Why High Performers Need a Different Career Transition Playbook

 A few weeks ago, I created a poll asking my LinkedIn connections what topics they’d like to see me write more about. While career transitions didn’t receive a lot of votes, they generated an incredible number of private messages. I hadn’t realized how many people in mid- and senior-level roles were quietly thinking about change.

Career transitions look different for everyone, but here is some timely advice I’ve been sharing repeatedly in those conversations.

1) Use the holidays to reflect, not to act.

The end of the year and the start of a new one naturally invite reflection. They also tend to trigger big, life-altering decisions. New Year’s resolutions are the obvious example. Like many resolutions, decisions made during this period are often reactive rather than strategic and don’t always serve long-term objectives. Reflection is useful. Premature action often is not.

2) Separate discomfort from misalignment.

Fatigue, boredom, or friction are often interpreted as signs that someone is in the wrong role. Sometimes that’s true. Often, it isn’t. Discomfort can come from seasonal pressure, organizational dysfunction, or being under-utilized rather than from a fundamental mismatch. Before assuming a wholesale change is required, get specific about what actually feels wrong. That clarity reduces reactive exits and helps you design a smarter transition if one is truly needed.

3) Not all career trajectories are linear, nor should they be.

Some great thinkers (such as Arthur Brooks) describe a “spiral” trajectory for high performers, often moving through 4 distinct careers in their lives. I personally prefer to think of it as a slingshot. Career transitions often require taking a few steps back, which can feel deeply uncomfortable for high performers used to forward progress. But those steps back create space and load you up to launch (slingshot) into your new trajectory. Purposeful movement away from your current trajectory can be exactly what enables a stronger launch into the next one.

4) Detach your identity from your current title before you move.

Career transitions are hardest when your sense of self is tightly tied to a role, level, or external validation. When who you are is anchored to what you do, even positive change can feel like loss. Start loosening that attachment early. You don’t need to know your next role yet, but you do need a sense of value that travels with you. That’s what allows transitions to be intentional rather than fear-driven. A practical first step is paying attention to how you introduce yourself. For a long time, I led with “I own a business” or “I’m an entrepreneur.” When I sold the business, those labels no longer fit, and one can feel lost without a new identity. Career transitions work the same way. Titles change. Identities evolve. Learning to separate the two makes change far less destabilizing.

Want to Learn More?

I highly recommend reading the book Strength to Strength by Arthur Brooks (and if you do, I’d love to know your thoughts!).