This guest post from Kelly is part of the “reader stories” feature at Get Rich Slowly. Some stories contain general advice; others are examples of how a GRS reader achieved financial success or failure. These stories feature folks with all levels of financial maturity and income. Want submit your own reader story? Here’s how.

When I was younger, I’d always planned to be a professor in the social sciences field. I studied hard through college and was accepted into a top graduate program in my chosen discipline. But after spending three years in my program, I realized (much to my dismay) that it wasn’t a good fit for me. I ended up switching programs and completed a different degree altogether.

When I graduated at the age of 26, I immediately moved across the country and then had to decide on a new career path. Although I’d worked at summer jobs and part-time jobs since the age of 16, I’d never actually had a real grown-up job. I interviewed for a few positions, but didn’t find anything that spoke to me. So, I decided to start my own business instead.

Minding My Own Business
The prevailing wisdom on starting a business is to do what you know. The thing that I knew how to do was standardized test preparation (for tests like the SAT and ACT). I got involved with test preparation after studying countless hours for the GRE for graduate school admission. I decided that I should use that knowledge for something, so I went to work for one of the major test preparation companies. I worked there on the side during graduate school and then later worked for a private company.

After several months of extensive reading and a meeting or two with the people at SCORE, I was ready to get started. At the time, I was single and without any consistent source of income. I’d also just moved, so I had no social connections and had to start everything completely from scratch. I had a small cushion of savings that I had built up during graduate school, though, which allowed me some flexibility.

My business started very slowly as I experimented with gaining clients. I got a few clients from Craigslist and two from a very pricey magazine advertising experiment.

During my first year, my fledgling company brought in about $20,000.

The next year revenues doubled, and then they doubled again. In year three (which was smack in the middle of the economic meltdown), revenue crossed over into the six-figure territory and has continued to increase every year since.

Barriers to Success
Starting a new business is always challenging, but I faced some extra challenges as a single person.

Most obviously, I didn’t have another source of income to fall back upon if my business didn’t succeed. This was actually a positive in many ways, in that I quickly realized that if I didn’t work, I didn’t eat. It was also pretty empowering in those early days to be able to support myself on something that I had literally created from nothing.

Health insurance was another major factor, and one that almost kept me from starting my business. My graduate school insurance lasted a few months after I graduated, so I used that time to start looking for an individual plan through As a fit, healthy, non-smoker, I didn’t anticipate having much of a problem finding a policy. However, individual health insurers can reject applications for the smallest of reasons, and my application got rejected by at least five companies. Luckily, I finally found one company that would insure me. It’s expensive, but I will never, ever drop the coverage since I’m not likely to ever find coverage again.

Buying a house was also tricky as a single, self-employed person. Well, that’s not true. Buying my place was disturbingly easy. I bought a small condo in 2006 (the height of the housing bubble), shortly after I moved. Although I didn’t have an actual job, or a history of steady employment, I was given a 7.0% stated income mortgage (a.k.a., liar’s loan).

However, when the rates started dropping a few years later, I wanted to re-finance to a shorter term and that’s where I started running into trouble. Although I had plenty of income at that time to support the mortgage, the mortgage company kept requiring more and more documentation because I was self-employed. One refinance fell through altogether, but I was eventually able to refinance twice in the past two years (lowering the term each time).

One unhappy surprise that comes along with being a single, small business owner is taxes. Self-employment tax (having to pay both the employer and employee portion of Social Security and Medicare) is already shocking in itself. But since I’m single and don’t have children, I have virtually no deductions that I can take other than those related to my house.

One of the only tax-reducing mechanisms available to me is a retirement account. I have a Solo 401k, which allows for contributions for up to $49,000, depending on business income. I have been maxing out my account for the past few years, and this has saved me a bundle on taxes.

The Single Advantage
There were a few factors that made it much easier for me to start a business as a single person:

  • I had an immaculate credit score. My parents taught me how to use checking accounts, savings accounts and credit cards from a pretty early age, and I took those lessons to heart. I’m pretty sure the only reason I was able to get my house was because of my credit score.
  • I was able to get through graduate school with no consumer debt or student loans. Based on my GRE scores (which, ironically, eventually led to the creation of my business), I received a fellowship that paid tuition and a small living stipend. I had a tiny undergraduate loan, but the payment was very small. Had I had large debt, I would have had to get a “real” job to service the payments.
  • I always had my eyes open for extra ways to make more money. Both during graduate school and the early years of my business, I took on all kinds of side-hustles. Among other things, I mystery-shopped, took internet surveys when they were still lucrative, started a text-book selling business, taught classes for other businesses, did freelance editing, found temporary jobs on Craiglist, and worked at a summer camp. Each little bit helped while my company was still getting off the ground.

As a recent GRS commenter pointed out, there aren’t a whole lot of stories out there about single, successful entrepreneurs. Not having a partner to fall back on can make starting a business a lot more difficult, but it is quite satisfying to build something awesome all on your own.

Reminder: This is a story from one of your fellow readers. Please be nice. After more than a decade of blogging, I have a thick skin, but it can be scary to put your story out in public for the first time. Remember that this guest author isn’t a professional writer, and is just learning about money like you are. Henceforth, unduly nasty comments on readers stories will be removed or edited.

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