During my recent three-month sabbatical, I learned so much and was journaling a lot. Eventually I wanted to synthesize all of my reflections. So I came up with a process that’s become surprisingly impactful: pick the most important lesson each day, and write it down as a single sentence.

I now have over a hundred key lessons from the last few months, and it’s very powerful stuff.

How it’s impacted me

By re-reading the insights several times a week, I’ve changed in a number of ways:

  • It’s super-charged my growth overall. I adapt to new lessons faster than before, while in the past I needed to run into a quote/realization a number of times before it stuck with me.
  • It forces me to think clearly. I have to distill the most important takeaway. That’s hard, and very useful.
  • It makes lessons very memorable, because they’re catchy in their “one sentence” format.
  • It sparks curiosity in me, because I’m on the lookout for the next thing to learn.
  • Seeing all my learnings makes me feel more confident and relaxed about my growth overall.

I think most importantly, it’s helped me be a better me, faster. So that’s why I’m sharing with you.

Recent examples

Feb 24: “The secret to being boring is to say everything”

This was a quote I saw that day. It’s something I’ve been practicing when writing and designing lately: you have to choose a key message to convey, and then cut all the rest.

It’s hard!

The quote eloquently explained the “less is more” concept, and I’ll be taking it with me as a rule of thumb.

Feb 25: Only discuss solutions after people clearly see the problem

As an entrepreneur, my mind quickly jumps into “we can fix that!” mode. Every day I’ll come up with a handful of solutions to problems big and small. I can’t help it!

But when working with other people — particularly in a remote company, like Lookback— that may not always be useful, or even appreciated. Especially if people don’t even see the problem I’m addressing in the first place.

So this insight is applicable when communicating, like in team meetings: when raising topics, I can start by making sure there’s clarity about what the problem is and how it affects us.

And only after I’m successful in that — if we all agree that it’s actually a problem — can I help steer the conversation into solution mode. And that’s when I can present my ideas.

Much better.

Feb 28: When you can’t articulate something, go out and find the words

I was recently in a situation with a group where our collaboration just wasn’t working. I concluded we didn’t understand one another, and on my part, I wasn’t expressing myself clearly.

I often find myself in that situation. I love to learn, read, experiment, and will often have learned or intuited something that I can’t properly explain yet. My writing, I should tell you, is really part of a longer plan for myself to become clear and to structure what I’m seeing and learning.

Either way, the situation in question was resolved more easily once I had gone back and meditated on what I was feeling, so that I could really communicate it. And once I did, everything was easier.

My lesson is to keep up this behavior: take a pause the next time I feel that way, and don’t come back until I’ve clarified — within myself — what it is I’m really feeling or thinking. In order to be able to collaborate and discuss things effectively.


Those are some of my examples. Again, I only actually write down the headline itself, not the actual explanation. The explanations were just for you.

If you end up using this idea, I’d love to hear from some of you how it works and what you’re learning!

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