Contemplating the Next Adventure, Charting a Path Forward.

Finding your path toward your true calling.

The process of contemplating the next adventure in my life started a little over 24 months ago. I could not have imagined that the second half of this period of contemplation would have up-ended our nation the way it did. Politically and socially, things got a little weird. I am sitting here writing this after almost a full year of not really interacting directly with anyone outside of my family.

To go back to where it all started, you can take a trip to my thoughts two years ago to see what I was thinking then. This next one will be what I am thinking now.

I will start it out with a self-coaching exercise.

In a perfect world .

There is a common question that coaches often ask. The question is a variant of, “If money were no object, and if what you wanted to do was guaranteed to work, what would you do?” I get why the questions is good. It puts one in touch with their passions and desires so that they can focus on charting a course toward making that a reality.

I have been spending some time (and given the coronavirus, probably too much time) pondering this question.

I revisited all my old side projects and startup ideas and realized quickly that building a ‘thing’ — a startup or a product- was not really at the core of what I enjoy. I enjoying building products, but with everything I do the part I enjoy the most is working to create a team to create a project.

Reflecting on my past ‘good memories’, they all centered either on helping a founder, working with an employee to become a better version of themselves, or massaging a team to become a ‘superstar’ team.

I did explore (and am still exploring) the idea of a venture studio, but the part that excites me the most about a venture studio was not the money, it was all about people. When I thought about the ‘perfect world’ question, I imagined the day to day of running a studio and what I realized that no matter what I have done, either at the startups I worked at, with my consulting work, running the accelerator, or the fund, the part I enjoyed most was enabling the founders. The coaching part was the part that I looked forward to.

The common thread that runs through the startups I have worked at, the accelerator, the fund, and all my various consulting engagements was all about people, strategy, leadership, teams, and growth (both business growth and the growth of each individual at an organization).

I toyed with the idea of a leadership academy online (this was during the pandemic) — and again, this idea of helping people become better and more capable versions of themselves is the part that brought me joy.

The common thread that keeps coming back is that this is the part of the work of working with startups I like the most.. it is the founders. It is helping them to discover and embrace their own agency — to help them to become ‘actors’ on the stage. It is helping them to step into themselves, to be the support system for them to undertake a hard personal journey.

Over the past year, I have found joy in both the paid coaching work I have done and the unpaid help I have given to numerous founders. It makes me full.

The feedback I have received from others has confirmed this. When I asked others what I need to be doing with my life, the responses where either, Startup Community Builder or Coach.

I have many ideas for startups, but what has become clear to me is that my passion is helping people.

I still do not know exactly what the future holds, but I do know that coaching others, either in the context of a company, or directly as a coach, is going to play a part in my future.

To do my own startup, to work at a VC fund, a Venture Studio (either my own or at someone else’s), work at someone else’s startup, or in the corporate space- I know that I will somehow end up gravitating toward coaching and helping people be better versions of themselves.

In a high growth startup, growing leaders is the only way you can scale.

In a fund, helping your portfolio companies founders be better leaders is the best way to make returns.

In order to make our world better, we need leaders, and the best and highest use of my time is helping to grow them, and then teaching them how to grow and support leaders.

It may have taken me some time to see clearly my own ‘North Star’ — the reality is that I have known this for a very long time — it just took a pandemic to get me to listen to my own inner voice.

I am going to keep doing what I have already been doing for the last 20 years — focus on becoming a better version of myself, and helping others to do the same.