11 questions from Tribe of Mentors by Tim Ferriss

Reflection is good for you

Dan Barrett
5 min readMar 3, 2018

I was inspired to do this by Richard’s post, which was in turn inspired by @jukesie’s post.

In their posts Richard and Matt answered questions from Tim Ferriss’ book ‘Tribe of Mentors’.

Quoting Richard:

Ferris had just turned 40 and was wanting to answer some fundamental questions about life. Not knowing what his own answers would be to these questions, he asked over 100 people how they would answer them. The book is their answers to the same basic 11 questions, and is full of amazing life advice from amazing people.

I just turned 40 too, and I am amazing¹. I thought that I would give it a go.

Full disclosure: I haven’t read the book, but I will — it sounds great. I got the 11 questions from the sample chapter from Tim’s blog, which I really enjoyed.

It can take me a long time to write, but for this I’ve tried not to deliberate too much. I answered 10 of the 11 questions — question 10 stumped me a bit. Right…


ONE: “What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?”

I can’t think of a book that I’ve given as a gift more than once. I did write a blog post about 3 books that helped me in my work. Of those, I’d pick ‘Boyd: The Fighter Pilot Who Changed the Art of War’ by Robert Coram. This is a biography of John Boyd, the influential late twentieth century American military strategist. The military aspect doesn’t interest me, but Boyd’s works and theories (in particular the OODA loop) have crossed over into many other sectors, including ‘digital’ strategy.

I first heard about John Boyd from my colleague Robert, who is very wise and well-read. John Boyd didn’t publish many works, but reading his biography was a really effective way for me to learn about his ideas, and his struggles. Telling the story of how these ideas and influence played out over decades, often with unintended consequences, was especially relevant in the context of work. Overall it was thought-provoking and particularly humbling.

A second book would be ‘Infinite Jest’ by David Foster Wallace. It’s the novel that’s stuck with me for the longest after I’d read it, even though I can’t remember what happens in it. I found it to be incredibly sad, funny, and true — with a resonance that went beyond the words and the characters and somehow described how I feel about life much of the time.

TWO: “What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)? My readers love specifics like brand and model, where you found it, etc.”

Digital kitchen scales. The cheapest available (around £10), from Argos.

THREE: “How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?”

I’m not sure about “success” here. Still, in my third year of university I didn’t work hard enough and I didn’t do as well as I should have done in my degree. It was a privilege to be there, and I wasted the opportunity. I didn’t know what I wanted to do afterwards, and I struggled to get a job. After being miserable and aimless for the best part of a year something switched², and it sorted out my work ethic after 8 years or so of coasting. It made me realise work was important, and rewarding, and that I need to continually test myself and grow. I can’t say hand on heart that I’ve never coasted since, but I try not to.

More recently, failure to get a promotion led to me defining a role with a bit of a personal work mission, and led to 18 months of the best work I’ve done.

FOUR: “If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)”

“Never stop playing.”

FIVE: “What is one of the best or most worthwhile investments you’ve ever made? (Could be an investment of money, time, energy, etc.)”

My Tascam 414 4-track cassette recorder. It was a significant purchase 20 years ago and I’ve used it to make music ever since. I find the constraints that the device puts on me make me more creative. I also like the fact that I’ve scrupulously looked after it, because it’s always been precious.

SIX: “What is an unusual habit or an absurd thing that you love?”

I take pictures of things that are orange.

SEVEN: “In the last five years, what new belief, behavior, or habit has most improved your life?”

Writing on the internet.

EIGHT: “What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?”

Work is not a soap opera. Try not to participate if things are getting melodramatic. If your life is missing a grand narrative with intriguing subplots then maybe try some great fiction. Don’t whinge — be positive. Stay humble.

Ignore anything related to hierarchy unless it’s ‘ignore hierarchy’.

Ignore any advice that involves not at least trying to achieve something you believe in.

NINE: “What are bad recommendations you hear in your profession or area of expertise?”

A tendency to bring in third parties to ‘solve’ problems when those problems can’t be solved in the relatively brief time of a commercial engagement.

ELEVEN: “When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do? (If helpful: What questions do you ask yourself?)”

I listen to music, particularly things that are long and that you can zone out to. Some recommendations:

Increasingly, I go for a walk. I don’t consciously ask myself questions, my mind doesn’t really work like that.

¹ Your mileage may vary

² My mum and dad were really important in this. I feel I let them down, but they’ve never pressured me and have always supported me



Dan Barrett

Head of Data Science at Citizens Advice. These are my personal thoughts on work.