The Quitting Problem
During a conversation with a fellow coach this week, I had a realization that shook me to my core. For the past five years, I’ve been clinging to an identity as “the person who made it,” and with that, reluctant to put myself in situations where that identity might be challenged. I realized I’ve been dipping my toes into new challenges without fully diving in, because failure would threaten how I see myself. In essence, I refused to “quit” being the person I thought I was, even when that identity was holding me back from what I could become.
Annie Duke, former poker champion turned decision strategist, calls this the “quitting problem.” In her book, aptly named Quit, she explains how our aversion to quitting often stems from identity protection. We’d rather continue down a failing path than admit we need to change course. We see quitting as failure rather than a strategic decision to reallocate our resources toward something more promising.
While my own realization came during a coaching session, I’ve seen this pattern play out in business countless times. This struggle is particularly common for founders and leaders. I’ve seen countless brilliant people who built companies around their expertise - whether in design, engineering, or finance - struggle to evolve as their companies grew. The financial consultant who built a successful firm can’t stop delivering billable hours for clients. The technical founder can’t resist rewriting code their team produced. Once the company’s greatest asset, their expertise becomes its greatest bottleneck.
One clear sign of having stepped into this trap is when you’ve noticed you’re the person everyone’s waiting on. Decisions stall until you weigh in. This leads to stalling growth despite having more resources than ever. And you find yourself constantly switching between high-level strategy and in-the-weeds execution.
A second related sign appears in how you respond when problems arise. Do you jump in to fix them yourself, or do you coach the person responsible through finding a solution? The former feels efficient in the moment but creates dependency and reinforces your outdated identity as the problem-solver-in-chief.
The third and final sign is that ‘what am I even doing?’ feeling when you’re not directly contributing. If a day filled with one-on-ones and strategy sessions leaves you feeling like you haven’t ‘done anything,’ your sense of value might still be tied to personal output rather than the outcomes you enable. I remember finishing days of back-to-back meetings feeling frustrated and restless - despite having aligned the team on our quarterly priorities and unblocked three critical projects. My brain was still wired to value shipping code more than enabling others to ship code.
So what’s the path forward once you’ve spotted yourself in this trap? For leaders and founders alike, it requires a fundamental shift in how you measure your contribution. This isn’t just semantic. It’s existential! You need to reframe your expertise as being most valuable when used to guide others, not when applied directly. Your specialized knowledge needs to become a tool for developing your team rather than a reason to keep doing the work yourself. The very skills that got you here won’t get you there - they need to evolve from doing to enabling.
This means finding new metrics for success. Instead of tracking how many problems you solve, track how many your team solves without you. Rather than measuring hours worked, measure the impact created by the systems and people you develop. Take pride in building the best team rather than being the best individual contributor.
I remember struggling with this transition many times before. In the early days of my career I built my identity around being the person who could solve any technical problem, who could write code faster and better than anyone else. When my role grew from individual contributor to building a company, I felt like I was abandoning what made me valuable. What I eventually realized was that my greatest contribution came when I stopped doing what initially made me successful.
The tricky part is that these identity shifts are rarely ones we can navigate alone. Our identities are often our biggest blind spots. External perspective - whether through coaching, mentorship, or trusted peers - is crucial for seeing where we might be holding onto outdated ways of defining our value.
A coach once asked me: “What if your most valuable contribution isn’t what you do, but what you enable others to do?” That question changed everything for me. It gave me permission to evolve, to strategically quit being the person I’d been so I could become the leader my company needed.
So ask yourself: What identity might you need to let go of to move forward? What story about yourself is keeping you anchored to patterns that no longer serve you or your team? The willingness to strategically quit - to release who you were to become who you need to be - is a leadership skill worth developing. As for me, I’m working on quitting my identity as “the person who made it” so I can become the person who helps others make it. Turns out letting go is harder than holding on, but that’s where the growth happens.
