2018 is all but over, there are only 12 days left in the year. By just about any measurement, I’d say it was a decently successful year. I traveled to and through some new states including Texas, New Mexico, Florida, Louisiana, and Colorado. This was my first full year at Automattic. We moved across the country and bought a home. My team and I did our meetup in Playa Del Carmen back in March, and the last 5 days of this year, Kristen and I are heading to Switzerland to snowboard the Swiss Alps. It was a fun, comfortable year.

2019 is about getting uncomfortable. It’s about evolving. I’ve always followed the “sage” advice of tripling down on your strengths – getting better at what you already have an aptitude for. I’ve always been strong, so I lifted weights for years and became stronger. I’ve always been a decent student, so I went back to school and picked up a Master’s degree, graduating back in March.

It’s time to start tripling down on my weaknesses.

Now: I’ve never been a New Years resolution type of guy. In fact, I’ve never actually made one. I’ve always considered resolutions as “things people break.” I’ve always looked at motivation like a going and coming, fleeting feeling. Some days you’re motivated, some days you aren’t. I’m a firm believer in cultivating discipline, routine, habit.

Discipline, routine, habit, callousing the mind – this is the ethos of a man named David Goggins. I had read Jesse Itzler’s Living with a SEAL back in 2016 before it was well known who the person who trained Itzler, acting as the catalyst of the story was. I watched Joe Rogan’s interview with the man in February where he gave a condensed version of his life story. Then, nine days ago when it released, I picked up and read his book/autobiography “Can’t Hurt Me.”

It’s probably impossible to give someone like David Goggins a fair shake when recounting parts of his life, so I encourage you to buy his book or do your own research on him. For those of you who have never heard of him though, this man:

  • Completed three hell weeks in BUD/S (the hardest evolution of arguably the toughest military training in the world).
  • Completed the aforementioned training on broken legs.
  • Completed 52 ultra marathons between the ages of 30 and 42, winning some of them and finishing top 5 in most of them.
  • Holds the world record for pull-ups completed in 24 hours at 4,025.
  • Did I mention he did all of this with a hole in his heart? How about a learning disability? One of the few black men in special warfare? The list goes on.

This is just the tip of the iceberg. Again, if you have any interest or doubts – do your own research. If none of this impresses you, you’re not being honest with yourself and the world around you.

The book was the icing on the cake in helping me determine what I needed to do next. I know I’m capable of doing more, and I decided to commit to something that I didn’t want to do, every day, for 100 days. As David Goggins would say: I’m going to do something that sucks, every day.

The Plan

The plan is two-fold, but it starts like this:

  • Every day, for 100 days, I’m going to run at least a mile.
  • Every day, for 100 days, I’m going to write about and share that progress.


The why is the easiest part of this whole thing: because I hate running. I am a 260 pound man (at least at the start of this). The reasons why are a bit more complicated, but stick with me:

  • Why Run? Because I hate running, and there’s something to be gained from doing something you don’t want to do every single day.
  • Why one mile? I loathe running as it is, knowing I have to get up and run at all every single day is going to require immense willpower for me. Setting an unrealistic goal like “5 miles a day” or “300 miles in 100 days” is going to set me up for failure. Perhaps I end up doing a lot more, perhaps I end up getting just 100 miles at the end, the point is I know physically I can do one a day, the rest is willpower.
  • Why Share? Mainly because I’m not Mr. Social media. I’m a private person by nature, an introvert. It’s going to be uncomfortable sharing my slow miles and paltry distances. I’m doing this for me, but perhaps people will see my big ass do it with the hopes that realizing anyone can.
  • Why 100 days? After the first quarter of 2019 there’s a lot of work and travel obligations I’m not fully sure how to work around yet. I also want an opportunity to re-evaluate and modify my goals and 100 days feels like a good initial number and goal.
  • What about rest? Injury? The tentative plan is to lightly jog or even walk the mile every 7th day as active recovery, but I’m still going to complete the mile. I’m going to listen to my body. The plan is to not miss any days, but if I have to, I will make them up the next training session, and be complete within the 100 days no matter what.


I’m going to post each and every day of the 100 days on this site.

Date: X/X/XX
Day: X of 100

I will also be using my Nike Run App and FitBit Versa to track miles and time.


  • I’m interested in seeing how fast I can get, both in short distance running and endurance. Putting a number on this now seems silly, since I have no idea what I’m doing or talking about.
  • I’d like to culminate all of this in completing some sort of challenge as a new way to test myself, perhaps a marathon or obstacle run. More to come as the challenge evolves.
  • Ultimately, however, the main benefit here isn’t how fast I get, how far I can go, or about doing or completing any races. It’s not about trophies. The real trophy here is forcing my mind to do something for me that it doesn’t want to do. I surmise I’ll find the most real benefits there.

I’m far from perfect. I’ll never be as strong as a lot of people, as smart as a lot of them, or as fast. What I can do, though, is become the strongest, smartest, and fastest version of myself. 2019 is about taking the first step in that direction.

Last year, I donated – this year, I’m suffering.

Are you interested in following this journey? There are some buttons on the right to help make that happen. I don’t run ads, I don’t e-mail, I just post.

This post proudly written in Gutenberg, the new block editor for WordPress. I’m really starting to like it.