20 Things No One Ever Tells You About Being Self-Employed

There's a lot of stuff online telling folks to quit their jobs so they can freelance at "what [they] love." That all sounds great in a blog post and even better in an e-book that a blogger can sell (for just $9.99!) but it doesn't really cover all the stuff you need to know before you make the jump.

Like, what happens when no one wants to pay you to do what you love? Because the market for GOURD ART might not be strong enough to support you.

Jus' sayin'.

This year marks my 12th anniversary of self-employment so I'm going to tell you everything that's not in those books. All the stuff about freelancing that's not so great. Maybe I should write an e-book about the sh*tty side of working from home, but I'd rather you put your hard-earned money toward a bottle of Apathy Anti-Bad-Mood Spray.


20 Things No One Ever Tells You About Being Self-Employed

  1. That you will go through amazing amounts of toilet paper and that no matter what, you will always be the one that changes the toilet paper roll when it runs out.
  2. Two out of your three meals each day will be a bowl of cereal.
  3. Your friends and relatives will assume that you are always available to accept their packages and drive them to the airport. They will call you during your work day to chat but if you call them in the evening when you're free they will tell you that they are "busy with family stuff and can't talk."
  4. After a few years, the blush of daytime solitude wears off and you get a little bit lonely.
  5. You can accomplish two or three times what you did in an office environment in half the time but your clients won't get you feedback until Friday afternoon. And then they will want those drafts back by Monday morning.
  6. No one will give you a paycheck just for showing up. You either earn money or you don't.
  7. Sometimes you earn the money but don't get paid and that's going to hurt. This has only happened to me twice in twelve years but the memory still smarts. Once, someone just flaked and never wrote a small check which was pretty consistent with his management style. The other time I had to cover a sub-contractor's invoice because my client was unhappy. Both hurt my bank account but it hurt my heart even more.
  8. You have to be the accountant, the bill collector, the IT department, the blogger, the administrative support and the travel agent. If you're lucky, you can find someone good to help you out, but it rarely makes good financial sense long-term and often takes just as long to explain it to someone as it does to take care of it yourself.
  9. Because you don't care about Federal holidays anymore, you'll catch yourself working on more than one of them and wondering why no one else is picking up the phone.
  10. The first $700 you earn each month will go toward health insurance.
  11. You will either be too busy or not busy enough. In the not busy times, you'll have time to put lots of proposals together thinking that only a few will come back in. The challenge will be that they come back in at the same time. Making you too busy all over again. It's a cycle that is well-documented among freelancers. Check it out.
  12. It's very likely that you'll be better at managing a remote relationship than your clients will be. All the stuff that really helps - like BaseCamp and DropBox and such - may be beyond the realm of possibility for your client. Last year, I worked with someone who could only use a fax machine. A FAX MACHINE.
  13. You'll get to know your UPS driver on a first-name basis.
  14. Eventually, you'll wind up taking projects you don't really want because you need the money. Because you always try to do your best some of those projects may be wildly successful for your client. This success will send a whole bunch of other people your way with more work that doesn't have anything to do with "what you love." And then you'll have the decision to make all over again, only this time it will be easier because you won't have to decide whether its worth it to give up your benefits. Because you don't have any.
  15. Over time, you will become incredibly relaxed about personal hygiene tasks once considered essential.
  16. You'll get incredibly bored by "what you love." Maybe not every day, but many days. Ongoing professional development is an essential part of my week. You must keep learning just for the sake of keeping the brain engaged.
  17. Even though you have more time to go to the gym and get abs of steel? You will never put the time in to have abs of steel. At best? You'll work off the equivalent of one or two bowls of cereal every couple days.
  18. Every piece of feedback every boss ever gave you will suddenly make total sense when you hire other people to help you do a job.
  19. Your family and friends have absolutely no idea what you do for a living. Sometimes you don't even know what you do for a living.
  20. Other consultants will steal your ideas. Potential clients will assume you don't need money and will do their best to get your advice without paying for it. Your printer will always run out of toner the day an RFP is due. Travel on your own budget is not nearly as glamorous as traveling on your employer's budget. You'll rue the day you complained to your former boss about your travel budget.

Sure. There are definite positives - I don't have to wear pantyhose, for one - but this blog post isn't about all that. Do you freelance? What are the pros and cons you struggle with in your business?



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