Running Your Business On The Road (with Kids)

Last month I took a trip with my family to Ohio. A coworker of mine was getting married in Indianapolis, and we have friends on the way, near Toledo, and I have some family in Northern Indiana. So we thought, let’s make a weekend of it.

One of the biggest benefits of working for yourself is having the ability to set your own schedule. Pair that with homeschooling, and you get this double-whammy, double-stuffed “flexibility Oreo.” But of course, in the modified words of Uncle Ben, “With great [flexibility] comes great responsibility.”

When you’re an employee, typically you work in the office and you don’t work outside the office. But I’m not a fool. I know that hasn’t been true for many people for many years. Today, you’re expected to be reachable at all times… but that’s a whole other conversation.

Regardless, when you’re a small business owner, the lines between business and home become much blurrier. And if your business is inside your home, good luck. Now, there’s a lot that can be discussed on the topic of work/life balance, but let’s focus on vacation for a minute.

When you’re living a flexible life, things can get messy pretty quickly if you’re not careful. I’m speaking from experience. One example: This past fall we went down to Atlanta for a week to celebrate Thanksgiving with some family, and it was awesome; best Thanksgiving ever. There was plenty of downtime. I had my computer and access to WiFi, so I was able to get some work done. Everybody else knew what was up. But I still had to dart out unexpectedly from time to time to take a phone call, or answer an urgent email, or show up a few minutes late to the dinner table after everybody else was sitting down. And I just can’t shake the feeling that I might have made other people feel… cheated?

My wife says that’s too a strong word, but I think she’s just being nice. Whether or not she felt a certain way, I was a little disappointed in myself that I didn’t draw clearer boundaries. One way to do that: Communication.

Communication is crucial all. the. time. And it’s especially important when it comes to preparing for a trip with your family and establishing expectations beforehand.

This isn’t really business advice. This is relationship advice.

In addition to communication, you also need a healthy dose of flexibility. You never know if you’re going to get a flat tire, or if you want to make a detour to see the world’s largest ball of twine or something. You need to be ready and willing to give a lot of patience, give a lot of grace to your family. You can ask for a little bit of flexibility from other, but I think it’s much more important to be willing to go with the flow yourself. We’re talking about vacation after all and it’s your family’s time.

There’s a spectrum. One end of it, you need to work so you can afford to pay for a vacation, but you also need the vacation to recharge you and make the work worthwhile. And when you’re with your family, love on them and give them your time and your attention as much as you can. Also, work ahead. Before taking a trip, I like working a few extra longer days to prep and get ready so I’m not feeling like I’ve fallen behind (too much) when I return from vacation.

You’ll find a rhythm and routines. The more that you spend in between work and play you’ll learn what you need. So I’m not going to be overly prescriptive with this. Everybody’s situation is going to be very different, just like everybody’s marriage, everybody’s family, everybody’s work style, and everybody’s business is going to be different. Take time and find your flow. But whatever you end up doing, I would encourage you to go – hop in those muddy waters in between vacation and work, take time and leverage the flexibility that you have as a self-employed individual.

Don’t get too busy to relax and rest, and go explore, and have an adventure, and take a long weekend to celebrate your friends wedding in Indiana. Or whatever other simple moments and amazing people your life has in store.

Share the Post:

Related Posts