Nineteen years ago I made what seemed like an obvious decision to work for myself. The decision was in part a desire for more freedom, but it also reflected a spate of challenging bosses I had experienced. I was ready to bet that I would be a better boss of me.
While the decision did provide some relief, it also provided plenty of challenges. On the plus side, I didn’t have to face managers who included but were not limited to (snarky-alert):
—The Screamer: This type of manager is near extinct because society will no longer tolerate it. Screamers lack self-control or believe their volume will elicit the best performance. As a young consultant, I worked for a screamer who improved my game but at a cost.
—Charlie Fun-Time: This manager has a great golf game or some equivalent. There is often an annoying chasm between his jovial personality and the anxiety the team feels to perform. Relationship driven, Charlie is able to finesse his way through the corporate maze, which is a definite skill but hardly inspiring.
—The Quiet Introvert: This manager doesn’t really want to be managing but by virtue of strong skills and track record, the introvert has been catapulted to a place he doesn’t want to be. Highly competent, he is often joyless in the pursuit of team goals.
—The Double Checker: This boss loves details and insists on combing through everything, no matter how attentive his team is to the minutia. This leaves the team dispirited because of a perceived lack of trust.
—The Endless Strategist: This manager has vision but lacks an understanding of how to get the trains to the station on time. Practical considerations are not a strong suit, reducing the likelihood of success. This team shifts from feelings of inspiration to pessimism and defeat.
Going solo, I would no longer face the challenges these types of bosses posed, but I also wouldn’t experience the benefit of some of my great managers. Great managers do the obvious but apparently hard-to-do things. The elite managers I experienced took genuine interest in me as an individual; they led me to the answer but didn’t give me the answer. Most important, they always had my back.
My favorite manager told me to start the day by walking from one cubicle to another, saying hi to people by name (this was before cubicles were replaced by remote offices). “The name means a lot,” she counseled.
After I put myself in the driver’s seat, I discovered that managing me was harder than I thought. The good news is that I haven’t fired myself. Almost two decades in, I am still at it and ready to share a few important tips. Specifically:
—Prepare to be a mix of cheerleader and tough-love giver: You need the supportive, “I can do it,” voice as well as calling yourself out at the first sign of slacking or resignation. In my hands, I carry one pompom and one boot for the proverbial kick in the pants.
—Get comfortable wearing many hats: At project start, I wear a sales hat, project delivery hat, finance hat and technology hat but there are more hats (e.g. mediator, negotiator). I can never say, “That’s not my job.” It’s like the plaque on Harry Truman’s desk that read, “The Buck Stops Here.” Otherwise, the bucks literally stop.
—Manage short-term and long-term thinking: Most organizations have people designated to think long term — strategy, partnerships and competitive differentiators, for example. There are also people who focus on the “now” — sales bookings, product releases and messaging. As a company of one, I have to think both short and long term. I have to manage the risk of getting stale with the risk of taking on too much “new.”
Even though I am better today at being my own boss, I still grapple with a few thorny issues. For example, getting accustomed to the roller-coaster experience still requires effort. I know to expect a pace that goes from busy, to quiet, to busy to who the hell knows, but the unpredictability can still fray my nerves and send me to reread Andy Grove’s book “Only the Paranoid Survive.”
I also know to value the slow periods, which consultants commonly refer to as “beach time.” Downtime is very useful in recharging my engine. For me, this translates to more tennis, hobby writing, baking and time with friends. Still, in the midst of all these fun activities, I will find myself wondering what things I should be doing to spur on business.
It turns out that I am my toughest boss. There can be no mercy when it comes to sustaining a sole proprietorship, and on top of that I have high standards. For those pursuing this path, remind yourself that selling is job one, rejection is seldom personal and persistence wins the day. The price of freedom can be high, but I wouldn’t have it any other way.
