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Have you ever hit a big milestone—one you thought would feel amazing—and instead, you’re like, “Wait, that’s it?”

You got the job. You crossed the finish line. You checked the box. And five minutes later, you’re already on to the next thing. Or worse—you feel a little empty, maybe even disappointed.

I don’t think that’s because you’re ungrateful. I think it’s because you’ve been living by someone else’s definition of success. And if you’re wondering where those definitions come from, look no further than the culture we’re raised in. It feeds us a script about what “making it” should look like.

The Success Playbook We Rarely Question

In the U.S., we live in a capitalist-first culture. And whether we realize it or not, we’re spoon-fed a script about what “success” should look like. It usually sounds like this:

* Make a lot of money.

* Get the big job title.

* Work long hours—because hustle equals ambition.

* Collect degrees and credentials.

* Show it all off with travel, brands, and lifestyle.

Now, none of this is bad. Honestly, some of it can be great. But here’s the catch: if you’re chasing these things because you think you should—or because that’s what everyone around you is doing—you’re going to feel sorta hollow and empty when you get there.

The Comparison Game

And then there’s comparison. We look around and think, “Well, they did it, so maybe I should too.”

That’s exactly what happened when I went for my MBA. Most of the business leaders I admired had one. So I thought, okay, I need that too. And while that degree never once got me hired, I’ll admit it gave me confidence in a boardroom.

But let’s be real—that’s not the degree speaking. That’s me outsourcing my self-worth to a piece of paper. What I really wanted was authority and belonging.

That’s what comparison does: it makes you believe if you just had the thing—the degree, the Fendi handbag, the fancy beach or ski vacation—you’d finally feel successful. Spoiler: you will, but only if that’s how you define success.

Redefining Success

Here’s the shift: success isn’t a moving target. It’s a way of life. And the only way to feel it—really feel it—is to define it for yourself.

Here’s a little exercise I use with my clients (and myself):

* Write down your definition of success. Don’t overthink it—just get it on paper.

* Ask yourself: Why is this my definition? Write down the answer.

* Ask again: Why is that the answer?

* And one more time: Why is this the answer?

Each “why” pulls you deeper—past surface-level goals into the values and purpose underneath.

Let me show you how this played out for me.

Back in 2017, here was my definition of success:

* Land a fabulous, high-profile job.

* Finish a vomit draft of my book by the end of the year.

* Lose 10 pounds.

Here’s what happened when I put that list through the “why” filter:

High-profile job

* Why? Because I wanted to feel important and respected.

* Why? Because I thought if people admired me, I’d finally feel secure.

* Why? Because underneath all the ambition was a fear that without status, I wasn’t enough.

Finish a book draft

* Why? Because I wanted to be able to say I was an author.

* Why? Because I thought having “author” next to my MBA would make me more legitimate.

* Why? Because I believed credibility came from labels, not from having something meaningful to say.

Lose 10 pounds

* Why? Because I wanted to look like I belonged in Los Angeles.

* Why? Because the beauty standards here are unforgiving.

* Why? Because I thought if I fit the mold, I’d be more lovable.

Unpacking each of these so called definitions of success showed me that none of them connected to my actual values. They were all seeking external validation - and they were goals, not ways of being. No wonder I felt an odd sense of emptiness and like “what, that’s it?”

Here’s how I define success today: Listen with curiosity, courage, and compassion while creating content and experiences that help people love, learn, and laugh.

See the difference? Instead of goals shaped by comparison and culture, this definition is rooted in what matters to me. It’s not something I can check off a list. It’s something I can live into every single day.

The Bottom Line

Culture and comparison will always offer you a version of success. But if you don’t stop and ask whether it’s really yours, you’re going to keep hitting milestones that don’t mean anything to you.

So grab a pen. Write your definition. Ask why, and then ask why again. And don’t stop until you land on something that feels like you or gives you clarity on what needs to be course corrected.

Because success isn’t out there waiting for you at the next finish line. It’s in how you’re living your life today.

If someone came to mind while you were reading this—please send it their way. You never know the impact a well-timed message can have.

Related Content

* Why Can’t I Stick With It? 🔄

* Is Uncertainty Blocking Your Career Growth?

* Unlocking Your Life Purpose

Perks for Paid Subscribers

Moonshot Mentor paid subscribers get weekly journal prompts to spark personal and professional growth, guided meditations to help them center, reflect, and reset, plus exclusive career development and career grief workshops that build clarity, resilience, and momentum.

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Journal Prompts

Here are 4 journal prompts for paid Moonshot Mentor subscribers. These will help you dig deeper into your own definition of success and notice where culture and comparison may have shaped it.

Does Success Feel Flat to You? 😶