An exercise I sometimes share with clients, especially those who are rethinking their career aspirations around a big life transition, is the Odyssey Plan. It comes from the book “Designing Your Life” and it asks you to develop 3 different 5 year plans, with significant personal and professional milestones mapped out.
The exercise rushes you — you’ve got 12-15 minutes to come up with 3, so you can’t get bogged down in details. Drafting several plans keeps perfectionism and indecision at bay. (It’s often easier to think of many ideas than a single one.) You give each plan a 6 word “catchphrase” representing the unifying principle behind it. Once you’ve concocted some plans, you can start asking questions to get at the underlying values and ambitions it reveals.
Here’s a set of videos with an overview of the whole thing, from the creators. I don’t subscribe to all of their ideas or mental models, but I think there’s a lot of good in the exercise. So ignore any stylistic quibbles, and give it a try if you’re feeling stuck.
