It was May 2018, I was 37 years old, and I was ugly crying on my couch.

I was terrified that I was destined to forever be an administrative assistant. Not that there’s anything wrong with that – I’d been an assistant for years, but I was afraid I was stuck and it was my fault.

While everyone else had racked up years as bankers, lawyers, doctors, or other reputable professionals – I left corporate America in my 20s to try different things. I produced a documentary, I took writing classes, I freelanced babysitting, planning weddings, and whitening teeth. I went to conservatory for 2 years to become an actor which meant I needed a day job. So over the next decade, I worked at a startup doing bizdev, at a hedge fund stocking the fridge, at a web development company as an admin. My resume looked completely disjointed and unfocused.

That day, my friend encouraged me to reach out to my network. “I don’t have a network,” I said. “The only person I could ask for a reference is my old boss Dan who moved to Paris and I haven’t spoken to him in a decade.”

She said: “Reach out anyway.”

So the next day, I sent Dan an email asking to be my reference and threw out: btw if you know any startups looking for someone with my skill set, let me know.

Not 15 minutes later I received a response: “I happen to be in town right now. Let’s meet up!” It was Wednesday; by Friday Dan gave me an offer to head operations for Shoott with two t’s – a startup we came up with to see if we could improve the gig economy for photographers.

That was 6 years ago. I had no idea what I was doing, but I was so excited. Early on, we did all the dumbest things like mistakenly undercharging a client, then emailing her asking to pay us more. The client said: "Why would I pay for your mistake?" We said, "Oh yeah, you’re right, our bad." And went from there.

We’ve grown a lot since those days – Shoott is now in 58 US cities, we support over 700 photographers, we have a 4.9 star rating on Google, we’ve completed over 175,000 photo sessions, we’ve been featured by The Today Show, Oprah Daily, People, and Elle, and I’ve also been named a Forbes Next1000 Entrepreneur.

We’re proud of these highlights; but the truth is, Shoott is still here today because we learned to take risks and pivot. Doing this in real time is scary and unsexy because everything is a risk when you’re doing something new.

My Co-Founder Jen and I are both children of immigrants from Taiwan that were pressured to follow a straight and narrow path. But we found ourselves replicating the side of the immigrant experience that we’re often told to avoid, which is putting yourself in situations where you need to rely on your ability to survive and figure things out. So many AANHPI folks come from people that took immense risks and are the OGs of pivoting. Don’t know how to do something? Figure it out as you go!

Running Shoott has been nonstop learning things as we go and just not giving up. I had to learn social media from scratch at almost 40. It was painful at first, but now I comfortably run our social media and we have 20K followers on Tiktok and 50K followers on Instagram. Not bad.

So if you feel like you might have a calling that you don’t know how to make a reality, I encourage you to try some part of it. Trying may seem like a potential waste of time and effort, but it’s the fastest way to gain clarity. For example, by working a short stint at a nonprofit, I learned that nonprofit work was not for me. When I started Shoott, it felt like a better fit, but I had no business running a business, at least on paper. My cofounder Jen wasn’t better – she was a hard-working straight C student that left the workforce for a decade to raise 3 kids only to get divorced – most people wouldn't bet on her either.

But no matter what the world might see when they look at you, you have to know you. What are your strengths? What types of things do you have almost unlimited energy for? My cofounder Jen was the bridesmaid that happily pulled all-nighters with me making all these DIY crafts just so I could have the budget wedding of my dreams. I knew we could work hard, we could make it to the other side of challenges, and we loved doing bonkers projects together.

We brought these parts of ourselves to Shoott, so when things felt uncertain, we stayed true to our passions which helped us navigate all the challenges. Our days can be hard, but our work is really gratifying. We’ve become sharper, stronger, and more resilient. We’ve learned that for us, taking risks and simply trying things - has freed us from wondering if we’ve left our potential on the table.

We’re proud to share that in 2023, Shoott had $9MM of annual revenue and just reached breakeven on a small team of 12.

So consider this your sign to take risks you’ve been contemplating – I can honestly say that nothing I tried was ever a waste of time or energy – it just provided more clarity. And you never know what you can achieve.