My First Year as a Business Owner

It’s crazy to think that just one short year ago, I quit my job to start a travel business.

I walked away from an amazing career that I loved and people who had truly become family to me over the 14 years that I worked in higher education.

A lot of people thought I was insane for quitting my job. And let’s be real, I was.

I lived off a single income, and I had no partner to support me while I pursued my dreams. There was no backup plan.

“What about health insurance?”

“Won’t you be lonely?”

“Can you actually make a living doing that?”

“What if it doesn’t work out?”

Trust me, all of these (and many, many more) were doubts I played in my mind over and over before I made the decision. I thought about it for over a year, and I questioned myself probably more than anyone else did.

But the reality was, I wanted something different for my life. I had done many things in my career that I was proud of, and I am incredibly grateful for what I had, but I no longer felt challenged. I was burned out. And I didn’t see a path forward in that line of work that fueled my passions. It was no longer a fit.

I wanted to work remotely from anywhere. And most importantly, I wanted the freedom that most 9 to 5 jobs just cannot provide.

It was my goal to create something for myself that could grow larger than just me. I wanted to create opportunities for other people to travel like I had and see the world in a different way. And I couldn’t do that if I was working more than 40 hours a week at a job that no longer served me.

I knew if I kept working full-time while starting a business on the side, it was going to take me way longer to get where I wanted to be. The only thing that would force me to give 100% was if I was all-in without a safety net.

If there was one thing that the pandemic taught me, it was that I wasn’t meant to work for someone else.

I still remember the day I quit my job so vividly in my mind. I’d been having a really hard time making it official, even though I’d been thinking about it for weeks and had made up my mind.

The thing about quitting your job is that many people fantasize about it, but few people actually follow through—until you actually do it, it’s just a pipe dream.

And it’s absolutely terrifying.

I drafted up my letter of resignation after I was done for the day, thought of how I was going to tell my boss and my team, and then I sat there in my office with a signed resignation letter in a total state of panic.

I sat there for over an hour, paralyzed with anxiety.

I texted my former boss, Kristen, who’d always been a mentor to me and who I greatly respect and admire.

“Do you want me to talk you into it or out of it?” she asked.

“Into it,” I quickly texted back.

And then she said the magical words of encouragement that I desperately needed to hear:

“You have been an exceptional employee and a brilliant leader. You have a business plan. You have a passion for traveling and want to devote your time and energy to your future. You deserve to be happy. You deserve to live your life however you see fit.

So hit ‘send.’ Draw your line and go home and have a cocktail.”

I so clearly remember my finger hovering over my mouse, shaking uncontrollably as I worked up the courage to click that button. I felt like I had my finger on a trigger, and one small motion was all that stood between me and changing my life forever.

I took a deep breath, said f*ck it, and I hit send.

What came after that was a rush of relief combined with sadness, excitement, and a side of fear.

There was no turning back now, and nothing could have prepared me for what came next.

Sure, I knew owning a business would be hard. But I’m smart, I’m resourceful, and I can do some crazy shit when I set it as an intention, so I knew I could do it if I really wanted to.

But I also severely underestimated how challenging entrepreneurship was going to be.

In one year as a business owner, I have learned a lot of important lessons. More lessons than I learned in 7 years of college, grad school and 14 years working in higher education and leadership combined.

They say being an entrepreneur isn’t for the weak, and that’s no f*cking joke. So here’s the good, the bad, and the ugly that I learned during my first year.

Working remotely from my AirBnb in Mexico City after quitting my job

You’ll work more hours as an entrepreneur than you ever will work for someone else, and with little to no recognition. You won’t count your work hours anymore, because it really doesn’t matter. Nobody will see you working in your home office until midnight, eating every meal with your laptop beside you to save precious time. All you can hope is that your hard work pays off eventually.

Nobody is looking over your shoulder, making sure you meet deadlines or staying on task. You get to choose your own schedule, which is amazing, but it also means you need to be incredibly self-motivated and disciplined.

You’ll realize not having a boss is a blessing and a challenge, all at the same time. You’re now your own boss, which means nobody is in charge of you but you, and there’s also nobody to take the blame if you don’t succeed or take the heat when you mess up.

It’s incredibly lonely at times, especially if you’re used to working as part of a team and want to bounce ideas off someone else, share your victories, or vent about your setbacks.

There’s no guarantee of clients or sales, and your income can fluctuate at crazy unpredictable levels, especially at the beginning.

You have to pay for your own health insurance, you don’t get PTO, and “vacation days” quickly lose their significance, as you’re never truly on vacation or out of touch from your business, no matter where in the world you are.

You’ll spend tons of money on coaches, courses, workshops, and professional development so you can master your craft, and some of it will be a waste. Some of it you’ll never even have time for, despite your good intentions and desire to learn absolutely everything.

You’ll realize you not only need to be good at your field of work, but you need to learn how to do everything else to run a business too. You’ll become CEO, CIO, and CFO, and then some, all wrapped into one—you’ll become a graphic designer, sales person, photographer, videographer, bookkeeper, accountant, copywriter, content strategist, web designer, and so many other roles that you never knew existed (or cared to learn).

You’ll be uncomfortable, and often.

You’ll cry, a lot. But you’ll work through the tears because nobody else is going to do it for you, and the work doesn’t go away.

You’ll have to sell your business idea to people and put yourself out there—the hardest thing for an introvert like me who doesn’t like the limelight. You’ll need to overcome all kinds of fears and do scary things you don’t want to, like be on camera and self-promote.

You’ll lose friends, and relationships will be tested. You’ll find out who actually supports you and wants you to be successful (and you might be surprised how many people actually do). You’ll let some friendships go while you cultivate new ones.

You’ll try lots of things, and you’ll fail. And then you’ll fail again.

But you’ll also succeed—people have to be doing this for a reason, right?

There will be milestones and celebrations, like getting my first real customer who wasn’t a friend, selling out my first trip, quitting my side-hustle within 4 months of starting my business, hitting a $28k sales month, and making 6 figures in 6 months.

You’ll make connections far beyond what you thought was possible. You’ll find likeminded entrepreneurs who understand what you’re going through, and in those shared struggles, you’ll find your tribe.

You’ll challenge yourself in ways you never thought possible, and you’ll accomplish things you never even dreamed of. You’ll soon realize that what you wanted a year ago is no longer enough, and you’ll aspire for more.

You’ll change. You’ll change and grow in beautiful ways and become more resilient every day.

You’ll realize that there’s a hell of a lot more to life than punching a clock, and your only regret will be that you didn’t figure that out sooner.

Feeling free in Costa Nova, Portugal

So here’s to surviving my first year as an entrepreneur.

To everyone who has supported me along my journey, offered words of encouragement, booked a trip with me, listened to me vent, dried my tears, gave me business ideas, helped me with IT issues, said my name in a room of opportunity, and believed in me when I didn’t believe in myself:

Thank you, from the bottom of my crazy little entrepreneurial heart. It truly takes a village, and I couldn’t have done this without you.