A Learning a Day

15 years ago, on this day, I committed to writing a learning a day. This commitment has changed my life. When I share this, I’m often asked for examples of how it has impacted me. So, here are 15 things I’ve learnt from the act of writing every day:

(1) Discipline is a muscle. I missed many days in the first 2 years as I struggled with getting to consistency. I had to find shortcuts (e.g., sharing a quotes every weekday) to ensure I didn’t miss days. Growing up, I was often in awe of people who were disciplined. I just didn’t seem to have what it takes. Writing here taught me that it was just a case of making an effort.

(2) Today’s post will be #6318. Showing up every day to write has given me confidence in my ability to be disciplined about other things. When I make a commitment now, I know I can see it through. In fact, if I don’t see it through, I think there’s something wrong with my motivations for it. Why else wouldn’t I be able to follow through?

Making and keeping commitments is integrity. The word integrity comes from the word “integer” which means whole. This integrity has increasingly made me feel more consistent and whole.

(3) Learning is hard. To learn and not to do is not to learn. This means learning only happens when we change how we operate. I learnt over time that this blog would more accurately be described as a “reminder a day” instead of a “learning a day.” It has taught me that learning something new every day is challenging. We have to give ideas time to simmer before they get synthesized and applied to our lives. But, since learning is the goal, I’m good with the name “a learning a day.” It is, no pun intended, a good reminder of the goal.

(4) The biggest challenge with learning, the kind that changes how we operate, is synthesis. It is easy to summarize and hard to synthesize. When we synthesize, we boil things down to their essence and either create a mental or augment an existing mental model. Most good writing is summary. Great writing, on the other hand, is synthesis.

(5) Learning is everywhere. We just have to be willing to see.

(6) One of my bigger motivations when I started writing was to become better at dealing with failure. I vividly remember a moment a few years in when I made an embarrassing mistake and experienced some glee. It took me a moment to ask myself – why am I feeling this sense of glee? And the response that emerged was “No need to think about tomorrow’s blog post.” A win.

(7) Pausing to reflect on what worked during the day has been a great reminder of just how much I take for granted. It is what accumulated privilege does to you. Over these years, I’ve been fortunate to be educated at great schools and work at wonderful companies for great people. I’ve become significantly more privileged over time and it is so easy to take that for granted and falsely attribute all the good things to “hard work” or “hustle.” Both have played a role – but the biggest factor is simple that privilege leads to more privilege.

(8) Being happy doesn’t make us more thankful. Writing everyday has often been a gratitude practice and I have observed a causal relationship between how grateful I am on any given day and how happy I am. Thankful people are happy.

(9) Our ability to write is a reflection of our ability to think. As I’ve shared many times over the years, the word “essay” comes from the French word “essayer” which means “to try.” When we write, we try to figure things out. This practice is the biggest investment I’ve made to improve my quality of thought. Writing often helps us write better – like most other skills in this life.

(10) There are a lot of pithy quotes about the importance and impact of making a small improvements every day. It’s true. I’m still a person with many flaws. But I’m exponentially better as an individual and a human than I was then. Little drops of water do make an ocean.

(11) The benefit of reflecting every day is that you see some fascinating patterns about your own behavior. The most consequential is realizing the impact of good sleep. Good sleep is the single biggest driver of productivity and optimism.

Related, some days we’re the pigeon and some days we’re the statue. On these statue days, the most important thing we can do is go to bed. No point trying to salvage such days. Best to focus on making tomorrow great after some rest.

(12) I’ve written a lot about relationships over the years. The single best lesson I’ve learnt is that good relationships can last for a reason, a season, or a lifetime. Don’t try to over extend a natural lifecycle. Put differently, the cliche that you have to let go of those you love is very true. It doesn’t have to be someone’s fault (though sometimes it is). Often, it’s just about the chemistry – it takes two to tango.

On the flipside, if the chemistry, do everything you can to share your appreciation and keep it that way. Great relationships and trusted partnership are a very special thing. We appreciate them more as we age.

(13) The biggest lesson I’ve learnt from my reflections as a parent is that every choice has trade-offs. As every strategy has trade-offs, attempting to manage my time and energy as a parent has been the best strategy lesson of them all. We have to say no to things that don’t matter to be able to say yes that do.

(14) Confidence is saying “this might not work, and that’s okay.” Confidence was the #1 reason I started writing here. My hypothesis was that writing about what I struggle about will help me develop my confidence in my ability to deal with them. That hypothesis has panned out. I don’t remember the struggle of the moment at this time ten years ago. But I do know from all that daily writing that I managed – with plenty of help from people around me I’m sure – to find a way through. That realization definitely helps put things in perspective.

(15) Very little is in our control in the grand scheme of things. And, yet, if we focus on our circle of influence and responding constructively, so much more “feels” in our control. We have to hold both thoughts at once. These kinds of contradictions are surprising. That surprise is the essence of learning.

(one last thing) A wise friend used to end his emails to me with a note to “be kind to yourself.” That might just be the biggest gift writing every day has given me. It has made me realize that we must live from wholeness, not from our wounds. And that comes from being kinder – to ourselves and others. The universe is unfolding as it should. We never know if a good day is a good day. So there’s no point over analyzing things. Instead, it’s best we just keep plugging away and be kind to others along the way – the universe will roll on just fine without us.

One of the biggest sources of insight about what matters to us and what we’re insecure about lies in what frustrates us about others.

One of the truths about the markets is that when the Federal Reserve Bank has to come out and say “everything is okay,” it probably isn’t.

When a CEO has to make a statement during a difficult time saying something isn’t a problem, it often is.

And when a football manager comes out to say they’re fully behind a player or when a board member says they’re fully behind a manager, it is a sign of trouble in the background.

Beware public endorsements that attempt to showcase trust. When things are going good, they’re not necessary. By the time they show up, they’re often a desperate attempt at arresting the slide.

One of my favorite excerpts about culture in Will Guidara’s “Unreasonable Hospitality” was about the unique language they used in Danny Meyer’s Union Square Hospitality Group.

“Constant, gentle pressure” was Danny’s version of the Japanese phrase kaizen, the idea that everyone in the organization should always be improving, getting a little better all the time.

“Athletic hospitality” meant always looking for a win, whether you were playing offense (making a great experience even better) or defense (apologizing for and fixing an error).

“Be the swan” reminded everyone that all the guest should see was a gracefully curved neck and meticulous white feathers sailing across the pond’s surface – not the webbed feet, churning furiously below, driving the glide.

“Make the charitable assumption” was a reminder to assume the best of people, even when (or perhaps especially when) they weren’t behaving particularly well.

The simplest way to describe culture is the phrase “this is how we do things here.” And all these phrases made it easy for everyone at USHG to understand that how.

Language creates culture.

WordPress sent me an email as part of a new email campaign this week – “April Site Stats.” As soon as I got the email, I went straight to the bottom of the email and clicked unsubscribe.

The WordPress team does emails well – they are thoughtful about their campaigns and use nice designs and good copy. And this campaign is a smart idea – give people stats and they’ll typically focus on how they can optimize them.

However, in my case, this is exactly what I don’t want to do.

I’m approaching 15 years of daily notes on this blog. And the only periods when I had a decidedly negative experience writing were during 3 short bursts when I attempted to optimize reach. The last of these was over 7 years ago and I have no intention of reliving that phase.

Optimization of any kind brings trade-offs. Choose what you optimize carefully.

The single hardest kind of honesty is honesty to self.

It is much easier to see things as we want them to be instead of how they are.

Choosing to tell ourselves the truth – even when uncomfortable – instead of what we want to hear is an act of great courage.

“Never let the future disturb you. You will meet it, if you have to, with the same weapons of reason which today arm you against the present.” | Marcus Aurelius

I was pondering this today – at what point does it become worse to worry about a worst case outcome vs. simply experiencing that outcome?

More often than not, better is faster in the long run.

Not always.

But more often than not.

In a world where information is just a click or scroll away, it is just as important to be clear about what we want to be stupid about as it is to be clear about what we want to be smart about.

Claire Hughes Johnson, in her book Scaling People, said something interesting about good managers “say the things you think you cannot say.”

It is a fascinating way to describe communication as a manager.

It got me thinking about a story from venture capitalist Fred Wilson’s post titled “Leading from the Heart.”

One of my favorite stories about this comes from a particularly difficult moment in my career where I had to transition a founder out of the company they started. It was the night before the all-hands where the CEO transition was going to be announced. I asked the founder if they were going to attend the all-hands and the founder said no. I then asked the founder what I should tell the team. The founder said, “tell them you fired me because that is what happened”.

The next day I stood up in front of the entire company and told the team the Board had asked the founder to leave the company they started and that the Board had asked a member of the team to step into the CEO role.

After the all-hands ended, there was a line of about twenty or thirty people long to talk to me. And every single one of them waited in line to tell me the same thing which was “thank you for telling us the truth.”

It was a powerful lesson for me. And like most of the lessons I’ve learned in business, I learned it from a founder and their team.

If you are struggling to build the level of trust you want with the team in your company, try a little more transparency, vulnerability, and honesty in your communication style. It will pay dividends.

As a recipient of many messages from leadership over the years, I’ve learnt that I prefer the truth. Plain and simple. No dressing required.

It is often there to see anyway. The camouflage just gets frustrating after a point.

It is why Claire’s idea and Fred’s story resonate deeply with me. I love the idea of saying things that people don’t normally say. And I think Fred is spot on about communicating with more transparency, vulnerability, and honesty.

It doesn’t mean it always works. There are many instances when it has backfired for me.

But, in the long run, I think it creates better cultures and higher trust environments. And that makes the juice worth the squeeze.