Distance as a service

How going indie helped me be more myself — and also took me further from many of the people I work with

About five years ago I worked with a serious executive coach for the first time. At the start of our work she put me through the usual battery of personality tests, and as we reviewed the result she expressed surprise. “You score very low on Achievement, that’s unusual for an executive,” she said. “And you score very low on caring, too — that must be a challenge.”

The puzzle to solve early in our work together was: If my profile looked so different from the average exec, how did I end up here? But the answer to that puzzle led me somewhere else: I’d be much happier on my own, or leading a small team of senior people, that I would be as a typical exec.

In the short term, that coaching helped me let go of what remained of my ego as an exec and to focus mostly on getting out of the way. But in the longer term, it planted the seed that grew into my indie work now. I already saw myself and organizations differently than most did; the way to get the most out of that was to step outside the organizations and help leaders see things my way too. Not all the time, but as a counterbalance to how they saw things on the inside.

Venkatesh Rao writes that this isn’t just about seeing things differently, it’s about relating to work in an entirely different way:

People take jobs where their inner realities will be most relevant to the inner realities of the company, allowing them to express those realities and be seen. For consultants though, it is less important to be seen and more important to be seen through. In both senses: you are an optical instrument that enhances the vision of another and your motives are transparent and easy to account for, just like a good optical instrument should have easy-to-correct aberrations and flaws.

Few books have made me wince more — in a good way — than Rao’s two-part bible of indie consulting, The Art of Gig. And few portions of the book made me wince more than this one:

Over time, it becomes hard for long-time indies to even relate to employees of client organizations and recognize their ordinary human needs in a business setting. Because you no longer operate in the context of a large organization, you lose the ability to operate in anything but an individual capacity. Don’t underestimate the slow erosion of empathy and emotional and lifestyle distancing that occurs as you log the years as an indie unless you do something to stop it. The longer you’re in indie mode, the stronger the impedance mismatch between your needs and client needs because you gradually lose the internalization of big-org needs at a business level and empathy for paycheck employee mindsets and needs at a more fundamental level.

Ooooooof. I feel this in my bones.

The double whammy of this distancing is that I was drawn to indie work in the first place because I didn’t identify with some of the core needs of most full time employees. Being indie for 18 months has reinforced my core motivations. It has definitely pulled me further from the base assumptions of a typical employee or manager. I’m more interested in autonomy than belonging. I’m more interested in excellence than recognition. I’m more interested in getting tested than in getting coached.

I don’t frame these tradeoffs with any judgment. One side isn’t better than the other. But the tradeoffs are real, and they are stark.

I have stronger business opinions now than I used to. I’m more interested in complicated problems than simple ones. I’m less accepting of organizational “muddling through” to protect people’s feelings, for better or worse. I’m less tolerant of poor performance.

A lot of this is because I’m “unburdened” by many of the typical people-centric tradeoffs that come from having an opinion. I externalize these tradeoffs to the client. (Or more accurately, probably, they externalize some of their cold-blooded thinking to me.)

How much of this is about the seat I now sit in, and how much of it is about “who I am”? Am I becoming harder or am I just hard enough? Am I oversimplifying or am I thinking more clearly? Am I dodging people problems or am I putting them in their appropriate context? It’s hard to say — only a longer track record of being right or wrong will help me say for sure.

But do I prefer the version of myself that has these strong opinions? Yes, definitely. I like being able to take an unambiguous stance. I like being able to say what I think. And I like the feeling of independence that engenders.

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I’m going to start adding a reading recommendation each week, just for fun. This week: An old article from The New Yorker, Where Do Eels Come From? It’s about exactly what it says it’s about.