When you work at your own startup, it's tough to unplug. That's especially true when you have a small team, with many of them relying on the work you do to get theirs done. Now, add your spouse into the mix and it's really challenging--both of you being "gone" at the same time can be rough on a small company. So what do you do? How do you relax and make sure your business keeps on track?

It really depends on your definition of "relaxing" doesn't it? For me (CMO of Dasheroo) and for my husband, John Hingley (CEO of Dasheroo), we relax when we know the stuff we need to get done, gets done. That's it. (Note: It is a benefit in this instance that we don't have kids, which we know takes a huge element of difficulty out of the equation.)

So how do we vacation? Brace yourself--it's the antithesis of what everyone tells you to do, but it works wonders for us.

1. Take a long flight.

We love to fly. We get a good amount of work done on the flight whether we have inflight Wi-Fi or not. We prepare for "not" having Wi-Fi by getting any documents we've been working on out of the cloud so there's no added pressure. And since there are few distractions it's somewhat settling. We prioritize the stuff we need to get done online while we're over land then switch over to offline mode as we go over water.

If we can get a quick nap on the flight that's a bonus, but we're rarely ever watching a movie or TV.

2. Don't unplug.

In this day and age where everyone is telling us to just unplug and get away, that's more stressful to us than keeping up to date on what's happening. And because it's the first year of our startup, we want to make sure we're not burdening a small team of people. We're making a commitment to the team, we're continuing to get our work done, and we're having a good time.

3. Make a time difference work for you.

Lots of times we find ourselves on the East Coast or Europe and we love that. We work in the a.m. and have a check-in in the p.m. We almost always continue to hit our daily 15-minute check-in meetings with the team if we're not in the air.

If we go the other way, to Asia for example, it's tougher. We can't get online as much as we'd like so we try to do a lot of our work beforehand and automate as much as possible.

4. Do your thing.

Make sure you make time to do the things you love: work out, run on the beach, lay out by the pool, get on a boat, eat, drink, or do nothing for many hours. If we hit a Wi-Fi connection at lunch we scan our emails to make sure sh*t has not hit the fan. Then we take our iPads to the beach and read something or send an email.

5. Travel a bunch.

Because we can work remotely (not everyone can), it doesn't matter where we are. So we're in the air almost every month going somewhere. And as long as the business continues to progress we'll try to be somewhere cool.

6. Take your dog.

We're lucky. We have a little guy named Dwight and we take him everywhere. The kid's been to Ibiza, Barcelona, Paris, Italy, New York, Oregon, Arizona, Austin, Miami, and the Caribbean, and he'll continue his journey. But there's nothing better than coming back to the hotel to a cute little pup wagging his tail to greet you. Wherever he is, it's home!

Dwight loves Virgin America!

Dwight, ready to deplane and have some fun!


OK, it might not be how everyone does it, but it's how one tech startup couple is having a lot of fun traveling and growing our company Dasheroo.

Published on: Aug 12, 2015
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