Two Years of Memos

I’m a bit late on this one, but at some point last year I shared what I learned from writing Monday Memos each week for a year. Now that we’re over two years in and over 100 of these weekly messages have gone out, I wanted to share my thoughts on what the Memos have taught me this year. The four lessons I started learning in the first year were:

I’m still very much a work-in-progress on all of those above. I still don’t communicate messages as frequently and in as many mediums as I believe I should. I still struggle with not taking certain things personally. I’m a person who loves options -thus truly committing is difficult because you do so at the expense of alternatives. And while I know writing helps me clarify my thoughts, it’s still painful to take time each week to set aside for it.

So while those are definitely still developing, there are three other realizations I’ve grown to appreciate the past year of writing weekly:

5. Take Mental Snapshots: Reflecting on where we were a year ago generates gratitude.

6. Don’t Try To Be Smart: Arriving at the best outcome is the goal, not demonstrating intelligence.

7. Do Hard Things: The harder it is, the fewer people try - and the bigger the reward.

Take Mental Snapshots

I typically have a 'weekly meeting’ on Mondays where I check-in with myself about 10 areas of my life to see ‘how I’m doing,’ and write a short reason why I’m feeling the way I am. Besides that, the weekly writing of the Memo is the only other weekly habit that I personally have (disregarding All Hands Meetings, one-on-ones, etc.). It’s fascinating to be able to recount what my thinking was for every single week of the last two years. Looking back, I can see where I’ve “overcome” a challenge I was wrestling with at the time, such as why we might raise prices and how to communicate that (May 2018). At that time, I really was scared that many parents and students would leave the program. I was proven wrong. I can also see where I’m having perpetual challenges, such as fostering a collaborative culture where we can set goals effectively even with those with whom we don’t usually work (Many in Q4, 2017). Based on recent Team Pulse Survey data, we haven’t cracked this one yet.

Allowing a snapshot into thinking at any given point in time has allowed me also to reflect on what were the largest or most pressing challenges or problems at that time and what was consuming my attention. This reminds me of an expression I learned when I was a kid hiking on the Appalachian Trail that I love: “The view of both the mountain and the spirit depends on where you stand.”

It’s so true. For all of us, we’re currently standing at different places on the same mountain and at the same time at different places in on our own personal mountains of self-discovery and self-growth. Being able to reflect on my mindset, challenges, thinking, and priorities at any point along the journey has made me more aware now as to when I’m disproportionately focusing on non-priority issues. It’s also made me more grateful of both the adventure itself and the progress that we’re experiencing as a team.

Don’t Try To Be Smart

This one shouldn’t come as a surprise, but it has taken me a long time to realize (and admittedly, I’m still working through it).

Early in my career, I thought that the goal of ‘knowledge work’ was always to be smart and to come across as smart. After all, that’s all of the (limited) feedback I received was about - when I did something smart, or at least came across that way, I would receive praise. As a ‘knowledge worker’ I felt I was being paid on the quality of my ideas and ‘winning the decision.’ If my boss picked my idea after the team discussion, then I had won. In order to do that, I needed to be smart and show how much I know about everything. It wasn’t until after leaving my last company that I have slowly begun to realize that having ’smart ideas’ is only valuable if you can implement them and make the change you desire. I thought that strategy was such a higher order level of thinking and tactics and execution were not as important, because they were just about ‘doing’ and not about ’thinking.’ Oof! How wrong was I!

Making a difference in a company is truly about finding opportunities to provide other people value, communicate that value to them, and then produce that value in a manner that costs you less than they are willing to pay for the communicated value.

It’s a very simple idea. And communicating value is a simple activity - not one that needs to be littered with ‘million dollar words.’ It’s a tough habit to break when you learn it early in your career and one I still struggle with today, though I do feel like I’m slowly coming around.

The amount of Memos that I’ve completely written and then trashed because I tried to be too smart for my own good is laughably high. Earlier this year, I remember excitedly telling an LL Partner about a draft of one that I had written earlier that day that was essentially a unifying theory of centralization and decentralization in businesses using my own analysis of Uber, The Federalist Papers, Cryptocurrency, and LearningLeaders. The reaction I received was incredibly polite and supportive, but thinking on it afterwards, I couldn’t help myself from thinking, “Why am I trying to make this more complex than it needs to be? Am I still trying to sell smarts when that’s not my job anymore?”

A simple message that communicates value and meaning will never go out of style.

Do Hard Things

I wrote last year about Jerry Seinfeld’s routine for coming up with comedy routines. Apparently, he has a calendar in his house. Every day he comes up with a new joke, he takes a red marker and draws and X through that day. After a short while, he has a chain of red Xs that lasts weeks and months. He continues because he doesn’t want to break the chain. Seeing the previous commitments and follow-throughs not only trains him to continue doing it, but it helps him consistently produce jokes and routines that have allowed him to become one of the most famous names in entertainment. And it also helps him come up with innovative ways to stay on top of his game and the industry.

I think about this every week as I write the Memo. To take this one step further though, what I’m growing to realize is that once you develop a habit to do things that other people think are ‘hard,’ you’re willing to take on other related challenges much more easily. This could be running, studying, learning a language, eating healthy foods, or whatever else you want. After coming up with a joke every day for years, I’m sure creating ‘Comedians in Cars with Coffee’ was a piece of cake for Seinfeld.

The fewer people who attempt to do something (typically because it looks harder) the ‘rarer’ that skill/ability/demonstrated capability becomes. That in turn makes both those skills and the problems those skills allow you to solve more valuable. But the longer you do something, the less scary and difficult those problems seem. Writing weekly Monday Memos is never going to make me a million dollars, because writing a weekly memo isn’t that valuable of a skill. Reporters and journalists the world over do it better than I and with more frequency. But the last two years have definitely showed me that once writing weekly for two years, I’m less scared writing a book.

Fewer people write books than articles and thus typically books are worth more. Even more specifically, fewer people write best-selling books, which are worth more than the average book. I’m not there quite yet, but it’s becoming a more realistic aspiration by the week.

The foundation to do hard things, which other people are afraid to do, might just come from the habits and consistent action that bring us to the point where our courage expands beyond where it once was.

Baby steps to big dreams.