I just returned from a road trip to Long Island to see dear friends. The kids were plugged in to movies in back, so I actually had a long time to think while navigating around the edges of NYC. I also had a lot of time to listen to music and sing loudly, to listen to podcasts, and to talk to people on the phone, but the thinking is the point here.

This coaching enterprise is my first foray into really being (and feeling) self-employed. I have done some contract work where I was technically my own boss, but I made my client my boss. Now, I am, without question, the boss of my business. And that reality has a lot of pros and cons that go with it. The thing that I was mulling in the car as I stopped and went between Brooklyn and Canarsie, and between Canarsie and JFK, between JFK and the Southern State Parkway, was that perhaps the most important decision I make as my own boss is what kind of boss I intend to be. And the funny thing is that this same decision applies to all of us, self-employed or otherwise, because no matter your employment situation, you are surely your own boss for some part of your day. If you are not ever your own boss, I would seriously like to talk to you about that.

Slide1But I digress… being the boss of yourself at any time means you have some decisions to make about how you are going to handle that responsibility and what kind of boss you want to be. My old tendency was to be the taskmaster boss: making big (often unrealistic) lists of things that need to get done, cracking the whip on “down” time, demanding high levels of performance and imposing emotional consequences for a job not completed or not well done. My employee self was always scurrying, trying to get those items crossed off, but also always afraid of underperforming, rushing to move from one to the next but occasionally becoming paralyzed by the sheer amount being asked or the difficulty of making a clean decision when faced with harsh penalties. My employee self had trouble sleeping, would wake up early and run To Do lists mentally to ensure everything got covered. My employee self was not terribly productive, but sure was busy, and tired, oh so tired.

Slide2That’s not the kind of boss I want to be, and it really isn’t the kind of boss I am to myself anymore, although there is still the occasional pull in that direction. The boss I am now uses words like “learning curve,” “creativity,” “experiment,” and “balance.” The boss I am now sees value in her employee as an individual before, during, and regardless of the list of tasks that “need” to be done. The boss I am now wants to value growth and integrity over productivity and checklists. The boss I am now reassures her employee when things get hard and when she can’t, she calls in a friend to do it: “You can totally do this. You really can.” The boss I am now celebrates successes (even the really small ones), ensures adequate time for training and thinking, and occasionally insists that I go home early on Fridays.

Slide3And all of this is a choice. It’s a choice I make as a boss, as a self-employed boss, but it’s also a choice I make as an adult human. I get to choose to value my own growth and integrity over productivity and checklists. I get to choose balance and time with my family alongside of ambition. I get to choose how I talk to myself when I don’t get something right or when things don’t turn out the way I expected. I get to choose, even if it’s only for part of the day. Sometimes seeing myself as boss and employee in my non-work life helps me remember that these are all choices. The boss in me gets to choose how I will treat the oh so willing employee. The employee in me gets to ask questions and occasionally put her foot down if the boss is getting all kinds of crazy.

And here’s the funny thing, the part that will surprise absolutely nobody who’s worked for an excellent boss, when I am the best boss, I am not only honoring my values and feeling confident, I’m also insanely productive. It really does work best this way. The scolding and hardness only breeds discontent and feelings of incompetence. The encouragement and confidence creates new opportunities, abundant energy and creativity.

I love my boss. She’s awesome. How’s yours?

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