So you want to be successful?
What does that even mean?!
What Does Success Really Mean?
I’ve been thinking a lot lately about what success really means — and, maybe more importantly, what it feels like.
When any of us set out to do something — start a business, excel in school, or simply “be successful in life” — we’re all chasing something. Sometimes it’s tangible, like a car, a title, or a certain number in the bank account. Other times it’s more abstract — a feeling, an experience, or a kind of freedom.
Success looks different for everyone. For some, the pinnacle might be a Lamborghini. For me, that does absolutely nothing — I don’t even like to drive. So while many of us name these “markers” of success, what we’re really chasing is something deeper beneath the surface.
The “Why” Behind It All
In my MBA program, I learned about something called the Toyota 5 Whys, a problem-solving technique developed within the Toyota Production System. It was originally attributed to Sakichi Toyoda (the founder of Toyota Industries) and later popularized by Taiichi Ohno, one of the architects of Toyota’s lean manufacturing approach.
The idea is simple: when something goes wrong — or when you’re trying to understand what you really want — you ask “Why?” five times in a row. Each answer peels back a layer until you uncover the deeper reason or root cause.
It’s not a perfect science — “five” is more of a guideline than a rule, and the answers depend on your own awareness and perspective — but it’s ALSO a powerful framework for reflection (I’ve found).
Let’s say you define success as having “lots of money.”
Why? Because it would let me travel wherever I want.
Why? Because I didn’t travel much when I was younger.
Why? Because my parents weren’t into it.
Why? Because I’ve always associated travel with freedom.
So what you’re really chasing isn’t money — it’s freedom. The ability to go where you want, when you want. That’s what success feels like to you.
And I think most of our “success goals” work that way. They’re not about the surface-level thing. They’re about the emotion we think that thing will unlock.
Redefining Success Through 1987
When I started 1987, I was chasing success too. But after four years, a lot of lessons, and a lot of growth, I’ve realized that success has evolved for me.
Statistically, most businesses don’t make it past year one — or year three — or year five. We’ve built something that’s profitable, sustainable, and expanding. That alone is an incredible milestone. But this year, I started asking myself: Okay, but what does success actually look and feel like to me now?
When I worked in corporate, I had no control over who I worked for. Because of my work ethic, I would give 100% no matter who was on the other side of the table — even if that person wasn’t a good human being. And that powerlessness really got to me.
Now, as the CEO of 1987, I get to choose exactly who I work with — and that is one of the most rewarding feelings of success I’ve ever experienced.
The Power to Choose
Our team is built on loyalty and good energy. If you look at 1987’s journey, you’ll see the same faces and names again and again — because when we find good people, we stick with them.
I’m fiercely loyal to our fulfillment team (shoutout to OWD), to Sarah (my co-founder and our CGO), to our models, photographers, and everyone behind the brand. And when we’ve had the rare experience of working with someone who didn’t align with our values — and I later get to professionally, calmly say, “No, that person’s not a fit for us” — that’s what success feels like to me.
It’s not about money or status. It’s about freedom of choice. The freedom to only surround yourself with good people. To build a business rooted in kindness, respect, and alignment.
Building Something That Can’t Be Taken Away
Another layer of success for me is pride — knowing that I took something that existed only in my mind and turned it into a real, thriving business. Even if, hypothetically, it all disappeared tomorrow (which I hope it never does!), no one can take that away from me.
I built something from nothing. And that kind of confidence — that self-belief — is something no one can give you and no one can take away.
Success as Worthiness
I struggled with self-confidence growing up. There were people in my life who made me feel unworthy — like I didn’t deserve good things or success. So, part of what success means to me today is feeling worthy of where I am.
Worthy of this brand.
Worthy of our community.
Worthy of the life I’ve built.
That’s not something that happens overnight. It’s something that grows through years of showing up, proving to yourself that you can do hard things, and realizing that you deserve to enjoy them once you get there.
The Real Definition of Success
So what does success really mean? For me, it’s this:
The freedom to choose who I work with.
The confidence in what I’ve built.
The pride in knowing I beat the odds.
And the deep sense of worthiness that comes from doing it all with integrity.
If you’re chasing success in your own life, I’d encourage you to pause and ask yourself: What do I really want — and what feeling am I actually after?
Because chances are, what you’re really chasing isn’t a thing.
It’s a feeling.
PS this HOC collection drops Oct 24 at 10am et:
