I honestly liked freelancing better than running a company, but I think that’s mostly out of my own personal weaknesses.
As a freelancer, I could participate and collaborate as an equal in conversations, and express opinions without them meaning much of anything to anyone. I could try and fail; I could hold and abandon wrong opinions or ways of thinking; all without significant consequence or political fallout. Bonus: freelancers are always the underdog, so people’s natural prejudgments are to root for them.
(I say all this entirely with the benefit of hindsight, and I am not putting down freelancers—it’s just that the grass is deludedly green on the former side of my fence.)
One of the most frightening moments of my life was when I found myself waxing about what leadership was and wasn’t—and suddenly turned around and discovered there were people actually (WTF) following me, including people for whom single decisions I made could have a significant impact on their life.
I have always believed leadership to be about responsibility, not authority, but the weight of that statement means more when your everyday decisions have a legitimate visible impact that goes beyond yourself and your house.
Power is a useful thing for getting things done, but it’s something I never sought to have, something I’m often in denial of having, and certainly something I often wish I never had. I simply want my opinions and ideas to win when they’re right, and I want them to lose when they’re wrong, on the basis of merit alone.
I would a million times rather be a useful nobody than a useless somebody.
Most of my life I’ve been psyching myself up to believe I was powerful enough to make something happen that I wanted to see become reality. So to suddenly find myself in conversations where I realize I’m carrying a not-so-concealed weapon (“leadership”), that is perfectly apparent to everyone else, but not so myself, is personally terrifying.
Add to that an increasing number of eyes, judges, opinions, and the natural course of life’s various disappointments, and the pressure is not slight.
At some point, my fear of whether I was good enough was overtaken by the fear of whether **I** was good.
(No doubt, every day I acquire more empirical justifications for my self-doubts, but as far as capability is concerned I’ve long learned this peace: My opinion of my capability is irrelevant. If I am responsible, either I am going to carry out my responsibilities to the best of my ability or I am not.)
On the other hand, the nagging question of my goodness is harder.
Having seen and experienced firsthand the impact of a leader who was not good (to me), I pray most days (sometimes all day) not to become like that. But hearing thirdhand rumors of my motives questioned, and sensing apprehension and silence where there was once mutual respect and trust, always makes me spiral into questioning myself.
I know it’s human nature: the entire reason we put people on pedestals is to knock them down. And what a friend we have in schadenfreude—what a friend we have indeed, right?
Ultimately, I settle in a place of some peace about my doubts of my own goodness, too.
Because I can’t personally judge my goodness.
All I can do is search my heart and share my doubts with people who I know are not afraid to take me to task. I have to trust their assessment—both positive and negative.
Here’s the thing though: I’m not a good person by default.
Just like any other person, I am capable of doing wrong and hurting people.
And knowing that, all I can do is pray for wisdom and keep working on my own destructive and biased thinking, improving my decision making, and trying to constantly get perspective for how I can most usefully be a better person.
This is yet another reason to love Dee Hock’s instructions to leaders to spend 50% of their energy managing themselves.
At this point, I am absolutely certain that is my most important job.