Looking Back at 2018

Variations on a theme

This is my reflecting pose.

It’s no secret that I track a lot of information about myself. I know every book I’ve read in the past year, every TV show and movie I watched, how much sleep I got, how many times I meditated, how many steps I took… just to name a few. Part of me wants to go through each metric I tracked and dive deep into what the numbers are and what they might mean. God knows I’m not shy about diving into miniscule detail about pretty mundane things. For once, though, I’m going to show some restraint and actually try to extract some themes instead of deluging you with data.

After a couple weeks of reflecting on how the past year went, looking at the various data I collected, and talking with loved ones, here are the three key themes I’m taking from 2018:

1. Self-compassion will be my ultimate productivity hack

I have a hyper-active self-critic who thinks he’s the star of every show. He’s not shy about chiming in. Sale fall through? “Hello, why are you so bad at this?” Have a tough time figuring out what to work on? “You call yourself a productivity expert? You’re a joke.” Write something that didn’t garner much attention? “I always knew you weren’t very smart and now everyone else knows it, too.” It’s truly endless and at my lowest points, emotionally and in terms of productivity, it was because my critic had made himself far too comfortable in my brain.

For somebody as obsessed as me with personal development this is one part of my development that I haven’t really explored. I’m much more comfortable creating new systems and structure that help me take the action I know I need to take. I’d much rather read a book or do some writing or somehow just try harder. 2018 is when I finally started to learn that you can’t berate yourself into self-compassion (I know, right?) and that shutting up the critic in my head will probably do more for unlocking personal and professional growth than literally anything else.

2. I need to make decisions for sustainability

For the first half of 2018 I commuted full-time from Washington D.C. to my project in San Francisco. I would catch a 6:00 AM flight Monday morning (after a 30 minute Lyft to the airport), land in SF Monday morning, spend all day at the client’s office, work normal-ish 8–5 PM days Tuesday-Thursday (while fighting my body’s attempt to acclimate to the time change) and then either take a red-eye flight back to DC Thursday night or fly out early Friday morning and land in DC Friday early evening. Repeat for five and a half months. This is one example of me taking a situation at face value and basically martyring myself rather than seeking some concessions or changes that would allow me to work in a more sustainable way. I put myself in the mindset of a hockey player battling through an injury in order to not let my teammates down. I can’t do that.

This learning is largely around the idea that I have limits, both physical and mental, and although they can sometimes be ignored in the name of “powering through” or making the client happy, they represent a debt that must eventually be paid. In my case, it meant absolutely crashing at the end of May and requiring several months of recuperating to get back to anything close to approaching my normal operation.

I’ve spent most of my life looking ahead to the next thing. College was a finite time ending in a degree and entrance into the real world — so I might as well bear down and really do a good job. My abbreviated teaching career theoretically should’ve been a time where I was focused on the long-term but I think I knew early on that it wasn’t going to be my future and I was therefore simultaneously hustling on multiple side projects. I was teaching during the day, coaching hockey at night, and writing for my website during the snippets of blank space that I was able to carve out each day. Grad school was another unknown with a theoretically knowable end point but I was self-financing through student loans and didn’t have a clear sense of what I was going to do afterward. I had to ignore sustainability in the name of hustling to figure out what the hell I was going to do to justify the incredible debt I was taking on to give myself this experience (hence the copious side projects, organizing TEDxClaremontColleges, starting a company, and non-stop work). Only now, three years into my work with The Ready, am I starting to realize that I don’t need to be killing myself in the name of figuring out the next thing. The next thing is this thing. I need to be growing in my roles and responsibilities at hand — not grinding myself into a dust in order to figure out what I need to do next.

I think part of me has worried that the flip side of not hustling is complacency. 2018 taught me that what I’m actually looking for is sustainability and that until recently I’ve never felt like I could be in a place to work sustainably. I have a lot of bad habits and mindsets to unravel (see learning #1 regarding self-compassion) but acceptance feels like the first step.

3. Action does not (and will never) equal progress

Are you sensing a theme here?

I’ve always been powerfully motivated to be productive. Call it a Protestant work ethic combined with Catholic guilt, a childhood and adolescence spent playing extremely competitive ice hockey where there was always somebody looking to take my spot in the lineup, being the oldest of five boys and always wanting to be a role model for my brothers — the reasons are surely numerous and profoundly psychoanalytic. What it means in practice, though, is that I’ve always been comfortable taking non-stop action toward success. What’s the next action? What do I need to do? Repeat, forever.

Working in a self-managing company requires an ability to pick through a truly overwhelming amount of possible actions (I could literally do anything I want) and pick the best ones given any number of contextual factors (my energy, what the company needs now, what the company will need later, what Slack is telling me, what my email inbox is telling me, etc.). Instead of getting good at distilling this information down to the most essential things to do I’ve gotten too good at capturing every possible thing I could do and then surfing along the top of all of them. Instead of going deep on the most essential one or two projects at a time I’m able to do the most inessential work across 7, 8, or 20 projects all at once. The end result is a ton of work without much to show for it.

This is the lesson that fills me with the most angst. It’s the one that feels like the largest squandered opportunity and the one where I should’ve most obviously “known better.” Without letting my critic get too engaged at this point, let’s just say that this lesson is going to inform the largest part of how I work differently in 2019.

What now?

I’m not particularly interested in distilling these lessons into bullet lists of “things to do” because I think they retain more of their usefulness in their more complex and ambiguous form. Suffice to say I will continue reflecting on these in the weeks and months to come and future writing will (hopefully) peppered with ideas that were born of the lessons above. For now, though, I’m going to get back to the most important project I could possibly be working on, in a sustainable way, while I tell my self-critic to take a hike!

I’m Sam. I work for The Ready in Washington D.C. I tweet. I write a newsletter called The Deliberate. I take pictures of mostly boring things.