Originally posted on Substack on April 11, 2025
Today I am celebrating ten years as an entrepreneur. This date would have come and gone completely unnoticed if I hadn’t needed to submit some business paperwork earlier this week. Exactly ten years ago, I registered my business with the Hawaii Department of Commerce and Consumer Affairs. I’m so proud that my 24-year old self had the foresight and courage to take such a big step. I can’t imagine what my life would look like if I had gone the traditional route. Would I be sitting in a cubicle right now watching the minutes tick by until I can clock out? Who knows.
A decade ago, armed with an undergraduate psychology degree and a strength and conditioning certification, I had dreams of one day building a business working with athletes on their mental and physical fortitude. My boss at the private psychotherapy practice I was interning with pushed me to start a mental coaching business. He knew I wanted to go into Sport Psychology and he recommended that I just go ahead and get started already. He taught me to swim by shoving me into the deep end, and I will be forever grateful.
In fact, his son was my very first client.
It was a few years later while in grad school for Sport Psychology that I accidentally launched my current career. On a whim, I signed up for a metalsmithing class at the local art academy and decided that if I, a poor graduate student, should pick up a hobby it should be one that could make a little money while I study full time. I soon started selling my handmade jewelry at pop-up shops and online via Etsy and my own website. By chance, an earring design that I created in that first metalsmithing class took off on Instagram, and the rest is history.
Reflecting on a decade of what felt alternatively like flailing around hoping to stay afloat and throwing shit at a wall to see what will stick, I’m realizing I learned a few things about life and work. Here’s ten of them:
1. Define success
What would it take for you to consider this entrepreneurship endeavor a success? Is it a certain amount of money? Is it achieving a specific milestone? Is it the ability to financially support yourself while having the freedom to live a vibrant life outside of work?
One of the first things I learned while working with athletes is that success looks different to each individual—and that every person needs to answer this question for themselves before they set any goals. Chasing someone else’s idea of success is a recipe for endless dissatisfaction.
2. The rules are merely suggestions
Who says your day needs to start at 9 and end at 5? Who says lunch is only an hour? Who says you can’t take off Tuesdays or work weekends? Who says you can’t book an impromptu trip to Japan because a cheap flight popped up? Who says you need to strive for endless growth at the expense of your sanity?
3. You are not your job
As a youth athlete, my life revolved around sports. All of my time outside of school was dedicated to becoming the best athlete I could be (wrestling, in my case), which meant that when my wrestling career ended in college, I lost my sense of self-worth. I had poured my entire being into a sport and didn’t know who I was without it. It took many painful years of soul-searching to discover who I was off the mat.
With this in mind, I’ve been very conscious about separating my identity from my businesses. I’m proud to say that the pie chart of my life is divided among a variety of things that I am equally passionate about—jiujitsu, travel, being a dog mom, etc.—and work is just one slice.
4. Be flexible
Have an idea of where you want to end up, but don’t waste your time meticulously charting the path to get there. Life is unpredictable, and those carefully plotted points will inevitably change. Adhering to a rigid vision of what your journey should look like is how you miss life-changing opportunities, but embarking on this journey with the understanding that the path isn’t straight allows you to spot new possibilities you might otherwise overlook.
5. Seek knowledge
One of the best things I did in my self-employment journey was to seek out people in the community I admired. I wanted to know what their paths looked like, how they got to where they are now, and what advice they’d give someone in my position. I had so many cups of coffee with entrepreneurs in all kinds of fields, and those conversations helped shape my own ideas of entrepreneurship.
The biggest takeaway from these meetings with successful business owners was that it always feels, to some degree, like you’re figuring it out as you go. That was incredibly reassuring to me back then—and after ten years, I can confirm it’s still true.
6. Create community
Being a small business owner can be lonely, especially as a sole proprietor—and double especially if you work primarily online. Most of my peers have “normal jobs” with normal hours and the luxury of leaving their work at work. I couldn’t relate to their work lives and they couldn’t relate to mine. I was fortunate to find a network of other small business owners early on, and many of us have stayed close to this day.
As an added stroke of luck, my partner is also a small business owner. He runs a bespoke fine furniture shop, so we can share little wins or commiserate when things get tough. Though we have very different businesses, we deal with many of the same issues and benefit from being able to bounce ideas off one another. Surrounding myself with the right people has made self-employment a lot less lonely.
7. Imposter syndrome
It’s real. Everyone feels it. Get over it.
8. Play to your strengths and find those who balance your weaknesses
Just because you can do every job in your business doesn’t mean you should. You may have to wear all the hats in the beginning, but one of the most important things I’ve learned is that your job as a business owner is to continually seek out people who are better than you at certain things.
There are endless tasks that need to be done to run a small business. Figure out which ones you’re capable of doing—and which would be better done by someone else. Those are the people you need to hire.
9. Know when to walk away
Not every opportunity is for you, so it’s important to know when to walk away. I once left a lucrative partnership after realizing I was jeopardizing my company’s future for a (really big) paycheck. When I raised concerns about protecting my designs, the response I got was, “I don’t think you understand how much money we make you.” In other words: “How dare you question the way we handle your intellectual property—we more than compensate you for it.”
Yes, I made a lot of money with them. Yes, opportunities like this are rare. But walking away was easier than I expected. I realized I’d gladly trade instant gratification (and an earlier retirement!) for long-term protection of my company.
I’ve always believed that walking away from something that isn’t right for you creates space for opportunities that wouldn’t otherwise exist. (See #4: Be Flexible.)
10. Celebrate your victories, no matter how small
A classic overachiever move: set a goal, accomplish it, and immediately focus on the next, bigger, more ambitious goal. My advice? Don’t move the goalposts the second you hit a milestone just because there’s still more you want to accomplish. Work becomes an awful drag if you can’t even celebrate your own wins.
One of my biggest regrets as an athlete was not celebrating my victories because I was so focused on the next big goal. It went like this: I just need to win this match, then I’ll feel accomplished. Actually, winning this match didn’t feel as good as I thought, but when I win this tournament it will definitely be worth celebrating. Okay, winning this tournament wasn’t enough, but winning the league championship will be. Okay, actually, winning the league championship wasn’t enough, I need to win the state championship. Well, now that I’m a state champion, I just really want to be a national champion. This is how I spent my athletic career, and I regret it.
Now, when I catch myself thinking this way, I slap my inner self upside the head and pat myself on the back for whatever milestone I’d been tempted to overlook. That’s exactly why I’m celebrating ten years of entrepreneurship with this post (and fancy sushi takeout). Thanks for reading.