On Being King of a Shrinking Castle

Those of us who have been self-employed for a number of years sometimes joke that we are now unemployable. We’re used to being king of our own castle. We make our own rules. After having that autonomy, returning to a workplace and the need to comply with company process would be hard.

Not everyone gets on with self-employment. It requires discipline, consistency, and the ability to self-manage. You have to do this for yourself; it all stops with you. As someone who has always sweated the small stuff, it suits me. I’m a planner, an organizer, I work hard and get stuff done. I like being king of my own castle, because I can get more stuff done without anyone else knocking my carefully laid plans off course. Much of this is baked into who I am, but I’ve taken a step back recently and realized that often I cross from staying organized and being reliable into making unreasonable demands—mostly of myself, but sometimes of other people. Anyone close to me has at one time or another had the misfortune of getting in the way of a Rachel-shaped steamroller fixated on Getting Stuff Done.

I have found myself becoming so accustomed to being in charge that I start to micromanage every aspect of my life. I’ve heard the same sentiment voiced by other self-employed friends. In a workplace, even the most introverted of us is forced to work with and around the needs of others. Working alone, we can often avoid that, and that inflexibility then creeps into the way we see the rest of our lives.

While being organized and reliable as a business owner is important, there has to be balance. The more we obsess about our plans playing out as we had imagined, the less we leave ourselves open to new things and to new people. When I travel (which is often), I plan my time as usual and don’t make any concessions to the struggle to find wifi and work in hotel rooms. To keep to my plan, I need to get back to my hotel after the conference day ends to make sure I can tick items off my to do list, get the planned things done. When a friend asks me to dinner, I can feel the panic of uncompleted tasks looming. I often decline, or I go but then spend the whole evening worrying about what will not get done.

By sticking to the plan I might have a clear to do list, but I lose the chance to spend time with my friends and peers making new connections and strengthening old ones. I’m king of a castle whose walls protect my plans and my world, but that world is shrinking.

There will always be times when, as a business owner, you will have to work incredibly and unreasonably hard in the short term. Being reliable is important, getting things done matters. However, the aim of self-employment for most of us was to free ourselves from the demands of a 9 to 5. We squander that freedom when we start to surround ourselves with rules and demands upon our own time. Worse, we squander the chances we have to make real and lasting connections with those around us.

I heard the quote at the top of this column from Yitzchok Willroth—the keynote speaker at a conference I am also speaking at. The quote speaks of the balance I want to regain. There are times when I and my business need me to look out for myself, to put my things first. However, the happiness that lies in being there for others matters too much to put off until later. This year, when I have turned forty, is as good a time as any to ask: if not now, when?