2017: Annual Review

2017: Annual Review

Just a quick fyi, this post may contain some affiliate links.

The Oh So Essential Annual Review

Without measurement and adjustments it’s damn near impossible to grow and improve. So with that in mind, this is my annual review for 2017, I’m hopeful that the increased transparency helps keep me accountable to making even better decisions in 2018 and beyond.

Measured Change

Quite a few things happened for me and my family in 2017, here are some notable things:

  • We had our first baby which has been an incredible step forward for us. Being a father is both amazing and exhausting in so many ways but I definitely wouldn’t change a thing about it.
  • We moved across the country, coming back to the DC area from the San Francisco Bay Area. This was partially motivated by the baby but largely fueled by our love for all things DC, especially all of the friends and family we have in the area.
  • I took a new job, leaving Nuna and joining [SourceClear] as their Chief Security Officer. This was an exciting step forward for me and my career in terms of learning opportunities, new challenges, and a very much needed fresh start.
  • We bought our first house together back in the DC area. This one has been interesting amidst the baby and work as it’s a little bit on the fixer-upper spectrum, we’ve both been able to demonstrate our handier and creative sides (side note, my wife far supersedes me on the creative front) while working together to build something we both love.
  • On the health and fitness front, unfortunately I’ve largely hovered in the same place without making much in the way of gains, I’m currently coming in at 215 and about 33% BFP (according to my Fitbit Aria) which isn’t terrible but could be way better. By terrible, I'm using my previous fitness state about 7 years ago as the very low bar. This is definitely an area for improvement for me though, so I can maximally function as a father and husband.
  • I started to commit to a few daily routines which has really helped me maintain a discipline throughout my entire day, in no particular order this includes:
    • Setting a todo list of the most critical stuff to get done
    • Meditation
    • Learning a new language (or something new)
    • Prayer and/or bible study
    • Keeping up on just enough news but not getting sucked in
    • Reading
  • I started to take notes on most of the books I read so that I have something to look back towards that isn’t just a pile of highlights. I have a collection of my own thoughts and takeaways as well as useful visuals.


Last year was a pretty epic turnaround for me in terms of reading, I finally stopped talking about it and made it a huge priority for myself. The books I read last year include (note some of these are re-reads):

  1. Zero to One
  2. Data Driven Security
  3. Red Team: How To Succeed By Thinking Like The Enemy
  4. Becoming Batman: The Possibility of a Superhero
  5. Leadership Transformed
  6. The 4-Hour Work Week
  7. The Cyber Security Dilemma
  8. Ancient Chinese Thought, Modern Chinese Power
  9. Practise to Deceive
  10. Turnabout and Deception
  11. The Thirty Six Strategems
  12. The Lean Product Playbook
  13. The 22 Immutable Laws of Marketing
  14. Blue Ocean Strategy
  15. Extreme Ownership
  16. Born For This
  17. The Art of Strategy
  18. The Happiest Baby
  19. Content Machine
  20. A Spy’s Guide To Thinking
  21. A Theory of Everything
  22. The Effective Executive
  23. Unrestricted Warfare: China’s Master Plan to Destroy America
  24. Stealing Fire
  25. Anticipating Surprise
  26. Analysis Without Paralysis
  27. Dark Money
  28. The Prince
  29. The Art of War
  30. Competitive Intelligence Advantage
  31. The Book of Five Rings
  32. Daring Greatly
  33. Battle Studies: Ancient and Modern Battle
  34. Business War Games
  35. How to Measure Anything in Cyber Security Risk
  36. The Phoenix Project
  37. A Burglar’s Guide to the City
  38. The Open Organization
  39. Battlefield of the Mind

Yes...I know you were thinking it, I am indeed a huge dork. But with that in mind, anyone who follows me on Twitter will get a sneak peek into the sorts of articles, books, and podcasts I’m digging into at any given time.

What Went Well

  • Setting and sticking to clear boundaries between work and the rest of my life has notably improved for me. I used to be completely consumed by work, checking emails constantly, up until the early hours of the morning working only to pick it up again the next morning, and never saying no to anything. I find myself still hustling but doing so on my terms now, which is very refreshing. One book in particular really helped me with that, The Effective Executive, in addition to my wife being there for me!
  • Disabling notifications on my devices, this has been an incredible step in helping me stay focused throughout the day. I also find that this has helped me in my personal relationships as I’m not constantly pulling my phone out in the middle of a conversation with someone else, I can focus on being present with people.
  • Opening up with people has been a very intentional goal for me, I feel it’s gone pretty well at home, in friendships, and at work. I got a lot of feedback throughout the year that sounded like “wow, you’re not a robot, that’s awesome.”
  • Career development in general has been progressing in the direction I want it to. I have learned a TON about business, strategy, and relationships this year. All the things I thought I knew pretty well but once I started really studying, listening, and talking with mentors I was able to fast track my development on this front.
  • I had the honor of speaking at some major conferences this past year, such as BSides Las Vegas, DefCon, and the Military Operations Research Society Summit; that was amazing.

What Didn’t Go So Well

  • Once we started moving around a lot and when the baby came my volunteering/serving efforts pretty much vanished. I really want to re-establish this as a cornerstone in my life moving forward.
  • I ebbed and flowed a lot with my eating and drinking habits, in a pretty unhealthy way. I didn’t do much in the way of meal prep or adhering to an eating schedule and I gave in to sweet stuff, social drinks, and drinking in general far more frequently than I would have preferred.
  • In work and personal settings I let myself get too emotional at times which leads to my more assertive, dominant personality traits coming out over my calculated, analytical, and empathetic adaptive self. I think meditation is helping a lot with this, but as with most people, I am still a work in progress.
  • I didn’t take nearly as many pictures as I would have liked to have in retrospect, especially of my family when we are out either out and about enjoying ourselves or at home taking it easy.
  • I stopped coding almost entirely this past year, a habit/skill I need to dive back into in 2018 to both stay sharp and continue growing.

Aspirations for 2018

Now for the fun part, the aspirations for 2018.

  • Be a more present father, husband, and friend for people in my life.
  • Learn things outside of my comfort zone.
  • Lay the groundwork to start a company of my own that addresses a problem I believe needs to be solved.
  • Resume volunteering my time and resources to change lives for the better.
  • Train my body, mind, and spirit to be more like Batman, a resilient, powerful, ass-kicking machine for good in this world!

In a future post I might break all these down in OKR format, could be a useful way to further keep myself accountable :)

About Robert Wood