The Odyssey Plan ⛵️

Hey everyone,

If you know me, you know I’m a big planner. I often spend a lot of time thinking about the future, setting goals, daydreaming about aspirations, etc.

While the benefits of thinking about the future have a limit, I do think it’s important to be intentional about where we’re headed. It’s the whole “fail to plan, plan to fail” thing.

With that in mind, I found a helpful planning framework this week called The Odyssey Plan. The plan, based on a book from two Stanford professors, incorporates elements of design thinking and allows you to take an iterative approach to ideating/brainstorming about how life might look in the next few years.

person working on blue and white paper on board
Photo by Alvaro Reyes on Unsplash

Essentially, you come up with three 5-year plans. The first describes what life would look like if you continued on your current path. The second plan pertains to taking a completely different path (i.e. what you’d do if plan #1 wasn’t an option). And the third is what you’d do if money and social expectations were no object.

The idea is that the exercise allows you to reflect on what you come up with, and eventually figure out what feels right and what your real goals are. The intended outcome is a comprehensive vision rather than just focusing on career trajectory.

I’ll admit the whole “life design” or “lifestyle design” thing sounds hokey, but I think there are some good takeaways from this process. After all, if you aim at nothing, you’ll hit it every time.


Pete’s Picks ✅

  1. Podcast episode: I heard a great episode of How I Built This about the founding of McBride Sisters Wine. It’s got all the elements of a great story and then some—the sisters grew up across the globe from one another and didn’t know the other existed until they were both adults. This one won’t disappoint.

  2. Series: I’ve been in a spooky mood lately, and got really into Unsolved Mysteries on Netflix. It’s exactly what it sounds like, but there are some real head-scratchers in there. If you’re a true crime fan, this is for you.


Have a great week,

Peter