On Taking Big Risks, Embracing Change, and Losing it All

What I've Learned After 5 Years in Business

The first time someone paid me $1,200 to design their website, I thought I was rich. It was the most money I had ever received at once and it made me feel invincible. So much so, I packed my belongings into square brown boxes and moved out of my parents' house two weeks later. Although I didn't have enough money for the second month's rent, I trusted that if I had earned the money once, I could do it again.

This was it, I thought.

My one-way ticket to freedom and independence. I was desperate to leave my hometown and move to the city where my friends lived. I wanted to prove to myself, and everyone else, that I could do this on my own. That I was smart. That I could write my own paychecks and build a business based on the things I was passionate about.

The first year in business was all passion.

It was an intoxicating fever dream. I had just moved to Oakland, CA, joined a co-working space I couldn’t afford, and was taking BART into San Francisco every morning like a real, grown up adult. I was riveted by my own life. I couldn’t believe I was a business woman working for her own company. Not to mention, I loved the work I was doing, the people I was meeting, and the relationships I was building. It was, to me, one of the most defining periods of my youth.

I rode that momentum into the second year, straight into the pandemic, and created a signature coaching program called Personal Brand Accelerator, a 3-month course to help people build their personal brands.

The pandemic was a fantastic time for business. People were bored. No one had anywhere to be. Taking a personal development course was a sure-fire way to stay occupied and feel good about yourself in the process. After the first session completed, I’ll never forget the phone call my mom made to me. She said, “Anna, it works! It really works!” And I knew we had done it, that this course was special, and that I was accomplishing some far-away purpose I was destined to fulfill. I remember thinking, wow, if I can do what I am doing now for the rest of my life, I will be so happy.

By the end of my second year, I was leaving Oakland and driving solo across the country on my great American road trip. As I drove past state lines, I documented my travels and created videos on TikTok, eventually dubbing Boston my new home. I signed the lease for the first apartment I saw and settled into my new life, 3,000 miles away from my family and friends back in California.

The buzz I created on social media was enough to catapult me into the third year, and we started off January with a bang.

I hired a new assistant. We had a full course of students. And I had gained dozens of thousands of new followers from sharing my road trip across the country.

But you know how it goes. What goes up, must come down. Once the dust had settled and the novelty of my new home had worn off, I slipped into what felt like a self-induced coma. I was lonely in a new city where no one knew my name. I ate savory pizzas and rich desserts to escape that loneliness. I drowned myself in one too many cocktails at the bar just to feel something. My old self, and the possibility of my new self, were at odds with one another. My old self fighting to stay, my new self fighting to exist at all.

After my pity party, I decided, on an evening in May, on the step of my stoop with an ice cream cone in my hand, that I was going to do something different.

I would change. Utterly and completely change. I need to get it together, Anna. Lick. It’s time to grow up. Lick. Lick. I mean it, Anna. Lick. No more partying with strangers in the streets and emotionally eating until you're physically sick.

Lick.

People passed me by on the sidewalk in groups, and I just kept licking, and thinking, and licking, and thinking. And the next morning, I actually did it. I started to change. I made myself balanced meals, took long sunset walks around the Charles River Esplanade, read more books, wrote morning pages, and even started running.

Unfortunately for me, that was also the summer I ran out of money.

The pandemic was over. My first few years in business had been great, but then I was smacked in the face by the reality of it. Businesses aren't just about making money, they’re also about keeping and growing it, too. Nobody had ever taught me how to do that. I didn't take a course on this, I didn't study business in college, I was just a girl with an idea and an insane amount of blind enthusiasm. My confidence was not a product of experience, but of fantasy. I dreamed I could do it, so I did. But eventually, that wears off and when it does, you have to prove to yourself that this thing, this wild beast of a thing that you've set out to create, can stand on its own two feet without you constantly having to rescue it. I hadn't proven to myself I could do that yet, so I floundered for a bit, angry and constantly in a debate with myself, talking myself off the ledge.

Eventually, the tides turned, and by the beginning of year three, my content on TikTok and Instagram was enough to generate new business and bring people through the doors again. Another fabulous season of business. Money was flowing in effortlessly. Credit cards got paid off. Savings were growing steadily. The community I was building was growing deeper and more connected. I loved the work we were doing. And for the first time ever, I made $40,000 in one month. My life became a dream I never wanted to wake up from.

Then, something happened that would change its course forever.

In the span of a few hours, I lost it all. Everything I had worked for, everything I had saved, almost all of the money I had to my name was gone in an instant. In a flash. It was as if the rug had been swept out from under me. I had been scammed.

People always think it'll never happen to them.

You believe you'll be smart or savvy enough to know when someone's trying to deceive you. In retrospect, I assume most people would have realized what was happening before I did. But I was alone. I had no one to fact-check with. The men who had scammed me over the phone had disguised themselves as my heroes, my companions, heroically trying to save me from "identity theft." And I believed them, desperate to free myself from the situation they had thrusted me into. I wanted to be done with it. I wanted it to be over, so I trusted them, and they betrayed me.

When I finally realized what had happened, that I had just lost everything, my rage bellowed out of me like an eruption from a volcano. I told the scammers to fuck off, hung up the phone, and screamed at the top of my lungs, so fiercely, it felt like trying to shatter the sky. I sobbed uncontrollably and pounded the steering wheel with my fists, as my dog, Laurence, sat in the passenger seat watching me. He was so scared, didn’t look at me for days afterward.

After that, there was nothing. Silence.

Money is like a blanket. It keeps you warm at night. Without it, you lie there naked and exposed, left in the cold, yearning for its comfort and regretting not having appreciated it more when you had it.

The next day, I met my partner, Trevor, and life would never be the same.

I told myself that I would make all the money back and that it would only be a few months before things would return to normal. I coached myself with positive affirmations, wanting to believe things weren't really that bad. This was not life-altering. But it was.

Year five was the hardest year yet.

I was back on the ledge, angrily contemplating the proposition of abandoning my business and working for someone else. I could hardly afford to pay my bills, my dad had to loan me money. I hated how vulnerable I had become, that I had to rely on people again and ask for help. The beginning stages of my relationship with my partner were etched with desperation and vulnerability. "This isn't who I am," I would tell Trevor, "I promise it hasn't always been like this." Although, I’m sure I was trying to convince myself more than I was trying to convince him.

It was a combination of a lot of things: losing all that money, starting a new relationship, moving in with my partner, a lull in new clients and business, that really made showing up online with my usual confidence and charisma pretty difficult. I was not the same person anymore, and I didn’t feel ready to tell people what had happened to me. It was just too raw and under-processed to share online. I knew I would eventually talk about it, but I needed to lick my wounds for a while.

So I continued on, just grateful to make it through another day.

There were times I considered getting a second job as a waitress or a dog walker, purely to meet my expenses. But every time I got serious about looking, I would book a new project or an invoice would be paid. It almost felt like the universe telling me to endure the discomfort. I just had to accept that this was part of the deal. There would be good years, and shitty years, and this was a shitty year, but it wouldn’t stay like this forever.

It took a full 15 months for my business to show signs of improvement, but eventually, things started to get better. New students joined PBA and we further developed the 1:1 coaching aspect of my business. By the beginning of the sixth year, we were on an upswing. I had found my stride again. Life would never be the same as it was before the scam, but it didn't need to be. What became most important was building towards the future, instead of romanticizing the past.

As I look back on what the last 5 years have meant to me, I have so much love for them.

Having a business feels a lot like being in a wishy-washy relationship. It’s up, it’s down, it’s all around. Some months are good, others are not. Some years are prosperous, others are not. I’ve stood at the ledge so many times and said, “I’m going to jump. I’m really going to do it this time.” But I don’t. I always turn around, vowing to devote myself to whatever it asks of me next. I’ve never been a mother, but I wonder if it feels a bit like that. I’d imagine your children drive you crazy, but you’ll always stay, no matter how bad it gets. You're their mother, after all. They still need you.

Recently, my friend asked about the source of my security. "When everything was stripped away, where did it come from?" she asked. I paused for a moment, thinking that I wanted to be honest with her. I didn't want to say the first thought that came to mind; I wanted it to be the truth.

After a long while, I said, “It came from my relationships. I had to draw strength from the people in my life who showed up for me during that time.”

After we hung up, I thought about it some more. While it’s true, my relationships were a great source of support, the greater lesson I learned was in the power of equanimity. Losing that money felt like being stripped of my autonomy and control. I regained that sense of control, not by earning more money, but by learning to endure the discomfort of having none.

As I think about what the next five years will bring, I draw comfort from the experiences these last five years have given me. My confidence no longer feels like a figment of my imagination, but is firmly built on the rock of experience. From enduring the pain and coming out the other side, transformed and wholeheartedly ready to face what’s next.

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