What do I want to be when I grow up, take 5. Structured introspection at choice point.

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

2. Analyze the Past

3. • First I opened up a spreadsheet and listed
most major projects since college.
• I rated each projects on a
satisfaction/happiness/engagement scale.
OVERALL
Things I've Done
Community Organizing 8
Non-profit BoD 9
Startup 7
Post-Startup Biz Exec 4
Integration w/ New Parent Co 6
Systems Building 7
•List anything that takes up a lot of
time, ie jobs, hobbies, volunteer work,
etc
•Try to get a 5-8 examples
• I hid the OVERALL
ratings column.

4. • Next I broke it down by factors.
Factors
tribe /
teamwork
fun social
utility
legend money Average
Things I've Done
Community Organizing 10 4 10 6 0 6.0
Non-profit BoD 10 6 10 10 0 7.2
Startup 7 8 5 8 8 7.2
Post-Startup Biz Exec 4 4 5 6 8 5.4
Integration w/ New Parent Co 7 6 4 8 8 6.6
Systems Building 2 6 5 6 8 5.4
•Think through the factors that might have provided satisfaction in
each different project
•Add those as column headings
•Examples: teamwork; social impact; autonomy
•My preliminary list is below.
•Rate each project 1-10 on each factor.
•Average the ratings for each project.
contribution to something
meaningful; right livelihood
street cred, fame, glory, ego boost

5. • Unhide the overall column.
Factors
OVERALL tribe /
teamwork
fun social
utility
legend money Average
Things I've Done
Community Organizing 8 10 4 10 6 0 6.0
Non-profit BoD 9 10 6 10 10 0 7.2
Startup 7 7 8 5 8 8 7.2
Post-Startup Biz Exec 4 4 4 5 6 8 5.4
Integration w/ New Parent Co 6 7 6 4 8 8 6.6
Systems Building 7 2 6 5 6 8 5.4

6. • Where are the contradictions?
OVERALL Average Comments
Things I've Done
Community Organizing 8 6.0
Non-profit BoD 9 7.2
Startup 7 7.2
Post-Startup Biz Exec 4 5.4
Integration w/ New Parent Co 6 6.6
Systems Building 7 5.4
•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.
Should be different but
Averages are the same

7. After going through the process above, I discovered my story didn’t correlate. For example, 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. On the other hand, 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.
OVERALL Average Comments
Things I've Done
Community Organizing 8 6.0
Non-profit BoD 9 7.2
Startup 7 7.2
Post-Startup Biz Exec 4 5.4
Integration w/ New Parent Co 6 6.6
Systems Building 7 5.4

8. • So I added Engineering.
• I, also, made some comments where I thought
this framework was too narrow or missing
factors.
Factors
OVERALL tribe /
teamwork
fun social
utility
legend money craft /
engineering
Average Comments
Things I've Done
Community Organizing 8 10 4 10 6 0 3 5.5 made life long friends
Non-profit BoD 9 10 6 10 10 0 8 7.3 downside: stress of budgeting
Startup 7 7 8 5 8 8 10 7.7
Post-Startup Biz Exec 4 4 4 5 6 8 4 5.2
Integration w/ New Parent Co 6 7 6 4 8 8 7 6.7 good personal growth, too extroverted for the long term
Systems Building 7 2 6 5 6 8 10 6.2
Better but still a bit off.
More on that to come.
Patience is requested.

9. Project Yourself Forward - Too Simple Version

10. • 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.
Factors
OVERALL tribe /
teamwork
fun social
utility
legend money craft /
engineering
Average
Things I've Done
Community Organizing 8 10 4 10 6 0 3 5.5
Non-profit BoD 9 10 6 10 10 0 8 7.3
Startup 7 7 8 5 8 8 10 7.7
Post-Startup Biz Exec 4 4 4 5 6 8 4 5.2
Integration w/ New Parent Co 6 7 6 4 8 8 7 6.7
Systems Building 7 2 6 5 6 8 10 6.2
Things I Could Do
Role in Startup - Anticipated 10 10 6 9 9 8.8
Role in Startup - Tested 9 8 8 ? 9 8 8.3
Story Social Media - Anticipated 3 6 9 9 9 7.2
Story Social Media - Tested 7 5 6 7 9 10 7.4
Watch TV 1 4 1 1 0 1.4
Play Games 5 9 1 5 0 4.0
Build Games 4 8 5 7 10 6.8

11. Project Yourself Forward – A Better Model

12. Factors
OVERALL tribe /
teamwork
fun social
utility
legend money craft /
engineerin
g
Average Comments Rank
OVERLL
Rank
Average
Dif
Things I've Done
Community Organizing 8 10 4 10 6 0 3 5.5 2 5 3
Non-profit BoD 9 10 6 10 10 0 8 7.3 1 2 1
Startup 7 7 8 5 8 8 10 7.7 3 1 2
Post-Startup Biz Exec 4 4 4 5 6 8 4 5.2 6 6 0
Integration w/ New Parent Co 6 7 6 4 8 8 7 6.7 5 3 2
Systems Building 7 2 6 5 6 8 10 6.2 3 4 1
0
Adding in Weighting - Dropping Out Money 9 mismatch
weighting--> 1.0 1.0 1.0 1.0 0.0 1.0
Community Organizing 8 10.0 4.0 10.0 6.0 0.0 3.0 5.5 2 3 1
Non-profit BoD 9 10.0 6.0 10.0 10.0 0.0 8.0 7.3 1 1 0
Startup 7 7.0 8.0 5.0 8.0 0.0 10.0 6.3 3 2 1
Post-Startup Biz Exec 4 4.0 4.0 5.0 6.0 0.0 4.0 3.8 6 6 0
Integration w/ New Parent Co 6 7.0 6.0 4.0 8.0 0.0 7.0 5.3 5 4 1
Systems Building 7 2.0 6.0 5.0 6.0 0.0 10.0 4.8 3 5 2
0
I 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 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. I added weighting and experimented
with different weights.
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 had no impact on any factors except Social Utility. Increasing that
improved the model
OVERALL Average Comments
Things I've Done
Community Organizing 8 6.0
Non-profit BoD 9 7.2
Startup 7 7.2
Post-Startup Biz Exec 4 5.4
Integration w/ New Parent Co 6 6.6
Systems Building 7 5.4

13. • 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!
• Here’s a template you can copy and use.

14. Factors
OVERALL tribe /
teamwork
fun social utility legend money craft /
engineering
Average Comments Rank
OVERLL
Rank
Average
Dif
Things I've Done
Community Organizing 8 10 4 10 6 0 3 5.5 2 5 3
Non-profit BoD 9 10 6 10 10 0 8 7.3 1 2 1
Startup 7 7 8 5 8 8 10 7.7 3 1 2
Post-Startup Biz Exec 4 4 4 5 6 8 4 5.2 6 6 0
Integration w/ New Parent Co 6 7 6 4 8 8 7 6.7 5 3 2
Systems Building 7 2 6 5 6 8 10 6.2 3 4 1
0
Adding in Weighting - Dropping Out Money 9 mismatch
weighting--> 1.0 1.0 1.0 1.0 0.0 1.0
Community Organizing 8 10.0 4.0 10.0 6.0 0.0 3.0 5.5 2 3 1
Non-profit BoD 9 10.0 6.0 10.0 10.0 0.0 8.0 7.3 1 1 0
Startup 7 7.0 8.0 5.0 8.0 0.0 10.0 6.3 3 2 1
Post-Startup Biz Exec 4 4.0 4.0 5.0 6.0 0.0 4.0 3.8 6 6 0
Integration w/ New Parent Co 6 7.0 6.0 4.0 8.0 0.0 7.0 5.3 5 4 1
Systems Building 7 2.0 6.0 5.0 6.0 0.0 10.0 4.8 3 5 2
0
5 mismatch
1) Add weighting
Template and formulas here:
https://docs.google.com/spreadsheets/d/16fLLRcCQw6Fl3w7UBJQUswGGNQumEao5yg0V3cBac2I/edit?usp=sharing
2) And Add Rank.
3) Then dropping out money…
4)Improved the model

15. Factors
OVERALL tribe /
teamwork
fun social utility legend money craft /
engineering
Average Comments Rank
OVERLL
Rank
Average
Dif
Things I've Done
Community Organizing 8 10 4 10 6 0 3 5.5 2 5 3
Non-profit BoD 9 10 6 10 10 0 8 7.3 1 2 1
Startup 7 7 8 5 8 8 10 7.7 3 1 2
Post-Startup Biz Exec 4 4 4 5 6 8 4 5.2 6 6 0
Integration w/ New Parent Co 6 7 6 4 8 8 7 6.7 5 3 2
Systems Building 7 2 6 5 6 8 10 6.2 3 4 1
0
Adding in Weighting - Dropping Out Money 9 mismatch
weighting--> 1.0 1.0 2.0 1.0 0.0 1.0
Community Organizing 8 10.0 4.0 20.0 6.0 0.0 3.0 7.2 2 2 0
Non-profit BoD 9 10.0 6.0 20.0 10.0 0.0 8.0 9.0 1 1 0
Startup 7 7.0 8.0 10.0 8.0 0.0 10.0 7.2 3 2 1
Post-Startup Biz Exec 4 4.0 4.0 10.0 6.0 0.0 4.0 4.7 6 6 0
Integration w/ New Parent Co 6 7.0 6.0 8.0 8.0 0.0 7.0 6.0 5 4 1
Systems Building 7 2.0 6.0 10.0 6.0 0.0 10.0 5.7 3 5 2
0
4 mismatch
Template and formulas here:
https://docs.google.com/spreadsheets/d/16fLLRcCQw6Fl3w7UBJQUswGGNQumEao5yg0V3cBac2I/edit?usp=sharing
5.Doubling social utility…
6. Improved it further

16. Project Yourself Forward – The Messy Reality

17. There’s a discussion of this
slide in the companion
Medium article, last
section.