“The Pathless Path” tells Paul Millerd’s journey of going from traditional employment (GE, McKinsey) to embarking on a journey to follow his interests and eventually becoming a writer after going through difficult times due to health problems and loss of loved ones. Watching videos of Paul, I loved his calm energy. He’s very affable: humble, goofy, and excited like a grown up kid. His book resonated with me because I’m in a similar life stage, on a sabbatical, exploring different interests and paths beyond my software engineering career at big tech companies.

Here are some of my notes from the book:

• If work dominated your every moment, would life be worth living?
• The longer people stay at a company, the higher odds that they would become what the company wanted.
• Prime candidates for burnout were those who were dedicated and committed, trying to balance their need to give, to please others, and to work hard.
• The most common regret? Not staying true to themselves in their lives and focusing too much on what others expected of them.
• Misery tax: This is the spending an unhappy worker allocated to things that keep you going and keep you functioning in the job. For me, it was a mixture of alcohol, expensive food and vacations.
• Arrival fallacy: The idea that when we reach a certain milestone we will reach a state of lasting happiness. For years. I believed that once I had achieved an imaginary future leadership position, I would then finally be able to be myself.
• Life scripts are culturally shared expectations as to the order and timing of life events in a prototypical life course. Most of these moments occur before the age of 35: graduating from school, getting a job, falling in love, and getting married. This means that for many people, expectations of life are centered around a small number of positive events that occur while we are young
• My biggest barrier was my inability to imagine an alternative life. I started looking for another job. I still thought the perfect job was just around the corner. There was no dream job to be found.
• We must let go of the life we have planned, so as to accept the one that is waiting for us.
• I hadn’t set out to prototype a life beyond full-time work, but through freelance projects, coaching, paid speaking, writing and connecting with people online, I achieved the same result.
• Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown… They learn to sidestep the manipulative manager, or change jobs every couple of years, plan vacations, stay busy, and get drunk during the weekend. Uncertain Discomfort < Certain Discomfort + Coping Mechanism
• Most people want to contribute, help, and engage with the world. People in their 60s and 70s, while they often don’t have full-time jobs, they enjoy working part-time, volunteering, learning new things or finding other ways to contribute.
• The spirit of a mini-retirement is about testing different circumstances to see if you want to double down on them or change directions.
• I’m orienting my work around taking every seventh week off from work no matter what.
• On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It is to actively and consciously search for the work that you want to keep doing. Once you find something worth doing, working backward to build a life around being able to keep doing it.
• What I want to keep doing, such as mentoring young people, writing, teaching, sharing ideas, connecting people, and having meaningful conversations, is worth fighting for.
• Despite dealing with post-traumatic stress disorder, many of the soldiers wanted to return to dangerous war zones. Why? Because at war, they felt part of something, deeply connected to the men and women they were serving with.
• The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything. Which means you get to start early the work of figuring out what does mean something.
• If your success is not on your terms, if it looks good to the world but does not feel good in your heart, it is not success at all.
• Oprah Winfrey argues that each of us has a personal calling. The best way to succeed is to discover what you love and then find a way to offer it to others in the form of service.
• Instead of thinking about what I want to do and how I want to live, I start instead with what I don’t want to be doing and what failure looks like.
• Biggest risks for me are spending my time doing things that undermine my ability to stay optimistic and energized, and obviously running out of money.
• Only by taking action do we learn and only by learning do we discover what we want.
• “What would I end up doing with the increasing earnings?” I decided I would use the time to write. Then I realized that there was nothing stopping me from doing that at the moment. So I decided that instead of scaling my course, I would write this book.

The book also has a good bibliography, referencing works from Agnes Callard, Eric Fromm, and David Whyte that I look forward to reading. Overall, I enjoyed reading about Paul’s journey and his perspective on work.

“Stop Asking Questions” is Andrew Warner’s book where he offers short lessons on how to be a good interviewer and podcast host. There are lots of great tactics that can be applied to everyday conversations. Here are my notes from each section:

4. What’s a win for you
Reassures the guest that you care about their needs, establishes trust

• What would make your team happy to hear us talk about?
• Why did you agree to do this interview?
• How can I make this interview as useful for you as it will be for me and my listeners?

5. Join the resistance
“I never failed” → “It’s amazing to talk to someone who always got everything right”
“I’m not a worrier” → “I don’t usually get to talk to people who are 100% confident”

6. Discover topics they crave
Look for shoved facts during the conversation:
“Sorry I’m late. When you go through a divorce, everything takes longer …”

7. Reciprocation
If only one side shares vulnerable information, they will feel resentment. If you want people to be open with you, you need to be willing to share first

8. Promotion stopper
You can use this phrase: “We’ll get to that, but first let’s finish talking about ….”

10. Because
Just ask “Because?” to let the guest elaborate

11. The dramatic lowball
I threw out a number that was absurdly low for her. I asked “Are you doing at least a million dollars in sales?” She shot back, “We’re doing 20 or 30 times that.”
I gave her a number that was almost an insult. Instinctively, she felt the need to correct the record.

12 . Share a higher purpose
Give the guest a mission they can buy into and support, examples:
– “Greg, I want to record an interview so good that decades from now when your great-great-grandkids wonder how you built your business, they’ll come listen to what we record today.”
– “We both believe in pushing ourselves physically. I think I might be able to do my first solo 26.2 mile run, but I’m still at only 14 miles. Would you help me?” –

13. Stop asking questions
Question after question sounds needy. Instead of asking “How did you get your first customer?” I said, “Tell me how you got your first customer.”

14. Put the words in someone else’s mouth
“What do you say to someone listening to us thinking, ”James is only happy now because he has money in the bank.“ I imagine someone listening to us thinking …. What would you say to that?

15. Pre-ask the shocking before the interview
Would he mind if I asked him about it so he could address it?

16. A time when you
A lot of advice can sound cliche. But when you share advice through stories, it becomes memorable and actionable. Ask “Do you have an example of that?”

17. Stop asking most questions
Instead of asking “Who’s the most important person you hired? I go with ”Who’s an important person you hired?“

18. Use double-barreled questions
Double-barreled questions are questions that address two different issues. When reporters ask double-barreled questions, their subjects answer the easy part and ignore the part they don’t like.

“Is it inappropriate for me to ask …”

20. Sorry to interrupt
“I’m sorry to interrupt, but …”

21. Avoid train crashes
Have an emergency question ready like “What’s your motivation?”
“Listening to you, I can see you work hard. I have to pause and ask: what’s your motivation?”

22. Home run questions
The peak-end rule is a cognitive bias. Humans tend to remember two aspects of an experience more than anything else: the peak (i.e: most intense) and the end.
When an interview ended, I thanked them, and told them they did well, and mentioned one specific thing I liked from our conversation.

Pre-Interview
You might be tempted to send over a list of questions before the interview. I found that shortcut to be much less effective.

Interview Structure: Hero’s Journey

(Asking reddit founder) “True of false” You guys saw that Digg was doing well and said, ‘Let’s jump on that bandwagon“

Joe Rogan’s style: The host moves quickly through multiple subject areas, looking for what’s new and fascinating. “Forget about the flamethrower.” (switches subject)

Ask your audience: “I’m going to interview [whomever]. What questions should I ask them”

Stop looking for guests individually and instead look for sources of guests – search for idea fountains
Interview idea fountain: “Companies acquired in the last 3 months” or “Amazon’s upcoming book section”

How to say No
When it’s time to say no, depersonalize it. Put the rejection in someone else’s mouth. Did you promise your sponsor you’d focus on a certain type of guest? Say so. If there’s no one else to point to, blame your higher purpose and guidelines.

“I admire what you have planned for your company, but when I interview founders of smaller companies, my audience complains and sends me angry emails. It’s not worth it for you and me to get that kind of treatment”
“In recent years my audience has complained when I feature investors instead of entrepreneurs”

Tools he uses:

• Descript [Editing Software]
• Semrush [which websites send people to my guest’s website to understand their marketing]
• Pipedrive [CRM]
• Sachit Gupta – creatorsmba.com
• Fusebox – audio player for your website

Not Giving Up
I couldn’t give up because I had already scheduled more interviews. I had to keep going because I’d already committed to interviewing them and others. The best way to ensure you keep going is to schedule interviews ahead of time. Let your commitment to another person drive you even when you doubt yourself.

The book was a page turner, I couldn’t put it down after starting. The descriptions of his manic state were very engaging and I could imagine myself as a manic CEO. It’s a good read if you’d like to build empathy towards people with bi-polar disorder.