Reverse Engineering My Life

Reverse Engineering My Life: using myself as a case history with various asides, details, and instructions.

For a quick overview, here’s the slideshow version with more images and less text.

Five years ago, at a point of life transition and in search of new projects, I had the unsurprising thought that I might be able to predict what I’d find meaningful in the future by doing a systematic review what I’ve done in the past.

I’m numbers guy so it involved numbers.

And I can’t even add a few numbers without opening a spreadsheet so I started a spreadsheet.

It worked out pretty damn well.

I’d like to give a shout out to Dr Dave and Shrink Rap Radio, a great psychology interview podcast. His #520 with Barbara Bradley Hagerty inspired me to write this up. Also, to my good friend John Owens of Mooseheart Coaching for providing invaluable assistance and challenges during this latest round of deciding what I want to be when I grow up.

Step 1 — Analyze the Past.

The process:

First I opened up a spreadsheet and listed major projects since college.
● Anything that takes up a lot of time (jobs, hobbies, volunteer work, video games) counts.
● Try to get a 5–8 examples.

Next I gave each project an OVERALL rating on a satisfaction or happiness or engagement scale. Your pick. Each project gets rated 1 to 10.

>● Now hide the OVERALL rating column.

Then I broke it down by Factors.
● Think through the Factors that might have made you happy in each different project. (Perhaps engaged is a better term than happy.)
● Add those as column headings
● Example: Work with team; Social impact; Autonomy.
● Rate each project 1–10 on each factor.
● Average the ratings for each project.

> ● Unhide the overall column.

Where are the disconnects?

● Does the order shown by the averages pretty much match your overall assessment?
-● Yes, great! Proceed to the future.
-● No — then:
— ● What’s missing?
— ● Add Factors.
— ● Rate the new Factors.
— ● Does that fix it?
— ● Iterate
● Note that the relative order and obvious contradictions are more important than the actual numbers.

After going through the process above, I discovered my story didn’t correlate. Two items with quite different overall ratings ended up with the same average.

I had to ask myself why did I like Systems Building and dislike the Biz Exec crap. (Apologies to happy Biz Execs.) This was pretty easy to answer. One involved building things immediately and concretely…what I’ll call Craft or Engineering.

The other occasionally bordered into baby-sitting.

I liked working with folks to set personal and enterprise goals and trying to make those harmonize. I liked marshaling the resources and setting up the framework to get shit done…but you know, that’s pretty close to Engineering if you define Engineering broadly as finding, building, assembling or inventing a collection of elements and then crafting them to create a desired effect. I had very little patience with folks that weren’t intrinsically motivated and was happy to give maximum slack to those that were. Downside: if someone was having serious problems and didn’t tell me, I’d notice when their corpse began to smell.

So I added Engineering. Also, I added Comments to point out factors that weren’t taken into account.

This got me much closer but still not really there. For the sake of this discussion, let me assume that I’ve hit a ‘good enough’ version and take the next large step. I’ll loop back and refine this.

Step 2 — Project Yourself Forward : Too Simple Version

The Process:
● List things you could do next.
● Think through how they would likely rate on each factor.
● Determine the top few and explore them in real life to see if your assessment is accurate.

I then listed a lot of options and boiled it down to the top two and then did what I could to test my assumptions. The results were pretty darn good. The illustration below shows some results along with just a few other hypothetical options thrown in for a baseline.

Step 2 revised — Project Yourself Forward: A Better Model

The Process:
● Add weighting to the Factors to allow differences in importance.
● This tweaks the averages: switch to Rank as your key indicator.
● Test all Factors by first zeroing and then doubling the weight to see what Factors are irrelevant and which are key.
● If necessary, test new Factors. Iterate between including or excluding Factors and changing weighting to get your story as consistent as possible.
● It should never match perfectly. Remember reality is always messier than you can effectively model!

You can see the resulting spreadsheet below. There’s a template you can use shared as a Google Spreadsheet.

I’d listed the Factors I considered major and by luck they were close enough in relative importance for some patterns to immediately emerge. I did need to do a few passes to include all the Factors that seemed highly relevant.

However, the more Factors, the more likely that some are going to be more important; in the current model they’re all equally weighted. Perhaps, say, you like teams but also a high level of autonomy and have to experiment with the trade off.

In my case Money was a distortion.

What I discovered:

Money was not a Factor in satisfaction. I dropped it out because I was planning ‘retirement’ and didn’t need it to be a Factor. Surprisingly the model got a lot better. Thinking it through, it was really only a factor in how much time I could afford to devote to any project. It was not a source of satisfaction in and of itself.

Doubling the weighting on all Factors had no impact except Social Utility. Increasing that improved the model further.

Step 3 — Project Yourself Forward : The Messy Reality

You say someone stole a strand of your hair, you say it’s missing but you don’t know where. — Dr John — Zu Zu Mamou

Once I had everything in a nice package, it was time to start messing it up; the order to chaos ratio was way too far to the side of tidiness. And, besides, I was retiring in part in order to follow an impulse that I wanted to write. I’d been feeling vaguely trapped by the time and bandwidth demands of my job. Wouldn’t I want to be getting outside the box of previous experience? I felt that growth might be elsewhere.

Now then, there are apparently folks that undergo personal growth effortlessly like a balloon floating up into the sky. That’s not my case. I’m in the “all my truths are bought in blood” Nietzschian tradition.

Carl Jung’s writings have always provided a useful framework for me. He distinguishes appropriate tasks for the first half of life from the mission of second half. In the first half, we play our strong suits in order to make a place in the world…hopefully pulling in income and accomplishments. In the second half we need to turn and face down everything in our makeup that we’ve chosen or been forced to exclude.

I don’t know if things now fit so tidily into that sort of life history (or perhaps I’ve just had to do it backwards) but I do believe that is a useful distinction. I added separate columns for Learning and Growth. Learning extends what you do well into new realms. It leads to mastery and works the flow. Growth is often movement into pain, inadequacy, and residual childish reactions. It is the world of dreams and ill-formed impulses. It brings the excluded into relationship with our everyday selves. There can be a flow here, too, because this is often a creative process but it can also be stumblingly painful.

Writing, in my experience, can be essay-like on the learning side (done to clarify thought, advocate, etc) or aimed poetry-like at growth by bringing forth from the depths. If one is a specific case of more widespread issues, ones scribbling can even border over into art. I had no such ambition but I did want to explore writing. I, also, intended to keep some irons in the fire on strong-suits side.

Here’s the spreadsheet again on the diastole of ordering process. A bit more hypothesis testing and flailing and it might be time to tidy up and re-evaluate.

Summed up: my attempt to reverse engineer personal satisfaction proved a its value…much more than I expected…and has stood up to a few years of testing the results to boot.


I decided a year or so back that if I was going to write, I might as well seek readers. I’m replacing my old system (spam everyone I know who might be interested) with a mailing list. You can sign up for that below. I’ll let you know when I publish something.

Berkeley Backpacking Biz Lifer, System Builder, Coder, Community Organizer, Music and Evolutionary Biology Geek. Sign up and my projects at

Berkeley Backpacking Biz Lifer, System Builder, Coder, Community Organizer, Music and Evolutionary Biology Geek. Sign up and my projects at