Are You Accumulating Career Debt?Short-term comfort feels good, but building long-term equity feels better.
There’s a quiet anxiety that settles in when you're good at your job and the pay is pretty good, but you have a nagging feeling you’re falling behind. It’s the paradox of being comfortably stuck, and it’s a feeling I know intimately. My biggest career mistake was a sin of omission. I stayed on a team I loved, in a role that was comfortable, for at least a year longer than I should have. The money was good and the work was familiar. It felt like the safe choice, but it was the riskiest career move I ever made. I was accumulating a massive debt I'd have to pay back with painful interest later on. I call this Career Debt. Career debt is like financial debt. It feels good while you’re accumulating it, but terrible when you see the bill. In tech, we obsess over paying down technical debt in our codebases but completely ignore the career debt accruing in our own lives. It’s the same principle: you make short-term compromises for comfort that compound into long-term problems. The opposite is Career Equity—the ownership you build in your future by making intentional, often uncomfortable, investments in your growth. The danger of career debt is that it accumulates silently. Unlike a credit card, you don't get a monthly statement listing the interest you’re paying for staying comfortable. We go into debt unintentionally, through a series of small compromises that feel right in the moment. Recognizing the types of debt you're carrying is the first step toward building back your equity. In today’s article, we will focus on minimizing or eliminating Career Debt. I will write a future article on how to maximize Career Equity. If you are finding this article useful, you might also enjoy the most popular posts from A Life Engineered this year: 1. The Debt of ComfortThis is the most common form of career debt, and also the most seductive. I learned about it the hard way. When I was a senior engineer in Amazon Tickets, I stayed in the role because it was comfortable. We were solving a fascinating customer problem, the engineering was interesting, and I genuinely liked my teammates. On the surface, everything was great. But deep down, I knew I wasn't pushing myself. To make matters worse, for a time, I was reporting to a manager who was a level below me. It was an impossible situation. He couldn't grow me, and I stagnated even though I was high-functioning in my role. That period of comfort set my career back, and it took me the better part of two years to recover the lost ground. Think back to this time, two years of not growing makes me feel like I lost a part of my life savings at a casino. Every successful person I know from the corporate world has a similar story of staying on a team for too long. It happens because inertia is a choice. It's easier to do nothing than to do something, but doing nothing is still a choice—one that quietly accrues debt against your future. What felt like a secure position was actually a losing bet against my own future. Actionable Advice: To avoid this trap, you need to conduct a "Growth Audit" every six months. In my story, this simple exercise could have saved me years of grief. Ask yourself three brutally honest questions:
If the answer to one or more of these is "no," the next step isn't to panic. It's to shift from a statement to a question. Instead of accepting "no" as the final answer, a high-agency person uses it as a starting point. Ask yourself:
Posing these questions is the first act of agency. It forces you to look for solutions before you conclude that your only option is to leave. 2. The Debt of "Yes"This is the debt of the overachiever and the people-pleaser, and for years, interviewing was my version of it. At Amazon, I conducted nearly 1000 technical interviews. I became a "Bar Raiser," which is an interviewer from outside the hiring team who is trained to be an objective steward of the hiring bar. It’s a crucial role, and I eventually became a Bar Raiser trainer and a leader in the program. The thing about interviewing at Amazon is that it’s almost all voluntary. As I was coming up in the company, saying "yes" to it was a great investment. I found the process fascinating, became a coding interview junkie, and the skill was useful for my rapidly growing teams. But as I progressed, the return on investment diminished. I had already learned the lessons interviewing could teach me, yet the requests kept coming. Recruiters would ping me, and because I was good at it and it felt helpful, it was just so easy to keep saying yes. Each "yes" was a small withdrawal from my bank of focus, leaving less time for the deep work that my senior role required. It was a classic "Debt of Yes." It’s a debt that feels like teamwork and ambition, but the bill eventually comes due in the form of burnout, a string of minor accomplishments instead of major wins, and the frustrating feeling of working hard but standing still. Actionable Advice: My usual advice here is to do a "Yes Audit," but we're going to switch it up. Instead of auditing your "yeses," I want you to start a "No Ledger." Saying "no" is one of the most powerful ways to build Career Equity, because it creates the time and space needed to work on things that truly matter. If you find you aren't saying "no" very often, it's time to reflect on why. Here's your exercise: Pull up your calendar and emails from exactly one year ago today. (If you're reading this on the day of publishing, September 17, 2025, go to your calendar for September 17, 2024). Look at that day. Look at the emails, the meetings, the tasks, the commitments. Now ask yourself: How many of those things truly mattered in the long run? How many could you have said "no" to, and what was the ultimate cost of your "yes"? Most work is inconsequential and doesn’t move the needle, but we believe the exact opposite in the moment. By looking at the past we can disabuse ourselves of this self-sabotage. 3. The Debt of SilenceThe debt of silence is like a small, nagging toothache. It isn't debilitating, just a pain that doesn’t feel right sometimes. You know you should deal with it, but that would involve the inconvenience of finding a dentist, scheduling an appointment, and taking time out of your day. So you ignore it, hoping it will go away. But the underlying decay silently worsens. One day, you wake up in excruciating pain. What could have been a simple filling has now become an emergency root canal, something far more painful, expensive, and disruptive. This is exactly how the debt of silence works. It is the accumulated cost of every difficult but necessary conversation you have avoided. I learned this lesson the hard way early in my career. When I was a junior engineer, I saw that a critical project was going to be late because of an issue outside my direct ownership. I could have sounded the alarm a month earlier, but that would have meant interrupting senior people and rocking the boat. So I stayed silent. When the news finally broke, the project was in a full-blown crisis. My silence didn't prevent the bad news, it just made it a thousand times worse. That experience taught me a vital lesson: Bad news delivered early is just news. Bad news delivered late is terrible. This applies everywhere:
Uncomfortable conversations are just that: uncomfortable. But you must weigh that temporary discomfort against the guaranteed, long-term pain of your silence, not the comfortable feeling of saying nothing. Actionable Advice: The 10-Year Test. Take a moment and run a thought experiment. Imagine it’s 10 years from today, and you're in the exact same place in your career. Same role, same problems, same pay (adjusted to inflation). Ask yourself one honest question: "Am I okay with that?" If the answer is a deep sense of disappointment, know that you can change that outcome, and it’s easier than you think. Your career is like a massive ship on a long voyage. A tiny, one-degree course correction today will land you on a completely different continent a decade from now. That one-degree nudge is the uncomfortable conversation you’ve been avoiding. It’s the five seconds of courage it takes to send the email or Slack message that breaks the silence. All you have to do is be okay with a small amount of discomfort today to steer your ship away from the island of regret. Your Debt is a SignalReading this might feel uncomfortable. Identifying your own debts can bring on a wave of anxiety or regret. But this feeling is not a judgment, it's a signal. Your career debt is a check engine light for your professional life. It’s a clear indicator that the path you’re on is no longer aligned with the destination you want to reach. Ignoring the signal doesn't make it go away. It only guarantees that a small problem will become a big one. The goal, then, isn't to live a life with zero debt. It's to become a conscious and intentional investor in your own Career Equity. Every uncomfortable action you take—auditing your growth, saying a strategic "no," or starting a difficult conversation—is a direct investment in your future self. Choose the discomfort of growth over the comfort of regret. New Podcast Episode - Dave AndersonDave Anderson went from a Midwest cubicle to Amazon director, saved 85% of his income, and walked away from everything at 42 to achieve complete financial independence. In this conversation, he reveals Amazon's hidden promotion secrets, why the company lost its way before Bezos left, and the brutal math behind early retirement.  Paid subscribers get an extended 30-minute discussion on his specific investment strategy and unfiltered predictions about Big Tech's future. Swarm-Coding With WarpLast week I challenged myself to build and ship a Chrome extension to the Chrome Web Store in a single day-not just a prototype, but a real, installable extension that people could actually use. Using Warp's multi-agent system, I orchestrated AI engineers like I used to at Amazon: one handled frontend, another backend, another tests, and yes, one even wrote decent documentation. After 18 months away from shipping code, I went from blank screen to published extension in under 24 hours.  Warp is free to try but for a limited time, my friends at Warp are offering their Warp Pro plan for only $1. Use code LIFEENG to redeem here: https://go.warp.dev/life-engineered New YouTube Video - Scaling Through OthersMost people think "scaling through others" means breaking work into smaller chunks and delegating—but that's exactly why they never become true leaders. In my new video, I reveal the force multiplier principle I learned during 20 years at Amazon that helped me influence over 450 developers without a single one reporting to me. The difference between those stuck at senior level and those who break through is mastering this one counterintuitive approach to leverage that nobody teaches you.  A Life Engineered will always be a free publication, but if you’d like to support it, we’d be honored if you upgraded your subscription. Paid subscribers get the full experience, including access to the archives.
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