The Contradiction Between Having Freedom and Building a Business

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There’s a lot of people selling freedom.

Companies who are hiring remote workers promise the freedom of being able to work from anywhere. Blogs, podcasts (like the one I host) and Youtube channels centric around being an entrepreneur promise the freedom of being able to build your own thing. 401K plans and financial planners promise financial freedom if you follow a certain set path.

I don’t have a problem with freedom. Last year we even hosted a conference where the tagline was “own your day”.

But my question is — once you have freedom, then what?

Freedom is this elusive and attractive fairytale dancing off in the distance. It’s this idea and dream that once you attain it, everything will be gravy. Freedom will finally be the day you can wake up when you want, work on whatever you want (including nothing if you so choose), and say whatever you want to whoever you want.

I’m not posing this question because I’m going to hand you the answer on a silver platter. I’m posing this question because it’s a current struggle in my life and I think it’s a topic worth talking about.

Why I Originally Wanted Freedom

In college I worked for a moving company called Square Cow Moovers (yes, brilliant pun).

At the time, I remember waking up in the mornings, sipping my coffee on the patio of my apartment in Austin, TX reading a book, only to get into the best part of the chapter and then have to dash off to work. I remember thinking about how much I couldn’t stand that someone else controlled my time and my life.

I wasn’t upset just because I had to put my book down and get to work. I actually enjoyed work. I just wanted some kind of choice in the matter. If I did wanted to show up a bit later, I wanted the option to do that. If I wanted to work from home that day and not put on pants, I wanted that option too.

In short, I wanted freedom in my work. I wanted to choose when I worked and what projects I worked on.

I knew in my heart that punching into someone else’s clock wasn’t something I would do for the rest of my life.

So for the next 5 years, I put my head down. I worked on building skills that helped me start making money outside the 9–5 walls and eventually helped me walk away from a job altogether. It was a gradual and difficult process, but one that landed me actually where I want to be — not working for the man, owning my time, and getting to do work I want.

That being said, for the past five years I haven’t taken my foot off the pedal. I felt like if I slowed down in my work, I might have to go back to someone else’s clock. If I slowed down, I couldn’t pay off student debt. If I slowed down, someone (I don’t know who) would beat me and that was unacceptable.

Slowing down was not an option.

But right now, my wife and I are on a once in a lifetime trip to New Zealand and for the first time, we’re not planning a conference or taking on a major client project. We paid off our debt. We got to a place where our income streams are coming in each month regardless of the effort we’re putting into them (i.e what some people call passive but I call massively delayed income), and we have a bit of financial runway in the bank.

For the first time we don’t have a crazy itinerary for where we’re supposed to be and don’t have meetings on the calendar. I’ve batched recorded several of my podcast episodes in advance plus the 17-hour time difference from New Zealand back home means I’m actually receiving fewer inbound messages on a day to day basis.

For the first time, I have the freedom I wanted for so long and honestly, I don’t know how to handle it.

To Build or to Be? That is the Question.

Having freedom wasn’t the only reason I wanted to be an entrepreneur. I also wanted the opportunity to build something bigger than myself.

The contradictory thing I face now that I’ve achieved the very, very early stages of freedom — do I spend all my time hiking and traveling or do I put my head back down and work toward building the thing that can impact a lot of people? 

I do enjoy business, a lot. But at this stage in my life I’m also enjoying getting to travel with my wife.

I’m finding a tension between these two driving factors as an entrepreneur and as a human — to enjoy life in the moment or build something bigger than me?

I’m not the kind of person who would be content just working 4 hours a week and checking out to sit around all the time. I would go nuts.

And much as I would love to wrap up this blog post with a 3 point takeaway, I’m still working through this problem myself.

That being said, I created a list of questions I’m working through to help with this whole contradiction I’m facing between work and life. If you’re facing a similar struggle, I don’t think these questions will get you 100% clarity but maybe they can help get you 60% of the way there.

  • Am I content with sacrificing the size of my business in order to have a more full life, or do I need it to be the biggest company ever?
  • Am I willing to build in “heads down time” for my company amidst a sometimes hectic travel schedule to make sure my work can get done?
  • Will my business suffer if I’m not on hand 24/7 (aka can I leave for several hours without it imploding)?
  • Will I be fulfilled knowing I could be doing more to grow my business, but instead I’m spending time on life experiences?
  • What gives me meaning? (i.e What makes me happy?)
  • How much money does my business (or do I) need to make in order for me to be comfortable?

I’ve found that asking myself these questions — not just once, but on a regular basis, has been incredibly helpful in getting daily clarity of my goals. It makes me realize that more often than not, the stress I’m feeling is not coming from my own goals, but from false expectations I’m putting on myself because of what I see from others.

I should be doing more. I shouldn’t be traveling, but focusing on my business 24/7. I’m never going to be a successful entrepreneur because I’m spending too much time seeing the world in an RV.

These are the voices I have to push back on every day. If you’re anything like me, you probably have voices trying to create a dialogue in your head as well. I think it’s up to us to ask difficult questions like the ones above to really figure out what we want and how to get it.