It’s not exactly going as planned.

Taking a look back at an “Odyssey Planning” exercise from 5 years ago and what’s next.

Back in the spring of 2017, my old friend from college, Sean, reached out about creating a virtual book club to go through Designing Your Life. Five of us got together on a weekly video chat to go through the chapters and exercises and help each other think about what might be next for us. One exercise I thought was fascinating was creating “Odyssey Plans.”

What is an Odyssey Plan?

I’ll let the author explain it himself in this video below. (If you’re interested, there’s also a whole playlist that goes into it in more detail.)

The Plans

As Bill mentions above, the idea isn’t really to “plan” it out but to develop a few different ideas and possibilities to spark some directional movement. It’s been 5 years since I created these plans originally, and they cover a 5-year span, so I thought it would be fun to share these fantasies and see how closely they lined up with reality in the end—sort of a “How it started vs. How it’s going” kind of thing.

Plan 1: Leaning into Design Leadership & Love Life

This plan was perhaps the most “predictable” of the bunch since it followed the trajectory I was currently on. The general idea was to build up my design cred and eventually lead a design team, build up some passive income, and do the whole get married and have kids thing back in Seattle.

Plan 2: The Small & Fluffy Business Owner

This one played up one of my fantasies of owning a pet supply store and getting a pet-related product onto Shark Tank. I have always loved cute fuzzy animals and would love to incorporate more puppies in my life. I’ve had lots of pets in the past, and it seemed reasonably doable.

Plan 3: DIY Rustic Real Estate Empress

This one was more about my interest in real estate, crafting, hosting events, and creating a community. The idea was to eventually open a shared community space that also included some crafting areas. I really liked this idea, but at the time, I was the least confident about how I’d pull something like this off, and it seemed the least related to my current trajectory.

Reality

I think about this old Steve Jobs quote a lot, especially when I’m looking back at where I’ve been.

“You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future.” — Steve Jobs

After looking through the original plans, I noticed several elements that actually kind of panned out somehow, though the timing was a bit different. And some things I tried but decided not to pursue. So I thought it would be fun to quickly sketch out the “Reality” version, looking back at the past 5 years in the same format.

Things that went a little differently

• I tried the pet sitting/dog walking thing for a bit. I realized I don’t really enjoy picking up other people’s dog shit, so that’s a no-go.
• I went to Shoe School and actually made a pair of (very ugly) shoes by hand. I also tried Japanese woodworking. Both of these require a lot of work and space to make a mess. I still have all my leather and wood supplies but haven’t used them since. Maybe someday I’ll get back around to it when I have the studio space.
• I got into a much healthier and happier relationship in 2018 with Shawn, who I’ve known since my Art Center days.
• I ended up in a “Design Director” role much earlier than I had expected, which might have accelerated my “oh shit, now what do I do with my life” crisis.
• I danced in Brazil when work surprised us with a trip down to the Brazil office. And I ended up getting several trips to lovely tropical locations paid for by work or scholarships.
• Left Oakland but ended up in Los Angeles instead of Seattle. I think we are planting roots in LA, but I still miss both Oakland and Seattle.
• I ended up learning more about real estate through grad school and started a little bit of investing through Fundrise.
• Finally launched my online store to sell some of my craft/art stuff. Totally not profitable last year. But I wasn’t able to spend much time on it while in school, so hoping to do more now that school’s over.
• Two of my plans included opening a physical retail space. Really glad I didn’t end up trying to open a shop during the pandemic.

Next up

So, what’s next? I just started my job as an Assistant Planner at Gruen Associates. I think one of the cool things about working at GA is that they’ve done a lot of work in LA over the years, so it’s neat to be able to physically experience it as a “user” when I go around town. It’s like the warm fuzzy I get seeing one of the apps we worked on in the hands of real users... except this is a more “immersive physical reality” kind of thing.

When I drafted these Odyssey Plans five years ago, I never imagined this outcome was even a possibility. To be honest, I often second guess myself and wonder if I should have stuck to the more “predictable” trajectory career-wise. But I’m really interested in seeing how this side quest plays out, so I think that’s a good sign.