Getting to Time Off as an Entrepreneur

With the heat of summer settling in, most people are busy contemplating vacation plans and time with families and friends. They’re having fun and recharging. Meanwhile, many entrepreneurs struggle to enjoy time off, even when they manage to squeeze it in. Wanting a fresh perspective, I asked Greg, an entrepreneur who owns an IT company, about his former struggle with vacations. When Greg started his company, he was working so hard that he couldn’t even IMAGINE the idea of taking time off.   

The Trap

"It took a helluva pace and effort to keep the business going and the bills paid. In fact, it took pretty much all of my energy, effort, brains, and brawn. I was proud of it, even as I was on a slow but steady physical and emotional downhill slide.

I was in the office from the early morning until I was late for dinner. I was in meetings, on the phone, and driving to meetings while on the phone. When our first son was born, I left the hospital a few hours later to go to a meeting — I can’t remember with whom.

I stuffed a little free time in here and there. I took a day or two of vacation if my family was going somewhere. I'd be on and off the phone and computer. I didn't understand why my wife thought I was 'not really present.' Someone had to run the business and pay the bills or we wouldn't enjoy these vacations at all!

Someday I'd get the business to a point where it would be making a ton of money — or we'd sell it — and then I'd have all the time off I could stand. Someday I'd get all the surfing, reading, climbing, snowboarding, and family time I wanted."

These two ideas — “Right now I just can’t take time off” and “Someday I’ll be able to” — are so common among Awesome’s clients that it’s almost universal. This struggle can go on for years, sometimes indefinitely. And if it goes on long enough, it can lead to burnout, depression, anxiety, health crises, or divorce. Fortunately for Greg, something changed for him before things got that far:


"Somewhere along the line, someone suggested that it might be possible to get a little free time to relax and think and play. None of that sounded very good at the time. I was engaged with all the challenges of the business and slowing down wasn’t compelling. But over time I began to think that maybe I should look for ways to enjoy life more. Alone. With friends. Especially with my family. Maybe. But only if it wouldn't hurt the business"

How often do all of us have those little voices whispering in our ears?  When was the last time you told yourself something like that?  What did you choose to do about it?  Most entrepreneurs are really worried about how dependent the business is on them.  In essence, they’re worried that their baby will die if they look away for even a moment.  Is that really true, or just a fear?  Fast forwarding a bit, Greg decided to try acting on those voices and take a little time for himself.

Learning to Unplug

"It was odd at first: going to a nice restaurant — the kind where I'd take a client — and sitting alone and reading a book while they brought me an espresso. It was odd, but I returned to the office recharged.

I started squeezing recreational activities into the day. I made plans to pick up a friend at 6:15am to go surfing four days a week — picking him up got me off my pillow and on track with my new habit. If the waves were good, I'd be so focused on surfing I wouldn't be thinking about the business. If the waves were terrible, we'd have a coffee and then go home.

Then there was weekend camping with no access to devices. When I returned, everything in the business was fine. Rejuvenated, I was a better boss and I made better decisions. I added rock climbing to a couple of afternoons. Then my wife joined in and date nights were reborn. Only this time, I wasn't on the phone or thinking about the business.

Little by little, I was creating more free time in my life. And I was surprised to see it wasn't detracting from the business. In fact, the business did fine with me 'disconnected' for all these hours and days. 'Maybe I could take time off' turned into 'Maybe I should take more time off.'”

Greg did something really wonderful here. He listened to his inner voice, and then acted on it, starting with small steps and building new habits. Greg’s description may make it sound easier than it is — but trust me, it isn’t. Rebuilding healthier habits is something most of my clients are working on. As a coach, it’s so rewarding when my entrepreneurs take time for themselves and begin to blossom again — and their families and companies benefit too.

So now that you’ve heard Greg’s story, what’s yours?  What is your inner voice telling you that you could do for yourself today?


Want more time off but not sure where to start? Take your first step with the Wheel of Awesome.