Everybody talks about the importance of learning — from experience, from mistakes, from successes.
And there is no doubt we take away something of the many events tucked into our days. Based on the actions and reactions we observe, we develop mental models to navigate the external world.
The more seismic an event relative to others in our lives, the more likely we are to extract its lesson. Being frequently late to the bus sucks but rarely forces us to overhaul how we think about getting around in the way, say, being late to an international flight might.
For most of us, even those who claim to be serious about self-improvement, this is how we drink the coffee of our learning: passively, incidentally, splash of cream, bit of sugar. Hey some of this stuff will stick right?
It will. But there are two problems with this approach:
- It takes many loops of the same action-reaction pattern for the learning to passively slip into our consciousness
- Because we learn the most from events that are relatively more consequential, by definition we are taking most of our learnings from a small subset of events in our lives. This reduces both the total number learnings and their likelihood of being accurate
So if we want to increase our rate of learning, passive osmosis or even the odd year-end reflection doesn’t cut it.
What does? I wager that it’s active reflection on our days to extract value from the long tail of smaller events, meetings, outcomes. The stuff of every day.
I started doing this daily in the beginning of the year — jotting down one thought about something I learned. The learning could relate to anything: a monumental epiphany about my life’s priorities is as acceptable as what CitiBike stations I should avoid at rush hour. And, most importantly, I tried to do it every day.
Reviewing it now, it’s humbling to think how much space life affords us to understand the world and ourselves better — and how many learnings bypass us because we chose not to examine our days here.
But I click-baited you to read this with the promise of an actual list of my learnings. Here are some of my favorites from 2019.
1. Getting really bored is a great way to figure out what you want in life.
And I don’t mean like binge-watch Game of Thrones bored. But like bored-bored. I took some time off work recently and found that the little voice of meaning/direction was loudest when I was just hanging out on my couch or staring ahead at a blank screen on a long flight.
2. To maximize growth, look for the opportunities that will let you make the greatest number of high-impact decisions per unit time.
Running towards — not away from — responsibility is the ultimate growth ‘hack’. (h/t Joe Kraus)
3. I sometimes avoid asking for help.
I have a tendency to think not knowing somehow reflects negatively on me. The first step, as usual, is becoming aware of it. The second is a very subtle reframe: a reminder that not knowing doesn’t mean I am not good at something. It just means I am not good at something yet. Framed this way, I’ve found myself much more comfortable asking for the resources or advice I need to be successful.
4. Others won’t get my journey.
No matter how hard I try to create a cohesive narrative to explain why I am doing what I’m doing. And that’s ok. My life doesn’t need to ‘make sense’ to others. Ultimately I am the one who will live with my decisions. For someone ordained in the mystic traditions of the Church of the Rat Race, this discovery is a welcome and hugely liberating bit of white magic.
5. A user manual is a great tool for any team leader.
My experience has shown that it can effectively reduce anxiety and increase productivity (as the article linked promises) because it makes clear upfront what often takes years to discover: habits of communication, effective working styles, things that push people’s buttons. I also found it to be a useful, if vulnerable, exercise in self-discovery: to understand and formalize how I work best, share my strengths and weaknesses, or even just the times of day I am most productive and don’t want to be disturbed.
6. I tend to make decisions seem way more important than they actually are.
Blowing up the stakes of quotidien decisions may be an effective trick I developed to force myself to dedicate a ton of mental resources to doing granular analysis, as if I can somehow arrive at the perfect decision just given enough time and focus. And it got me this far, so I’m grateful for it. But it’s an approach that’s fundamentally anxiety-driven and doesn’t align with how I want to be — as a person and as a professional.
7. Feeling uncertain is actually a good thing.
I felt a lot more uncertainty this year than in the past. And I’m glad I did — I think it suggests I am finally moving away from the illusions of certainty that plagued my early and mid twenties. I am coming to terms with not being able to rigidly control my life, and from traveling the path others think is right. Uncertainty means I can now ask and, one day, answer questions I’ve been avoiding like what’s actually meaningful to me?
8. Take some beatings. It’ll do you good.
I definitely took some this year. Coupled with a growth mindset, it will dial up your confidence because it gives you real world data that says: you can take a beating. You’ll be ok.
9. People are better at coming up with ideas alone.
Most traditional group brainstorms are a waste of time because people aren’t incentivized to think outside the box (for fear of being judged), it’s easy to avoid contributing (by riding others’ coattails) and you’re time bound (there are only so many ideas you can voice and explain in a session). To have an effective one, ask others to prepare a list of ideas alone, ahead of time. Then bring them to the group to choose the best ones — selection being a function where groups are actually quite effective.
10. Run from prestige.
This advice from Paul Graham really hit home: ‘prestige is especially dangerous to the ambitious. If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. It might be a good rule simply to avoid any prestigious task. If it didn’t suck, they wouldn’t have had to make it prestigious’. (from his fantastic How to Do What You Love)
11. I’d benefit from spending less time debating ‘should I?’ and more on ‘how can I get more data to make a better decision?’ (h/t David Fong)
12. When making a decision, fall in love twice.
We tend to value most the first idea we come up with, and give it more credence than other ideas. But there’s no reason the first idea will inherently be better. Confirmation bias just fools us into making it so. Some of my best ideas and decisions this year came when I was willing to let go of my attachment to the first option that I liked. (h/t Decisive by Chip and Dan Heath)
13. It’s not weird or wrong to feel panic in stressful situations.
I used to judge myself a lot for this, expecting to somehow Sean Connery my way out of every difficult scenario. That’s BS. This year I learned that many of those who remain calm when the alarm bells ring have just been through it before. And others just learned to look calm on the outside. There’s no magic here.
14. Look for leading indicators for failure.
When putting together any strategy, ask: how will I know things are going wrong before they actually do?
15. Better to oscillate between a 2 and a 10 than be at a simmering 6.
Got this idea from the patron saint of productivity, Tim Ferriss and I really liked it. Choose to be relaxed most of the time (a two out of 10) but when you’re on — be ON (a 10) kinda like… Mr. Miyagi? In any case, avoid the simmering 6: always sort of on, sort of anxious, ready but not quite.
16. Team events matter.
For a long time I didn’t realize the role they play in creating team cohesion. It just seemed like the stuff of corporate playbooks. But this year changed my mind. Giving the team opportunities to create social bonds outside the office is essential to productivity and morale. Or, I should say, creating these opportunities won’t save a team but not doing it will definitely hurt a team.
17. If you get a new manager, take ownership of the transition.
To make sure nothing gets lost, don’t expect your new manager to project manage the transition. Take ownership (and make your manager’s life easier) by putting together a presentation of what you’ve been up to and follow it up with an email. Include things like key challenges, specific contributions, and the plan going forward.
18. Separating time into work (weekdays) and play (weekends) is not how I want to live my life.
First, seeing past the traditional dichotomy allows me to work on passion projects (like The Tea Party) and explore new topics in my ‘downtime’ without feeling like I am somehow wasting my ‘time off’ by not making thorough use of my Disney Plus subscription. Second, it reframes the whole week as an opportunity for fun and curiosity, as opposed to the 5-day week being the ‘price’ I pay for a 2-day respite. That math doesn’t work in the long-run. Or any run.
19. I sometimes take my mom and dad for granted.
They won’t always be around. This year I realized how nourishing it is to spend quality in-person time with them. Doing more of it will make me happy.