Reflections on two years as a full-time small business owner

I have been studying art since I was a wee little kid. I dreamed of a glamorous life of long nights covered in paint and days full of inspiration. Even as a child I would fall asleep thinking about my next painting and wake up to spend hours drawing and sketching before anyone else got up.  I went to art school for college, because it was the natural choice, but even while studying at The School of the Art Institute of Chicago, I never truly believed that one day I would "just" be an artist. The most I hoped for was to find a job that was somehow art-related.

I had many jobs. They were great jobs, with missions that I believed in. But I came to realize that I was an entrepreneur trapped inside an employee's body, and life. Anyone who knew me in 2016, knew that I was on the verge of a nervous breakdown. I had been running my art studio as a "side hustle" in addition to my demanding full-time job for 6 years. I wasn’t getting much sleep. I was barely eating and not spending any quality time with my family. I was the definition of burning the candle at both ends. Something had to change. Would this be the year that I would finally take the leap and go into my art business full time? 

To say it was not an easy decision would be hilarious to anyone who witnessed this process. All I talked, thought, or dreamed about was the day when I could work for myself and escape the hamster wheel I felt trapped in. But being a Virgo, I am extremely risk-averse and terrible at making big decisions. So, I enlisted everyone I have ever met and their mothers to help me decide if my little art ketubah studio could really go the distance. The first lesson I have learned in two years of running my own business is Don’t. Do. That.

Lesson 1: Trust your Gut

Headshot by Sarah Deragon
Running a business is no walk in the park – they don’t call it a hustle for nothing. It is a journey fraught with mistakes, hidden landmines, failed experiments, learning opportunities, and many a happy dance.

The thing is, that everyone has opinions about your business – how you should run it, what you should sell, what direction you should expand, etc. The unsolicited opinion-sharing goes double if you’re part of an immigrant community or family like I am.

While most advice is given in good faith and with the best of intentions, the bottom line is that others may be on the ride next to you, but you're the one in the driver's seat -- and time is your most precious commodity.

You can't be all things to all people. Your business is your baby alone -- for better or worse, and while input is great, ultimately you are the one doing all the work and assuming all the risk. I have learned to trust my instinct, pick and choose my trusted advisors carefully, and take everything else with a mountain of salt.  

Lesson 2: Save for a Rainy Day (or the slow season)

Being in the wedding industry, I was always aware of the seasonality of my business – the summer months would always be busier than winter. That said, I didn’t feel that full impact until that first slow season that I didn’t have another salary to make up the difference. If you’re going to take the leap, planning is key. Lesson learned. 

Lesson 3: Pay Quarterly Taxes

Otherwise, you are going to cry come April 15th. I did. Literally. 

Lesson 4: Invest in the Business and in Making Work Life Better

When we relocated to the Bay Area from Texas, we had to downsize. Obviously, because everything is bigger in Texas. When we were delegating which room would have which purpose in our new home, naturally I gave the larger bedroom to our kids and took the smaller one to be my studio.

I “little housed” my studio to make it as functional and pleasant as possible, but as the business grew in the last year and a half, the studio launched an attack. Every day it would arm itself with more and more boxes, papers, scraps, and brushes until it became a dangerous landmine that I no longer enjoyed spending time in.

Another lesson learned -- take the needs of the business seriously.

With our big move to Los Angeles around the corner, we have invested in a home with big, bright studio with all the storage I need. This time the kids can get the smaller room -- it'll make them closer, right? 

Lesson 5: Take time off

I know everyone says this – self-care, self-care, self-care, the name of the game.  Part of the appeal of quitting my day job was having the flexibility to chaperone a school field trip or to take a day off to binge read Nathan Englander's latest novel.

What I have learned in these two years is that when you're self-employed it's even harder to take time off. Sure, you don't have a boss to get permission from, but it is nearly impossible to resist the temptation to be glued to the computer or easel, working every minute. But resist you must! Burn out is real, and you don't want to go there. 

Lesson 6: Find your community

with my Business Bestie Evie from Urembo Asili


Self-employment can be lonely. We moved to California only a few months after I quit my day job, and my first year in a new city and working alone was very quiet. While I was busy and enjoying my work, I found myself going days without any adult contact. I realized that as much as I love being a solopreneur, I also love being around people and I missed it.

I set out to solve this challenge and discovered Craftcation – an amazing conference in Ventura, California, for creative handmade business owners just like me. It took me a while to decide to splurge on the trip to Ventura (did I mention that I am risk averse?). Would I even remember how to speak with other human adults after being holed up in my studio all this time? But going to Craftcation and discovering my community of creative, hard-working women all over the country was one of the best investments in my business, and in my mental health.

I have attended twice now, and the relationships I have made keep me going strong, working hard, and feeling supported all year long.

At Craftcation with Sara from Nymph in the Woods

Lesson 7: Celebrate the Victories


Seriously though, you are doing it. Through the long days, and sometimes the long nights, through the stress and sweat and hard work, you are building something. And when the successes come, it is the best high of all, because you know they are all due to your hard work.

I am well aware of the sacrifices I am making to grow this studio – first and foremost, my time away from my kids (or the times I am distracted while with them). But my kids also admire what I am doing. The other day when a news crew came to the studio, my eight-year-old was home for spring break and you would have thought it was Hannukah, her birthday and the last day of school all rolled into one with how excited she was.  Spending time with my daughters is important, but so is being a role model for them. They are proud of me and that in itself makes it all worth doing.

It has been two years almost to the day since my last day at a formal job. What I know now is that to be "just" an artist, I have to be a businesswoman first. I am incredibly grateful for the lifestyle that my art studio has helped me achieve. It has given me freedom (moving to California for one thing!) and built my confidence.

When people ask what I do for a living, I say I am an artist. It took me a while to learn to say it without giggling or being self-deprecating because it took me a while to believe that it was the truth. 

For the first time, I feel like my career is on track. It challenges me and excites me and most of all, it inspires me. I have learned that growing a business in and of itself is a creative endeavor... and on top of that, I get my hands dirty with paint every day! 

But the best part of it all is all the amazing people I get to work with. You come to me with beautiful visions and ideas, and it is my privilege to be able to bring them to life. You, my customers, inspire me and delight me and surprise me-- and I am honored to be able to paint your stories.

Thank you for being on this journey with me.  As a token of my gratitude, I send out an art gift every month. Get yours here



  • Sara

    Girl, I love this! I’m in the process of taking mine full time and you inspire me all the time. I’m so glad we got to meet at Craftcation! (and I LOVE that pic of us!)

  • Amber Collins

    I love this! I’m a little over a year into taking my passionate, creative side hustle to a full time business. I can relate to all of this, especially the taking time off. My creative brain can run at odd hours which doesn’t always work with family life. :)

  • Angie Chua

    ANNA! I love this and I had no idea about the QuickBooks thing! I too just passed my 2-year mark and I need to take a moment to celebrate that.

  • Jessica Pritzker

    So great! Love this. And love your work! Incredible that you get to do what you love.

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