The Courage to Define Success for Yourself

The Question I Wish I Had Asked Sooner

“Am I making this decision because it’s what I truly want, or because it’s what success is supposed to look like?”

It sounds like a simple question. But for much of my career, it wasn’t the question I was asking.

Instead, I asked the questions ambitious people are taught to ask:

What’s the next opportunity?

How do I keep growing?

What’s the smartest career move?

What do I need to accomplish next?

There is nothing inherently wrong with those questions. Ambition has been an important part of my journey. It has pushed me to take risks, step into unfamiliar spaces, advocate for myself, and continue growing both professionally and personally.

But somewhere along the way, I realized there was another question I should have been asking:

What does success actually look like for me?

It is easy to inherit someone else’s definition of success without realizing it.

We are surrounded by visible markers of achievement: impressive titles, promotions, higher salaries, bigger responsibilities, beautiful homes, and increasingly ambitious goals.

You reach one milestone, celebrate briefly, and almost immediately begin thinking about the next.

For women in leadership, there can be another layer to this. Many of us have spent years proving that we belong in rooms where decisions are made. We learn to be prepared. We learn to deliver, negotiate, adapt, lead, and keep going.

That determination can take us incredibly far.

But constantly proving that you are capable can also make it easy to forget something important: You are allowed to decide whether the destination is one you actually want.

Not every opportunity needs to be accepted simply because it represents advancement. Not every higher salary automatically creates a better life. Not every prestigious title is worth what it may require from you. Choosing differently does not mean becoming less ambitious. It means becoming more intentional.

As I have grown in my career, my definition of success has evolved.

I still believe in setting big goals. I still want to challenge myself, grow as a leader, and pursue opportunities that once might have seemed out of reach. But I have learned that the best decisions cannot always be measured by a title or a number. I think about alignment more now.

Does this opportunity move me toward the person I want to become?

Does it support the life I am trying to build?

Will I be proud of this decision even if nobody else is impressed by it?

Those questions are different from asking whether something looks successful from the outside.

They require a level of honesty that a résumé never will.

One of the hardest things for an ambitious person to define is enough. There will almost always be another level to reach. Someone will always have a bigger title, a larger salary, a more impressive accomplishment, or a seemingly perfect life. If success depends entirely on comparison, the finish line will continue moving.

I am learning that confidence is not only believing that I can achieve more. Sometimes confidence is knowing that I don't have to chase everything I am capable of chasing. It is being able to pursue the opportunities that genuinely matter to me and walk away from the ones that don't, even when they look impressive on paper.

That shift has changed how I think about ambition. Ambition without intention can become an endless pursuit of the next thing. Ambition with intention becomes something much more powerful: choice.

And if I could go back, I would not tell my younger self to dream smaller. I would tell her the opposite. Dream big. Work hard. Take the opportunities that scare you. Ask for more. Walk into rooms before you feel completely ready. Learn everything you can. But while you are building your career, remember that you are also building a life.

Don't spend so much time asking whether you are making the “right” decision that you forget to ask whether you are making the right decision for you.

And once you make it, trust yourself. I don't know that asking this question sooner would have changed every choice I made. In fact, I suspect many of my decisions would have been exactly the same. But I would have made them with greater confidence. I would have spent less time wondering whether I was following the right path and more time appreciating the path I was creating.

Today, I still ask myself what comes next.

But now I ask something else first:

“Is this what I truly want, or is this simply what success is supposed to look like?”

The answer has become one of the most valuable measures of success I have.