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  • Cy Tidd

How to Work on Interesting Things

Updated: Jun 14



I have a weird job. That's what I say when someone asks what I do. I have a job title. It has very little in common with my day-to-day. That means my days are usually very interesting. Here's a list of stuff you need to do to work on interesting things.


1. Be curious. About everything. Learn a little about a lot. Learn a lot about the things that interest you. It's okay if the topics change.


2. Act like someone other people want to be around. This is how to do it, from Peter Kaufman's guide to multi-disciplinary thinking:

"Here’s your 22 second course in leadership. That’s all it takes. You don’t have to go to business school. You don’t need books. You don’t need guest speakers. All you have to do is take that list that’s in Emily’s head, and every single other person in this room, every single other person in the whole world, has this list in their head – trustworthy, principled, courageous, competent, loyal, kind, understanding, forgiving, unselfish, and in every single one of your interactions with others, be the list!"

3. Get angry about very little. Anger prevents learning and turns you into a jerk. Very few people want to be around other angry or distraught people.

  • It helps if you carry around as few identities as possible.

  • The side effect of rarely getting angry is you're generally happier and will have more energy to learn.

4. Finish some things.

  • Not everything. Then you'll work on stuff other people know how to finish, and they won't need you. Also, you'll likely be bored.

  • Cultivate an "absent-minded professor" persona. Forget to do minutiae. You'll discover you won't be stoned out of your village.

  • You do have to produce some value, however. You will be stoned out of your village if you're completely useless.


5. Listen. Get very good at listening. It's a skill.


6. Create slack in your day.

  • You need time to think, and time to do. They're different. Schedule accordingly.

  • If other people can put things on your calendar, use "defensive calendaring" and schedule blocks of time for yourself. Do whatever you want in them.

7. Write something every day. Hone that skill. Learn to write things other people like to read. Putting ideas and images in other people's heads when you're not physically present is magic.


8. Understanding does not equal agreement. The greatest barrier to listening is assuming you have to agree with the other person 100%. You don't. You can disagree 100% with whatever they're saying and still have them want to keep spending their time with you.

  • If someone does not understand what you are saying, that is not their problem. It's yours. If they don't understand after you're done explaining, then you don't know what you're talking about enough to explain it using language they can understand. Go figure that out and come back.

  • Listening to another point of view is only threatening if you've adopted an identity from someone else without really thinking about it.

  • If you get angry about a topic you haven't really thought about, chances are you've joined a tribe without realizing it. Tribes have their own talking points. If you get mad at someone when they calmly question your world-view, then it's not your world-view. It's somebody else's and you're mad because you've just realized you haven't really thought it through. Be purposeful about the tribes you join.

9. Be harmless.


10. Laugh at almost everything.


11. Be interested in everyone. When you're listening to someone, make them feel like they're the most important person in the world in that exact moment. Be present.


12. Be gracious. Maya Angelou said it best: "At the end of the day, people won't remember what you said or did, they will remember how you made them feel".


13. Before you speak, ask yourself three questions. Does this need to be said? Does this need to be said by me? Does this need to be said by me right now?

  • It's okay if you don't get a word in. If you can't get a word in, nobody present is likely in a brain space to listen to you in the first place.


14. Get enough sleep. You can't operate at optimum capacity if you're tired and irritable. Everything you do - and I mean everything - is impacted by your ability to rest and recover.

  • Find out how much sleep you need (hint: it's not 4 hours), and do everything you can to get it. Life pays you dividends when you get enough sleep.


15. Gravitate towards the problems nobody else has solved yet. They'll be hard things. Hard things are interesting things. If it were easy to solve, someone else would've done it already - and they wouldn't need you.

  • You'll know you're working on interesting things when you cannot really explain what you do to people, and you still have a job.


16. There are more books in the world than there is time to read them. Stop reading when you're bored, and read something else.


17. Be a vault. Do not gossip. People will tell you things if they know you won't turn around and blabber it to everybody you know. You will learn things about an organization and environment that will help you understand why a hard problem exists in the first place.

  • You will sometimes learn critical information that someone else should know. I usually ask my source if I can pass on some bits. I'll tell them why it's important. Use your best judgement. You will learn over time if your judgement is good or not.

18. Find out why people do things.

  • You will not be able to ask them directly. Be cautious about asking "why". People get defensive when they don't know. Humans rarely know the actual reasons they do things, so asking "why?" is a great recipe for creating defensiveness.

  • Defensiveness is a giant concrete barrier a million miles wide. It's a signpost that you're not listening very well and asking dumb questions. Yes, there are dumb questions. They all start with "Why did you..."

  • Try to get to a level of understanding where you can describe the environmental pressures that led someone to decide one thing or another. Focus your attention on changing the environment. Behavior follows incentives. Work on the incentives.

19. Learn the different ways humans process information. Understand how cognitive biases work. Human brains are glucose hogs and biases are the cognitive shortcuts brains use to save energy to keep things like the heart and lungs running. Know how the shortcuts work.


20. Understand how cognitive dissonance works. A very great deal will suddenly make sense to you.


21. Don't attempt to multi-task. It does not exist for humans and you make yourself less useful every time you do it.


22. Remember: all human dysfunction is a result of improperly communicated expectations. We're really bad at communicating with each other, so the dysfunction will never go away. But it can get better.


23. None of us are getting out of this alive. Every day is a gift. Work on something that's interesting. If it's not interesting, go find something else. If you die tomorrow, that silly thing you're wasting your time on will be done by somebody else. Plan accordingly.

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