Are You the Worst Boss You Ever Had?

Alternate Title: I’m Taking Labor Day Off, Dammit!

If you are a freelancer, self-employed, sole proprietor, business owner like me, then one of the major reasons you got into the business was to be your own boss. Maybe it was just time for you to go out on your own, maybe you couldn’t handle the cubicle environment. Or maybe you just really hated every boss you ever had (if so… maybe you were the common denominator!). Either way, you worked hard and built up a business and now you are your own boss. Hurray!

But if you are like me as well, you find that by being your own boss you’ve lost several… let’s call them “benefits”, of being gainfully employed. Here’s a short list of things I hear from others developers all the time:

  • Health Insurance? No way! I totally save money by just paying for doctors visits whenever I need something.
  • Retirement? Ha! I’ll retire when Google buys out my business. Totally gonna happen!
  • Vacation? Sure, I’ll take a break now and then. I like to call it “Casa del Starbucks”. Gets me energized for the rest of the week.
  • Spare time? Totally. That’s when I just code for fun or build sites for non-profits.
  • Sleep? … uh…

You can see where I’m going with this. Basically, if I compare the way I treat myself to ANY of my previous bosses, I would have quit with both middle fingers high in the air years ago.

Considering I have an awesome family, home, friends and family nearby, I seriously don’t have any excuse to NOT be vacationing. Worse yet, why do I put up with going to social gatherings and not being able to get my mind off some piece of code that’s not cooperating, or some client email that irked me? When I was employed with others previously, things like that always were “red flags” to me that something was off — that work-life was taking over personal-life in bad ways.

But suddenly, laughing about the idea of taking Labor Day off is the norm for me and the majority of self-employed folks I know. Really, most of the time, I don’t even realize there’s a holiday on the calendar until someone says: “Have any plans for the long weekend?” Uh… try not to work til midnight? How’s that? Do I honor all hard laborers in America with that sacrifice?

No. No you don’t. And if any of your former bosses asked you to work Labor Day you would have pulled a Maria Shifrin dance break on the spot!

So Starting Now, I’m the Best Boss I’ve Ever Had

So Starting Now:

… I will fully embrace every National Holiday like it was my birthday. Groundhogs will be kissed, Laborers celebrated, Poems will be written to Presidents and MLK will be honored in this house. And every one of them with friends and family nearby.

… I will afford myself every insurance and pension that I believe I deserve. I’ll thank myself profusely for this when I’m old and can’t enjoy kissing groundhogs anymore.

… I will set aside 10% of profits each month to go towards a 4 week vacation. That’s right, vacay-ing European style, because that’s what I’d want my employer to support

… When I am sick I will not sneak to the computer to “answer a few emails”. I’m sick, dammit! Leave me alone, bad-boss me!

… When I miss a deadline, I will not berate myself in front of myself and my other… ok, some things just don’t work with this analogy.

… If I work late one day, I’ll come in late the next morning. With style, with coffee and doughnuts, without fear or anxiety that I don’t deserve it. I do.

Truthfully, I’m not prepared to put on a party this Labor Day like I’d want to, but you better believe I’m taking it off. What about you? How will you be the best boss you’ve ever had?

CC BY-NC-SA 4.0Are You the Worst Boss You Ever Had? by Matt Cromwell is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.