Success. It’s something we chase for years, even decades. But do we even know what we’re really chasing? When’s the last time you stopped to consider what success means to you?

A definition of success was handed to many of us early: work hard, climb the ladder, earn more, collect the titles, stay busy. There’s nothing inherently wrong with this type of ambition or the external badges we wear designating our achievements. The problem creeps up when those things become our default definition of success… and we forget to ask: at what cost?

The Invisible Trade-Offs

When I talk with clients, peers, and even reflect on my own career, I notice a common thread: success didn’t always feel successful.

It looked good on paper, sure. But behind the scenes? Exhaustion. Resentment. Disconnection. A life that was supposed to be full but felt somehow empty.

Sometimes, the problem isn’t that we’re chasing someone else’s version of success. It’s that we’ve been so busy doing—responding, achieving, fixing, helping—that we’ve lost sight of what we’re working toward. And who we’re becoming in the process.

Success isn’t the enemy, but unconscious striving might be.

5 Prompts to Reflect On

If you’re feeling the nudge to reimagine what success means to you, here are five prompts to begin exploring:

• What has your current definition of success cost you? Be honest. Has it impacted your health? Your creativity? Your relationships?
• Where did your definition of success come from? Family? Industry? Cultural or social expectations? A version of you from a decade ago?
• What would success look like if no one else could see it? Strip away the accolades and LinkedIn headlines. What would feel fulfilling just for you?
• What fear comes up when you think about changing course? Naming the fear doesn’t make it bigger, it makes it more manageable.
• What are you already doing that feels aligned, even if it’s small? Sometimes the clues are right there. Follow what feels grounded, expansive, or simply true to you.

Flipping the Script: New Definitions to Try

Redefining success doesn’t mean you have to burn everything down. More often, it’s an intentional recalibration, a transition that occurs over time. Here are a few alternate definitions of success to try on:

From Proving → to Belonging

Instead of constantly striving to prove your worth, practice being in it. Notice where you naturally bring value without performing.

From More → to Meaning

Choose depth over accumulation. Focus not on more metrics, but on more time, more peace, more you.

From External → to Internal

Check in with yourself before chasing the next goal. Ask yourself, “Who am I becoming through this?” and “Is this who I truly want to be?”

From Default → to Design

If your career was set to the default setting, what would happen if you broke away and designed your own path instead?

Success, On Your Terms

This work to rethink your definition of success isn’t about abandoning ambition. It’s about gaining alignment. You can still strive. You can still lead. You can still care about growth and achieving excellence.

The difference is that you get to choose. You decide what success means to you in this season, with your values, at a pace that honors your life.

If you’re ready to do that work in good company, my group program is designed for exactly this kind of reset. Cohorts begin monthly, and you can learn more here: The Transitions Careers Career Reset Program.

Interested in more probing questions to get you thinking about the state of your career? Join our free Career Conversations where we dive deep into topics like this one.