As an entrepreneur, you don’t really get time off.
You have to make time, sometimes against all odds.
Most people I know who are entrepreneurs and business owners work 365 days per year in some way, shape, or form. When they take a weeklong vacation, they’re still checking emails and responding to urgent messages. It’s one of the things that’s a bit of a misnomer when it comes to “entrepreneurship.” Most people think becoming an entrepreneur is what will give them freedom, when in reality, running a business may give you more choice, but less freedom in the traditional sense.
Everything is on you.
I’ve had many vacations where I’ve ended up spending a full day in the hotel room, working late nights based on shifted time zones, or working from my phone in every taxi ride to maximize the time. Other vacations have been more low key and I’ve been able to check out more fully. In both cases, the responsibility and accountability remains — ultimately, no matter what happens, it’s on me, which means I need to (or get to if we want to reframe it in a more positive light) keep tabs on all of it.
So, how do you manage time off as an entrepreneur when you never really have the luxury of stepping away completely?
1. Set the expectation that, at some point during your time off, you will have to work.
This is a combination of setting that expectation with your traveling companion(s) and with yourself. You might only need to work for 20 minutes one morning, responding to a few emails.
Or, you might need to cancel your entire afternoon of scuba diving because there’s a fire you need to put out in your business.
If you don’t have an expectation that you’re not going to work at all (or that you “shouldn’t” have to work at all), you won’t resent the little moments where work inevitably pops up. When I go on vacation, I do everything humanly possible to get the big stuff sorted before I leave, but I’m also honest with myself about the fact that I may need to jump in here or there while I’m away. And I’m totally fine with it.
This is part of being a business owner.
Acceptance here is key.
2. If you have to work regardless, you might as well travel more often.
This is how you have your cake and eat it too.
In the digital age, the blessing and the curse is that cell phones work everywhere and WiFi is almost universally accessible. You could be in the most remote place and still be able to connect to the Internet. The challenge here is that our society has become accustomed to asking for things from people even when they’re on vacation. It’s a benefit that you can work and remain connected from anywhere, allowing more flexibility in your life and schedule.
So, instead of taking one vacation per year and hoping nothing unpredictable happens during those 7–14 days, travel more often.
Take mini vacations, or work weeks in other countries, and remove the pressure of feeling like if anyone disrupts you during your time off, it’s all over. For example, I just got back from Greece, and of course, two important client presentations popped up in the calendar for the week I was returning, which meant lots of preparation from the team with input from me. I did everything I could to plan in advance, and still, I had to work. If this had been my only trip for the year, I might have resented having to work. But because I am fortunate enough to travel more often, I was able to do what needed to be done without feeling like my whole vacation was “ruined.”
3. Find ways to remind yourself of your passion for your work.
If you love what you do, then it doesn’t have to feel like work.
At least, not all the time.
Whenever I get stressed about work while traveling or on vacation, I remind myself I chose this path for myself. I wanted the responsibilities that came with owning a business. I wanted to work for myself, and to choose the people I worked with. So instead of complaining or resenting, I always have the option to choose differently, and remembering this is motivating and uplifting.
Most of the entrepreneurs I know work nights and weekends. And they don’t do it because they have to (although sometimes that’s certainly the case). They do it because they’re passionate about what they do, and they enjoy spending time doing it. And while I don’t expect my own employees to work weekends, I know that answering a few emails on a Sunday and prepping for my week ahead makes my Mondays a whole lot more enjoyable.
The key to sustaining yourself over the long term as an entrepreneur is finding little moments along the way to be grateful.
When I took this most recent trip to Greece, it had been a long journey getting there. I knew I had emails to respond to, I knew I was going to have to catch up on some work eventually. But as soon as I got to my hotel room, I went straight out to the pool, jumped in, and leaned into the moment.
You might not get an entire week off work, but you can make little pockets of time for yourself.
And in those moments, pause, take a deep breath, and feel grateful.
