;s me when I need something.&quot; </blockquote>
<h2>Takeaways</h2>
<p>After listening to Brian Chesky, here are my top 3 takeaways:</p>
<ol><li>I agree. Recurring 1:1s are not needed at the CEO / C-suite level. The direct reports are senior enough executives to discern when an escalation or a private 1:1 is needed.</li><li>Brian Chesky mentioned Jensen Huang (Cofounder &amp; CEO of NVIDIA) and that he also does not do 1:1s with his 60 direct reports because (a) he wants a culture where there is no privileged access to information; and (b) he gives people feedback right there in front of everybody because feedback is learning and learning from mistakes, other people&#39;s mistakes, is the best way to learn.</li><li>Ethan Evans shared that Jeff Bezos felt 1:1s at the executive level were low-value, and he stopped having any 1:1s himself. Jeff felt that 1:1s with very senior employees often turned into an arena for complaining about one another, which was a waste of time. At the executive level, leaders should handle their own interpersonal challenges without needing the CEO to intervene.</li></ol>
<h2>Conclusion</h2>
<p>When you look at other top tech CEOs like Jensen Huang at NVIDIA and Jeff Bezos at Amazon, a pattern emerges.</p>
<p>They&#39;ve all moved away from traditional 1:1s at the executive level for practical reasons.</p>
<p>This isn&#39;t about abandoning communication - it&#39;s about being intentional with how leadership time is spent and creating cultures where transparency and collective problem-solving take precedence over private, recurring check-ins.</p>]]></content:encoded>
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      <title>Career &amp; Personal Challenges Faced by Women in Tech with Chaitali Narla</title>
      <link>https://jasonyoong.com/women-in-tech-chaitali/</link>
      <guid isPermaLink="true">https://jasonyoong.com/women-in-tech-chaitali/</guid>
      <pubDate>Wed, 05 Feb 2025 22:12:44 GMT</pubDate>
      <description>Chaitali Narla went from Google intern to Engineering Director (5x promotions) in a decade. As a tech executive (Google &amp; Stripe), career coach, and mom…</description>
      <content:encoded><![CDATA[<p>Chaitali Narla went from Google intern to Engineering Director (5x promotions) in a decade.</p>
<p>As a tech executive (Google &amp; Stripe), career coach, and mom to 9-year-old Saanvi, Chaitali shares bold lessons from her demanding tech career while balancing motherhood and family. </p>
<h2>This Week&#39;s Discussion</h2>
<p>In this fireside chat, Chaitali and I dive into:</p>
<ol><li>What it takes for rapid career growth.</li><li>The biggest challenges women in tech often face in their careers and personal lives.</li></ol>
<h2>Video</h2>
<p>Here is a <a href="https://youtu.be/ijM7ZcCMWk0">link to the full discussion</a>:</p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/ijM7ZcCMWk0" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>Lessons Learnt</h2>
<p>Here are the key takeaways from our discussion:</p>
<h3><strong>Find sponsors, not mentors (especially for women)</strong></h3>
<p>Establish two-directional relationships with stakeholders closer to your work (e.g. manager, product partner, senior IC engineer, peers) who can not only advise you but also have skin in the game. </p>
<p>You help them by being part of their org or being project collaborators—use Ethan’s <a href="https://www.lennysnewsletter.com/p/the-magic-loop">Magic Loop </a>with these partners.</p>
<h3><strong>Know that titles DO matter, it helps with having to double-prove yourself as a woman</strong></h3>
<p>Chaitali had to double-prove herself many times and experienced the change when her title was software engineer vs. tech lead. </p>
<p>The appropriate title saves you time and energy from having to put your credentials on the table every time. </p>
<p>Negotiate for the title you deserve, build your network, and have strong allies to help you voice your opinion. </p>
<ol><li>Do not assume your allies know your struggle. Chaitali experienced this as a new mother nursing when she was asked to travel multiple days for a work summit, and she shared the impact that has. Speak up, educate them, and direct the allyship.</li></ol>
<h3><em><strong>“You are not technical enough”</strong></em><strong> — how to respond boldly and strategically</strong></h3>
<p>Chatali experienced this multiple times, and her response evolved with seniority:</p>
<ol><li><strong>In more junior roles, she did too much “glue work”</strong> (e.g. bringing teams together, facilitating a discussion, reviewing other people’s docs) which are important tasks but do not add up to promotable artifacts. Avoid this trap: Be confident to say no and give a clear reason why your current work is more impactful: <em>“I would love to help, but I cannot drop ABC for XYZ reasons.”</em>   Make time to do work that is viewed as technical artifacts, such as code and design docs. Block your calendar.    Leverage glue work for your growth.    Example #1: If you orchestrate a meeting between many different teams where you reach a consensus that was previously at an impasse, and you moved it along, write down the meeting notes and send them to leadership (it’s now an artifact).    Example #2: If your comments in a design doc changed the course of that project and improved the design, write it down and have that artifact ready to show how you are a technical influencer in your org.  </li><li><strong>As a manager, that question was less about Chaitali and more on her organization</strong>—meaning, does she have senior and staff engineers who can represent the organization appropriately—is their technical brand strong and are they getting stuck in glue work.</li><li><strong>In more senior roles and when talking to a peer, Chaitali would respond: </strong><em><strong>“Are you technical enough?”</strong></em></li></ol>
<h3><strong>Build a personal Board of Directors to overcome the lack of role models (especially at the executive levels)</strong></h3>
<p>Your goal is to collect many viewpoints and to learn specific skills needed at that time, whether that is executive communication or organization design. </p>
<p>Have a mix of genders and seniority levels. </p>
<p>At any given time, Chaitali has 5-7 (includes an external coach for a fresh perspective) and actively shifts the roster based on current career needs.</p>
<h3><strong>Turbocharge your career with side quests—things not part of your core job that you are not asked to do, but you pick up to do yourself. </strong></h3>
<p>Hone your skills via learning environments, build your network, attract sponsors (the thought is: <em>“If you bring this much rigor to our side quest, you must be good at your day job”</em>), and find your ikigai. </p>
<p>Example side quests: conduct recruiting activities and interviews, run a team event. <a href="https://www.chaitime.chaitalinarla.com/cp/151120357">Read more here</a>.</p>
<h3><strong>To overcome self-doubt (very common with women), take an ownership mindset approach and accept that you will have failures</strong></h3>
<p>Go into the role confident you will make it happen, be prepared to adapt, and sometimes you have to fake it till you make it. <a href="https://levelupwithethanevans.substack.com/p/overcome-imposter-syndrome">Read more about overcoming imposter syndrome here.</a></p>
<h3><strong>The top 2 reasons top performing women in tech get stuck at the Senior Manager leve</strong>l</h3>
<p>Not putting themselves up for the role and not advertising themselves enough (thus, people don’t you think are ready). Every day, you must look for those moments to build your reputation and brand. <a href="https://www.chaitime.chaitalinarla.com/cp/151502881">Read the 3 principles that drove Chaitali to Google Director.</a></p>
<h3><strong>Grit and pushing through friction are 2 things Chaitali would advise her younger self</strong></h3>
<p>As you get more senior, you experience more frustrating moments, and it takes more time for outcomes to show—thus, a key skill is staying with it and working till you’ve reached the finish line. </p>
<p>Don’t give up too early.</p>
<p>Additional resources Chaitali referenced: (a) Carla Harris on <a href="https://youtu.be/gpE_W50OTUc?si=oaZLEjmGFBiWV8_p">sponsorship</a>; (b) Tanya Reilly on <a href="https://www.youtube.com/watch?v=KClAPipnKqw&amp;t=0s">glue work</a>; (c) Dan Na on <a href="https://www.youtube.com/watch?v=8bxZuzDKoI0&amp;t=0s">pushing through friction</a>; and (d) <a href="https://www.chaitime.chaitalinarla.com/p/work-life-tapestry">Work Life Tapestry</a>.</p>
<h2>Conclusion</h2>
<p>Thank you Chaitali for the thoughtful and thought-provoking chat!</p>
<p>Connect with Chaitali on <a href="https://www.linkedin.com/in/chaitalinarla/">LinkedIn</a>, subscribe to her newsletter (highly recommended) <a href="https://www.chaitime.chaitalinarla.com/">ChaiTime</a>, and if you want to sign up for 1:1 coaching with her, <a href="https://form.jotform.com/250167679403057">fill out this form</a>.<br /></p>]]></content:encoded>
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      <title>Olympic Gold: Habits for Peak Performance with Justin Best</title>
      <link>https://jasonyoong.com/justin-best/</link>
      <guid isPermaLink="true">https://jasonyoong.com/justin-best/</guid>
      <pubDate>Sun, 26 Jan 2025 21:04:58 GMT</pubDate>
      <description>Justin Best is a two time Olympian, Gold Medalist at the Paris 2024 Olympics in men’s four rowing, and an analyst at Union Square Advisors. He is an…</description>
      <content:encoded><![CDATA[<p>Justin Best is a two time Olympian, Gold Medalist at the Paris 2024 Olympics in men’s four rowing, and an analyst at Union Square Advisors.</p>
<p>He is an inspiration, a great Team USA ambassador, and an organizational machine BEAST. </p>
<h2>This Week&#39;s Discussion</h2>
<p>In this fireside chat, I sit down with Justin to discuss:</p>
<ol><li>How Justin does it all.</li><li>Motivation and achievement at the highest levels. </li><li>Time management, sleep optimization techniques, breaking down big goals, sacrifice, career advice, and favorite Olympic memories.</li></ol>
<h2>Video</h2>
<p><a href="https://youtu.be/x6vvkQ52jvc">Watch the full interview here</a>.</p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/x6vvkQ52jvc" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>Lessons Learnt</h2>
<p>Here are some key takeaways from our discussion.</p>
<h3><strong>Takeaway 1</strong>: Balancing investment banking with Olympic training</h3>
<p><strong>Run your calendar on automatic.</strong> </p>
<p>The key to Justin’s rigorous schedule is siloing work vs. training so that he can focus 100% on one at a time and decompress:</p>
<p>Here&#39;s a look at a typical day in his schedule.</p>
<ul><li><strong>5:30am</strong> wake up</li><li><strong>6:20-8:45am</strong> training #1 cardio on the water, interval or steady-state</li><li><strong>9:30am</strong> arrive at work via BART (train)</li><li><strong>9:30am-5:30pm</strong> at work doing deal support, execution, mandates, and anything that needs to get done</li><li><strong>5:30-8pm</strong> training #2 weights and indoor rowing machine</li><li><strong>8-10pm</strong> complete unfinished work (sometimes till 11pm)</li></ul>
<p><strong>The next day</strong>…run it again!</p>
<p><strong>Optimize your energy and recovery.</strong> </p>
<p>Justin is strategic with caffeine, taking approximately 200 mg every few hours, with a 3pm cutoff to avoid sleep disruption. </p>
<p>The key to deep sleep, is a cold room (65°F), white noise, comfortable mattress, and sleeping on your side or stomach (not your back—it makes you more prone to snoring and reduces oxygen intake). </p>
<p><strong>Work like an Olympian—Be an organizational machine with compartmentalized work streams.</strong> </p>
<p>Justin has an organization system of checklists and notes per project. </p>
<p>For example, he will have 5 simultaneous checklists prioritized by <strong>immediate</strong>, <strong>medium</strong> (due 1-2 days from now), and <strong>long-Term</strong> (due 1-2 weeks from now) — this system helps him stay locked in and avoid boom and bust situations which cause stress and anxiety.</p>
<p>Set clear expectations and work to go beyond them. </p>
<p>Justin over communicates, gives work in progress (WIP) updates, and blocks out his calendar so his team knows when he’s in training.</p>
<h3><strong>Takeaway 2</strong>: Motivation and competing at the highest levels</h3>
<p><strong>Visualize your goals and work backwards from controllable inputs. </strong></p>
<p>At age 17, Justin visualized himself as an Olympic Champion in 10 years…crossing that finish line, seeing and feeling what it looks like. Being hyper-competitive, Justin is addicted to optimizing every input to drive outputs.</p>
<ol><li>And where did he learn most of his motivation, visualization, and working backwards methods… YouTube! He would watch what the best people in the world were doing. </li><li>His new goal is to close $50M in overall deal transactions. </li></ol>
<p><strong>Run full speed at what you want and hedge your risks. </strong></p>
<p>A prime motivational driver for Justin to live with urgency was while he was in college, Justin’s cousin lost his battle to brain cancer at age 27. </p>
<p>It hit Justin that we all don’t know how long we have, so go full speed because you can figure out many things (like a job) later. </p>
<p><strong>Turn pain into motivation.</strong> </p>
<p>On tough days when Justin is exhausted and needs a gut check, he watches a video recording of their Tokyo 2020 Olympics performance, where they <strong>got 4th place by ONE SECOND</strong>. </p>
<p>Recalling that painful experience refuels his motivation to get up and get it done. </p>
<p><strong>The hard truth about sacrifice to be world-class.</strong> Justin’s hardest obstacle was the personal sacrifices—less time with his fiancée, not attending friends’ weddings, not going out on Friday nights. He kept rowing his top goal and priority.</p>
<h3>Takeaway 3: Career advice</h3>
<p><strong>Find excellent mentors and leverage them. </strong></p>
<p>Find people you want to emulate and reach out to them. Put yourself in the physical locations where they are and bridge those connections. </p>
<p>You can be the smartest, but if you don’t have a group behind you, you won’t move forward (<em>that’s how business and the world works</em>).</p>
<p><strong>When you disagree with a boss/coach, know where they are coming from and approach it productively.</strong></p>
<p>Whenever Justin disagreed with a decision, he first sought to understand their 10,000-foot point of view.</p>
<p>He then bridged how they got to that decision, and then made suggestions to those points rather than attacking the decision. </p>
<p>It’s a give and take in being accommodating but pushing back on the important points.</p>
<h2>Conclusion</h2>
<p>Here are some of Justin’s favorite Paris 2024 Olympics memories (outside of winning gold).</p>
<p><strong>Connecting with athletes all over the world. </strong></p>
<p>At the Olympic Village, Justin saw how the power of sport brings athletes together—there were athletes from Russia, Ukraine, Palestine, Israel, all coexisting without altercations. </p>
<p><strong>And…GETTING ENGAGED ON LIVE TV! </strong></p>
<p>Justin may have one of the best proposals ever (surprise, family and friends, Eiffel Tower, live TV, after winning gold, and 2,738 roses). You can watch the full proposal on <a href="https://youtu.be/q0Ori0ID2hM?si=dpyeBjd3cR6Qxk1k">YouTube</a>.</p>
<p>Thank you, Justin, for the motivational chat and being a great Team USA ambassador—we look forward to rowing with you soon! </p>
<p>Connect with Justin on <a href="https://www.linkedin.com/in/justinbest30/">LinkedIn</a>, support <a href="https://usrowing.org/">US Rowing</a>, and learn more about <a href="https://www.teamusa.com/">Team USA</a>. </p>
<p><em><strong>Find your “Olympic Champion” goal and live life with urgency.</strong></em></p>
<p><br /><br /></p>]]></content:encoded>
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      <title>What Your Manager Won&apos;t Tell You: The Art of Managing Up with Wes Kao</title>
      <link>https://jasonyoong.com/managing-up/</link>
      <guid isPermaLink="true">https://jasonyoong.com/managing-up/</guid>
      <pubDate>Wed, 09 Oct 2024 19:02:49 GMT</pubDate>
      <description>Welcome to this week’s free article of Level Up: Your source for executive insights, high performance habits, and specific career growth actions. Wes Kao…</description>
      <content:encoded><![CDATA[<p>Welcome to this week’s free article of Level Up: Your source for executive insights, high performance habits, and specific career growth actions.</p>
<p><strong>Wes Kao</strong> — is an entrepreneur, speaker, coach, and advisor. </p>
<p>Here are some of her career highlights:</p>
<ul><li>Co-founded Maven (a platform for live online courses; raised $25M from First Round &amp; Andreessen Horowitz).</li><li>Co-founded the altMBA with bestselling author Seth Godin.</li><li>Advised CEOs of Section (Professor Scott Galloway), Outlier (co-founder of Masterclass), and Morning Brew on go-to-market, positioning, and growth.</li></ul>
<p>Wes currently works with founders and senior leaders via 1:1 executive coaching, typically in areas like setting a high bar of excellence, leveling up their strategic communication, and managing lean teams with ambitious goals.</p>
<h2>This Week&#39;s Discussion</h2>
<p>In our fireside chat, I sat down with Wes to discuss:</p>
<ol><li>​Key principles when managing up.</li><li>Observing, understanding, and building trust with your manager (including insecure managers). </li><li>​Fin​​esse when managing up to intense senior executives.</li><li>Handling unreasonable expectations.</li><li>And what Wes learned from Seth Godin.</li></ol>
<h2>Video</h2>
<p><a href="https://youtu.be/VsJar8v7NtU">Here is a link</a> to our discussion.</p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/VsJar8v7NtU" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>Conclusion</h2>
<p>Here are some key takeaways from our discussion.</p>
<p><strong>Managers WANT YOU to manage up to them, and it creates a virtuous cycle.</strong> </p>
<p>When you manage up, your manager believes in you more, your manager gives you more autonomy, you get more leeway to make an impact, your manager sees the impact, and they give you more autonomy. </p>
<p><strong>The best operators do not just ask their manager, instead, they OBSERVE them and pattern match.</strong> </p>
<p>Many managers are unable to clearly articulate exactly how they want to be managed up to. Thus, do not rely solely on their manager. </p>
<p>Three clues to look for:</p>
<ol><li>What are the questions that my manager usually asks me when I bring up an idea or challenge?</li><li>What are the questions that my manager asks other people?</li><li>How does my manager present their own ideas? This will tell you what they value. </li></ol>
<p><strong>Turn a yellow spot into the sun—there are always ways to bring excitement and energy to elevate your work.</strong> </p>
<p>Understand how your work drives value and identify how you can elevate it in the eyes of the rest of the company.</p>
<p> You can make something boring into something exciting (e.g., Simplehuman turned trash cans into an iPhone-like product). </p>
<p><strong>Get to the point as fast as possible when communicating with C-level executives.</strong> </p>
<p>Wasting 3-minutes on background or pleasantries will frustrate busy executives. </p>
<p>View presentations as two-way guided conversations (not one-way TED Talk speeches) with the goal either to get buy-in or poke holes to make a better decision and align on next steps. </p>
<p>Also, do not feel like you need to finish your full message/spiel before taking the win and just moving on. </p>
<p><strong>Managers, use TACS when giving feedback.</strong> </p>
<p>Tactical, Actionable, Concrete, and Specific. </p>
<p><em><strong>“To increase my standards”</strong></em><strong>—the biggest thing Wes learned from Seth Godin.</strong> </p>
<p>For 3 years, Seth tore Wes’ work to shreds and set unreasonably high expectations. </p>
<p>That taught her how to reframe the problem to meet the standards (it’s the leader’s responsibility to constantly break frames).</p>
<p>Note: Your skills, background, and experience become less important as you advance in your career. Rather, your judgment and ability to set high standards for yourself and other people become more important—this is what makes a senior leader a force multiplier.</p>
<p>If you&#39;re looking for more insights from Wes, follow her on <a href="https://www.linkedin.com/in/weskao/">LinkedIn</a> and subscribe to her <a href="https://newsletter.weskao.com/">newsletter</a> for high-performers (highly recommended). </p>
<p>Wes also teaches a <em>very</em> popular Maven course on <a href="https://maven.com/wes-kao/executive-communication-influence">“Executive Communication &amp; Influence for Senior ICs and Managers”</a> and you contact her here if you want <a href="https://www.weskao.com/coaching">1:1 executive coaching</a>. </p>]]></content:encoded>
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      <title>What a Series B Co-Founder looks for in their Leadership Team with Dee Murthy</title>
      <link>https://jasonyoong.com/series-b-co-founder/</link>
      <guid isPermaLink="true">https://jasonyoong.com/series-b-co-founder/</guid>
      <pubDate>Tue, 28 May 2024 21:53:01 GMT</pubDate>
      <description>​Dee Murthy — known for his candid advice and hot takes — is the Co-Founder of Ghost, a private B2B platform for surplus inventory. Ghost raised a $20M…</description>
      <content:encoded><![CDATA[<p><strong>​Dee Murthy</strong> — known for his candid advice and hot takes — is the Co-Founder of Ghost, a private B2B platform for surplus inventory. </p>
<p>Ghost raised a $20M Series A and $30M Series B. Dee is also the Co-Founder of Five Four Group (the holding company for fashion brands and services) and a Co-Host of Group Chat, a popular business, culture, and current events podcast.</p>
<h2>This Week&#39;s Discussion</h2>
<p>In our fireside chat, I sit down with Dee to discuss:</p>
<ol><li>​What Dee looks for when hiring leaders &amp; executives (and how big company leaders get startup attention). </li><li>Common advice that is BS.</li><li>How to cold email Dee to get a response (he gets 500+ messages a day).</li><li>​How to successfully scale a startup (plus a lesson Dee learned the hard way). </li></ol>
<h2>Video</h2>
<p><a href="https://youtu.be/32eC_QBAZg0">Watch the full interview here</a>. </p>
<figure class="video-embed" style="position:relative;padding-bottom:56.25%;height:0;overflow:hidden;margin:1.5rem 0;"><iframe src="https://www.youtube-nocookie.com/embed/32eC_QBAZg0" style="position:absolute;top:0;left:0;width:100%;height:100%;border:0;" loading="lazy" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" allowfullscreen></iframe></figure>
<h2>Lessons Learnt </h2>
<p>Here are 4 hot takes and 2 pieces of advice.</p>
<h3>Chaos Experience is Priceless</h3>
<ol><li>If you’ve only worked at big companies, startup founders think you’re unwilling to get your hands dirty. </li><li>What counts as chaos? Failed startup.   Hyper-growth (e.g. Uber 8 years ago, not 2).   Big company operator on a small, under-resourced team that built something special.   </li></ol>
<h3>There is no work/life balance…speed at a startup is everything</h3>
<ol><li>Know what you are signing up for.</li></ol>
<h3>In-person is a requirement for executives</h3>
<ol><li>Startups are already impossible. </li><li>Always interview in person (no Zoom interviews). </li></ol>
<h3>Executives have 90 days to deliver results before getting axed</h3>
<ol><li>Compare that with the 90-day onboarding plan for big companies. </li><li>Why? Because 90 days in startups is 1 year for big companies. </li></ol>
<h3>How do I guarantee an interview for an executive role?</h3>
<p>Strong referrals and warm intros.</p>
<ol><li>90% of Ghost’s executive team are network referrals (the non-referred executive came via a recruiter). </li><li>80% of leadership jobs (per Forbes magazine, 2023) come through networking connections.</li><li>A strong network is your most powerful, portable long-term career asset. </li></ol>
<p>If you want to learn how leaders build great networks and use them to their advantage, consider Ethan’s on-demand course, <a href="https://ethan-evans.mykajabi.com/">Leadership Networking.</a></p>
<h3>Use the ‘Airport Test’</h3>
<p>Never underestimate likeability. If it comes down to you and another qualified candidate, likeability will be the tie-breaker.</p>
<ol><li>The ‘Airport Test’: If I got stuck at an airport (or on a plane) with this person, do I feel energized or drained?</li><li>Small talk is an important skill set to disarm people. </li><li>The ability to talk to all walks of life signals you can handle all types of personalities. </li></ol>
<h2>Conclusion</h2>
<p>Here&#39;s what Level Up Community Members said about our episode:</p>
<blockquote><em>“Really insightful event - Dee was an absolute banger of a guest!”</em>   <em>“I also really enjoyed his blunt honesty.”</em>   <em>“I was so happy to be able to talk to Dee live. I also felt that I could relate to all the questions that everyone asked. The knowledge I gain today will help me take the next step in my career.”</em>   <em>“Great event. Thank you for bringing Dee.”</em> </blockquote>
<p>Follow Dee on <a href="https://www.linkedin.com/in/dee-murthy-8a3557/">LinkedIn</a>, <a href="https://twitter.com/deemurthy">Twitter</a>, listen to his podcast <a href="https://podcasts.apple.com/us/podcast/group-chat/id1311062310">Group Chat</a>, and check out roles at <a href="https://www.ghst.io/">Ghost</a>.</p>]]></content:encoded>
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