You Can't Define Success If You Don't Know What Enough Is

Listen to the full Podcast Episode on Apple Podcasts | Spotify | Watch on YouTube

You did the thing you said you wanted to do.

You got the promotion. You made it to the senior level. You built the client base, hit the revenue number, got the title on the business card. Maybe you even have the family alongside it, the partner, the kid, the apartment that finally feels like a home.

And somewhere in the quiet after that, you felt it. That hollow little pause before you started looking for the next thing.

That feeling has a name. It's what happens when you've spent years chasing success without ever defining what enough looks like. When the finish line is always moving, you never get to stop running. And the arrival you've been working toward keeps arriving empty.

Why "success" is a trap without a definition of enough

Most of us inherited our definition of success. The good school, the competitive job, the climbing trajectory. Jess Wass, co-host of Rewritten and founder of Reworkit, describes it clearly: we get fixated on milestones. I'll be happy when I get this promotion. When I get into this school. When I hit this number. And then you get there, and you're already looking at the next one.

Teresa Sweeney calls it the hamster wheel. The carrot that's always dangling just ahead, close enough to feel real, far enough to keep you running.

The problem isn't ambition. Ambition is fine. Goals are fine. The problem is chasing without clarity. When you don't know what enough looks like for you specifically, not for your industry or your peer group or the version of you that was twenty-two and trying to prove something, you hand the definition of success to everyone else. And they will keep the bar moving indefinitely, because it serves them to do so.

Without a personal definition of enough, success becomes an endless negotiation with an invisible standard you never set.

How it shows up at home

The hamster wheel doesn't stop at the office door. It follows you home, into the weekends, into the decisions you make about your kids' schedules, your own free time, what you're willing to let go of and what you tell yourself you should be doing.

Jess talks about it in the context of toys and birthday parties. The pressure as a parent to provide the specific learning toy that teaches the specific skill, or your kid is behind. The birthday party gifts that multiply until a child is fatigued from opening them. The extracurricular schedule that consumes every weekend because if your kid isn't in swim and soccer and dance class, you're not doing enough.

It's the same mechanism. No definition of enough means someone else fills the gap. And in parenting, that gap is filled with guilt, comparison, and a low-grade sense that whatever you're doing, it isn't quite sufficient.

The relief comes from asking the question you've been avoiding: what actually matters here? Not what should matter. Not what other parents are doing. What do you actually care about? Because once you're clear on that, the rest becomes noise you can name and set aside.

What redefining success actually requires

Jess describes the moment her definition of success crystallized. She was building her coaching business, and a client told her how meaningful their work together had been. It lit her up in a way nothing else had.

And she thought: if I could only ever help one person, that would be a thousand times more meaningful than anything else I could do.

From that moment, everything else became a trade-off she could actually evaluate. What was she willing to give up to keep doing this work? Her answer was: a lot. The prestige of Brooklyn. The idea of a growing revenue number. The version of success that looked impressive to people who didn't know what she actually wanted.

What she wasn't willing to give up was the work itself. The flexibility. The autonomy. The ability to step away when her daughter needed her and come back without asking anyone's permission.

That clarity, knowing what she was protecting and what she was willing to release, is what gave her a real definition of success. Not a number. Not a title. A feeling she could recognize when she was in it.

This is what redefining success requires. Not a vision board. Not a five-year plan. The honest answer to two questions: what is the thing I'm actually protecting, and when will I know I have enough?

The one question that changes everything

Jess uses a reframe she describes as a little morbid, but more useful than most planning frameworks she's encountered.

If I died tomorrow, would I feel like I hadn't even started yet?

She's lost people in their thirties. People who worked hard their whole careers building toward a retirement they never reached. That reality, not as an abstraction but as something she has lived, is what keeps her from postponing the life she wants.

The question isn't meant to be dark. It's meant to cut through the noise of everything you think you're supposed to be doing and get to what you actually want to have done. Not at retirement. Not at some future milestone. Now.

When the answer is: I haven't even started, that's the signal. The definition of success you've been operating under isn't yours.

The permission nobody is waiting to give you

Teresa shares a story from an internship: a senior banker, asked what he regretted most, described missing his children's entire childhoods in pursuit of a career that, at the top, felt like it hadn't been worth it.

The look on his face, she says, was heartbreaking.

Nobody told that man to miss the birthdays and the soccer tournaments. He made choices, every day, that accumulated into a life he was grieving while still living it. And the tragedy isn't the career. It's that nobody made him choose. He chose, without ever asking himself if this was what he actually wanted.

The women Teresa later observed, the ones she wanted to emulate, did something different. They had extreme clarity on what mattered to them, and they protected it without asking for permission. They just did what they needed to do and let people question it if they felt the need to.

That's not a personality type. It's a practice. And it starts with knowing what you're protecting, which starts with knowing what enough looks like.

You will not accidentally arrive at a life that feels like yours. You have to define it, name what enough means, and then stop negotiating against yourself before you've even asked the question.

That's the work. And it's worth doing before you get to the top and feel that hollow pause.

Want to hear the full conversation? Listen to Episode 102 of Rewritten: Real Talk for Working Moms Who Want It All on Apple Podcasts | Spotify | Watch on YouTube

If this resonated and you want to get clearer on what success actually means for you, I work with women one-on-one to do exactly that. Book a free consultation at reworkit.co/schedule-a-consultation.

Jess Wass is the Founder of Reworkit, a leadership development and coaching company, and co-host of Rewritten: Real Talk for Working Moms Who Want It All. She helps women ditch the script they were handed and build a life that's actually theirs.