Project Pillars


Over time I’ve found myself with the recurring issue of what to do next. This is a problem that is also faced by most teams / companies and one of the more successful ways I’ve seen them take this challenge on is by comparing the costs / benefits of each effort and using that as a metric in the decision process.

Thus the point of these pillars is to initiate a process that will help me compare my numerous projects so I know what the best prospects are at any one time.


Approx. the points for each project by adding them up.

Max is: 5 Min is: -3

So likely stick to the positives. We can label in Trello like:

  • High opp - green [5+]
  • Medium opp - yellow [3 - 4]
  • low opp - red [-3, 2]

  • is it cool (0, 1):

  • am I excited (-1, 1):

  • will i learn something (0, 2):

  • is it valuable (0, 2):

  • how much does it cost (-2, 0):

  • total:

Is it cool (0 - 1)

This is a super subjective thing but I think coolness lends itself well to both keeping me motivated and getting kudos / long-term value out of projects, so it’s useful to have.

  • 0 - not cool
  • 1 - cool

Am I excited to build it (-1 - 1)

If I’m not excited to build it, motivation may be hard to come by. Moreover, if I’m not excited to build it then the other things better be damn good for me to waste my time doing something I don’t necessarily want to do.

  • -1 - ugh I don’t want to do it
  • 0 - meh
  • 1 - hecka yeah

Will I learn something (that I want to learn) (0 - 2)

Projects don’t necessarily need to be cool in their end form. It’s possible to build something solely for the passive rewards of better understanding the domain. I want to encapsulate that.

  • 0 - won’t learn anything I’m excited about
  • 1 - will learn something I’m excited about and that’s useful
    • like async in a new language
  • 2 - will learn something I’m excited about and that I think is valuable to me, my growth, and future plans
    • like AI, new paradigms, new design systems

Is it valuable (0 - 2)

Value comes in a lot of forms and I want this to be as generic a rubric as possible cause I love doing an array of things and would like this to be a simple one-stop shop. Thus I’ll delegate the value scoping to more specific planning sessions (like Qs or Hs) and leave it high-level here.

  • 0 - low value - A minor improvement / build, unlikely to see a meaningful change, $0
  • 1 - medium value - A significant improvement / build, good chance of meaningful change
    • infra: saves 1 hr / month
    • product: 100 views / month, $1 / month
  • 2 - high value - A large improvement / build, high chance of meaningful change
    • infra: saves 10 hrs / month
    • product: 1000 views / month, $10 / month

How much does it cost (-2 - 0)

Now a cost / benefit analysis isn’t complete until we talk about cost. Similar to value, the cost of something really depends on the scope but here we’ll stick to a high level but I’ll provide some guidelines that could be used to gauge.

  • -2 - high - A quarter+ of time
  • -1 - medium - A ~month of time
  • 0 - low - A weekend or weekday week of time

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