When considering a major career change, it's easy to get trapped by the "sunk cost" of your existing industry expertise and identity. The key to making a successful long-term pivot is to consciously ignore what you've built in the past and focus on what will bring fulfillment and growth over a multi-decade career.
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When your business no longer feels aligned, trust your instincts to make a change. The required pivot may be disruptive and risky, especially if the current model is commercially successful, but your internal wisdom is the most reliable guide for long-term fulfillment and integrity.
At age 44, Matt Spielman reframed his career pivot not as a risk, but as a mitigation of a greater one: staying on the wrong path. He believed waking up at 55 having not pursued his passion would be a far worse outcome than the uncertainty of starting his coaching practice.
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Pursuing a more fulfilling career doesn't require risking financial ruin. Instead of taking a blind leap, you can vet a new direction by "trying it on"—shadowing professionals, conducting informational interviews, and testing the work in small ways to understand its reality before making a full transition.
When facing a major career crossroads, the goal isn't to find the objectively "best" option, as it's unknowable. The key is to make a decision based on intuition, commit to it fully, and refuse to entertain "what if" scenarios about the paths not taken.
The best long-term strategy isn't the one with the highest short-term growth, but the one you're genuinely passionate about. This intrinsic motivation leads to sustained effort and eventual success, even if it seems suboptimal initially. It's about playing the long game fueled by passion, not just metrics.
Deciding to pivot isn't about perseverance; it's a cold, rational decision made when you've exhausted all non-ridiculous ideas for success. The main barrier is emotional—it's "fucking humiliating" to admit you were wrong. The key is to separate the intellectual decision from the emotional cost.
John Grisham's career change wasn't solely a flight from the pressures of law. He was pulled by the "huge dream that became all-consuming" of becoming a full-time writer. This illustrates that a powerful, positive vision for the future provides more sustained motivation for a difficult transition than simply the desire to escape a negative situation.
Major career pivots are not always driven by logic or market data. A deeply personal and seemingly unrelated experience, like being emotionally moved by a film (Oppenheimer), can act as the catalyst to overcome years of resistance and commit to a challenging path one had previously sworn off.
Before a major business pivot, first identify what can be let go or scaled back. This creates the necessary space and resources for the new direction, preventing overwhelm and ensuring the pivot is an extension of identity, not just another added task on your plate.
The pivot from a pure technology role (like CTO) to product leadership is driven by a passion shift. It's moving from being obsessed with technical optimization (e.g., reducing server costs) to being obsessed with customer problems. The reward becomes seeing a customer's delight in a solved problem, which fuels a desire to focus entirely on that part of the business.
