Actually, I Don’t Want Coaching to be my Job.
I was talking on the phone with an old friend I had not heard from since I left Seattle Washington over 20 years ago. They found me through this blog, so I know they will read this. But, to them it is mostly a repeat of our conversation.
After some small talk, they asked me how I liked being a “full time” investor and coach.
“But, I’m not,” I said.
We then talked about my leaving the W-2 world and I explained why. I explained I liked working in a corporate environment. It was a nice change from running the consulting group. I also explained that I’d like to find and work with the right start up. One that has a really great idea for a product or service and could use the unique experiences I could bring to the party.
One of my unique strengths is I can cross the technology-business barrier and see the bigger picture and more to the point, how technology fits into solving business problems. I can go deep into the minutia of technical details and I can comfortably sit in a boardroom and distill the details to the salient points. I easily manage people and have always earned the respect and loyalty of those I managed.
We also talked about what I am doing now.
I explained how I toyed with the idea of full time paid coaching and then realized it took the fun out of it. I still mentor, in fact I picked up a new “student” yesterday, but paid coaching is just wrong for me. We also talked about the Field Guide for Investors. I walked them through how it came about, what my original idea for it was and how it has morphed into something with its own destiny. I also explained that I think I have a great opportunity to nudge it more in the direction I want with respect to commercial investing. I am building content and a support structure to help others learn to invest in commercial projects.
But, mostly we talked about what I was building and why. We chatted about the transition to commercial investing. We talked about raising money in that environment and how different the private money aspects were than on the residential side of the world.
Then the magic question. He asked, “so, what DO you want to be when you grow up?”
I know I will re-enter the corporate world whether I go to an established firm, a start up or form a start up, I know it will happen and I know it will be sooner rather than later. I won’t do it because I have to, I will do it because I want to do it. When you aren’t dependent on a salary, you can obviously pick what you want to do but more importantly you can do it without having to worry about financial matters. In other words, you can do the right thing without hesitation.
Right now though, I am putting most my work energy into the following:
- Refining my commercial investing strategy
- Sharing that strategy with others through mentoring
- Refining the tools needed to support that strategy like a specially targeted version of RIPP and FastDraft
- Sharing those tools with others
Once I get those tasks completed, I will then decide on the next steps.

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