Reflections on a Year in Learning

By July 2020 COVID-19 had grown from an obscure virus in central China to a worldwide pandemic. Most areas in the United States were under lockdown, with stay at home orders in effect across many states. As I quarantined in my apartment, only venturing out once a week to pick up groceries (ordered online to reduce contact with others), there was plenty of time to think. For me, there was one topic that was stuck in my mind: the future. Not just the uncertain future of the world at large, but what I saw for myself in the coming years. I sat down with my journal, a pen, and three days of uninterrupted time. It took the entirety of that time, but by the end I had created what I’ve come to call my “3 year plan.” This plan offered a rough outline of what I wanted to see out of the next 3 years, and what I would need to do to realize that vision.

Now, in June 2021, it has been almost exactly a year since I first put together my 3 year plan, and I wanted to offer some reflections on my experience over the last year. This piece will cover the thought process behind the initial plan, as well as some of the lessons I learned that transcended individual domains. Over the coming weeks I’ll be publishing additional pieces that offer a deeper view into specific pieces of the last year. I should begin with an admission that this is not the first time I’ve tried to put together a long term plan. For years, I’ve been drawn in by the promises of “personal productivity” and have read many books¹ and blog posts discussing how we can do more and be better. Through a personal synthesis of this content I’ve developed a system for planning and acting on a daily, weekly, and even monthly basis. However, my past attempts to expand my planning to larger timescales have fallen short. I would meet my goals on a month by month basis, but they would be missing a unifying thread. Thus, at the beginning of 2020, a fresh decade, I decided to try again. The start of 2020 found me taking time off between jobs and exploring potential futures. I spent time going deep on chess, learning yoga, blogging, improving my handwriting, and all of the other areas of the human experience that had struck my fancy. But here, once again, all of these explorations were self contained, and there was no story that tied them all together. I was determined to understand that story, but given past failures, this time I wanted to make a couple of changes to the process.

The first thing that I wanted to change was the scope of my planning. Past iterations had seen me planning for 5 years, 10 years, or even planning my whole life. I’ve now come to the conclusion that, in most cases, life is too variable for plans longer than 5 years. However, I opted to aim for the even shorter 3 year time period because it aligned with some known milestones in my life. At the end of my 3 year plan I would be turning 30 and my girlfriend would be finishing her PhD. This offered an anchored endpoint to which I could attach my long term plan.

Having identified the timeframe, I needed to answer the question of the theme. The entire goal of setting up a long term plan was to connect all of my previously disparate monthly/weekly/daily goals. This was essentially answering the question “where do I want to be in 3 years?” At the time I kicked around a lot of ideas: writing a novel, building a startup, traveling the world, building a house. What came up during all of this time is that fundamentally I’m not sure.

For a while I was frustrated by this, locked between a desire to set up a long term plan and an uncertainty about how to orient that plan. What eventually helped me resolve this was the recognition that uncertainty is ok and sometimes figuring things out can be an end in itself. This led directly into the idea of building a plan around exploration. Instead of setting some major milestone, I would focus on exploring all of the domains of human existence that interested me. An astute reader may see a parallel here between this description and what I was doing before the plan, but there is a crucial difference: intentionality. With this new structure I was explicitly saying that exploration and discovery was the goal, not doing so incidentally.

Within this framework of discovery, my next task was to breakdown the projects, skills, and fields that I was most interested in learning about. After writing everything down, I was able to identify three broad domains that my topics were falling into:

• Physical: I value physical excellence and think that caring for our physical existence is a key part of living a good life. This domain included topics such as weightlifting, running, mobility training, martial arts, and calisthenic skills.
• Creative: Creative is another one of my core values. The topics here fell roughly into three categories: visual arts, writing, and music.
• Professional Development: I am a software engineer by trade, and there are many areas that I’m interested in that could serve to further my professional life (not necessarily all engineering related). Topics here include conducting effective communication, design, programming language semantics, and product management.

Using these domains as a rough structure I decided on time blocks for each topic of interest and assigned them over the course of my plan. Here I’ll just share year 1 as it’s the one that’s been completed and had the most detail initially:

• Physical: Mobility + Handstand (6 months), Running (6 months)
• Creative: Visual Arts (1 year)
• Professional Development: Effective Communication (6 months), UI/UX Design (6 months)

It should be noted that my goal during each of these is not to become an expert, but instead to build a strong baseline. In the end my goal is to know more about the field, and what I would do if I wanted to pursue it further in the future.

Future articles will cover each of these domains in depth, but there were some take aways that transcended the domains. First and foremost, that even the best laid plans can go awry. I developed a series of debilitating headaches in November 2020 that put me out of commission for much of the month. Even with a long term plan it is important that you can make adjustments as your life situation changes.

A big success from setting out the 3 year plan, was a new appreciation for the impact of self imposed limits. In past iterations of my personal planning, I would try to do everything at once: do a little drawing, a bit of writing, a bit of music. I would be focused on one thing, and then find a new article online, or a bolt of inspiration that would cause a complete change in activity. This time around, I’ve set out explicit time in the plan for each of these to be a focus. Now whenever I have a thought outside of the current activity, I write it down and file it away for the future. This is a huge relief to my mental load because it lets me focus on one task, without worrying that I’ll be losing out on other activities.

The final take away from year 1 has been the importance of structure, especially when you are new to a field. For the first six months of my journey into the visual arts, I jumped around a lot: I drew some lines, some hands, some cubes, a bit of perspective, some animals, and some doodling. While this was fun, ultimately it wasn’t really helping me develop as an artist. At the start of 2021 I signed up for some structured art courses, and those really helped give my exploration more direction. The simple fact that I had a weekly/daily structure I could follow along helped me learn much more about the field than my previous dabbling.

Now that we’re coming to the conclusion of year 1, I’m gearing up for year 2. This is the longest I’ve ever stuck with a long term plan, and I am confident that I can see it all the way through.

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