New Year’s Resolutions or OKRs?

Yesterday morning I did some quick reading on why New Year’s resolutions fail and I realized that I’ve viewed the concept of New Year’s resolutions in a very unhealthy way. I’ve historically focused on how they fail not because New Year’s resolutions are inherently doomed but to justify my dislike for them. This is so inconsistent with how I approach everything that it was a very uncomfortable shock for me. Thankfully, after reading all the Arbinger Institute books, in 2019 I conditioned myself to look out for this exact trap. I found it ironic that the inverse of what the Internet generally feels results in most New Year’s resolutions failing is what I had already committed to doing in 2020.

Throughout 2018 and 2019 I’ve gradually adopted something similar to Objectives and Key Results (OKRs) for personal and professional goal setting. Most OKR literature warns that nobody gets it right the first time. I’m very happy with the progress I made in 2019 but I consider this to be my first real attempt at this kind of OKRs. Until now everything I’ve done has been an internal process that I haven’t measured properly or shared with anyone. All my 2020 objectives are intentionally very abstract and my key results are all measurable. I’ve done my best to set key results I feel are both aggressive and not impossible but I still feel some of my targets are somewhat arbitrary. Below are my OKRs for the first quarter of 2020 with 2 caveats:

  • I have not included my family OKRs because most of my online audience lacks the proper context to appreciate them or to hold me accountable.
  • I have omitted any objectives or key results that are sensitive. I’m not planning anything nefarious but I have goals that require a certain degree of confidence on behalf of my employer or others. For example, I have not published any of my objectives dealing specifically with WePay’s product architecture or engineering organization.

OKRs were created by the legendary Andy Grove. I encourage anyone unfamiliar with OKRs to read John Doerr’s book, Measure What Matters, and to consider how OKR concepts could benefit their situation.

Level Up

Who doesn’t want to level up? This is primarily about learning and development.

  • Spend 4 hours per week writing articles or mentorship feedback. I enjoy writing and it helps me organize my thoughts. Writing forces me to think more thoroughly about concepts I feel are important and increases the quality of what I share with others. Writing is also listed first because my 2019 goal to write more was a complete failure.
  • Consume at least 25 hours of audio books per week. 25 hours of audio per week is not as much as it sounds. I commute a minimum of 10 hours per week and currently listen to audio books while commuting at 2.5x. Not considering when I skip back that should be about 25 hours per week already. I haven’t been measuring this so I’m concerned my metric is off. Nevertheless, this is not an area I’m looking to improve. I want to make sure I sustain and measure my current behavior.
  • Complete 3 Kindle or physical books. On the surface I don’t like the idea of measuring the number of books I complete because it could incentivize me to choose easier or shorter books. Despite devouring whole libraries of audio books I haven’t been reading physical or Kindle books at all. There are plenty of things I’d like to read or reread that aren’t available as audio books and this is an area I am looking to improve. One book per month is infinitely more than zero.
  • Build a personal application using a new technology. Long past are the times when I could learn Ruby in my hotel room while on vacation and write a Ruby Unit Test framework just because I couldn’t find a JUnit clone. I still want to experiment with technologies and concepts that are new to me but I haven’t been doing that as much recently. Building a simple application with something new to me will be a hands on success I can build on.
  • Find a new mentor in technology leadership. Everyone needs mentorship. I need to find another person that can provide me with essential feedback and guidance.
  • Read 3 technical papers. I have collected a long queue of technical papers but haven’t allocated time to read them. This is intended to be another starting point I can build on.

Have a Mind Like Water

Focus and time management are extremely important to being effective and productive. These ideas are based on lessons I’ve learned from books like David Allen’s, Getting Things Done, David J. Levitin’s, The Organized Mind and Roy F. Baumeister’s, Willpower. It’s important to spend my time deliberately and to get things out of my mind so I can focus on what I’m doing.

  • Get my Things inbox and today list to zero items every day. I have become disciplined at keeping track of what I plan to do by leveraging concepts from the Getting Things Done framework and an application called Things. Any thoughts that interrupt my focus get put into my inbox and my today list contains everything I’ve scheduled to be done on that day.
  • Perform daily reviews every day, including weekends. There are two parts to this key result. Until recently I’d been fairly consistent about performing daily reviews except on weekends. It was difficult to make as much progress as I would’ve liked at home and I was catching up each Monday. The second part is the review itself. It usually takes me fewer than 10 minutes to measure the day’s activities and review the next day’s plans. I also spend about 30 seconds considering each item on a short list habits I’m working on. I find that if I reflect honestly and daily on each habit I have more conscious influence over my automatic behavior during the day. There are a maximum of 5 habits on my list at any time and I remove items once the behavioral feels automatic. My current list is:

Don’t finish others’ sentences. It’s amazing how much I’ve noticed this since I’ve been paying attention to it. It’s used very often in scripted dialogue to demonstrate that multiple people are thinking the same thing. In real life, however, you run the risk of someone not feeling heard or actually not being heard. When done from a position of authority there is an even greater risk of losing the message that was intended.

Don’t plan what you’re going to say while others are speaking. This is mentioned in numerous books about management and listening and has been on my list for a very long time. I’ve gotten very good at noticing when I’ve started doing it or am about to do it so it doesn’t happen very often anymore. I’ve always considered myself to be a multitasker and this has been particularly challenging for me. Though it’s something I still need to pay attention to I see a noticeable difference in the quality of my conversations when I do this so much less frequently.

Don’t stay in bed once you’ve woken up. This is very straight forward but also one reason I’ve been able to do my daily reviews consistently. I won’t cite anything specific but there is plenty of data available that suggests doing this, at best, doesn’t add value.

Read name tags and address people by name. This is related to lessons in the Arbinger Institute book, Leadership and Self Deception. It helps make my interactions with others more genuine and meaningful.

Drink less caffeine. I already don’t rely on caffeine and simply want to drink less of it. I’m not eliminating caffeine, but caffeine is everywhere! I want to ensure that I drink things for enjoyment and not simply because they’re available.

  • Perform weekly reviews every week. During my weekly review I quickly review the previous week and look over short lists of long term items I want to do some time that aren’t currently planned.
  • Be everywhere I’m supposed to be. I have many appointments, have to keep a strict schedule and I don’t want to miss or be late to any virtual or in person meetings. When it’s necessary to reschedule something I want to provide sufficient notice. It’s part of my daily review but this key result will still be the most difficult for me to measure accurately.

Pay It Forward

I feel fortunate to be in a position to add value to communities of entrepreneurs and technologists. It’s important to me that I give back to others for too many reasons to go into right now.

  • Publish 3 articles. This is a supplement to the time I plan to spend writing aimed at give back to the community. I published one article last year and one per month sounds ambitious. Still, I don’t have a good sense of how much time I would need to complete most of the many works I have in progress.
  • Make 12 in-network referrals. It is important to me that I am connecting people in my network with one another in relevant ways. An average of one connection per week sounds reasonable to me.
  • Speak 3 times at events or in podcasts. Before publishing this goal I scheduled a TED-style talk at Hack Reactor and planned an interview workshop both in the first weeks of the year. I now also have another event tentatively scheduled in March, so this feels like sandbagging. In the OKR spirit I haven’t adjusted my goal based on my behavior after I set the goal. I will have a record of the original goal I set and the result which will help me set better goals in the future.
  • Become an advisor for a startup. I provide lots of informal guidance and feedback to early-stage entrepreneurs and technology leaders at small companies. My goal is to become a formal advisor to at least one additional early stage company. It’s important to me that I create relationships with the right companies and I’m not sure I’ll be able to accomplish this in a single quarter.
  • Host and follow up with 8 mentorship sessions outside work colleagues. I want to improve and measure the mentorship I provide to aspiring entrepreneurs and engineering leaders. I also want to participate more in mentorship platforms like Plato. I’m a big fan of what they’re trying to do and want to contribute to their efforts. There is plenty I can do to make myself more available through natural means and to improve my availability on platforms like Plato. I don’t know how much of this I already do because I haven’t been tracking it.

What are your goals for 2020?

Technology Executive, Startup Consultant, Investor