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Do You Want to be Your Own Boss?

Self-employment looks appealing for someone who wants to quit a job they hate. Working for yourself, however, does not mean total, or instant, freedom. Being the boss will put you in direct contact with the obligations from which you were once shielded.

I am more or less satisfied with my current job. That doesn’t mean there aren’t days, usually around 3 PM, when I don’t entertain ideas of getting up from my desk, picking up Matthew’s harness and walking out of the building and into a new adventure. So far though, I am willing to see this job through.

Here’s one way to put things in context:

“For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.”–Steve Jobs

A Few Considerations Before You Jump

As a self-employed entrepreneur you will need to work twice as hard to enjoy the benefits you had as someone else’s employee. You will need to pay for your own health and life insurance, account for your full share of taxes, cultivate your own retirement plan, and cover your own vacation and sick leave. Sick leave… Haha. We haven’t even begun touching on the expense of day-to-day operations. Working for someone else generally means you will have a steady check and benefits even in slow months. If you cannot meet the obligations of maintaining a business with enough money left over to pay yourself, you are probably not ready to fly solo. See Bob Bly’s article that goes into more of these logistical considerations before leaving your job.

The idea that you can be your own boss is something of a mirage. Someone outside of your control will always call the shots. If your clients aren’t satisfied, your clients won’t buy your product or service. True, you can pick and choose the assignments you take, but you don’t get a complete picture of what it is like to work for someone until you’ve actually started working for them. Trust me; you will eventually wind up working with people far worse than the supervisor you thought you hated.

Are you prepared to stake your reputation on resolving conflicts with difficult customers? Working for someone else means personal differences can generally be kept within a department or within the company. Working for yourself, however, means you are the company, and the negative repercussions of personal differences could taint the customer base you serve. Word of mouth is just as good at destroying as it is at promoting.

But, you say, I am a creative type whose only boss is my mind!

Can you feel me patting your head?

There is a difference between doing something as a hobby and doing something to make a living. Even authors who spend hours working on the next bestseller are beholden to their readers to keep the royalties flowing. If readers aren’t buying what they have to say, it’s going to be a while before they can enjoy the flexibility of writing from a balcony overlooking a sun-swept beach.

Given all my warnings, you may have gotten the impression that I am against your dream to start your own venture. On the contrary, I am squarely in your corner, but I despise marketers who make it seem as though the only key ingredient to successful self-employment is desire. You need time, talent, and the tenacity to persevere when the chips are down, because more than 90% of businesses fold in the first five years.

Essential Questions

  • Think about the kind of work you can still see yourself doing in five years.
  • Network inside and outside of your current job to learn your trade and identify potential clients.
  • Keep your eyes and ears open for partners or contractors who can help lift your business idea.
  • Keep your day job and work for a couple clients after hours to get a taste for self-employment.
  • Start putting money aside that could sustain you for up to a year.
  • Minimize, or outright eliminate, any looming debt that could hurt your credit.
  • Familiarize yourself with the tasks you enjoy doing and those tasks you would rather outsource.
  • Do not leave your current job under negative terms; your boss could be an asset.
  • Expect the unexpected. If you’re injured and can’t work, who will pick up the slack?

Final Thoughts

Self-employment is an exciting prospect, especially if one day you find yourself looking up and realizing you’ve been living someone else’s dream. There is something appealing about setting your own schedule, determining your own worth, and having something to show for your hard work, but that’s just it. Going into business for yourself full-time means hard work. I will be the first to admit I myself am not there yet.

Are you up for the challenge? Are you contemplating starting your own business, and if so, what’s currently holding you back? If you already took the plunge, what was it that motivated you to go for it? Sound off in the Comments!

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My blog is a collection of advice I wish someone had shared with me when I was young and targets subjects like personal finance, careers, and relationships. It publishes Mondays with the occasional bonus article. Sign up to have fresh content delivered straight to your inbox, no SPAM!


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