Ep. 1 - First 4 Weeks of Project Ulysses

So what does a 26 year old do on a sabbatical after leaving three lucrative white collar professions?

Travel around the world? Nope. 

It's funny because my parents actually suggested I just buy a one way ticket to travel somewhere. I'll do this eventually. But it's actually not a "want" of mine at this point.

What has continued to occupy my time are personal projects. Can't call them "side" since they have become my main endeavour. 

This post, and a series of it to follow have been inspired by the Startup podcast that tracked the creation of Gimlet Media (Thanks Andy and Scott for introducing this to me) + further encouraged by others to release more content on my journey and thoughts (Thanks Shubham and Vikram). 

So, being the creative genius I am, I named this the OMD Series. If you don't know what OMD stands for just think about it. Through this series I hope to take you on a ride through my journey of exacting the various sets of personal projects I conduct. 

The first project I'll introduce as part of this series is Project Ulysses.

So what is the project?

To perform introspective design. As the name suggests, the participants do self-directed or guided introspection and work to create systems that fit their personal design. For this I gathered 8 professionals from different professions, age groups, industries, gender, stages in career and personalities. 

I meet with each participant one-on-one twice a week for an hour + the participant spends 15minutes a day 3x a week doing personal reflective exercises. Estimated 25hours/week of time commitment on my part. 

I originally committed them for 18 weeks but I'm now realizing (Week 4 as I write this) most may go through faster. Faster as in, 9 weeks. This is also due to realization that a concurrent execution plan (#agile) may be more effective. Confirmed again how bad humans are at forecasting anything. 


How it's going so far?

It's fun. I actually find myself looking forward to the one-on-one sessions. #winning.

I've also been collecting feedback weekly and most have been positive so far so that's been great. I mean, the problems I'm trying to solve for them are problems I'm actively learning about myself so we are aligned here. 

There definitely is a sense of adding value to someone else's life in doing this project. Especially since I am literally interacting with the customer. 

I've also been discussing my project idea with various individuals in the Toronto Tech scene and have been getting very supportive feedback. Kind of like pitching I guess?

I was surprised but the number of people who've applauded me starting these projects on a sabbatical at my age have been enormous. While I know I want to be as intrinsically scorecard driven as possible, getting external encouragement helps. 

I wouldn't look at it as a means of external validation though... but just emotional support from the spectators as I run my marathon. 

The four weeks haven't been without bumps though. I started with 8 but now I'm down to 6. Mixed feelings about this. I think long term it's for the best. But we'll see. 


Wait so why is thing thing called Ulysses? Why the hell are you doing this? To find out, subscribe to my newsletter to get updated on the blog for future stories AND get 3 learnings I found valuable from the week. 


Daniel LeeOMD Series