10 Things We Learned about Being Self-Employed

~ by Maria Benner

Scott and I have both been working full-time on our art business, Real Art Is Better, for about four years now, and we’ve learned a few things about being self-employed.  So here are the top ten.

  1. Most people were not supportive when we started working for ourselves.  They told us we were being too risky, that we would become a burden on our society’s safety net, and that we were slacking on building a retirement.  This reaction was a big surprise to me, because I was always under the impression that self-starters and entrepreneurs are respected role models in America.  I learned that first we had to prove ourselves to these people, before they would start taking our business seriously.  After four years, some people still ask me what I’m doing now, as if being a Business Manager is not enough.
  2. There is no regular paycheck.  People expect us to pay our bills on time, but when we send out invoices, we have to wait for weeks to get paid.  Most times I have to send reminders.  We have to keep a very close eye on cash flow, and keep a list of IOUs.
  3. Hiring a tax accountant was one of the best things we did for our business.  We were using TurboTax, and I wasn’t doing our taxes correctly.  Also, it’s nice to know that if we need advice about a business decision that could affect our taxes, we can ask our tax accountant.
  4. Speaking of taxes, there are a lot of extra taxes for the self-employed.  We have to pay a self-employment tax, and contribute more to Social Security.  We also found out about the Business Property tax.  Turns out the Municipality of Anchorage collects a tax on business assets if they total over $20,000.  Luckily, we don’t fall into that category, but we were really confused when we received that notice.
  5. We spend a lot of time dealing with administrative tasks like book keeping, setting up our annual health insurance plans, reading and negotiating contracts, collections, etc.  Sure was nice to just focus on my job, knowing that my employer had a team of people working on such tasks, but I guess I’m learning more about the real world this way.
  6. We work almost every day.  In the last two months, we’ve taken five days off.  Sometimes if we decide to take a day off mid-week, we’ll make that happen, but we have to plan ahead.  We had more time off when we worked for someone else.  However, we can work while we’re traveling, so our jobs don’t hold us in place, and we can take more trips.  We just can’t be gone for more than two weeks before the business starts to suffer.  Luckily, we like our jobs, so we don’t need a lot of time off from them.
  7. When it comes to planning our day, we have a lot more flexibility.  We go running in the morning when the air quality is better, then sit down to a nice breakfast, and then get to work.  We end up working until 6 or 7 PM, as a result, but we don’t mind.  During the working part of our day, we are very productive, working straight for several hours, with a short break for lunch.  One of the best things about being self-employed is not having to wake up to an alarm, and not having set hours.
  8. There are days when things are going really well, and we think our business is unstoppable, and there are days when we experience a set-back and have doubts about the future of our business.  Those days are actually beneficial, because they motivate us to think outside the box to generate more income, but I still don’t like them.
  9. Working for yourself means there are fewer filters for your ideas.  Sometimes it’s nice not having to gain someone else’s approval before acting on a great idea.  Other times, it would be nice to have a second or third opinion, so we end up Googling, or crowd sourcing, or talking to friends and family instead of coworkers.
  10. Setting and following standard operating procedures is important.  That’s a given at a company, but when we started our business, we were just flying by the seats of our pants.  We’ve spent a lot of time figuring out and honing procedures.  The learning curve has been huge!

In conclusion, we both agree that we prefer working for ourselves, and our goal is not to have to work for someone else in the future.  However, we constantly have to be on our toes to keep the business rolling.  No slacking allowed.  One of my favorite quotes is, “If you don’t build your dream, someone else will hire you to build theirs.”


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