Making Deliberate Decisions about the Evolution of My Career

A Seven Year Retrospective and Looking Ahead to What’s Next

  1. What emotions come up when I envision myself in this future?
  2. What would I miss about this option if I don’t choose it?
  3. What pushes me away from choosing this option?

Scenario 1: Keep on Keeping On at The Ready

The obvious option is to keep doing what I’m doing at The Ready. I don’t know how else to really say that what I do at The Ready, in almost every aspect, is my dream job. We exist to change how the world works and we use ourselves as the first and best test environment for a better future of work. Fully self-managing, self-set compensation, fully distributed, great benefits, three times per year in-person retreats in excellent locations, crazy access to well-known clients who trust us to work on gnarly problems… it really doesn’t get much better for consultants.

Scenario 2: Internal Leadership Role Elsewhere

I’ve always felt a tinge of imposter syndrome for having never worked in a large bureaucracy like the ones I consult with everyday (other than my extremely brief foray in the American public school system as a teacher). Would I be able to bring the type of change The Ready is hired to bring if I were a leader in a “regular” organization? Would I fall prey to the same things I see the leaders I work with fall prey to? Would the toolset I’ve developed at The Ready serve me well if I had to operate from the inside? I don’t know — and part of me is curious to find out.

Scenario 3: The Indie Shift

I always assumed I’d be an indie of some sort. When I started making money from my first website in 2009, I figured I’d be doing some version of that for the rest of my life. Even after going to graduate school, I figured I’d have some kind of solo coaching/consulting/writing endeavor that would form the cornerstone of my career. It was while I was studying independent work as a research project that I became aware of holacracy, sociocracy, and other fascinating organizational theories. Once I found The Ready, I put the dreams of an independent career on the shelf so I could focus as much as possible on building this company. Even while pouring myself into The Ready, though, I’ve always kept one foot in the indie world by writing as much as I can, particularly through my The Deliberate newsletter. Sometimes I catch myself thinking and feeling that The Ready is still just a detour from the indie career I’m supposed to be creating for myself.

Scenario 4: The Wildcard

Must my career continue down the organizational consultant/coach route? All three scenarios above are basically just reformulations on the same raw ingredients (with maybe a bit more ambiguity in the actual work to be done in Scenario 3). Should I be casting my net wider, though?

A Third Way Emerges

Obviously, there are options outside of the four I just described and as we like to teach our clients, there’s almost never a simple binary decision to be made. There’s always a third way. What’s the third way between, or mixing, these scenarios?



Organization design guy at The Ready.

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