Being Your Own Boss Is Great Except for the Hours

The primary complaint with the typical 9 to 5 schedule is that it simply leaves you TOO FREAKING TIRED to do anything personally fulfilling after work.

From the moment you wake up, to the moment you go to bed, you’re in constant motion — either preparing to show up somewhere, plowing through something, or preparing to leave.

There’s no “you” time.

Weekends are a much-needed respite that typically only give you enough time to recharge for the week but offer little chance for you to make headway in personal pursuits — like learning new skills, traveling or spending a lot of time with family.

Five days on… two days off. The math just doesn’t add up.

I thought when I became fully self-employed I could fix all the glaring problems with the “employee schedule” by simply doing the opposite of what I didn’t like.

Well, I’m here to tell you that these proposed solutions did NOT work out like I thought they would. Not even close, actually.

Here are some some assumptions I had about entrepreneur life that turned out to be false:

1.) About sleeping in…

What I thought: “Six a.m. is too early to wake up! When I’m my own boss I’ll make my own schedule and wake up when I feel like it!”

What I found: If you read biographies or stories about the world’s most successful people, you’ll hear over and over again that they get up at INSANE hours like 3 a.m. and 4 a.m. to start working. Of course, I never wanted to do this. I figured that even if I stayed up late, as long as I got sleep, it didn’t really matter when I got up the next day. Eight hours is eight hours, right?


Unfortunately, getting up early makes a huge difference. Waking up at 5 a.m. or 6 a.m. allows me to have an entirely different day than waking up at 10 a.m., simply because I’m getting a 4-5 hour jump on projects when I’m primed to be most productive.

There’s nothing going on that early in the morning. I can wake up, get my coffee, hit the gym (if it’s a training day), come back, get a solid three hours of work in and be ready to go by the time the rest of the world is buzzing.

I’ve also tested waking up early to do work vs staying up late and I’ve found that the quality of my work waking up at 6 a.m. is far superior to the quality of work staying up until 3 a.m., even if I get eight hours of sleep in both instances.

Ben Franklin was right when he said “Early to bed, early to rise… makes a man healthy, wealthy and wise.”

And that really sucks… because I love sleeping in.

Unfortunately, I can’t.


2.) About free time to work on projects…

What I thought: “I don’t have any time to work on hobbies/skills/projects I enjoy. When I work for myself, I’ll make time in the middle of the day to do things that are important. There’s no boss here except me!”

What I found: I was really convinced that once I controlled my own schedule I’d be able to do what I wanted, when I wanted and fit everything else in around that.

To an extent, that is true. I do have a good amount of flexible time to do what I want.

BUT (and this is a big “but”), I’m still accountable to MANY people. In fact, I’m accountable to more people now than when I actually had a regular job. Even though I don’t have a boss, I have clients, partners and colleagues who depend on me daily to help them with things.

And that’s something worth thinking about — even if you ditch your boss, you’ll still need the support of other people to make it on your own. Nobody is an island.

Additionally, since I don’t have set work hours, any time (and every time) is a possible working hour. If something comes up, I have to handle it. There’s no calling in sick and having someone do my job. It’s all me.

Some days I have literally a dozen meetings.

Rather than doing what I want, when I want every day, I have to use scheduling services like Calendly and Google Calendar to keep me on track every single day.

Most days, I don’t have a gigantic block of free time in the middle of the day to do whatever I want. I may not be stuck in a cubicle, but I’m probably busy working at Starbucks (my office of choice).

So while the ability to work on my passion projects certainly exists, it’s not a free-for-all. Lots of things still have to get done, and just like a regular working Joe, I need to make sure I’m meeting my obligations.

(P.S. When I do work on my own hobbies/pursuits, I always use the Seinfeld Solution.)

3.) About comfort…

What I thought: “It’s so hard to stay focused at work. I’d love to be able to work somewhere quiet and comfortable, like my bed. When I have my own business, pajamas for work every day!”

What I found: Working from home, especially from the comfort of your PJs, is a perk that infomercial kingpins have touted about self-employment for years.

“Imagine the thrill of working from home!”

LOL. The reality is that for me, working from home sucks. Not because it’s not enjoyable, but because I simply can’t get anything done at home.

First of all, my apartment isn’t that big — so it’s not like I have miles of space to spread out.

Then, between the TV flickering in the background, the fridge calling my name and Sara frolicking scantily clad (at my request)… I really can’t get anything done.

I HAVE to leave the house.

To be honest, I actually prefer separating work from home because it allows me to create a psychological distinction between the two spaces and feel much more relaxed in the “work-free” home environment.

And working in your pajamas is literally the fastest way to guarantee feeling completely unproductive for the day. Trust me, I tried today… and barely got this post finished in time. In fact, if I have to work from home, I’ll make a point to get dressed as soon as I wake up.

(This is a quick little psychological trick that discourages me from doing unproductive things or just flopping on the couch.)

Despite all this, I wouldn’t trade self-employment for the world — and even though it doesn’t mean I get to sit at home and binge watch 30 episodes of “Game of Thrones” on a weekly basis, it’s still one of the best decisions I’ve ever made.

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