Work Shouldn't Be Fun

When I was in high school, I remember talking with a guy from my hometown named John. He worked construction, hard physical labor, and I really liked and respected him. Somewhere during the conversation he said something I've never forgotten.

"Work shouldn't be fun, if it was, they'd call it skiing."

At the time, I accepted it as fact. He was older than me, wiser than me, and, truthfully, I hadn't met anyone who genuinely enjoyed their work or met anyone who built their life first and then built work around it. That simply wasn't the model I saw growing up. People worked, they paid the bills, and then they tried to enjoy whatever time they had left over.

Then I experienced it for myself. My first job out of college wasn't exactly fun. I liked the people, I learned a tremendous amount, and it was a great opportunity, but I never woke up excited to go to work. Looking around, that seemed completely normal. The Sunday scaries were common, people joked about hating Mondays, and almost everyone seemed to believe that work was something you endured so you could enjoy evenings, weekends, and the occasional vacation.

I accepted that for a long time, until I started asking different questions. Why couldn't work be fun? Not every task, not every meeting, and certainly not every difficult conversation, but why couldn't the overall experience of building a career, or better yet, building a business, be something I actually looked forward to each day?

That question led me to starting my own business and to building it a certain way. I wanted to create work that funded the life I wanted to live, not a life that revolved around work. I wanted to use my strengths, work with people I genuinely enjoyed, create a schedule that fit my work inside my life not the other way around, and build something that I was excited to wake up and continue building.

One thing I've noticed over the last few years is that many founders unknowingly carry the beliefs they grew up with or the beliefs they developed during their corporate career, into entrepreneurship. They leave a traditional job looking for more freedom but then rebuild the same experience in a different form.

They accept clients they don't enjoy working with, they fill every hour of their calendar because busy feels productive, they continue offering services they've long outgrown, and they convince themselves that's simply what success requires. They built a business but they never stopped to ask what they actually wanted it to look like.

Maybe that's the real advantage of entrepreneurship. It's not unlimited income, flexible hours, or even being your own boss. It's having the opportunity to question assumptions that most people never stop to question, and intentionally build something different.

Which brings me to a question I've been thinking about lately, and maybe it's one worth asking yourself.

What have you accepted about work that you no longer have to accept?

Because maybe its not your strategy or marketing hold back your business.

It might simply be an assumption about work that you've never stopped to question.