Words of Wisdom 020: On solving hard problems

Happy Wednesday! Since this is my 20th post in the Words of Wisdom series, I thought I'd share a few reflections on the process.

Here are three things I've learned from writing my first twenty Words of Wisdom emails.

1. Writing leads to more writing. I currently have 18 other posts drafted to various degrees of completion. Begin a practice, and it will build momentum. The thousandth rep is much easier than the first five.

2. Writing leads to improving my thinking. I have 14 unfinished drafts because I will start to write something and be unsatisfied with my thoughts on it, so I then need to revisit it four or five more times until it is ready. That's true of many things, and continuing to show up leads to progress over time. If you want to improve your thinking, try writing things down, share your thoughts with others, and get thoughtful feedback.

3. To influence others, I need people to influence. More people need to grow in wisdom. If you know me, you know I'm not a big fan of self-promotion, and I'd rather talk to someone in a corner about hard things they are facing than be in the limelight. But that's the great thing about writing: I simply imagine that I'm writing to one person. Then a lot of people get to read what I've written. So sharing what I've written is a kind of stage. It's helpful because it keeps me accountable to share what I've learned with you.

But this will only be successful if the word gets out.

If you'd like others to learn from me, send them here and rave about me. I'm not very good at bragging about myself, but if you think what I'm writing is helpful, be bold, spread the word.

Okay, on to the Words of Wisdom for this week!

On solving hard problems

Difficult problems are the only ones worth focusing on. The more you grow in solving complex problems, the more valuable your skill set is.

There are different types of problems. Some problems are not complex. We know the answers and simply need the courage to live out the answer. But other problems are challenging to understand, let alone solve, and it is this second type of problem we are focused on today.

Below is a list of questions and helpful perspectives when solving hard problems.

When considering how to solve a problem, you must first understand the problem. If you can't name the problem, you won't have a clear idea of how to solve it. You might even waste time working on the wrong thing if you don't understand the problem.

How would you describe the problem?

What words best describe the dynamics that make up the problem?

What data do you have?

What are the key metrics that you can measure?

What data do you need to understand the problem?

What is the unknown? What can't you see? What is missing?

What are the conditions that make up the problem?

What is the simplest possible explanation?

What one thing, if successfully done, would help everything else or make other elements unnecessary?

Separate the different elements of the dynamics you see. What contributes to what? How does A cause B? How does B influence A?

Draw the problem. Visualizing the dynamics can be helpful to simplify.

What is a similar or related problem? Who else has seen this same or a similar situation? How did they solve it? What is different?

How can you solve part of the problem? Can you solve a related problem if you can't solve the primary problem? How are they related? What is different?

What is your hypothesis for a solution?

What is your plan? How can you run an experiment to see what might work?

How can you run the experiment as quickly and efficiently as possible?

How can you test the assumptions of the solution with the least time and resources? Is there a way to prototype the solution first?

What do you need to measure to learn if your experiment proves your hypothesis?

What did you learn from running the experiment? Did it work? What exactly happened? What specifically went wrong?

Was your hypothesis proven true? What assumptions were proven false?

What could be changed to make it better the next time?

What did you learn?

Who needs to know what you learned?


"It is foolish to answer a question that you do not understand. It is sad to work for an end that you do not desire."

G. Polya, How to Solve It: A New Aspect of Mathematical Method

"Talk with people you usually avoid. Pursue subjects you know nothing about, and experiences unlike anything you've done before. If you're not surprised — if you didn't feel your brain changing — then you didn't really learn. Don't be consistent with your past self. Only idiots never change their mind. Sacrifice the things you used to believe, and the ways you used to be. Learning leaves a trail of little deaths."

Derek Sivers, How to Live


What problems are you working on solving? I'd love to know.

Live wisely,


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