I’m going on two vacations in the next month. The first is a small weekend trip to visit my best friend for her birthday, while roaming around D.C. For the second trip I'll be spending a few weeks out of the country to spend time with friends and family I rarely get to see. It’s an exciting time of year — even without taking an actual vacation, the late-summer air makes everything feel casual and open.
Drinks start in the daytime and continue for hours until it’s dark and all that’s left are the streetlights above you. Long walks around parks and cities begin with no destination in mind and end up miles away, because there’s no reason to button up a jacket and head home. In the past, when I had a staff job, this was the time of year I would put in my requests for time off and put up my feet. When summer is good like this — and the rosé comes in buckets of ice by your table — the last thing I want to do is think about work.
Now things are different. As someone who is her own boss, there is no such thing as taking time off that is purely vacation. Yes, of course, no one is going to stop me if I run out for a day or week and decide to turn off my phone. But doing so means that money won’t get made, problems that might arise won’t get fixed, and progress on any number of current projects grinds to a halt.
Having a theoretically unlimited amount of work (and therefore income) in front of you means that no one is stopping you from doing the work you want to do, and creating your own life. However this also means that no one is going to help you, if you decide to take a personal day. And not only are you not going to get paid for the specific days you’ve taken off, you’re also not guaranteed that whatever you left at your desk is going to be there when you get back. In the world of self-employment, a week could be the difference between a huge job and nothing at all.
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So it’s easy to drive oneself crazy, never fully leaving your computer or phone behind, always thinking of the things you could do next or the things that are waiting for you back at the proverbial office. And when you love your work — which many self-employed people do — you find a sort of nobility in this.
The truth is that any of us could go at any minute, and the future we imagine we’re building is only real in our minds.
I tell myself a lot, when I’m in the middle of something that I should be enjoying and yet can’t pull myself away from my email, that I’m working toward a life where I have more freedom than I could even imagine today. I tell myself that I’ll own multiple properties and take cooking classes and long sabbaticals. I tell myself that I'll have a professional life balancing family, travel, and all of the good things we usually think come in direct conflict with our professional life. I imagine my future with more money, options, and time to get everything done.
But I’ve met a lot of incredibly-successful people — people who have a lot of money, and a lot of professional freedom — who are still not able to fully get off that hamster wheel, even during a vacation. I was just on the phone this week with a super successful man who has given up his entire summer to work overtime on a project that is way behind schedule. To him, the decision to get rid of his “me” time wasn’t even a question, it’s simply something that comes with the incredibly high levels of responsibility (and compensation) he’s achieved. Sure, he isn’t self-employed, but that doesn’t mean that someone who is their own boss wouldn’t make the same decision.
In fact, taking the full responsibility (and the working time that demands) seems like an even more obvious choice for an entrepreneur. The trade-off of being your own boss means that, no matter how big you get, the real problems always fall at your feet.
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As someone who is her own boss, there is no such thing as taking time off that is purely vacation.
Perhaps some of this is gender-based. I do feel a certain amount of pressure to perform and undertake responsibility because I am a woman, and because I know that this choice was not always offered to us. (Even my mother, an incredibly capable and financially-savvy woman, had to have my dad sign for her first credit card.) I want to prove that, as a woman, I’m capable of working just as hard and building things that are just as impressive. Even though terms like “girl boss” make me cringe, I know that there is, at least for our generation, that added pressure to prove people wrong about the supposed limits of our work as women.
I do feel a certain amount of pressure to perform and undertake responsibility because I am a woman, and because I know that that choice was not always offered to us.
However I want to be happy, and I don’t know that proving someone wrong or climbing a mountain for the sake of climbing it will achieve this for any more than a few minutes. The truth is that any of us could go at any minute, and the future we imagine we’re building is only real in our minds. Maybe I will have all the things I desire by 30, but maybe I won’t. So, I don’t feel comfortable in delaying life's pleasures and enjoying them at some later, unknown date (that very well might get put off year after year). I know that there are people who get a genuine thrill from working nonstop, and for whom “slowing down for quality of life” is something they must force themselves to do from time to time. But I’m not one of those people.
I want to work, yes, but I also want to enjoy my life now. And if that means losing out on a dollar here or a new project there, I think I’m okay with that. I’ll always have my laptop with me when I go away, but sometimes it’s best to force myself to forget about it. Because spending your life emulating a Pinterest quote that tells you to Never. Stop. Hustling. might get you more money, but I doubt it will buy you more happiness.
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