One of the biggest misconceptions in entrepreneurship is the idea that enjoyment comes later. Once the business grows, or once revenue increases, or once things finally calm down.
The assumption is that enjoyment will eventually follow as the reward for all the hard work. In my experience, that rarely happens.
I’ve worked with too many successful business owners to believe that enjoyment simply appears automatically once the business reaches a certain level. In fact, many owners become less happy as the business grows because the frustrations, complexity, and pressure grow faster than the systems around them.
That’s why I believe enjoyment needs to be approached proactively, not passively. There’s an old saying that happiness breeds success, not the other way around. I would actually take it one step further:
Happiness is success.
Because what’s the point of building a business that drains the life out of you?
Enjoyment is not selfish
I think many entrepreneurs almost feel guilty prioritizing enjoyment. They tell themselves things like, “I’ll slow down later,” or “I just need to get through this next stage.” But there’s always another stage, another target, and another problem to solve.
If you don’t intentionally create enjoyment along the way, you can spend years building a business that looks successful from the outside while becoming increasingly miserable inside it. And the irony is that frustrated, exhausted business owners usually make worse leaders. They become more reactive, less patient, less creative, and less energized. That impacts employees, customers, and ultimately results.
Enjoyment isn’t a luxury for entrepreneurs. It’s fuel.
A practical exercise
Here’s a simple exercise I encourage business owners to do:
- Make a list of everything that frustrates you in your business. It could be an employee issue, a software tool that constantly causes headaches, a lack of process, too many interruptions, meetings that waste time, unclear roles, customers who drain energy, or technology that never seems to work properly. Anything.
- Now look at the list and ask yourself a simple question: Which of these frustrations are actually within my control to improve? Because many of them probably are.
- Pick one item on the list that is within your control. Not ten. One.
- Make a plan to either remove that frustration completely or significantly reduce it. Maybe it means finally replacing a software system you’ve complained about for three years. Maybe it means having the difficult conversation with an employee you’ve been avoiding. Maybe it means creating a simple process for something that currently lives only in people’s heads. Sometimes the solution is surprisingly small relative to the frustration it removes.
When frustration goes down, enjoyment goes up
I’ve seen business owners tolerate problems for years simply because they became accustomed to them. They normalize frustration instead of fixing it.
But here’s the interesting part:
By definition, if you decrease your level of frustration, you increase your level of enjoyment.
It doesn’t require a massive breakthrough. Sometimes it’s just about removing unnecessary friction from your day to day experience as a business owner.
Keep picking away at the list
The goal is not to create a business with zero problems. That doesn’t exist. The goal is to create a business where the level of enjoyment meaningfully outweighs the level of frustration.
That happens gradually, one improvement at a time. One better hire. One clearer process. One improved system. One difficult conversation handled properly. One frustration removed.
Over time, those changes compound in a very powerful way.
Final thought
Too many business owners treat enjoyment like a finish line they’ll eventually cross someday after enough sacrifice, stress, and struggle. But maybe enjoyment was never supposed to come at the end of building a successful business. Maybe it was supposed to help create one.
