Why I keep shifting careers

I’ve had a very unusual “career” path. Actually, hold on.

career: a profession for which one trains and which is undertaken as a permanent calling.

Yeah, let’s not call it a career. It’s more accurate to say I’ve been working in some way or another for the past 23 years, with much more action than training or permanence.

For years, I felt a lot shame about this — I was a weirdo, an outsider.

But a lot has changed in the last 20 years, and thanks to the work of some really amazing people (like my friends Abby Falik and April Rinne), concepts like “gap year” and “career portfolio” are worming their way into mainstream consciousness.

I see the shifting as an integral part of an iterative process.

Here’s a graphical depiction of Newton’s algorithm for polynomial root finding:

Depending on where your initial guess is, it might take you more or less time to find the answer. But you always get to (one of) the answers.

I like to believe there is such an answer (or set of answers) for how I contribute to others.

From my rational culture, I have no way of knowing if it’s actually true, but I have found the belief itself leads to a mindset and actions that improve my quality of life (#pragmatism).

Every vocational experiment I run is an iteration giving me data about how accurate the hypothesis was.

Computer science
Cooking / Restaurants
Organic Farming
Ayurveda
Earthen Building
Chaplaincy / Death
Coworking Spaces
Event Planning
Executive Coaching
Conflict Coaching
Mediation

Some people hit a hole in 1! I’ve seen it. Not me.

The point is — like any series of experiments — to use the data from each one to influence the hypothesis of the next one.

What do I like to do with my days?
How much screen time can I handle?
How important is cash money to me?
With whom do I like to work?
What problems am I excited to solve?
What do I like to create?
What can my identity and community realistically handle?

There have been many days where I wished my journey was more linear.

But if I had really wanted that, I would have made vastly different choices with all the heaps of opportunities and privileges I had.

I didn’t.

There are other days when I can feel the wind of adventure blowing across my face. I am the D&D adventurer I spent my childhood imagining. I have no idea what will happen in the grand tomorrow and know that our infinite collective potential will rise to meet the challenge.

Once more unto the breach! 🗡️