Doesn’t it seem like 2020 has always been “the future!”. Technically as of this writing that’s still true… but almost assuredly for you reading this it is not true. What’s the future like, guys? Are you flying around in your jetpacks? Has the singularity happened yet I can’t wait for the world of tomorrow!

I wanted to write a huge, sprawling review of the past decade & a fully-imagined picture of the next decade; but this isn’t that. This post is not primarily about the past. It’s about the future. But to give context to that future, let’s briefly look at the past.

Last Decade

2010 - 2014

a young couple

Since the ball dropped on December 31st 2009…

  • Melissa and I were dating & working on-campus at KU.
  • I started to get interested in personal development and did a time-tracking project.
  • My back started hurting in earnest and I learned I’m not invincible.
  • I started doing my “Demetri List” - named after Demetri Martin, whose standup I stole the concept from
  • I started writing again (in this blog).
  • Melissa and I graduated with our respective degrees.
  • I got my first big boy job.
  • I lived by myself for a year.
  • I panicked about wasting a lot of time with nothing to show for it, and started what would eventually become “The Life Tracker”.
  • We got engaged.
  • We got married.
  • We moved in together. Got a couple of cats. Upgraded apartments a few times.

2015 - 2019

a slightly less young couple

The second half of the decade saw both changes and stability…

  • I did some continuing-education courses for fun online and learned more coding.
  • I rewrote the Life Tracker from scratch, a code base which I’ve lived on for nearly 5 years now.
  • I upgraded my career situation.
  • We bought a house and learned what it means to be homeowners.
  • We got pregnant and had an awesome baby, who’s quickly grown into an awesome toddler.
  • We started taking health more seriously.
  • We learned to cook.
  • We built and started actually using a pretty great home gym.
  • I started taking my continuing-education and personal development hobbies more seriously

Continuing my education and working on personal development stuff is the area of my life where I see the greatest potential to hit this target:

career Venn diagram

A professor once told our class that hitting that target, finding something at the intersection of those three things, was key to having a satisfying and enjoyable life. I wrote that down. I still think it’s a pretty great piece of advice. Once you think you’re there you can’t rest on your laurels… nor should you want to. It is for that reason that I have more content below this line.

Long-term Planning

About 2 years ago was when my original post-college-5-year-plan was supposed to end. I am happy to say everything played out pretty according to plan. I don’t have a graduate degree, and it took me roughly 6 years to get to the spot I wanted to be in 5 years… but aside from those two quibbles - I’m where I want to be. Now where am I going? Where do I want to be? More importantly, who do I want to be?

Those are my questions now.

Goal Mapping

When thinking long-term, it’s best to think first about who you want to be, not what you will have accomplished. Go from who you want to be to what does that person do? What do they have? What have they done to get to where they are? Then work your way backwards to medium-term goals. What will you need to do by when? You can then work your way further back to the short term goals, habits, and systems that are necessary to accomplish those medium-term goals. This maps your short-term behaviors to the long-term reasons why. It ensures you’re spending your time and energy in ways that move you toward who you want to be.

I don’t want to share my entire future outlook in this Column; but I do feel comfortable sharing an example from it:

In 5 years I want to be a music-capable individual. I’d like to be able to create new music utilizing some level of competence on an instrument. This means that in a year’s time I should probably have a good idea of what instrument I want to play. I should have ownership over that instrument. Musicians consistently practice their instruments. If I want to be a musician, I need to practice consistently.

2020 - 2030

a more less young couple

Given that we’re at the transition period between decades, it feels appropriate to think even more long-term than the standard “five year plan”. I’ve spent a decent amount of time thinking about the next decade. What do I want life to look like in 2030? How old will my family be? What milestones will happen between now and then? What do I need to start thinking about now?

The plan is not to set the next 10 years in stone. The plan is to think about them. Make a rough timeline, based off where I want to be in 2030, what my relationships look like, and what I will have accomplished by then… then adjust the plan as I go along.

Because that plan is subject to change, I don’t feel comfortable posting it to the general internet… but I cannot recommend this practice highly enough.

A System of Self-Actualization

I recently had one of those awesome total-brain moments of clarity. It was a purely theoretical (and beautiful) amalgamation of all the “me” things I’ve been doing for the past several years into one massive idea. I pictured of a system of processes, tools, and hobbies that come together to form a cohesive whole. Combining getting things done with habit change, with principle-based goal-setting, with quantified self concepts, with app development and writing. Put simply, I visualized a systematized method of self-actualization. Structured, yet flexible. Robust, yet only as intensive as you want. It’s very much in the center of that Venn Diagram from above.

Honestly it’s too big to talk about here. For a sneak preview of the framework, read this entire post. I’m pretty jazzed about the idea. I hope much about it will follow on this blog.

Before we go, though…

2019 in Data

In 2019 I…

  • Finished 69 movies (17 in theaters), 28 books (and gave up on 6), and 2 videogames.
  • Watched at least one television show on at least 90 days.
  • Logged 129 workouts - which is up 30% over last year, but still below the target of 3/week (156/year).
  • Tracked calories less frequently than any previous year, at 165 days fully tracked (compared to 213 days tracked on average from other years) Those days that I did log showed a marked decrease in calorie consumption, at 2475 (compared to 2785 calories/day on average from other years). My carb ratio is down, bringing the other two macros up. In turn with all the above, my weight has dropped by ~8 pounds after being steady for the past 6 years.
  • Wrote 26 Columns, including this one. One every 2 weeks.
  • Saw family 55 times and friends 127 times.

Top 5: Goals for 2020

  1. Complete 24 Gillespedia articles
  2. Have ZERO 3 day streaks without exercise
  3. To learn to play ~10 things on a guitar
  4. Transition the Google Spreadsheets based “Life Tracker” into the (likely AWS-based) Data Journal component of my new, as of yet unnamed system
  5. Some family fun goals we’re finalizing


I am not a product of my circumstances. I am a product of my decisions.
- Stephen Covey