The Hagakure #78: Win-Win

“The path that stops in the middle of the forest” (Thank you, S.)

As I write this, I have logged 882 hours of paid coaching over the last 3 years.

Becoming a coach back in 2021, I wanted to engage with different people in different places. I wanted to have flexibility, and own my schedule. And I wanted (as always) to learn as much as possible.

Coaching has delivered on all these.

The journey has had its ups and downs, more ups than downs. Being a coach, working for myself and on my own has been a powerful combination that forced me to reckon with a lot of things. There’s something about trying to help others get their shit together when you don’t have your own shit together that compels you to do the inner work. I certainly had my fair share of tribulations, some of which I’ve related here in the past.

I grew in ways I couldn’t imagine. While I’m clearer than ever about how little I know, I have paradoxically become a calmer person and more accepting of what I cannot control and what I cannot know. I still don’t have my shit entirely together, but let’s say there are less loose ends.

So much so that late last year I started seriously toying with the idea of going back to an operating role as an engineering leader.

Plot twist.

Why?

Becoming more confident in who I am (and who I’m not) led me to revisit my past in engineering management. A lot of it was difficult, exhausting. How much of that was due to the events, and how much of it was due to the way I perceived the events? How was that perception colored by who I was then? What would it be like today?

I have also learned a lot about what makes people tick, how the brain works, and I have been exposed to many different challenges from clients the world over. The more I learned, the more curious I got about the question, “what would it be like if I went back and applied this stuff myself?”

And let’s be honest: coaching can be lonely. You’re always the outsider. It’s hard to gauge your true impact. I never thought I’d say this but I started feeling like I wanted to belong to something again.

So that’s why I have taken the mental step of opening myself back up to full-time roles, putting out some feelers to executive recruiters I know, and letting the ball roll from there.

The In-Between

I don’t know what’s going to happen. I had been hearing the job market is tough, but now I can confidently state from experience: the job market is tough.

But whereas I think “past me” would be getting quite frustrated about all the ghosting, the slow moving interview processes, and the many folks who either don’t seem to know what they want or are being downright opportunistic… present me is somehow enjoying this.

For one, I thought I was a lot better at interviewing than I really am. Realizing that has been a bit of a tough pill to swallow—but ego is the enemy. I have been honing my approach, coming across as more direct, more pragmatic, more structured, less abstract and philosophical. Maybe I’ll soon write more about what this whole job search experience has been like.

The thing is that I care, but don’t care.

Whether I end up getting an interesting new job or not is outside of my control to a large degree. I’m focused on what I do control: preparing, reaching out, creating a little urgency in recruiters, asking questions for context. I don’t control the other side.

The key realization for me has been that my need—the itch to keep scratching—is to help others and to share what I know. Coaching is one way. Engineering management is another way. This newsletter is another way. Workshops, teaching could be other ways.

For the first time in my life, also per the suggestion of my therapist, I am allowing myself to exist right now in this in between. I’m still coaching while I’m interviewing for full-time roles. It may go one way or another. I don’t know. What I do know (provided I’m still breathing) is that I’ll continue sharing and helping others along their path while I keep learning and growing myself in the process.

Win-win.