How to Enjoy Your Work as an Entrepreneur

Illustration of a workshop full of tools tinkering away on a project

Tim Leatherman built his company to $100 million in sales, then 9/11 hit, and that number dropped precipitously for several years. Don Katz built into a public company that benefited from the .com bubble and IPO’ed at $25 a share, raising tens of millions of dollars. After the bubble burst, the stock dropped to $.04 a share, nearly wiping out the company’s entire net worth. 

Yet both of these companies bounced back to well above their original highs and are household names today. It took five or more years to turn around, but the founders don’t talk about that time as being full of misery. So, how did they manage to continue through such massive swings?

The answer they both give is joy in their work. In fact, Tim Leatherman kept a mantra that he would retire if he ever stopped enjoying his work. So how does one enjoy their work even when the outcome is so uncertain?

Keep creating whether you feel up or down

“Do what you love!” “Find your passion!” “Find what you love, and you’ll never work another day in your life!” 

These mantras are screamed at us day in and day out. They’re great and all, certainly fitting reactions to previous generations, who locked themselves in beige cubicles until their eyes fell out and they dropped dead of heart disease. But the downside is that these mantras can make people feel like they should be happy every second; otherwise they’re doing the wrong work. 

That’s insane. Every entrepreneur I’ve ever talked to or heard from had endured years of failure and hardship before their businesses got off the ground, and still, nothing is ever guaranteed, even after some level of success is reached. Businesses go through massive undulations of good times and bad. 

Yes, there is a point at which you can and should step away if the business is damaging your life and relationships, but I would argue that the bigger problem is feeling like we’re always supposed to be “having fun” when working on our businesses. 

Instead, what if you focused on the creation process, working on what you actually care about? What if you set a routine and stuck to it, regardless of whether you feel up or down on that particular day? 

So many writers talk about their routines of writing a certain number of words or hours every day. World record-holder for pull-ups, David Goggins, who you might assume loves working out, says some days he absolutely does NOT feel like starting his workout. 

There is intrinsic joy found in the processes we enjoy. If you don’t enjoy what you’re working on at all, it’s probably time to find something else to build. But, even if you’re working on your favorite thing in the world, it will still feel hard, and there will be days when it doesn’t feel “fun.” 

Let the worst-case scenario exist in harmony with hard work

Many entrepreneurs are scared of the worst-case scenario. I remember overhearing a conversation between founders before they’d even launched their business. One of them was obsessed with the idea of business insurance in case their company failed (like life insurance in case you fail). 

Not only does that not exist, but the mentality of always trying to prevent the worst outcome is exhausting. Instead of trying to figure out how to actually make the business work, they were worrying about what would happen if it didn’t. 

In his book, The Antidote: Happiness for People Who Can’t Stand Positive Thinking, Oliver Burkeman introduces the idea that if you make peace with the worst-case scenario, it won’t hold you captive. In other words, if you are okay with your company failing and can visualize how you’d be able to recover, then you can be free to work on the business, and research shows you’ll have a better chance of success. 

Set goals, then let them go

The psychology around goal-setting has been massively overplayed. For example, we’d read for years that to manifest success, all we had to do was visualize our goals and write them down. Uhhh, that makes no sense. You have to methodically work toward your goals to reach them. 

Seth Godin, who has been in the world of marketing for 30+ years, cites that the number one indicator of success is relentless consistency. The people who end up winning are patient and persistent enough to keep going for a long time. Tim Leatherman worked on his idea for seven years before making a single sale. At interact, we built for 18 months before getting a paying subscriber. We are the norm, not the anomaly. 

But, in every case where people put in years of work without payoff, there’s an underlying, easy-to-miss narrative that’s crucial to the story. In those years of effort, those entrepreneurs slowly let go of “needing” their goals to happen. Yes, no one ever forgets the desire to reach financial freedom and live the life they’d like without worrying about money, but in those years of hard work without payoff, what replaces that goal is a relentless passion to bring something to life. 

In almost every story, the entrepreneur works tirelessly to find solutions to problems, regardless of the payout. I know this sounds crazy. How can you stay motivated if you don’t keep an end goal in mind? By letting go, you’ll become more motivated to solve the real day-to-day problems, which, in turn, will lead to a higher likelihood of reaching your goal. 

There’s no shortcut, though. That’s why it can take years for entrepreneurs to internalize a reality with no guaranteed outcome. In fact, the more you try to force an outcome, the more miserable you’ll be. When we let go of our attachment to success, we can truly put in our best work (Pema Chodron).


Infographic of how to enjoy your work

There are three basic tenets of learning to enjoy your work. 

  1. Create when you feel up and when you feel down, because creating brings joy.
  2. Accept the worst-case scenario and know you’ll be okay even if it happens.
  3. Set goals, then, so you don’t become attached to them, let them go. 

Practicing these tenets daily will help you focus on the joy of building and creating, rather than needing something to happen to feel happiness. Letting go will bring joy, and you’ll be more likely to reach your goals. 

Business isn’t an all-or-nothing game. Joy can be found in both the successes and the failures. 

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