2019 Year In Review

Better late than never…

2019 was a kick in the ass. It was probably the most different year I’ve had to date in the last 5 years.

I traveled a lot less, worked a ton, worked more, and stayed more quiet than usual.

I got out of some bad habits and built some better ones – even if they are 11pm runs. A lot of things changed this past year, but if I boil them down to 2 key decisions.

The Two Primary Shifts I Made in 2019

Moving to Austin

Moving to Austin was something new for me. After not having a home for a couple years and going full digital nomad – I moved to Austin and signed a lease. I like it – I don’t love it. I miss San Diego – a lot. I miss New York – a lot. I had to make an emergency trip to NYC recently to get a jolt of city energy, but overall Austin haas been a good move. The fitness and the entrepreneurial environment are solid and this year I’d like to set up a system where I am based in Austin, but do more satellite short-term trips to different places and work on a “hub” living strategy. It’s amazing what just having a hub made possible.

Owning My Calendar

Jordan B Peterson wrote something last year that stuck with me.

Treat your schedule like the outline of a day you would very much like to have.

Something about that quote clicked for me. Up till that point, I treated my schedule like a bratty teenager treats rules they don’t understand – rebellious. I wanted to do whatever I wanted whenever I wanted.

But I took a step back this year and realized it actually wasn’t getting me to the places or do the things that a I wanted to do. So I decided to do something about it this year.

I started weekly and monthly reviews thanks to Taylor Pearson (he has a great course here) and I started using Woven Calendar to help me with this and it helped me so much that I decided to become an advisor to the company (you should download the app).

Discipline = Freedom

For a long time, I was focused on just doing whatever I wanted to do. But as it turns out – working off my daily whims sounds really nice – but it didn’t help me actually do what I wanted to do.

What did help? Writing down what I wanted to do and then working backwards from there to figure out how I was going to pay the price of admission to the goals that I had was the one thing that shifted things for me.

Major Highlights of 2019

1. I moved to Austin
2. I stayed put for 3 months straight (a new record for me)
3. Traveled to Malibu for Wild Ventures retreat.
4. I made my first (very small) angel investments.
5. I was intentional about expanding a few specific startup advisory positions.
6. Spent a week Portland for WDS
7. Did my 3rd Hell on the Hill event with Jesse Itzler
8. Renewed a love/hate affair with SF while traveling for Woven
9. Did a fall trip to Tahoe for Spartan Race and the Caveman Coffee crew.
10. Did an impromptu NYC “shot in the arm” trip NY “Jolt” trip.
11. Did my first stand-up comedy routine (3 states and counting). I’ve been having fun having a new hobby to test out when I show up to a new city.
12. Launched a new welcome trailer for IMPOSSIBLE TV and redesigned the site to be clearer about where IMPOSSIBLE is headed.

Things I Am Going To Do in 2020

I usually title this – things I want to do. Partially that’s been due to lack of planning. I didn’t have a plan for the year or where I’d be, so I’d just wing it and hope I get close.

With stability comes clarity – so here’s a few things I’m going to do this year.

1. Launch my first event (June). Stay tuned.
2. Run Rim2Rim2Rim
3. Launch the Mr. Impossible Challenge (Fall)
4. Knock 4 Things off MY IMPOSSIBLE List
   • Go to tactical awareness weekend (April)
   • Do Standup Comedy 100x (I’ve gone up a few times already and I’ll be sharing more about this soon).
   • 30 day parkour challenge.
   • 30 day Muay Thai challenge (Zach, I’m looking at you)
5. Launch at least 12 videos on IMPOSSIBLE TV
6. Launch a bi-weekly vlog
7. Go to Alaska finally
8. Do a quarterly retreat
9. Do 2 week kiteboarding trip (and get mediocre)
10. Do Hell on the Hill and get a decent time.

How did your 2019 go? What things on your #impossiblelist will you be doing in 2020?