Hey there, I’m Paul Millerd

I’ve been writing about our relationship with work since 2016 and have been obsessed with the mystery of how we have increasingly narrowed our conception of life down to something that centers around a job. If you’d like to follow along you can join 19k+ readers on substack:

My Story (Longer Version)

Hey there! Thanks for coming across my site.

The pic to the right is me hiking in Taiwan in 2018, I moved in September of that year on a whim after visiting a friend for a week earlier that year

Moving there changed my life.

Soon after arriving I started a deeper relationship with writing and ended up meeting the woman who would become my wife. Since meeting, we’ve lived in Taiwan, the US, Spain, Mexico, and Indonesia, never spending more than ten months in a place. So much of my journey has taken me by surprise since quitting my job in 2017 to wander into the unknown and much of that journey is highlighted in the book featured on this site.

The real story starts in Connecticut, where I spent the first 22 years of my life, never imagining I would wander more than a couple hours from my home, let alone halfway around the world.

Catching The Prestige Bug

Growing up, I had a knack for doing well in school and never really thought about the question “What do you want to do when you grow up?”

I spent most of my time wandering in the woods, hanging with friends and family, collecting basketball cards, and working on my jump shot, dreaming of playing in the NBA.

In college, I realized I wasn’t headed to the NBA and instead set my sights on the business world.

Towards the end of college, I found out about “prestigious” places to work like McKinsey & Company, Goldman Sachs or Google. My ego and drive to prove myself took over and I was determined to land a job at one of those places

I had a conversation with someone who told me I didn’t go to the “right schools” (meaning Ivy Leagues) and that I probably wouldn’t land a job in consulting. That motivated me further!

Paul Graham captures my mindset at the time better than I could:

Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.

In my senior year, I went a bit wild, applying to 150+ of those companies and getting rejected from every single one. I ended up landing a job at GE. After a few months of working in Cincinnati and being frustrated with the corporate world, I resumed trying to break into the prestigious world of the consulting industry.

As luck would have it, I found a random posting for a research gig at McKinsey on Monster.com (yes, really) and ended up landing the job.

I’d be lying if I had any lessons there for you about landing a job other than keep searching, don’t give up, and stay a bit delusional about your abilities.

McKinsey remains the best place I’ve worked and taught me how to write, create, work in teams, and lead others with compassion. Despite being in that environment, I felt the need to keep moving and after two years headed off to MIT to study systems engineering and get an MBA. Although I absolutely loved the freedom and curiosity of being in a University setting I have mixed feelings on whether I’d recommend it to anyone today (crazy expensive!)

Figuring Out What Matters

After business school, instead of continuing my smooth ascent up the corporate ladder, I became sick with a brutal case of Lyme disease. I spent the next two years not focused on work but on learning how to cope with uncertainty, reflecting on what really mattered, and developing skills to embrace my vulnerability.

For the first time in my life, I came face to face with my own fragility and realized that my identity revolved around a shallow notion of career “success” and that I didn’t really spend any time reflecting on what mattered to me. As I re-entered the workplace, I embraced a new attitude:

I had lost my health temporarily and had to slow my career trajectory a bit. At the time this really stressed me out. However, the process of experiencing this loss also made me realize it was survivable. It also helped shift how I think about risk. For example, at work I can take risks, try new things and pursue things I am passionate about instead of trying to fit in and being scared of being fired. Worst case is always losing my health, not my job.

I recently re-read this and it seems so obvious – yet at the time it was not!


As I recovered, I started focusing on the things I was good at and stopped worrying as much about pleasing others. I also started experimenting on the side, helping people more actively with their careers, and trying to share some of the lessons I learned.

This evolved into something a little more serious when I decided to create my first “side hustle” by setting up careerswithpaul.com (RIP!). Initially launched via an e-mail I sent to 100 friends, it was the first time I did something that was 100% terrifying but felt aligned with what mattered to me.

This experience gave me the courage to experiment in other ways, holding a group coaching workshop, building several customized coaching programs for founders and entrepreneurs, landing multiple paid speaking gigs, and a couple of freelance consulting gigs.

Quitting & Freelancing

While I now tell people “Don’t just quit your job!” that’s what I did. While I had thought about quitting for a while, the moment didn’t come until I had just arrived at a friend’s wedding in Florida. My boss at the time had a knack for soul-crushing e-mails and instead of ignoring the one he sent me while I was in Florida, I sent back a short “maybe it’s time for me to go.”

I now know that my frustration at work had everything to do with my own fear of being able to take the step to carve my own path rather than anything to do with that boss or culture. Deep down, I couldn’t ignore the pull to start a new chapter in my life.

I took the leap even though it cost me $24,000.

Over the next several months, I started my freelance consulting company and started laying the groundwork for what I thought would be a long-term freelance consulting career.

After leaving my job, I focused relentlessly on trying to land freelance consulting projects. In my first five months, I landed several gigs and was able to live life with much more freedom, all while earning more than I needed, proving to myself that I could in fact make this life “work.”

Self-Employment Helped Me Reimagine Life

After working on all these projects, I took some time off, and in that space, several creative projects emerged. This is when my old brand Boundless, my Podcast, and the Future of Work Mindset Assessment were born. None of those really turned into monetizable opportunities, but for the first time, I had found work that started to feed my soul. I was also noticing that I was becoming a calmer, more mindful, and more peaceful person and I didn’t hate it. I didn’t want to “go back” to the corporate world. I wanted to keep going. Here’s a reflection I wrote about a year after leaving my job:

I wouldn’t claim I am Mother Teresa, but relative to the person I was in the corporate world, I find myself being more patient, kind and generous to the people around me. The marginal blows of insanity and negativity in the corporate world slowly eat away at you in a way that is hard to put a finger on, but easy to spot once you get a bit of distance.

What I discovered in this period is that there was a deeper pull towards a creative life and that freelance consulting was only the short-term safe transition that would help me buy some time and fund my life while I figure out what the deeper journey had in store for me.

Living Abroad For The First Time

In April of 2018, I decided to take a month-long trip to Asia. That trip changed everything. During the trip, working from a cafe overlooking the ocean in Bali, I realized that I hadn’t been dreaming big enough.

As I worked that day, it was one of the first times I was working and didn’t really have any resentment towards that work. How could I with such a view? It was also the first time where I felt a little silly that I had spent almost a year freelancing and didn’t think about leaving Boston or New York to explore more of the world or visit friends.

In September of that year, I returned to Taipei and ended up meeting someone on a similar journey and we ended up getting married.

Life is pretty amazing when you let it be.

Given that I’m now committed to spending time straddling two worlds, I’ve continued to experiment with digital businesses such as writing, online courses, and consulting that might enable us to fund this life, travel, and spend time with people in meaningful ways.

The Pandemic Changed Everything

For years, starting in 2017, I chronicled my own journey disconnecting from my identity as a “worker.” I funded my life through minimal freelance projects and optimized around free time to think, wander, and write. While I slowly grew a humble audience of a couple thousand people, there were no viral moments. It was just a continuous process of me continuing to chase my curiosity.

And then the pandemic happened.

After we got married in 2019, we decided that we would travel for two consecutive years starting in 2020. February 2020. Yup, I know…

But we sort of got lucky. We were already working remotely and set out lives up to be adaptable and deal with change. When the world shut down in March 2020, we were in a beautiful location, the Canary Islands. We were”trapped” in round-the-clock paradise conditions in a 5-bedroom mansion living with five other people.

While it was a shock, we actually enjoyed the slower pace and spent a lot of time online. By April 2020, I suddenly had A LOT of people reaching out to me. People were starting to work from home, realizing this was going to be the case for a long time, and started to have deeper questions. WTF is going on with my relationship to work? Many people started waking up to the fact that much of their life before working from home had gone by as if it was a blur. People were asking questions: did they really want to commute every day? Did they really want to design their lives around a job?

I had weekly conversations with 5-10 people from around the world each week and that entire year ignited a flurry of ideas and thinking around our relationship to work.

In December of that year while living in Mexico, I decided I would write a book.

Over the next year, mostly in Taiwan (where we went back to enjoy relatively covid-free living) I wrote the book, studied Chinese, and spent time exploring the island with my wife.

I finished the book in January of 2022 after moving to Austin in the US after my wife had gotten her green card. I launched the book via a couple of tweets and newsletter announcements and put it out to the world.

Unexpected Success

My “best case” scenario when I launched the book was to break even. From the $7,000 I spent on editors and design I thought that if I could sell about 1,500 copies that would be a grand slam.

Well, I hit that in three months and then it kept selling, and selling, and selling.

I knew something special was happening when I was receiving e-mails in that first year with people saying “I’ve bought ten copies to give to friends.”

In December of that year, after a shoutout from Ali Abdaal, the book started selling even faster and in the first year, I sold 10,000 copies. I was blown away.

And what happened next shocked me even more. By the third month of the second year, I had already hit 10k books. Another shoutout from Ali Abdaal and a boost in the Amazon algorithm seemed to send the book’s sales into hyperdrive. That’s when Penguin reached out, and tried to buy my book, and I declined.

As of November 2023, I’ve sold another 30k books.

Who knows where it goes from here but this has been one of the most fun journeys of my life.

If you enjoyed my story, you DEFINITELY will like The Pathless Path