Show Notes
This episode tackles one of the quietest career crises high achievers face: the moment when the habits that made you successful start to hold you back. Adam opens up about a tension he's navigating — that the responsive, task-crushing, people-pleasing work style that earned him every promotion so far is the exact thing standing between him and the next level. Stephen and Adam unpack how identity shifts as you climb, why "does my boss like me?" eventually becomes insufficient currency, and what it actually looks and feels like to stop being a doer and start being a strategist, even when it's uncomfortable, even when you end up working until midnight anyway. Key Takeaways Early career runs on likability, and that's not a bad thing until it is. For most of your twenties and early thirties, the implicit promotion rubric is simple: Is this person generally capable and do people enjoy working with them? There's an inflection point where the game changes. At a certain level, career growth stops being about likability and starts being about owning a number, a budget, or a team outcome. The habits that made you great can become your biggest liability. Adam describes a specific trap: the emotional reward of clearing 100 small tasks in a day, and the guilt of ignoring a full inbox to do deep, strategic work that won't show results for a week. This is identity work in disguise. Your sense of competence and worth is tied to responsiveness, and unwiring that is genuinely hard, even when your boss explicitly tells you to stop. Letting go of reactive work is also the right thing for your team. The reframe that unlocked something for Adam is that doing long-term strategic thinking isn't a selfish career move dressed up as leadership. It's actually the higher-value contribution. Practical tool: Write your full responsibility list and show it to someone. Adam's most actionable move was writing down every single thing he felt responsible for and handing it to a trusted colleague for advice. From there, he looked for what he could hand off with a one-hour training and worked through the list one item at a time. Great managers measure success by the growth of the people around them. When Adam reflects on the leaders he's admired most, the common thread is simple: they saw your success as their success. Chapters The "Does My Boss Like Me?" Era (00:00 – 02:50) When Good Habits Become Liabilities (02:50 – 06:45) The Midnight Slack Spiral (06:45 – 11:30) Strategic Work Is the Team-First Move (11:30 – 15:00) Practical Steps to Reclaim Priorities (15:00 – 17:30) What Great Leaders Actually Do (17:30 – 22:00) The Claude vs. ChatGPT Moment (22:00 – 25:30) Robots and the Future of Work (25:30 – 27:05) Listener Reflection Question: What's one thing on your plate right now that someone else could do 80% as well as you, and what would it take to actually hand it off?
More from Identity Work
What would you do if you didn’t have to worry about money? Most of us start imagining a different job, a different schedule, or a beach somewhere. Eugene Luning asked Stephen a slightly different question: What if money were taken care of, but you had to stay in your current role? How would you approach the work you already have? Eugene is the director of The Union and Stephen’s spiritual director, a relationship that apparently began with Adam’s Christmas letter. He joins us to talk about ambition, anxiety, faith, and the pressure to figure out what our lives are supposed to become. We explore what changes when we trust that God knows where we are, and that the people and opportunities in front of us deserve our attention today. The conversation gets practical: using the space between meetings to reset, building small rhythms of gratitude, and recognizing when a commitment has become something we keep doing because we feel guilty stopping. Lexi joins us to talk about parenting guilt, and Eugene shares a story about his daughter leaving for college that brings the whole conversation home. Along the way, we discuss the humanity and humor of Jesus, Stephen maintains his unofficial count of Adam’s reading, and we consider whether a meaningful life might feel a little freer than we’ve been making it. Takeaways There is meaning available where you are today. Career planning can consume our attention. Eugene invites us to consider how we would treat our current work and the people around us if we felt less pressure to secure the future. Small moments of returning can become a way of life. A pause before a meeting, a reminder of past provision, or three things you’re grateful for can help bring your attention back to the present. Doing it once is a place to start. Pay attention to what you’re being drawn toward. Persistent friction can be a reason to reconsider a commitment. Asking what you want to give yourself to can help clarify what you need to release. Let your children experience being deeply loved. Eugene offers a simpler focus for the pressure of parenting: being interested in your children, helping them feel seen, and ending the day with them knowing you’re delighted they’re yours. Chapters 00:00 Introducing Eugene and the Christmas letter that started it 01:57 What if you stayed in your current job? 04:54 God knows where to find you 07:12 Connection and meaning in the present moment 12:02 Using transitions to practice presence 15:13 Anxiety as a reminder to return to God 20:06 Gratitude and building small rhythms 24:15 The pressure to keep doing good 28:51 Knowing when it’s time to move on 31:52 The humanity and humor of Jesus 35:15 Parenting guilt and helping children feel loved 41:15 Learning to receive love ourselves 43:10 Being set free for your work 46:57 Trends spotter 47:52 Is meaning in work found or created? 50:07 Where to find Eugene Listener Reflection Where are you waiting for your circumstances to change before you let yourself be fully present? What would it look like to bring a little more attention, love, or freedom to that part of your life today? Connect with Eugene Find Eugene’s writing at unionists.org and listen to The Unionists on Apple Podcasts.
You want people to know what you do. You also don’t want to become the person posting about "7 quick tips to earn $10m a year". How do you put yourself out there while still feeling like yourself? Adam and Stephen sit down with Harris Fanaroff, founder and CEO of Linked Revenue, to explore personal branding, humble brags, and the fear of being judged. Adam shares his four attempts at finding his voice on LinkedIn, from fintech commentary to weekly meaningful moments. Harris explains how sharing useful ideas and building relationships can create opportunities, even when you aren’t selling anything. We also discuss what to share early in your career, why human stories matter in a feed full of AI content, and how Harris approaches meaningful work through providing for his family and building a team where people can be honest. Four Takeaways Start with someone you can help. Thinking about what another person could learn from your experience gives you a practical way to approach posting without making every post a celebration of yourself. Your brand can grow from who you already are. Adam’s meaningful moments helped him notice more of what he values and gave others a clearer picture of him. Being thoughtful, curious, and consistent can carry professional value. Relationships build over time. Harris approaches LinkedIn as a place to share useful ideas, notice who engages, and start conversations. Those connections can become clients, collaborators, or a network to lean on during a career change. You can share while you’re still learning. Early in your career, useful observations, questions, and lessons from more experienced colleagues can give you something worthwhile to contribute. Fear of judgment often keeps people from starting. Chapters 00:00 Meet Harris Fanaroff 01:17 Personal Branding Without Narcissism 05:51 Adam’s Four Attempts at LinkedIn 11:26 Finding Your Why for Posting 15:02 Turning Engagement Into Relationships 20:04 Humble Brags, Ego, and Sharing Your Success 27:18 Getting Past the Fear of Being Judged 30:45 Algorithms, AI Content, and Staying Human 35:18 Practical Advice for Promoting a Podcast 39:09 Providing for Family as the Purpose of Work 41:23 Building a Vulnerable Team Culture 44:29 Is Meaningful Work Found or Created? 45:09 Favorite Places and Finding Time to Be an Adult 48:57 Where to Find Harris Reflection Question What is something you’ve learned or noticed recently that could help someone else, and what holds you back from sharing it? Connect With Harris Find Harris Fanaroff on LinkedIn or visit Linked Revenue.
What would it be like to start your career with AI? In this episode, Adam and Stephen explore how AI is changing the substance of entry-level work. Young professionals can now produce polished analysis, models, and presentations in minutes, but bypassing the struggle may also mean missing the judgment that struggle once developed. They discuss why speed is not the same as learning, how managers can help younger employees build judgment, and why time and human feedback remain essential even when AI can produce a strong first draft. They also consider whether every entry-level employee is now becoming a manager, with AI serving as their first team. Four TakeawaysAI is not simply making entry-level work faster. It is changing what the job requires, replacing some tactical skills with leadership, judgment, and strategic thinking. Struggle can be formative. Building the model or wrestling with the first draft helps people understand how the answer was created and recognize when something does not make sense. Efficiency does not guarantee learning. AI can help someone finish faster, but developing real understanding still requires time with the material. Junior employees need human feedback, peer review, and coaching. AI can challenge a recommendation, but a five-minute conversation with someone who has lived the problem can reveal what hours of research missed. Chapters00:00 Welcome and introduction 01:27 What would it be like to start a career with AI? 03:20 How AI changes the substance of entry-level work 05:30 What we learn through struggle 09:53 AI, homework, and the importance of time 11:49 How managers can help junior employees learn 15:02 Why human feedback still matters 17:16 Is every entry-level employee now a manager? 22:19 Evaluating the process, not just the answer 24:48 Trend Spotter: The language and future of AI 30:31 Showing appreciation for others 31:54 Closing reflection Reflection QuestionIf entry-level work now requires management skills, how should we change the way we train, coach, and encourage people at the beginning of their careers?
After more than 70 episodes asking what makes work meaningful, Adam finally has a working answer: learning with people who make him laugh while providing for his family.
Why can we accomplish ten things and only think about the one we left undone?