How To Never Work A Day In Your Life

A personal meditation on meaning, mastery, and the magic of who’s beside you.

There are few subjects more persistently misunderstood than the concept of ‘work’.

Work being that thing we spend the majority of our life doing.

That gives us resources to live the lives we want.

We talk about it constantly—how to approach it, how to find meaning in it, how to escape it.

But despite its ubiquity in our lives, most of us still fail to ask the right questions.

Last night, over a fantastic Mexican meal in Greenpoint with one of my best friends, we found ourselves circling around this very topic.

We’re both entering new chapters in our lives, and the conversation naturally turned to the criteria that determine whether or not work is fulfilling.

Three possibilities emerged:

• Love what you do.

• Love who you do it with.

• Work really hard at it.

At first glance, this seems straightforward: work should be something you love, something shared with good people, and something that requires real effort. \

A no-brainer.

But as we talked, we identified two common misconceptions that distort our thinking about work:

The first misconception is that success is simply a function of effort.

But effort, like most things in life, does not scale linearly.

If you’ve ever encountered the concept of superlinear returns, you’ll know that some inputs—insight, timing, leverage—can, and often do, matter far more than sheer labor alone.

Working hard is necessary, but it is no guarantee of success.

Trust me, I know this. I am addicted to the idea of working hard, something I have been trying to re-wire my brain on for as long as I can remember.

The second misconception is more pernicious (and controversial): the idea that we should “find our passion” and let that dictate our work.

But what if you don’t know what you love? Or what if you try something new and, at first, it feels terrible?

The truth is, passion is often the result of mastery, not the cause of it.

Many of us grow to love what we do only after we become good at it.

Hindsight tends to always be 20/20.

As an example, when I was a young kid, I thought skateboarding was way cooler than BMX.

But growing up mostly in the country, I had access to dirt, not pavement.

So I reluctantly picked up a bike, met some friends, and over time, it became the thing I loved—not because I was naturally gifted at it, but because it connected me to people and experiences that would shape my life (image making, creativity, graphic design, moving to NYC).

The love I felt was a byproduct of shared effort and camaraderie with the kids I was riding with (As seen in the video above of my BMX crew growing up).

I only was ever halfway decent at it, by the way.

Somewhere between BMX and now, DONDA happened, a place where I spent over five years of my life.

To this day, it remains some of the most chaotic, grueling, and tireless work I’ve ever experienced.

But at its core, it was just a group of friends who were tight-knit, relentless, and completely immersed.

We spent nearly every waking minute together: traveling, eating, partying, firing off memes in group chats, and stifling uncontrollable laughter in very-incredibly-serious meetings.

Also, we got to create incredible work in the process.

The same thing happened when I co-founded Rosaluna. I never set out to build an alcohol brand.

What I did set out to do was spend time with my best friend, (the one I had dinner with that sparked this post)—talking, building, creating.

And in the process, we became business partners, and the work itself became meaningful.

The lesson here is simple: we often misattribute our love for an activity, when in reality, it is the relationships formed within it that matter most.

I know not everyone gets to choose their coworkers, or even what kind of work they do, especially in the beginning.

I’ve had my fair share of jobs that were less about fulfillment and more about survival. I come from a big family…my mom raised five of us on her own, as a single mother.

So for me, work wasn’t optional. It was necessary.

I used to work the back-stock room at American Apparel during the day, then juice carrots at Juice Press overnight…just to afford a peanut butter bagel from the corner store. Not glamorous. Not fun.

That wasn’t about passion. It was about paying rent, and affording groceries.

But I knew deep down it was the sacrifice I had to make to break the cycle—to avoid living a life I didn’t want, working a job I hated, surrounded by people I couldn’t stand.

This path isn’t for the faint of heart.

It’s life with zero safety net.

But when it hits? It hits. And nothing feels better.

I now find myself in a similar position once again as I build Handstand.

At its core, it’s just another excuse to surround myself with incredibly smart, creative, and motivated people—people who are building in industries that excite me, challenge me, and (hopefully) shape the world for the better.

In that sense, it isn’t just a business; it’s a mechanism for connection, an engine for inspiration.

And in the same way that BMX as a kid and Rosaluna later in life became meaningful because of the people involved, Handstand is simply another iteration of this truth.

The work itself is a byproduct.

So, by the end of dinner, my friend and I had revised our ranking.

The correct order was now clear:

1. Love who you work with.

2. Love what you do.

3. Work really hard at it.

Everything else flows from this.

If you optimize for the right people, work ceases to feel like work at all. Instead, it becomes a vehicle for collaboration, exploration, and growth.

It becomes, in the truest sense, play.

I pinch myself every day over this realization.

Of course, there is a counterpoint: one could theoretically love their work and endure bad company for the sake of it.

Many people live this way—tolerating toxic environments in service of potentially higher ambition.

But it seems to me that this is an unnecessarily difficult way to spend the bulk of one’s waking life.

The only life that we know, as far as I’m concerned.

The real lesson for me (outside of having more epic dinners with your best friends) is this:
Fulfillment is not found only in a specific type of work, and definitely not in the sheer volume of effort expended.

It is found in the epic people you meet and get close with along the way.

Choose them wisely, and you’ll discover that you have never truly “worked” a day in your life.

Note:

Virgil Abloh, whose influence continues to inspire so many of us. Rest in peace.