The toughest boss you’ll ever work for is yourself.

When you work for someone else it’s easy to say that the reason you’re always stressed about work is your big bad boss and his (or her) mixed messages, unrealistic deadlines, and lack of boundaries.

It’s easy to blame your boss when you find yourself awake all night replaying the previous day’s failed proposal and wondering how they could have done things better, or when you get up at 1:30am to tweak slide #259 of tomorrow’s big presentation.

Many of us who work for ourselves made the decision to go off on our own at least partly because of bad boss experiences we’ve had.

Unfortunately, sometimes your new boss turns out to be a real hard-ass too.

Let’s start by talking about my boss, the Founder and Sole Employee of Denver Business Design Consulting, LLC.

First let me stress that his heart’s in the right place. He’s always talking about work/life balance and how great it is he can work at home with his young daughter. And he wants you to know that the whole “boss act” is just his way of motivating his employee to do the best possible job for his clients.

But here he is writing a blog post on a Sunday night, after spending Saturday and Sunday mornings tweaking and noodling on another work-related project.

What was that about work/life balance?

In preparation for this article I performed some rigorous Google-based research* into what types of behavior make a manager a Bad Boss. Here’s a rogue’s gallery of characteristics of the supervisor from hell—recognize any of them?

Eight Bad Boss Habits:

  1. Unhappy with anything except perfection.
  2. Motivates with Fear.
  3. Makes you work hard for low compensation.
  4. Unwilling to delegate anything.
  5. Has trouble communicating clear expectations, timelines or goals.
  6. Fails to provide rewards for big achievements.
  7. Doesn’t respect your time off.
  8. Way too picky.

Remind you of anybody you see in the bathroom mirror every morning?

Let’s take a step back and make something clear: I’m not in any way saying that the answer is to care less or accept half-assed results.

Number One, that’s a shortcut to failure.

Number Two, as solo entrepreneurs we do, and must, take personal pride in everything we produce.

But then there’s Number three: We have to set ourselves up for success.

Like most things, the issue comes down to questions of time and money:

Are you scheduling your projects so that you have enough time to do your best work? Are you pricing your products so that you can take that time and still make a decent living?

These are, of course, the most difficult questions to ask yourself. And they’re four times as difficult if you’ve got a partner and/or children involved.

But they’re also the most important questions to find answers to if you want to keep the lights on.

To answer them you need to get on top of the second item in the list: motivating with fear. Fear that nobody will buy what you’re making, that you won’t reach the right customers, that your online store has a fatal flaw that is leaking hundreds of sales a month.

Facing those fears and dismantling them, piece by piece, is the only way to put them to bed. Validate your products with a small group of the people you have identified as your ideal customers. Don’t ask if they like what you’re selling. Ask if they’ll buy one. Right now. Then smile and take their money, or smile and listen to their objections and go back to your shop and address them. And if their objections are ones you can’t address, then maybe those aren’t your ideal customers.

But Most Importantly: Good Bosses Know that Everyone is Human.

We’re not supposed to talk about it, but every entrepreneur and small business owner has days where it all seems like too much. That they’d rather clean the gutters of every house on the street than spend another five minutes checking social media or working on the next blog post. And that if they get another email or read another blog post about something else you could be doing to grow your business, you’re going to move to a yurt in Turkmenistan.

Even if you are the one and only employee of your business, you need to take time off. Take a mental health day. Turn the computer off at 5pm. Set the store on vacation mode and pay attention to the other things in your life, be they family, friends, pets, or yourself. A day, or week, or two weeks off won’t mean the end of your business, and when you get back you’ll be in a much better place when it comes to keeping things running and growing.

It sounds like hard work because it is hard work. But I get up every damn morning excited to get back to it, because this is the dream that I am building for myself.

And I’ll bet that most of you feel the same mix of terror and anticipation every day. We’re working without much of a net, but we’re doing it because we want to and not because anybody else is telling us to. So put on your Boss hat, grab your favorite mug, and give your employees a hug, or clap on the back, or barely perceptible nod of approval. And get to work doing what you need to do to become your own favorite boss.

*Google-sourced sources: