top of page

Sign up for our mailing list

Thanks for signing up!

  • Timothy Iseler

Be the Boss You Wish You Had

I played hooky from work last week. It was the middle of a workday, I had plenty to do, but I decided that the afternoon was too nice to spend it inside. Instead, I sowed spring vegetable seeds in the garden ahead of two days of predicted rain – the perfect time for gardening!

I do all of the time management things you are supposed to do when running a solo business – calendar blocking so that necessary tasks get addressed, paying attention to which activities work better at which times of day, keeping my quarterly & yearly goals in sight so I stay motivated, and choosing my meeting availability to accommodate different client schedules.

But you know what I don't include in my time management schemes? The kind of downtime that naturally occurs throughout the day when you work for someone else. Those short breaks while grabbing a cup of coffee or an unplanned conversation with a colleague – which allow you to relax, let new ideas bubble to the surface, or just disconnect for a moment – tend to be the first things to go out the window when you are both employer and employee.

There is an anecdote in the second chapter of Tara Brach's "Radical Acceptance" about Mohini, a white tiger at the Washington, D.C. National Zoo. Mohini spent most of her time at the zoo in a twelve-by-twelve foot cage, pacing restlessly back and forth. As times changed, the zoo modernized to give animals more natural habitats and Mohini was released into a new multi-acre environment with hills, trees, and a pond. Unfortunately, by that time the tiger was institutionalized. Instead of roaming throughout the expansive habitat, Mohini spent her time in a small corner where she paced restlessly in a twelve-by-twelve square.

Most people who work for themselves are looking to escape the rigidity that comes with having a boss. One person might want the freedom to pursue new or unconventional ideas and another might want more autonomy in creative output. Maybe you have a dream you've always wanted to follow and the only way to do it is to work for yourself. And, of course, some people just can no longer stomach the idea of taking orders from someone else, period. Whatever the motivation, working for yourself allows you to decide when and where and how to do your job.

But then something interesting happens. In order to juggle the responsibilities of being both employer and employee, many people start implementing the same procedures & policies they experienced at previous jobs. They adopt the same schedule as everyone else or start judging their work with an overly critical eye. They answer work email late into the evening or on weekends. Often there is even more pressure to be constantly on the clock as every coffee break or lunch hour becomes an opportunity to get just a little more done. In other words, they start pacing on the same small patch of land even though the cage has been removed.

But what if there was another way?

I was recently in a virtual networking meeting with several other self-employed financial advisors. One advisor, who I would guess is 10ish years older than me, was joining us from a two-week trip to Jamaica with his wife. It turns out they are big Deadheads and were there to spend several nights watching Dark Star Orchestra recreate Grateful Dead concerts. (I know an animal rights lawyer who similarly uses vacation time to follow Pearl Jam around the country.) This advisor explained that one of his goals when starting his solo practice thirteen years ago was to travel at least one week per year for every year that he remained in business.

That sounded like a great idea to me (maybe not the Dark Star Orchestra part, but certainly the travel) and I told the advisor that his ability to build his business around his life goals was inspiring. Before we ended the meeting, though, he gave me a well-meaning warning. "You know, I travel for thirteen weeks a year, but that doesn't mean I stop working. You can never really stop working when you work for yourself."

That's a fair point. Self-employed people will probably need to stay more connected during extended travel since all of the responsibilities for their businesses rest on their shoulders. It takes a lot of work to be both boss and employee – you get all of the responsibility for everything all of the time, with none of the stability of working for someone else. But, to invert Spider-man's catch phrase, with great responsibility comes great power: the power to do things differently than other people, to set your own schedule, to work wherever you want, to be the kind of boss you always wish you had.

Wouldn't you want to work for a boss who treated the star employee (i.e., you) like they were valued? Or who gives the top performer a little more leeway on schedule or remote work? How about a boss that doesn't expect you to reply to email once you leave the office? You can choose to be that kind of boss – and that top-performing star employee (again, this is you we're talking about) is going to be happier because of it.

Of course there will still be some long days or times when you need to pull yourself away from something fun to catch up with work. Of course. But that doesn't have to be every day. If you're going to put the time & effort into working for yourself – accepting all the responsibility with none of the stability of a straight job – you might as well be the kind of boss you would be proud to work for.

What goals will you set for yourself in your new role as Best Boss Around? I'm going to steal my colleague's one-week-away-per-year-in-business goal, but I'm also allowing more room to decide when stepping away from my office is the smarter long-term decision than sticking to a rigid schedule on a beautiful spring day.

Timothy Iseler, CFP®

Founder & Lead Advisor

Iseler Financial, LLC | Durham NC | (919) 666-7604

Iseler Financial helps creative professionals remove stress while taking control of their financial futures. As both advisor and accountability partner, we help identify current strengths and weaknesses, clarify and refine your long-term goals, and prioritize understandable, manageable, and repeatable actions to bring long-term financial well-being. Reach out today to take the first step.

31 views0 comments

Recent Posts

See All
bottom of page