Peter’s alarm went off at 6:30 a.m. He was already wide awake. He’d been staring at the ceiling for what felt like hours, his mouth dry and his stomach coiled with dread, watching his darkened room slowly fill with light. It was Wednesday.
There was nothing about this particular day that was different from the day before, or the one that would inevitably follow. That was precisely the problem. Peter was a mid-level executive at a firm whose mission was unimportant — both to this story and to Peter himself. He woke up, did his job, sometimes for up to 10 or 11 hours a day, ate dinner, and went to sleep. His routine had come to resemble running on a treadmill, and somewhere along the way, he’d lost track of how to get off.
For better or worse, many of us derive meaning from our careers. Research conducted by McKinsey in 2022 found that 70% of employees say their sense of purpose is defined by their work. Increasingly, studies show that we value purpose even more highly than we value pay.
More and more, people are leaping off of the treadmill — they’re becoming freelancers, independent consultants, and of course, entrepreneurs. Working for someone else used to be the expected course in life. The rise of digital connectivity has made it easier than ever to go into business for yourself. What’s more, those who have done it have no regrets — according to one statistic, 96 percent of those who work for themselves have no desire to return to a “regular job.”
Working independently isn’t for everyone. But if you decide to go it alone, the rewards can be significant.
The pros and cons of freedom
One of the biggest perks of being your own boss? There’s no one else telling you what to do. If you’re starting a business, that means you have the freedom to ideate your vision and then, if all goes well, bring it to life.
For a certain type of person, such freedom is a dream. But that doesn’t mean it isn’t work. If you’re someone who prefers to put in eight hours and call it a day, entrepreneurship is probably not the path for you. You’re going to go to bed thinking about your business, and it’s going to be one of the first things you think about when you wake up. There’s a good chance it will even seep into your dreams.
For some people, that’s a dealbreaker, and I get it. Freedom brings with it a fair amount of stress. But I’d also argue that building a business doesn’t have to be a jarring transition you make in a day. I held on to my day job for years after I started Jotform, preferring to chip away at it in the early mornings and evenings after I’d left the office for the day. When I did finally quit my full-time job, it was both because I was confident my business could stand on its own, but it was also because the lifestyle of being a founder appealed to me — I knew I wanted to be my own boss.
My suggestion? Go slowly. Test the waters. Do you have the drive to build something in your free time, on top of your other responsibilities? Or do you find that without the pressure of someone telling you what to do, you simply…don’t do it? It’s important to be honest with yourself about who you are before you take the leap.
Creative control
As much as I value being in control of my own time, that’s not actually my favorite part of running my own company. The best part, to me, is having control over my business and its objectives.
I’m a big proponent of bootstrapping for exactly this reason. Taking VC money typically means being forced to let go of the reins in a way that can potentially sink your business. One example horror story comes from ButcherBox founder and CEO Mike Salguero, who raised $30 million of capital for his first company. However, as is often the case, the venture capitalists had a completely different idea about how Salguero’s company should move forward, insisting on sticking to the strategy they signed up for rather than allowing Salguero and his team to pivot. Salguero found himself lashed to the mast of a doomed ship, unable to change its course. He recalled on an episode of HBR IdeaCast:
In that process, I lost the culture, I lost my place of work, I lost the ability to create the direction of where the company should go.
Suffice it to say, Salguero opted to bootstrap his next company, ButcherBox, which has been plenty successful.
I don’t deny that taking outside investments can pay off, and there are plenty of thriving businesses out there to prove it. But if part of your goal as a founder is to exercise agency over your company, bootstrapping is the way to go.
More and more people are becoming entrepreneurs and with good reason. Your time is your own, and you can forge your path forward in whatever manner you please. That said, it takes drive and discipline, and it’s certainly not always fun. But if you can make it work, the rewards will be well worth it.
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