The origin story of my coaching practice

Last year was tough. Good, but tough. In a period of just a couple of months I left my job, ended a six-year romantic relationship, and moved across town.

One of my favorite books, The Defining Decade, taught me that there are three significant categories of decisions that determine something like 80% of how our lives will look: work (what we do to meet our resource needs), community (who we choose to spend our time with; friends and lovers), and location (where we choose to spend our time and resources). Having just one of those areas be up in the air can be destabilizing.

I had significant shifts in all three.

At one point during all these shifts, I realized that I was going to run out of money. So I thought to myself (using one of the tools in my toolkit): what’s my hedgehog (ht Jim Collins) for this moment?

Adapted from Jim Collin’s book, Good to Great

As I reflected, I noticed a pattern among things people have said to me over the past few years:

  • “You’re like the most productive person I know.”
  • “How is it possible that you get so much done?”
  • “I don’t get it. Where do you find the time to do all this stuff?!”
  • “Your organizational skills are pretty unreal.”

Now, I went to MIT as an undergrad so most people attribute my organizational skills to that. There’s some truth to that, but if I’m honest, the process of writing my masters thesis took my organizational practices to the next level. I won’t bore you with the details, but suffice it to say that learning how to write that huge paper triggered me to dive wayyyyy deep into time management, self-mastery, personal systems, and things of that ilk (and if the details won’t bore you, I’ve written about how it all went down over here).

So at this point (back to the hedgehog hunt) I was thinking that folks would pay for my knowledge about getting things done. And I was definitely passionate about it. I wasn’t sure if I could be the best in the world at it, but hey, I wasn’t trying to do it forever…

And I didn’t need to rely on anyone but myself to do it. Although I knew that self-sufficiency wasn’t a crucial feature of my work in the long run, at this time of rapid transition the ability to be economically light on my feet felt critical.

Then I had to figure out how to share this knowledge with people in a way that made sense. Should I do group classes? support individual people? write something? As I thought about it over the course of a few weeks, I realized two things.

The first was that I really enjoyed being a mentor. Back in my youth group days, it was impressed on us that being mentored and mentoring was a necessary part of spiritual growth. At times, I had mentored (discipling was I think the term we used) up to four guys at a time and some of those relationships lasted 3–4 years! I knew from that experience (which was all of a sudden looking a lot like training) that I really enjoyed connecting with people one-on-one as well as seeing and supporting change over time.

The second realization was inspired by a wonderful, brilliant friend, Aisha Shillingford. Through our work at the Interaction Institute for Social Change, we were discussing a training series she had developed (which she was thinking of turning into a book?) about supporting movement leaders to be driven by love. I was totally inspired by her desire to go small and in as opposed to the societal defaults of big and out. Both scales are important, for sure, but I felt better prepared to do the former.

And thus my idea of productivity coaching was born. I would share my knowledge and experience about productivity with friends and other connections in one-on-one settings.

I started putting the idea out to a few friends (really like three people) and one of them (my good friend Erin – to whom I’ll forever be indebted) was interested. We hashed out the details over a few beers and then got started with our first session.

(Actually now that I think about it… it’s been almost a year since those first fateful days. I should probably circle back around with him and other people I’ve worked with to see if anything from our sessions is still sticking…)

Anyway, that’s the story as I see it. To date, I’ve worked with 10 people and I’m in the early days of working with the 11th and 12th. Crazy, right?

Ok. So. Why am I sharing this here? A few reasons:

  1. To make transparent (including to myself) how I understand the story about my beginning this work.
  2. To inspire other people who are at similar life moments.
  3. As a foundation on which to share more things in the future.

The more I do this type of work, the more I can see how this may be an important part of my life in the long-run. And as a communications strategist, I believe that communication isn’t an afterthought of work; it is a fundamental part of the work. It feels important to start publicly telling the story of this work as it goes along. Especially because I can already see things starting and needing shift. Example: My original frame for the coaching was around productivity, but that doesn’t seem like it fits anymore… and even the term coaching sounds a little patronizing at times…

Anyways… here we go!

Next up: a peek inside my shadow calendar, one of my latest experiments. Shout out to Julian for the nudge to write about that.

PS — thanks to the folks in the Evolutionary Leadership crew(s) who gave me feedback on this before it went live.


If you’re interested, you can find other thoughts of mine in even rawer form via my blog where I put out my unedited thoughts approximately once a day. You can also find me via my website, get my daily blog posts (did I mention they’re unedited?) via your inbox, or sign up for my weekly(ish) newsletter.