The Moving Goalpost Problem: Why “When I Hit This Milestone, I’ll Rest” Is a Lie

I’ve told myself this story more times than I can count. And it has never once been true.

When I launched Sarah Michelle NP Reviews, the goalpost was simple: survive. Get enough students to make this real. Once I had that, I’d feel settled.

I got the students. The goalpost moved.

Then it was: get to six figures. Then it was: when I hit a million dollars, I’ll finally feel like I’ve made it. A million dollars happened in seven months, and that was supposed to be the moment.

It wasn’t.

The goalpost moved again. Now it was: when I sell the business, then I’ll relax. Then the real life starts. Then I’ll have made it.

I sold. And for a moment, before the integration pressure and the contractual obligations and the reality of what transition actually looks like, I thought: this is it. I’m on the other side.

Also not the moment.

What the Goalpost Is Actually Made Of

The moving goalpost isn’t random. It’s not a character flaw or a sign that you’re too ambitious or not grateful enough. It’s a structural problem with how we’re taught to measure success, and specifically, it’s the habit of outsourcing the feeling of success to a number.

When success is a metric, a revenue figure, a valuation, a follower count, a title, it can never fully arrive, because metrics are always in motion. Hit $1M and the natural next question is: what about $2M? Close the deal and immediately: what’s next? The number gives you a momentary hit of validation and then resets the bar. That’s just how numbers work.

The problem is that most of us have been running this playbook since before we started building anything. Work hard, hit the goal, rest, repeat. But the rest part never comes, because the goal was never designed to provide it. Numbers don’t produce rest. Rest is a decision.

The Glamorization of the Exit

I want to be specific about the exit version of this, because I think it’s particularly seductive and particularly under-discussed.

Selling your business gets glamorized in a way that almost nothing else in entrepreneurship does. It’s treated as the finish line, the ultimate proof that you built something real, that you won, that you can finally stop running. The number gets announced, people congratulate you, and for a minute the story feels complete.

But exits are not a finish line. They’re a transition, and transitions are complicated, uncomfortable, identity-reshaping experiences that nobody really prepares you for. The business you poured yourself into is no longer yours. The people who depended on you are now someone else’s responsibility. The purpose that organized your days is suddenly unmoored.

I sold Sarah Michelle NP Reviews while pregnant, three weeks before we found out that our daughter Meadow had four heart defects. I went from closing an acquisition to becoming a mother to a medically complex baby in the ICU. The pressure during that period was unlike anything I had experienced: professional obligations, integration timelines, the name and face of the brand I’d sold still being mine to show up as, all of it while Meadow was in the hospital.

The exit was the right decision. I know that fully, and in fact, Meadow’s illness confirmed it in a way I couldn’t have anticipated. But it was not the arrival I had imagined. It was a whole new set of hard things that required a whole new set of capacities.

Success as a metric had nothing to offer me in that ICU. What I needed then, and what I think most of us need more of, was something the goalpost can never give you.

What I Mean When I Say Redefine Success

I know “redefine success” sounds like the kind of thing people say on Instagram with a picture of a sunrise. I want to be more specific than that, because it’s actually the most practically important thing I can say.

Redefining success means deciding, in advance, intentionally, in writing if you need to, what it feels like. Not what number it looks like. Not what title or milestone or acquisition valuation. What does it feel like to be living a successful life? What are the specific qualities of that feeling?

For me, when I got honest about it, the answer had almost nothing to do with revenue. It had to do with presence, being available for the moments that actually matter. It had to do with capacity, having enough left at the end of the day to be a mother and a partner and a human, not just a founder. It had to do with autonomy, working on things I actually care about in ways that feel aligned with who I am, instead of just what the market rewards.

None of that appears on a cap table. None of it shows up in a revenue report. But all of it is measurable, in how you feel when you wake up, in how you show up for the people you love, in whether the work you’re doing actually reflects the life you want to be living.

The Practical Version of This Advice

If you’re in a growth phase right now, heads-down, pushing hard, telling yourself the rest is coming, I want to offer you a few concrete questions. Not to slow you down, but to help you build in a way that doesn’t hollow you out.

What does “enough” actually feel like to you, not look like, feel like? Sit with that question. The answer might surprise you. Most of us have never asked it seriously.

When you imagine hitting your next milestone, what do you think will be different about your daily life? Get specific. If the answer is vague, “I’ll feel better,” “I’ll have more freedom”, you’re probably chasing a feeling, not a plan. What will actually change?

What are you postponing until after the goalpost? Rest, health, relationships, creative work, joy, whatever it is you keep saying you’ll get to later. The honest truth is that “later” rarely arrives on its own. You have to build it in now, even imperfectly, even in small doses. Because the goalpost is always going to move. The only way to stop running toward it indefinitely is to decide, now, not later, what you’re actually running toward.

I hit a million dollars in seven months. I sold a business. I did both of those things while navigating more personal complexity than I could have predicted. And the thing I know now that I didn’t know then is this: the goalpost was never the point.

The point was always the life you were building in between the milestones. That’s the thing worth protecting.

Decide what success actually feels like to you. Write it down. And then build toward that, not toward the next number that will move the moment you reach it.