7 Lessons I Learned from Paul Millerd

On writing, building an audience, the creative act, and living on the pathless path

Austin, TX

“I don’t actually know how to do what you’re doing.”

One year after reading his book The Pathless Path, I got to meet the man himself—Paul Millerd. When I was asking for advice on my own path of pulling out of pre-med to pursue writing, I didn’t expect him to drop this wisdom bomb on me.

“I have no idea,” he said. “I went to college in 2003. We had no social media. There’s now so much more resources and stuff. I wish I started writing more seriously earlier.”

While I admire Paul’s humility and honesty, he did happen to share some awesome advice with me that I wanted to pass along you.

1. Write For Smart People

One of Paul’s mottos: write for smart people. Go deeper.

When I discovered Twitter last year, I fell into the trap of thinking that I should talk about the trending things—like nutrition or copywriting—because that’s what everyone I saw was liking, retweeting, and building businesses around.

“Are you a midget? Here’s 5 ways to grow 12 inches taller in under 10 minutes and less than $5.” Algo-driven, advertising-style writing like this.

But all this repressed my own curiosity. I burnt out. I started to dread writing and creating, all because my own voice was muffled by this Twitter trap saying that I “should” study certain things or schedule Tweets.

I thought I wanted to be a health coach, but I knew I wouldn’t be fulfilled because I actually like spending my time in solo study, reading and writing. I don’t really want to be on calls all day, and as Paul told me, most coaches don’t actually like the act of writing.¹

This made me realize: I’m writing for someone very similar to me. I’m writing for one obsessive, ambitious intellectual. If I don’t write with the intention of writing for smart people, I’ll attract people who want the snackable content and petty platitudes. People who wouldn’t read an essay as long as this one.

As Paul said:

“Short stuff gets more views. Long stuff gets real views. People don’t remember short stuff. Long stuff will get you a good audience where people engage with it, remember it, and start to pay attention.”²

Even though my family does subscribe to my Substack, I’m not actually writing for them. I’m writing for myself and some of my homies, and creating should feel exciting, interesting, and fun!

So to remind myself of my audience, I treat each essay like a letter. In a H2 header at the top of every Google Doc, I address it to one of my smart friends (or sometimes an older version of myself).

2. Curiosity > Followers

Last year on Twitter, I got sucked into focusing on followers instead of expressing myself authentically. Likes, retweets, engagement—all that stuff superseded my curiosity.³

It took me almost a full year to learn the lesson Paul would go on to tell me:

“In the creator game, there's this surface level game: how do I grow followers as fast as possible? I actually think that's a stupid game. Do you care about the creative act? As a creator, you have to create the stuff that inspires you and that you can sustain over the long term.

Almost everyone will play surface level games, so once you internalize this, you’re basically not competing with anyone anymore because the only thing that matters is where you curiosity is going to take you.”

This even applies to how he thinks about booking podcast guests. Paul doesn’t care if it’s some big-name bad-ass. If this person just shares the same tactical tricks on every podcast, he can’t bring his heart to it, even if it goes viral:

“I don’t care. I can’t get excited for it. I can’t be motivated to do that, even if it would give me a crazy amount of views. So I’m ruthlessly protective of my own curiosity and energy.”

I deeply admire Paul’s honesty. Just like how an orchestra opens a symphony by tuning their strings to a single note, Paul is harmonized and fully in tune with his curiosity.⁴

But I was still curious: how does he know if he can’t sustain something? How is he honest with himself about doing things he likes doing? I’m still trying to work on this. I wondered how it shows up for him.

So I texted him, and he replied:

3. I Am Valuable (How I Met Paul)

Another thing that Paul told me is that at my age, I’m valuable. My competitive advantage is being young, living low cost, and being available:

“All the smart people who are 21 are wasting their talents at school. Not wasting, but at best, they’re not very hireable.”

I connected with him in the first place through an innocent Twitter DM. We briefly had talked before, and I just asked him if he knew anyone online or in Austin who needed a research assistant. He said he himself did but didn’t need help that very second. But he still gave me a brief project outline.

Then after taking a tiny $1 course called the Permissionless Apprenticeship, I saw an opportunity. Without him asking, I did some research from the podcast project that he outlined. I created a Google Doc for him that compiled some research I thought he’d find valuable.

He loved it. He told me that most people will email him about wanting to do Instagram Shorts or something but will never actually just send him one damn piece of content. 

As I later found out when meeting him in Austin, Paul actually just pulled that podcast project out of his ass. He created it for me because he loved my energy and enthusiasm.

This echoes exactly what Write of Passage founder David Perell said on Paul’s podcast:

“People are disproportionately willing to help young people who are highly curious and are high agency. If you are between 14 and 24 and you have ideas and you are hungry and you are willing to listen and learn and ask good questions, everybody will help you.”

Paul also showed me that I can think bigger. In the creator space, the obstacle is that there’s infinite ideas but not enough time to execute. Taste is treasure. It’s exciting when people like me take the lead and say, “this idea is awesome. You need to double down on it and do this.” 

So if I see an opportunity for someone, I can reach out and be the CEO of a project. The research I did for Paul was great, but the next step is being even more assertive.

This could look something like, “Hey, I’m going to go through all of your podcasts and be the project manager of pulling a book together for you over the next year. Give me $25K to do it.” The great part about a strong and clear ask like this is that it’s something that someone can say yes or no to.

4. Take All Online Advice Lightly

Going back to that Twitter trap, Paul said to default to thinking that everyone is full of shit about what they’re saying online.

But at the same time, since there’s no rules, still pay attention—with lightness. Try everything out. See if it works. Look for recipes, but don’t take any of them all too seriously. 

I’m still learning to unlearn from the scripts and stories I grew up with. What am I actually curious about? What do I want? Who am I? While it was wonderful to meet some fast friends on Twitter, there was still a mimetic skewing of media on my own curiosity.

What this translates to in my actions is less inputs. Less podcasts, less books, less newsletters. The only thing I’m actually actively reading is The Iliad. I haven’t listened to a podcast since May. For now, I don’t even feel called to consume many Tweets or almost anything created in the 21st century.⁵

Don’t get me wrong: I’m still open to people’s advice. But I’ll only take it if I feel excited. Regardless of the giver, something I’ve learned over and over is that following the feeling reveals everything. There’s no shortage of noise in society that too easily silences the stirrings of the heart.

As Derek Sivers wrote:

“You’re going to hear a lot of advice. Listen to it all, but pay close attention to what it does to your energy and focus. If it makes you jump into action, it’s good advice. If it makes you feel drained, sad, or lost, then it’s not for you.”

5. How to Spend My Time and Money

So then the question of money comes up.

For now, I’m in a really lucky position: I don’t have to work for money. My parents are paying for food and rent. I have the freedom to work on whatever I want. But because I’m a time billionaire, Paul said that I should be strategic with how I spend it:

“You need to generate ideas for what to do with your time. Do you want to spend 80% of your time writing on your own terms? 50? 30? 20? 10? And do you want to spend 90% trying to make money? Some things sound fun, but then when you’re doing them it feels like a job and you’re not learning anything and just producing money.

Don't just do what other people around you are doing. Try to default to the idea that what other people around me are doing might not be the best path for me, but how can I remix those things to make them my own?”

In the past few months, I’ve done a few paid projects with Paul. I was a research assistant and pulled together the juiciest parts of his podcast. I helped him script and outline a Youtube video essay on redefining ambition.⁶

I didn’t make much money, but I ate all these projects up because, like Paul, I’m at my best when I get to read, research, write, and puzzle ideas together.

But besides this, I didn’t really feel called to do any more projects. I still wanted to spend my time learning, so I invested in some life-altering experiences. The way it unfolded was perfectly unexpected, and I haven’t even written about most of them (yet). They tended to be at the intersection of introspection and psychology:

• I took Jordan Peterson’s Writing Course, Self Authoring. I reflected on my past, assessed my own faults and virtues, and set a vision for the next 5-10 years. I wrote about the course here.

• I went to Danny Miranda’s Be Light men’s retreat in Austin. The theme of the retreat was about loving everyone and everything in your own life, including yourself, your shame, and the people in your past who wronged you.

• I hired a trained therapeutic guide to facilitate my first psilocybes mushroom experience. It was one of the most beautiful and profound experiences of my life. I learned about a different dimension to reality. I learned why most of world is anxious. I saw what Steve Jobs was talking about.⁷

6. Play Games You Won’t Quit

I’ve been writing online now for almost two years. I love it, and I can see myself doing it forever. But it took some time for me to realize that I shouldn’t rely on my own writing to make money—at least for now. 

I told Paul about how while it’s amazing that I don’t have to work for money, there’s also this responsibility that I feel, like I should almost be doing more. But he said that if I like writing, keep at it and protect your time doing the things you like doing.

He spent as little time as possible trying to make money to fund the life he likes. He did this for 5 years, and now he’s recently had this phase shift where he can make money from the thing he loves! Paul’s now sold over 50,000 copies of The Pathless Path.

People will mention money and all these other things, he said, but just ignore them because you can make it work. It just might take longer. So I’ll keep writing, but I’ll also think more about building other businesses and CEO’ing some other creative projects.

Part of why I also got trapped on Twitter was because I was looking to make money online right away. But from what I’ve seen, a lot of these businesses are short-term ventures that people eventually bail on.

While I’m all for trial and error, Paul said that you can’t get any compounding returns if you play games that you’ll quit:

“If you've set up a game for yourself that you're going to end up quitting, that's the biggest risk. Almost everyone I've seen in the online creator world quits, especially Americans, because the wages for normal jobs are just really good.”

So because I’m not desperate to make money this instant, I’ll still create compounding returns with writing by doing it pretty much every day. No matter what else I do to make money, I’ll still abide by another of Paul’s mottos: write most days.⁸

7. “I don’t know what I’m doing.”

Almost 5 months ago, I had a hypothesis in my heart: I had to come to Austin. I had no job, a few friends, and figured that I’d figure things out by moving to a place where people like Paul (and me) existed.

I was right. I did track down my tribe. For the first time in my life, I’ve actually found friends. Aligned young people like me who read books, love ideas, and wipe the crust out of their eyes to go on sunrise runs.

And while it was wonderful to meet people like this, there’s still was a common theme that always came up: I don’t really know what I’m doing. I’m reading, writing, working on some paid projects, and living a life that’s aligned with the things I probably want to do forever. But when I first moved here, I would freak out because I still wasn’t really sure what I was doing.

As I learned from Paul though, you don’t actually have to know:

 “I don’t know what I’m doing and I’m 7 years into this path. Why would you expect to know what you’re doing? That's the default path. You go to med school for 7 years to pretend you know what you're talking about. I've met many doctors. Doctors don't know what they're talking about, but they're terrified to admit that to their patients, so they never end up serving them."

So what if this was a delusion? What if nobody actually knew what they were doing and we’re all just winging it in some way? 

Whenever I become aware of my anxiety stemming from this belief that I should know what I’m doing, I’ll just tell myself, “hey, it’s actually ok to not know what I’m doing. Nobody really does. Even Paul doesn’t.”⁹

How I’m Feeling Now

Phew. There it all is. Paul generously spent a few hours of his time with me in February, and it took me a few months to digest it all and live it out. I still don’t know what I’m doing, but now I feel way more okay about this. It’s a pathless path after all, and as Carl Jung wrote, “If the path before you is clear, you’re probably on someone else’s.”

To end this essay, I’ll share one wise Tweet Paul wrote last year that I’ve printed out for myself to see every day:

Tweet Link

---

---

Notes

1. Another lesson in here is that just because you like learning about something doesn't mean that you'll like teaching it or doing it for a job. Early on, I loved learning about nutrition and weight lifting, but I realized that I'd be bored and exhausted as a personal trainer. And even if I was just an online fitness coach, I would still be unexcited. This pointed me back to intellectually challenging solo study as an essential ingredient in my life.

2. If Paul started creating content about getting rich online, he’d attract a completely different audience. But he said that he can’t deliver on that. What he can deliver on is getting people to think deeper about their own lives, and this is something he can do with writing more books in the long run. Books are his product.

3. From what I read in some of Paul's other Tweets, meaningful metrics to pay attention to might include:

1. Comments: what are real people actually saying?

2. How many friends and positive connections have you made by writing online?

3. How does your audience impact your own behavior? Your audience should align with the way you want to live (ie, sending you reading recommendations).

4. One of the societal scripts to unravel here is the idea that work equals pain. It's almost as if something not “serious” couldn't be work. But whether that’s objectively true or not, it's not useful at all. This is why I love Paul Graham's prompt on figuring out what to work on:

“So try asking yourself: if you were going to take a break from ‘serious’ work to work on something just because it would be really interesting, what would you do? The answer is probably more important than it seems.”

5. I think that less inputs leads me closer to truth. Plus, it’s the only way you can learn something deeply because there’s actually time for contemplation. I spent the entire month of June reading Walden, and only by having more space and time was I able to integrate the insights onto my own clothesline of knowledge.

Less inputs will mean that I'll read a lot fewer books than I used to, which is ok. But taste—including trusting the feeling of quitting a book—will become increasingly important moving forward. Here I come, Penguin Classics.

6. I adore Paul’s definition of ambition: the most ambitious thing that you can do is find a path that’s true to yourself. For him, this is a slower pace than other people. But it took him a while to realize that this doesn’t mean that he’s less ambitious. He takes writing seriously. There’s an intense urgency not to go faster but to take advantage of the opportunity:

“Find what matters to you and take it deathly serious. And don’t take anything else serious. Once you have some sort of curiosity and creative habit, you can just decide: I’m going to write better than everyone else.” - Paul

7. The most surprising quote from Walter Isaacson's biography of Jobs:

"Taking LSD was a profound experience, one of the most important things in my life. LSD shows you that there's another side to the coin, and you can't remember when it wears off, but you know it. It reinforced my sense of what was important—creating great things instead of making money, putting things back into the stream of history and of human consciousness as much as I could." - Steve Jobs

8. I like this phrase because it removes the potential for routine rigidity and neurotically needing to write every single day, which really helps me out. I’ve been writing online for a while now and can easily pump out an essay every week while taking a day or two off once in a while.

And if I really needed to make money, I’d ask for help from my network and might even go check out startups or even work a more normal job like Uber or being a barista. If it comes to it, I know I can figure it the fuck out.

9. In a business, you sell X and get better understanding how to sell X to customer Y. What Paul and others are doing are exploring ideas, creating new things, and adapting to the environment of different opportunities. Figuring out what to do with things is a constant unknown. That's why some people hate this path, he said. But one metric that I constantly use for creation is from Paul Graham. Always produce, he said:

"The best protection is always to be working on hard problems. Writing novels is hard. Reading novels isn't. Hard means worry: if you're not worrying that something you're making will come out badly, or that you won't be able to understand something you're studying, then it isn't hard enough. There has to be suspense."

Thanks to

Paul Millerd

for sharing your time with me and inspiring me to come to Austin to find the others.