Start with the Lifestyle That You Want

When I look back on my journey to becoming an entrepreneur and my own boss, the biggest catalyst was my desire for more freedom and autonomy. Not prestige, fame, or money—just the ability to do whatever I wanted, whenever I wanted, for however long I wanted.

It was even something I wrote down eight years ago when I started my first business and became an entrepreneur.

At that time, I was grinding hard at an early-stage startup with a small team. While it was exciting to be in the trenches with other smart, ambitious people working towards the same goal of one day turning that startup equity into an IPO or big acquisition, I slowly came to realize that I didn’t enjoy this lifestyle.

Primarily for two reasons:

1. When the product was losing momentum, I didn’t have the freedom or autonomy to course-correct and pursue what I thought would be the best path toward success.

So while the hours were long and work never really ended, what was most demoralizing was still having too much red tape and too many cooks in the kitchen. Ultimately, when something isn’t fully yours, you can’t determine its outcome as much as you’d like. And once you start feeling that way, you inevitably put less care and effort into something.

I wanted to have my own business where I claimed all of the risk and also all of the reward. To be able to make executive decisions in an instant and pursue what I saw as the best path forward, and let reality tell me if it was right or wrong. I could work as hard on it as I wanted or as little as I desired, stay the course or pivot into a new direction that I was more interested in—all while being fully aware that I control my efforts and outcomes.

Admittedly, this is a double-edged sword, but whether I succeeded or failed, I didn’t want there to be anyone else to blame but myself.

That kind of freedom and autonomy is scary to many but liberating and invigorating to me.

2. Secondly, I still had to go to the office every morning to do something that I didn’t think had a high ROI and wasn’t enjoying. I really, really didn’t want my day to look like this: go into a physical office, do a daily standup, have other unimportant meetings, and be mentally drained before I even started any actual work.

This feeling prompted me to write down in my planner that my goal in five years was to “not have to wake up to an alarm, not have useless meetings, and have the freedom and flexibility to travel whenever and do whatever I want.”

These sounded like goals an ungrateful teenager would write, but working toward these ideals is what ultimately led me to where I am now, doing what I enjoy, with a lifestyle I wouldn’t trade for anything.

The process was gradual, though. I didn’t leave my startup job and immediately start a successful business that satisfied all of those criteria.

The first business I started with a friend was actually very hands-on in the beginning. We grinded even harder than we ever did at our previous jobs.

But every sale we earned felt like the most rewarding thing in the world—we truly earned it because we were nobodies at the time, and it was purely our decision-making and ability to execute that determined whether a sale happened in every sense of the word. It was a two-person e-commerce clothing business, and we did everything—from designing and sourcing to marketing, operations, packaging, delivery, and customer service.

Over time, we got the business to a stable point, found a storage facility that wasn’t our own apartments, and were able to hire some great people to manage more of the day-to-day operations, including packaging and shipping.

This was a huge leap toward giving me the freedom and autonomy (as well as the confidence) I had always wanted when I first decided to become an entrepreneur. And because we were the bosses, we were able to maintain a culture of not having stupid, endless meetings and allowed everyone to work remotely and asynchronously, wherever in the world they wanted. All we cared about was whether or not you completed your tasks well.

Rather than pursue relentless growth, we valued having a lifestyle business that supported our needs and gave us time back to pursue other interests that made us happy. I took advantage of that myself and became a digital nomad, traveling and living across the country for several years.

Simultaneously, I was growing a few other side hustles into full-time businesses with my partner. Some of these were content-based businesses, others were e-commerce, goods, or hospitality-based services, and some combined all of the above (i.e., Tiny Dice House & Tiny Dice Buddies). But they all started as creative passion projects that we consistently worked on little by little every day. Ultimately, that consistency paid off, and each of these side projects took on a life of their own and turned into full-time hustles.

From the beginning, we chose to do things that were relatively easy to get off the ground, could be iterated on as we went, and didn’t require much capital, especially if we were resourceful (except for the Tiny Dice House, but we were lucky enough to win an Airbnb competition to help fund some of that).

What each of these required instead was discipline, consistency, time, creativity, open-mindedness, and leveraging our skill sets in a unique way to create something delightful for others.

While my first business started by filling a gap in a niche market where demand wasn’t being met, my subsequent side hustles started from pursuing creative interests I genuinely cared about and felt that I could stay interested in over the long haul, regardless of public demand.

With all of the projects that Olivia and I worked on together, we believed that if we created things that brought joy and laughter to us and other people’s lives, the demand would follow—and we’d be able to figure out a creative way to make money from there.

More importantly, all of the side hustles we pursued aligned with our values of freedom, autonomy, creativity, and full ownership. We were doing what we found interesting, on our own terms, without being tied to a 9–5 schedule.

As with most successful things you see publicly, success was never overnight. But once I tasted this level of freedom (no useless corporate meetings, no office requirements, no alarm clocks, etc.), I couldn’t go back.

This also meant saying no to many ideas and opportunities that seemed lucrative simply because they didn’t align with the lifestyle I wanted.

None of our side-hustle-turned-businesses are generating the kind of “generational wealth” you see with extremely successful CEOs and entrepreneurs. But they’ve given us enough financial security to say no to things that don’t interest us and to avoid working with people we don’t want to. That balance—having a lifestyle that isn’t soul-sucking, chaotic, or constantly stressful, while still keeping your time, health, and a stable income—is priceless.

When you start a business, the natural tendency is to want it to become as big as possible. But achieving that level of growth comes at a significant cost. You end up sacrificing many other things to sustain it.

I respect and admire companies like FAANG (Facebook, Amazon, Apple, Netflix, Google) that have fundamentally changed and dominated their markets—and we need people to do this. But I’m also not naive about the lifestyle required to achieve that level of success. It’s not a tradeoff I’d want to make because it’s simply not how I want to spend my time. I went to school with some of the most talented overachievers on the planet, and many of them are now stuck in lifestyles they don’t want.

I’m fully aware that you can’t have your cake and eat it too. At this stage of my life, I want slow mornings. I want to enjoy my coffee under the sun, play with my dogs and goats, go down rabbit holes on whatever topic interests me that day, work on the parts of my businesses where I feel the most energy, have random intellectual conversations with my partner, and choose how I spend my days.

One of the best books that talks about the tradeoffs between becoming big versus staying small is Company of One by Paul Jarvis. In many ways, staying small, working for myself, having minimal overhead, and not managing employees is my ideal lifestyle.

So when someone asks, “What type of business should I start?” my answer is always the same: spend time thinking about the lifestyle you want first, then figure out what kinds of businesses or products will allow you to live that life.