
Among the many challenges of being self-employed, one in particular recently came up for me. The idea that regardless of what you are doing, it seems that there always has to be at least one foot in your business at all times. Of course, there is a nuance to how different businesses operate and therefore the role of a business owner will be different, but to me, this hits home.
I recently went on vacation with my family. An actual proper vacation to someplace we had never been before. Most people when they travel like this will put it for their paid time off, set up an out of office message and then check out.
One of the many benefits of self-employment is freedom and flexibility with my time and schedule. Because of this, I get access to more travel and time out of the office than the average vacation benefits package allows. However, most of these little trips and excursions I am always aware that I may have to do some work. To be honest, I am certain I will have to work, therefore I fully expect it and plan for it. Vacations are about new experiences, spending time with family and relaxing. So what makes this a problem is the fact that I never completely check out. This prevents me from feeling fully immersed in a trip, consequently, robbing me of the experiences and time with my family.
I referred to this most recent trip as a “proper vacation” due to the unique nature of the planning, the location and everything about it. It was just different, it was new, bigger, and expectations were higher. This caused me to want to immerse myself in the trip with my family and not have to work at all. Going into the trip I knew it was unlikely I could disconnect this way, but I was going to try. Once on the trip, I tried not to work and to trust my out of office messages and go all in. But just a few days in, I found myself getting aggravated, frustrated and seemed to have a short fuse. Traveling with kids can be challenging sure, but this was different. I realized that I was feeling guilty like I had abandoned something. it was becoming apparent this approach of ignoring work was ruining my vacation more than it was enhancing it.
What I realized was, that by ignoring all work I felt a complete lack of control. The feeling of not having control over my business was causing me to get frustrated and angry. I had to think about this for a while because giving up control over your work while on vacation was the idea right? Aren’t you supposed to check out and disconnect from work on vacation? That’s what I had always been lead to believe.
What was troubling to me was knowing that things that were going on that were not being handled. My emails weren’t being forwarded to someone else. There was no customer service department to cover for me. It was knowing that at the end of the trip I was going to have to deal with everything and I had no idea what that was looking like.
It ultimately came down to me acknowledging to myself that no matter how badly I want to and might need to, at this stage of my career I simply can not check out completely. Even if for my sanity and ability to enjoy my trip, I had to keep that one foot in. So I thought about it a bit and decided that rather than stew in the aggravation or give in completely to working throughout the trip, I had to figure out a balance that made sense. I decided I would give work just 20 minutes.
So one morning I grabbed my computer, sat on my bed and got to it. It is important to emphasize that I didn’t do any real work as I refer to it, only basic communication. I sent a handful of emails, keeping it short and brief, reminding everyone I was out of the country and couldn’t do anything until I got back in the office.

So, did it help? For sure, and for the same reasons that getting work done always helps. I felt back in control and out of the dark. Furthermore, I felt like I had a good idea of what I needed to do when I did get back. Just eliminating the questions mark of what faced me on Monday morning was enough to calm the temper.
I expected to go on this trip and not leave one foot in but it didn’t work. I learned a lot about how I operate in this position and adjusted which is all I can do. For now, I guess I will always have one foot in. It’s not ideal and likely not recommended but learning to confront it, and find the correct balance is the best way forward.
