Sabbatical Update

Month One

My paid three months off started October 1st. Sadly my plans are not going as well as I had hoped. I have four goals I’d like to accomplish by the end of my Sabbatical in January of 2022. Goals I think are good. Maybe?

  1. Regain my pre-Covid fitness level.
  2. Level up on Python and build proficiency in Cybersecurity by spending several hours a day on HackTheBox, TryHackMe, and BugBounty. Ending in December with a eJPT certification and at least one bug bounty complete. I have wanted to advance in these areas for a long time, but just have not had the time. I enjoy this stuff so much. I am working on my Linux systems 100% of the time again, and I have really missed that.
  3. Improve my leadership skills.
  4. Rest.


It’s been three weeks and my fitness goal has no progress. I am having trouble finding where to land. CrossFit again? HITT? Boxing? Heavy lifting? I just don’t know! I am forcing myself to do something by the end of this week and give whatever it is a few weeks at least, even if I hate it.

Level Up

This is the one area I am really making progress in. In three weeks I have learned so, so much. I am in the top 4% on TryHackMe, and I have almost completed the Pentester track on HackTheBox and the Bug Bounty track on HackTheBox Academy. I am also about 1/2 way through a Python book. So pretty solid here. I am spending about 4-6 hours a day on this goal.

Leadership Skills

This is a difficult one. Not just to accomplish, but to gauge progress on. I started on this about a year ago. I have some hard things that need doing, and it’s very exhausting to be honest. Career coaching and counseling play a big part in figuring this out. My mantra is simple. “I can’t lead others if I can’t lead myself”. So I am working on leading myself right now.


This one, I am pretty much just failing hard at. For good reason though. I am a dad. I am dad to many teens. I spend so, so much time driving kids to school, appointments, and events and such. Like it’s an insane amount of my time that goes to this stuff, not to mention just parenting and trying my best to love these kids and not burn out. The load is heavy, but it’s worth carrying, so I do. There is no sleeping in, there is no getting to bed early. I am still burning the candle at both ends, and it’s thankless work that frankly yields very little rewards in the now. It’s a long game I am playing and I hope that when it’s time for these kids to be adults, that they are good ones. I’ll rest when I am dead, right? Seriously though, I am trying to figure out how to build in rest. I do go for coffee after I drop off kids, and sometimes I go to a park and breath in the fall air, when it’s not filled with smoke and dust … because … Fresno.

I really did need this though. I am so thankful for where I work. A Sabbatical is one of the many, many amazing perks I enjoy working at Automattic (VIP). You might think about joining me, we are hiring.