A clever technique for choosing your yardsticks

Welcome to the first of The Monday 🩳

A big welcome to all the new readers! Our community grew by 50% since the release of the last essay, huge thank you to those who shared it. I’m so grateful for your feedback and the thoughtful dialogue on how we measure our lives and our relationship with work.

A new short form structure kicks off this week!

Introducing…

I’m actively working on several long form essays on the culture part of the system we call work, which touches on things like the American work ethic, burnout, leisure, and time off. It’s already 6000 words and still evolving, as I am currently adding the illustrations that bring the essays to life. I’ll release them as soon as they are ready.

Given the unpredictable length of time the long form essays can take, I’m kicking off a short form (→🩳←) component with something I’ve been pondering to bring a bit more consistency to the publication and keep the conversation going.

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On to this week’s 🩳 !

Define What You Want To Avoid

Combining two of the mental models from the last essay, The Yardstick and Inversion, we revisit the final question:

How will you measure your life?

A powerful perspective we can reference in answering this question is the reflections of those looking back on their lives as they face death. Bronnie Ware, a medical caregiver, compiles such wisdom together in her book The Top Five Regrets of the Dying - A Life Transformed by the Dearly Departing.

Below are their answers.

The Top Five Regrets of the Dying

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

2. I wish I hadn’t worked so hard.

3. I wish I’d had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish I had let myself be happier.

Number 1 and 2 are worth reading a second time, given the topic of work.

Using Inversion to Avoid Future Regrets

This technique comes from an essay titled “The Top of My Todo List” by Paul Graham, who started the famous incubator Y Combinator among many other things.

After considering the Top 5 Regrets, he shares how he could see himself “making at least 4 of these 5 mistakes.” To avoid making the same errors in his life, he inverts the top 5 regrets to define the behavior he does want.

Every day at the top of Paul Graham’s to-do list is the following:

1. Don't ignore your dreams

2. Don't work too much

3. Say what you think

4. Cultivate friendships

5. Be happy