Should You Be Imprisoned To Your Ambition?


“Sometimes I just can’t with the entrepreneur crowd,” she said. The funny thing is, both of us technically have been a part of it for the past five years. If you asked anyone, they’d label us as hard working, self-starters. Yet here we were, talking about our feeling of distance from the entrepreneurial hustle. And interestingly, within 12 hours, I found myself having a similar conversation with one of my other entrepreneurial girlfriends.

So what gives? We’ve each earned our own versions of entrepreneurial success in different capacities, but we have a ways to go with our ambitions as well. Why is it that we feel like something with the entrepreneurial lifestyle just doesn’t fit with who we are at our cores? It’s a question that has been plaguing my mind for a while now.

When I can’t find the answer, I usually look to my bookshelf. Thanks to years of spending time in bookstores instead of clothing stores, I have amassed a diverse mix of reliable voices I can turn to for reference.

But this time was different. I never opened a book. Instead, I found myself looking at their spines, recalling the wisdom between their covers. I had a number of books by and about rockstar entrepreneurs–the kind of stories everyone who owns a business dreams of mirroring someday. Their stories are all unique, but typically there’s a similar tale of their early days, where they worked 24/7, eating, sleeping, and breathing their business idea, all in hopes of surviving and eventually (hopefully) thriving.

When you start a business, everyone tells you that if you want to make it, you have to work hard. But then again, if you want to make it in anything, you have to work hard. The challenge with these stories and the conversations surrounding them though is that on one side, there is a glorification of working as hard as humanly possible and on the other, there’s this idea that hard work should feel like you’re imprisoned.

And here’s the predicament: if you want to create a successful business, it isn’t a short term game. Obviously, some companies, especially in the tech space, are playing a shorter game, but most of my girlfriends who own businesses aren’t in that category, nor am I. We are playing a longer game. Most of us are playing a creative one at that, building businesses that center on writing, photography, design, marketing, and so on.

So if it’s not a short term game and you commit to working hard, should it really feel like you’re imprisoned to your business?

It’s a conversation we have often. How do you find contentment in the journey when part of your role as a founder is to be focused on the finish line? None of us are new to this, but admittedly, I’m still learning how to work hard without subconsciously becoming a martyr to my entrepreneurial vision.  (I learned this the hard way.) However, I think I got closer to my answer as I sat in a French wine bar on a Friday evening in Omaha, Nebraska. A long way from New York, my office, my friends, and my typical work environments came some clarity.

It was 6:00 pm, and I was in search of a place I could grab a bite to eat and finish up the last few items on my to do list. As I walked down the cobblestone streets of Omaha’s Old Market, it felt as if everyone was celebrating the start of what would be a beautiful spring weekend. A saxophonist was playing on the corner and it echoed down the streets of the neighborhood, which resembled a setting from an old Western film. All the restaurants had opened up their doors and windows, welcoming in the warm air and hungry locals. There were even horse drawn carriages waiting on the corner for people in need of a lift. It was as picturesque as a Friday evening in an unknown city could be.

It wasn’t long before I found the French cafe. I snagged a little table, ordered a salad and some rosé, and quickly pulled out my laptop. Without thinking much about it, I got right to work, clearing out the last of my inbox’s email stragglers, checking off the to do list items, and finishing up work for upcoming projects. Once that last item was checked off my to do list, I finally lifted my head and exhaled. When I looked at the time, not much time had passed at all, yet it felt like it was the most productive I had been all day.

I sat there for a few minutes, just taking in this feeling of contentment. I thought, is that allowed? Am I allowed to feel content even though I’m still on the road to where I want to be?

I think in many environments, including entrepreneurship, there is this underlying idea that in order to create the life you want, you have to essentially imprison yourself to the process in order to get there. Eventually, you can have the glamorous office that inspires you. Right now, you are just plugging away.

Of course you have to work hard. Of course you have to log in long hours. Of course you have to persevere. But as I sat there, typing away in that picturesque environment, I started to wonder: if you are trying to find long game success (as I think we all are in some capacity), is treating hard work like it’s a prison sentence really going to make you joyful in the end or just drained of all energy and inspiration? If we place ourselves in environments that encourage us to find contentment in the journey, maybe it’ll be easier for us to continue down the path.

That doesn’t mean we all need to hop on a plane to Fiji and work under a cabana, though that does sound wonderful, doesn’t it? But maybe we could redecorate our desk spaces to create more calming, encouraging environments. Or bring our laptops to a park for an hour just for a change of pace. Or meet up with a few of our fellow entrepreneurs for a working brunch. The possibilities are endless when the goal is to create spaces that inspire you to not just get the work done, but to enjoy the process.

Contentment in the journey may not sound as flashy as a word like hustle, but who says we can’t marry the two? Entrepreneurship defines what it means to push boundaries. Maybe this should be the next one.