Recently, I challenged myself to commit to a gig by February 1 (see timer courtesy of Crushpath). My readers sent a lot of great feedback, questions…and a few very concerned head shakes. Some wanted to understand how I’m narrowing and filtering the options so that I’d be sure my next step was the right one. So with full-warning that this post is a bit of a selfie, here’s a snapshot of my process.

Getting to Know the Older Guy

Prior to starting the 90-day timer, I spent some time on what gets me up in the morning. Earlier in life, motivations were pretty straightforward (beer, money, opposite sex, beer), but with age, they’ve become more complicated. After seeing a pattern of ex-execs jump at the next “shiny metal object” job that came their way, I decided to dig deeper in the hopes of avoiding the wrong thing.

In a society infatuated with the self, there’s no shortage of tools designed to help people understand what makes them tick: Enneagram (I’m a 3), Myers-Briggs (ENTP), What Color is Your Parachute (mauve). I was even given a set of purpose cards (worst poker game ever). You could get caught up running self-diagnostics for months, but I think it’s best to pick one or two frameworks that fit your personality. Ultimately I found the most insights by asking myself: 1) When do you feel the most alive and why? 2) What do you want your legacy to be? 3) Who do you “want in the boat” with you?

I’ll spare you the navel-gazing details, but what I learned was this: I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives.

Clarifying and Learning

Once I had a sense of the goal, the process for attaining it seemed less Herculean. I listed out my “Must Haves” (e.g. creative control, dinner w/ family 4 out of 5 weekdays, intellectual interest) and “Can’t Haves” (e.g. long commute, board members who think they know best, overly crowded market).

I interviewed people with similar early careers, but different paths afterwards. People who had been founding CEOs, but had gone on to become venture capitalists, exec coaches, serial entrepreneurs, social entrepreneurs, nonprofit founders, whiskey-shillers, ranchers and confidence men (last one made up). I looked for people who shared my values and passions, and learned everything I could. Then I listed the most appealing options.

Extreme Narrowing

With list in hand, I jumped into a professional dating period that rivaled Warren Beatty in the 70’s. Lots of good people and ideas, but in Silicon Valley everyone wants to be CEO of their own thing. Also, it’s hard to commit to people you haven’t worked with before – and difficult to get two strangers excited about pursuing the same goals.

Realizing the process was taking too long and going in weird directions, I set the timer and committed to focus. Since then, I have become shark-like in my priorities. No meetings that don’t advance the goal. Always aware of my daily tasks. I even set up a war room in my office for managing priorities and scheduling.

Since then, I’ve only focused on options that get me excited. These could include starting something from scratch (company, social venture, nonprofit, fund), becoming “Founding CEO” for an early-stage start up, and even taking a shorter term executive role to help companies get to the next level (selling the company, raising a round, etc.).

I’m giving each opportunity a rank of 1-5 in three categories: Gut (do I just want to go do it?), Heart (am I emotionally drawn to it?) and Head (does it make sense to do it?).

For each line item, I drive hard to a decision. If the opportunity remains interesting to me, I’ll take whatever next steps are required to learn more to bring me closer to a decision.

The best filter I’ve found is to work directly with the team involved. There’s no better way to get to know the opportunity than rolling up your sleeves on something together. This is especially true for new careers – if you’re a mailman and want to be a hand model, best to try it out first.

Final Thoughts

I found it helpful to take time away from all the voices. Too much advice can cloud judgment, and often the advice is what those people would do in your situation, not thoughtful insights into your unique path. (But please keep your comments coming – I’m totally listening.) As a culture, we get so wrapped up in what other people think, it can be hard to find purposeful work. We put too much emphasis on personal brand and image over happiness. It’s a shame. Most people are too busy taking their own selfies to care anyway.

You can be as structured about this process as you want, but my experience is that the gut knows best. The more closely I listen to it, the better the options become.