Be Someone People Can Root For

January 28th, 2023: Greetings from Austin and welcome to the many new subscribers that found me from the Tim Ferriss shoutout this week.


#1 The Great Contemplation

This week I published a piece on Every talking about a broader shift I’ve been seeing in how people are relating to their work. I think many people are underestimating both how much things have changed in the past three years and also how much things will likely continue to change.

The industrial economy is shrinking. No serious person still working thinks working in an office is necessary most days of the week. Millions of boomers have started to loosen their grip on the higher rungs of power in the business world. The gravy train of “superstar” profits and wages in the tech industry seems to be slowing down. And people are waking up to the fact that it’s normal to talk about wanting more out of life than a life built around a career.

Here’s how I started out the piece:

If Tim Ferriss’s 4-Hour Workweek kickstarted the “first wave” of the post-industrial reimagination of work in 2007, 2022 was the year that a newer, and weirder, second wave began.

Unlike the first wave, which largely played out at the individual level, this one is happening at the societal level. While it is still early, this “great contemplation,” as I’ve been calling it, will likely shape the work stories that people use to orient their lives over the coming decade.

I then outline my personal work awakening, influenced by many of the ideas Tim Ferriss helped seed into the world in the 2010s, and how in 2020 a much larger group of people started to question the underlying assumptions about work in society.

#2 Be Someone People Can Root For

In Find The Others this week, we had a session on launching and running a newsletter and were talking about how sharing your ideas can be a generous act. A few reasons why:

First, no one has your unique experience and it might genuinely help someone else make sense of their own situation.

Second, you have something worth saying. People overestimate how much high-quality content there is in the world. As someone that writes about work, I still need inspiration myself. I get a lot of this from observations, conversations, and books, but surprisingly, don't find much writing about it that's all that interesting. Venkatesh Rao and Derek Thompson are probably the only two people who write about work I pay attention to that have a sizeable audience. When people like

start writing and about taking a sabbatical and her experience, I am pumped. Why? Because there is a lot more to learn from raw human experience than the same talking points that many mainstream new organizations push out.

Finally, there are many people who might like rooting for you. This can be hard to realize because the majority of people in the world don’t seem to spend much time rooting for others. It is easier to criticize than to cheer especially when we are talking about people trying new things. I sense this is because when we cheer someone on we are also making a metaphorical “bet” on that person and might feel that if the person disappoints us, our own reputation takes a hit too.

But I sense the bigger risk today is that people have no one that believes in them.

Root For Others & Also Give Them A Way To Root For You

It surprises me how often I connect with people who are clearly lit up by what they are doing but have not found a single person in their life that has told them to keep following that energy.

People are more likely to be mocked, peppered with skepticism, or met with silence in an average group for sharing something they aspire to do than being met with active encouragement.

I think people are easy to root for. If you look at others with a question on your mind, “what seems to be firing up this person?” you quickly find a lot of interesting things going on. We are often held back from even looking for these positive signs by our own insecurities. We are scared of standing out and end up projecting our fears onto others rather than paying closer attention.

But also, some people make it damn hard to root for them.

This is the point I was making in the newsletter Q&A session. If you are creating something, and are putting ideas out into the world, why make it hard to find you?

A newsletter is the easiest possible way to give others the chance to root for you. So I was delighted that at the end of our session, a few people said they would give it a go and put up a sign-up form.

And this is what Brian Reisman did after the session. He sent this landing page out and I loved it. Look at how much thought he put into it!


What helped them take action is reframing “I need to write every week and never disappoint people” to “I can throw something up and choose to share something if inspiration comes.”

Don’t overthink this stuff. Make it easy to root for you. Because one thing you’ll find is that in a world of billions of people, there are far more people than you think who are fired up about what you are too. We tend to place too much emphasis on what a random group of friends via circumstance think about us than the many more in the world who are interested in similar things.

But the art of being easy to root for is not something that comes naturally to most people and is something I’ve had to work to embrace a little more over the last year.

When people first started posting my book online I felt weird. Yet when I re-shared it and also started sharing my book sales number I noticed people were really excited for me. They wanted to root for me. This has also helped me work through some of my own insecurity about having bolder goals or actually having the courage to say things like “yes, I want to make money from my writing and book.”

Still, I didn’t expect this much rooting-for-me-ness

I shipped the essay at the top of this newsletter on Wednesday.

On Thursday, Tim Ferriss ended up sharing it on Twitter and in his weekly newsletter and it seems he read it too.

Tim Ferriss @tferrissThank you, @p_millerd, for a very thoughtful piece, and thank you to @jposhaughnessy for bringing it to my attention! Jim O'Shaughnessy @jposhaughnessy"I believe that @tferriss-- book laid the groundwork for this shift—has had a bigger impact on our collective relationship to work than people think." ~@p_millerd Tim was early to The Great Reshuffle party

This was quite cool but you know what was cooler? Seeing people root for me. Many of these friends I’ve gotten to know both online and in person over the past few years.


An emergent swarm seemed to form creating the illusion that I was moments away from being invited on Tim’s podcast. I’ve been joking over the past year that this is my only goal because, why not?

Tim’s team hasn’t reached out but I have staffed a team standing by watching my inbox.

But I don’t care about any of that. What mattered is that I was laughing all day seeing people root for me and support me. I was filled with gratitude and felt seen and can’t wait to continue to do that for others too.

Sometimes that’s all we need, right?

Who can you root for? How are you making it easier for others to root for you?

#3 You have ONE life - David Senra

I interviewed David Senra, the creator of Founders Podcast, this week. For the past five years, he has been reading hundreds of books and synthesizing them in his own unique style on his podcast.

It was fun to compare notes on betting on the internet, the desire to share ideas, playing long games, learning from weirdos from history, and how to balance work and family.

We also talked about:

  • Working 35-40 hours a week in high school by taking summer school classes
  • Deciding that “finding his life’s work” was the most important thing in the world
  • Why David thinks keeping his podcast behind a paywall was a mistake
  • Nobody understands the scale of the Internet
  • Ed Thorp as a role model for balancing entrepreneurship with fun and family
  • Lessons from David Ogilvy and Marvin Bower
  • “The only risk is not taking any”

He also messaged me after the episode and said “Can I buy $1k worth of books and give them away to listeners?”

Uh, yes?! I’ve also decided I’ll go beyond his $1k and give away even more books on my own than I expected. So far I’ve sent about 170 books to people around the world, including a bunch to a friend’s conference. If you want a copy, check out the episode for details.

#4 Layoff Reflections

A few people reached out after recently getting laid off. I asked if I could share their experience. Here is one person that go laid off from Salesforce:

I’m early 40s, and was supposed to make senior director this year. Glowing performance reviews. Boss literally told me before the holidays “you have nothing to worry about

I was on paternity leave over the summer and only took two months (instead of the 6 I could have) because I wanted to get the promotion.

So it hurt having worked so hard to just get canned via email.

It was also interesting to see how people I know reacted. I posted about being laid off publicly on LinkedIn. I know a lot of folks who didn’t and have otherwise not signaled publicly that they’ve been laid off. I had a handful of people immediately reach out with genuine concern and offers to help, which was really great and affirming but then people super close to me literally said nothing. As if they were unaware.

Which was really surprising, so kind of a jumble of emotions. There’s always so much talk in corporate about being a family and we care and all that, and then to just get canned via email despite being a high performer

Definitely felt bitter at first

Work is still such a hard thing to talk about and I wish more people would share their experiences.

We equate being unemployed to being a bad person because of how important work and employment have become in our lives.

Remember to check in on friends if they are out of a job and don’t project your own insecurity onto them on top of what they are feeling. They are probably already feeling bad enough.

#5 Two Reads On Starting & Shipping Things

Two people wrote about me this week and they are both worth following.

who I mentioned above argues that we should hit send so that people can support us:

When I started writing online a few months ago, I carried these lessons with me. I learned that people don’t mysteriously stumble upon your work if you’re keeping it safely bubble wrapped in a box.

wrote about how I helped him get started with his newsletter by saying nice things to him and then also acting as an escrow service, holding his cash until he followed through on his creative impulses,

Paul is a DIY your life path sorta guy (read his dope substack Boundless here) who left consulting and sorta roams around the internet like a self-employed buddha, helping people who feel ready to leave the corporate / 925 world behind. I definitely had doubts about him at first - like who the fuck is this guy he and what does HE get out of this, but after running several double blind experiments (meaning neither he nor I were aware of the experiment), I can safely say he is simply a good man.

He kept sending me kind messages that at least did not feel like they were bullshit:

And for a frail, young writer who was confident that everyone hated his work, that genuinely meant the world. Paul had no reason to reach out and say that unless he meant it. Or maybe this just means he pulled off the perfect crime that sunuva! But it seemed genuine and so I believed him.

Alex is hilarious and the essay is also just a good step-by-step guide on starting things:


#6 Find The Others

This week we had a “hot seat” coaching session with my friend Chris who is balancing his success in the corporate world with an emergent desire to create more. It raised a fun debate over whether a Master’s degree was worth it.

We also had a session on newsletters that inspired a few people to launch them.

We’ll have our next monthly “social” on the first Tuesday of February - the 7th.

Both are recorded and if you are interested in joining you can subscribe on substack for $20/month and get instant access or do the same thing on circle.

Only join if you want me to root for you :-)

Thanks For Reading!

I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support my journey, the best ways are to:

  • Buy or listen to my book, The Pathless Path (or message me if you want to bulk order at a lower price)
  • I’m looking for sponsors for 2023 for this newsletter or podcast. Please reach out or book a package here directly.
  • Subscribe to my podcast and leave a review
  • Join Find The Others if you want to hang with like-hearted generous weirdos.

In addition, I recommend all of the following services (affiliate links): for HD podcasting, Transistorfor podcast hosting, Podia or Teachable for courses, Skystra for WordPress Hosting, and Circlefor running a community

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