As an entrepreneur, it’s tough to completely retreat from work. With a little planning, it’s possible to take a little bit of the office away with you, but not have it completely ruin your holiday.

I was a solopreneur for years before I took my first proper vacation away from Sydney.

Money wasn’t the problem – at least not directly. What was keeping me at my desk was the almost neurotic fear of losing momentum if I stepped away for a single week. Most solopreneurs feel the same fear, mingled with guilt, of letting a few days go by without chasing every dollar that could have been earned during the downtime. Never taking a break is destructive, though, as it layers on the stress and deprives you of a much-needed pressure valve.

Fortunately for me, and for the people around me, I eventually figured out a few ways to take a real vacation without being sick with worry the whole time.

Enter the working vacation

It’s easy to mistake a freelance entrepreneur for a compulsive workaholic. We work such long hours, and with so few days off, that on the surface it looks like work is all we want to do in life. This is actually partly true – given the instability of freelance work, there’s no cosier feeling than having a full work calendar.

For many of us, getting work done actually does feel better than relaxing on a beach. At the very least it makes us feel safer.

But there’s no good reason to give up the work entirely on vacation. I’m able to work from any place with a decent WiFi, so I’m never entirely out of touch. During a trip I took to Bali a couple of years ago, I enjoyed the massages and the evenings out much more than I otherwise would have, knowing that I’d managed to putsome work-related brushfires out before leaving the hotel.

By making my trip into a working vacation, I was able to scratch the itch to be productive and enjoy my surroundings at the same time.

Don’t overdo it however

It’s good to get a few things done while you’re on vacation, but be careful not to overdo it. In my experience, the more I work, the more I find that needs to be done. This is how checking your email from the hotel gym can turn into an overnight work marathon before you know what you’re doing. If you’re sharing your trip with someone you love, you can spoil their good time by losing yourself in work when you should be enjoying your time together.

This was pointed out to me by my wife during our Bali trip. Fortunately, I came to my senses and strictly rationed my working hours for the rest of our stay. Every day, I gave myself exactly one hour to handle the most urgent matters before heading out for the day.

This took some planning. It didn’t matter whether I was in the middle of typing a word when the alarm went off, I stopped cold. Unfinished business was the price I forced myself to pay for taking on too much work. I gave myself another (strictly optional) 30 minutes before bed to handle whatever had come up while I was browsing overpriced souvenir shops during the day.

For the remainder of our trip, this is how I structured my day:

8am: Gym or Walk

9am: Breakfast

10am: Work / Business related (1 hour max)

1pm: lunch

2pm: Afternoon activity (hike, massage or sight seeing)

4pm: Final round of checking and responding to emails (30 minutes)

7pm: Dinner and entertainment

Plan, then do

I became an entrepreneur because I wanted to be in charge of my life. As an employee, working when other people scheduled work for me, I felt like all I ever did was work. Ironically, as a solopreneur my working hours are longer than they’ve ever been, and I have trouble pulling myself away for even a short trip.

To really enjoy my freedom, I’ve had to learn how to plan for a working vacation, prioritise the genuinely important work, and let the less-than-crucial stuff wait until I’m back in the office.  Before I left, I informed all clients around my availability during this period to ensure we had set times when they can expect to chat with me or expect a reply to their email.

We’re solopreneurs because we’re passionate about what we do. Productive working vacations help us stay on top of things while still allowing for some much-needed rest and recuperation. Make the most of this time to enjoy yourself and relax without losing full connectivity with your business.

Do you find it hard to take a vacation from your work? Have you developed any strategies around this?