How Much “Free Time” Do Entrepreneurs Really Have?

by / ⠀Entrepreneurship / August 11, 2014

beach free time

One of the primary reasons I quit my job 2 years ago was so that I would have time to do things that I enjoy.

Time to read, write, meditate and train my body.

Time to learn languages and master new skills.

Time to travel and spend time with my loved ones.

I needed free time.

The fact that my dead end 9 to 5 didn’t allow me this precious time drove me CRAZY — and I even wrote a manifesto of sorts to get it off my chest.

I think most of us here can agree that the idea of being able to wake up when we want to, make our own schedules and direct the flow of our own lives without living on someone else’s clock is EXTREMELY appealing.

But what is it actually like to be completely self-reliant, without a boss or organization to keep you in check?

Do you really have more freedom as an entrepreneur than as an employee?

The answer: Yes and No.

I didn’t know what to expect until I made the leap into full time self-employment. Now, I want to show you what I’ve learned over the last two years.

(This will be a two-part post.)

Today, I want to show you some of the BIG misconceptions I had about what my schedule would be like once I was completely self-employed…and why those assumptions were so wrong.

Then, the next time we talk (on Monday), I’ll let you inside my calendar and show you what my day-to-day schedule is like, along with the psychology behind why I make certain choices, and how I organize my life without someone else telling me what to do.

Keep reading!


First, let’s take a look at the average American employee’s work schedule. We’ll use 9am – 5pm as a basis of measurement. Most people work about 8 hours/day on average.

Average Employee Schedule

  • 6 AM Alarm goes off, wake up, curse, hit snooze button. Roll over.
  • 6:30 – 7:30 AM Getting ready for the work (shower, breakfast, etc.)
  • 7:30-8:30 AM Drive to work >> “OMG why is traffic so bad?”
  • 9AM At work, already ready for 2nd breakfast.
  • 9AM-12PM Work
  • 12PM-1PM Lunch  (perhaps a mad dash to Chiplotle?)
  • 1PM-5PM Work (dying….on the verge of complete exhaustion by 3pm)
  • 5:00:01PM GTFO

Then, of course, the inevitable commute back home to watch Shark Tank, eat dinner and pass out by 10:35PM so that you can repeat tomorrow.

Perhaps your schedule is a tad different here or there, but for the majority of young, working Americans…I know this layout is a pretty safe bet.

Misconceptions about the entrepreneur schedule

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.

5 days on…2 days off. The math just doesn’t add up.

When I became fully self-employed, I thought I would be able to 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 said: “6am 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:

Uhmmm yeah. I was completely wrong and this was a hard lesson. 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 and 4am 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. 8 hours is 8 hours, right?


Unfortunately, getting up early makes a huge difference. Waking up at 5 or 6AM allows me to have an entirely different day than waking up at 10am, 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 3 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 6AM is far superior to the quality of work staying up until 3am, even if I get 8 hours of sleep in both instances.

B. 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 said: “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 ScheduleOnce 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.


3.) About comfort…

What I said: “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 running around naked (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 —often in a collared shirt and tie.

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


What’s the BIGGEST thing that you’d change about your schedule?

These are just a few of the surprising realizations that have come to me after being out on my own for two years.

On Monday, I’ll go into extreme detail about how I set my life up to accommodate getting everything done — including the exact systems I use to keep multiple balls up in the air.

Image Credit:

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.