From Poverty to Owning an Accounting Firm: Here’s How She Did It

In just a few years, Katherine Pomerantz went from living below the poverty line to owning her own successful bookkeeping business.
In just a few years, Katherine Pomerantz went from living below the poverty line to owning her own successful bookkeeping business. Photo courtesy of Katherine Pomerantz

In 2014, I graduated from college and spent 15 months traveling the world. I’d often stop traveling for a few months to work side jobs and earn enough to travel more. Whenever possible, these jobs were in theater, my dream career.

I came home to get married, but my husband and I promptly moved again so he could start pursuing his Ph.D. Unfortunately, we moved to a rural state without enough paying theaters to keep me employed full time.

Instead, I worked 60 to 80 hours per week at whatever jobs I could find. I was hospitality staff at a golf club. I assisted a wedding planner. I was an office manager. I worked summer camps. I worked after-school programs. I tutored. I continued to take whatever theater jobs came my way.

Undeterred, I decided take my art part-time and began looking for a second career. I scored zero interviews in almost a year of job searching.

By 2016, I was depressed, worn out and lucky to make $300 a week. I was slowly realizing a hard truth: I knew nothing about money. I felt if I could figure that out, then life would get better.

That’s when I started reading The Penny Hoarder and learned about work-from-home opportunities like Ben Robinson’s Bookkeeper Business Launch program.

Not only did I complete Ben’s program, but by 2017, I owned a global accounting firm for creative entrepreneurs. I attended business conferences with the likes of Kyle Taylor, founder of The Penny Hoarder, who hugged me when I told him how his website changed my life.

While learning about money and specialized bookkeeping helped start my business, there are few key personal realizations that actually made it grow.

Money Doesn’t Have to Trap You

I’m not alone in desiring nontraditional employment. The rise of the gig economy shows that many are choosing to work outside the classic 9-to-5 schedule. If done well, the opportunities to grow your income are staggering.

Yet so many entrepreneurs fail. Many side hustles never pay off. How did I avoid this?

Well, I almost didn’t.  

I finished Ben’s bookkeeping program in 2016. By the time I shared a celebratory hug with Kyle in 2017, I had clients all over the world, and I wasn’t just doing bookkeeping anymore. My team also offered tax services, financial strategy and consulting.

But for the first eight months I was “in business,” I didn’t have a single client. All that incredible growth was crammed into four whirlwind months.

What changed in month eight?

When I “quit” theater to pursue bookkeeping, I thought I needed a certain type of client to support myself. There was clearly no money in art, so I had to pursue lawyers, dentists and other traditional business owners to make a living.

Except I didn’t fit in very well with traditional business. Of course, they didn’t hire me!

The people I actually wanted to help were people like me — creatives who owned a business because they simply loved the work. My new financial skills, and past theatrical experience helped these people the most.

Ironically, I had trapped myself in a dead-end job of my own creation. I thought the money was best in one area, so that’s where I tried to work.

Fortunately, no one hired me, and I was forced to examine my values — who I wanted to help, and why I was the right person to help them. Once I aligned my work to that purpose, I enjoyed it more and I made more money.

If you’re going to start a business, remember you can’t sell something you don’t love.

Sometimes We Need to Borrow Willpower

Katherina Pomerantz enjoying some time on her tire swing.
Photo courtesy of Katherine Pomerantz

Although my story has a happy ending, those eight clientless months were unbelievably hard.

My husband and I spent the first year of our marriage below the poverty threshold. Even working 80 hours per week, we lived on less than half the average American salary.

We were already exhausted and stressed, and I thought it was a good idea to invest some of our scant, precious dollars into building a business. Then, I quit my jobs because I didn’t have enough time to grow that business.

And I didn’t have a single client.

I’d like to claim that I’m brave, but the truth is, I borrowed strength from the people around me. I had no idea if I would be successful, but spending time with positive people always gave me little bursts of productivity. So I was very selective about spending time with certain friends during those hard months.

I also did everything possible to be around other successful business owners.  I went to conferences. I bought into expensive masterminds. My intention was never to make sales but rather to lean on the experience and mindset of successful people while I didn’t have very much of my own.

And it worked! Not only did I build an incredible support network of people who understood what I was going through, but these business friends also became my first referral partners. They are the reason I have clients all over the world, and they are the reason my income has never stopped growing.

Good Financial Habits Will Save You

If you read that I bought into expensive masterminds and thought I was spending recklessly, think again. The difficulties in my young adulthood taught me to be frugal, and I was very intentional about what I invested in my business.

So much so that I continued to shrink our debt. I never missed a bill. I budgeted like crazy, and I prioritized our emergency fund.

That’s the only reason we survived eight clientless months. I wasn’t digging myself further into a financial hole, but rather, I continued to solidify my family’s financial foundation, even if it was only a few dollars at a time.

These good habits allowed me to feel like an overnight success. When the money started rolling in, I had already cleaned up many of our financial messes. I had resources like The Penny Hoarder teaching me good habits, and I could focus solely on growing my business.

Quality of Life Matters

Portrait of Pomerantz
Photo courtesy of Katherine Pomerantz

With “success” came a whole new slew of challenges. There is a lot of pressure on businesses to perpetually grow. In the business world, the message is “more clients, more money, more markets, more opportunity, more everything”.

Added to this pressure were the bad habits I developed in my early adulthood. Because I was used to a 60-plus-hours-a-week schedule, I worked too hard and suffered periods of intense burnout. I doubled, and then tripled, my salary. But my fears of becoming poor again meant the pressure for more money never went away.

I needed to learn when I had enough. I needed to separate my success from a dollar amount.

And in order to do that, I needed to measure my quality of life: Where did I want to live? What did I enjoy doing? How did I want to fill my time — morning, noon, night and on the weekends? How much income would this life require?

These lifestyle goals are much more attainable and much more fulfilling, than any income goal I’ve ever set. Obtaining them makes me feel powerful and successful. In turn, I am a better business owner — even if I’m not obsessed with “growth.”

It is perhaps strange to attribute so much of my success to a lifestyle, but that’s what it took. I needed to be honest about the kind of work I loved doing. I needed friends who could help me experience the life I wanted. And I needed to shape my habits, and mindset, to fit my dream life.

KatherinePomerantz, an actress turned accountant, has capitalized on her artistic background to create the Chaos Money Framework, a signature tax service for creative entrepreneurs. Her financial expertise has been featured by Buzzfeed, Discover Card, IncFile and the Popcorn Finance podcast. Connect with her at