Hey, I'm Paul 👋
I left a path that made sense in 2017, and have been slowly crafting a much better path, an infinite game I want to keep playing. I don't have a "quit your job" pitch but I do hope you'll join my "conversation" exploring how we relate to work in a world still relying on scripts from the 1950s. I share my own reflections, research, and lessons in a newsletter read by 5,500+ from around the world every Saturday.
I don't make what I used to but have fun paying the bills through a mix of writing, consulting, coaching, and online courses on strategy consulting and freelance consulting. The best way to find me is on Twitter or through a curiosity conversation.
Full Story 👇
Hey, I'm Paul...
Hey there! Thanks for coming across Boundless. The pic above is of me hiking in Taiwan in October 2018, where I moved in 2018. For the last 2.5+ years, I've been living as a nomad around the world. I never thought I'd live in Taiwan let alone outside of Connecticut, where I grew up in a small town of fewer than 5,000 people.
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 that 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 got 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 Boundless, the Podcast, and the Future of Work Mindset Assessment were born. It became clear to me that I loved the work and the life I was creating. I was also noticing that I was becoming a calmer, more mindful, and peaceful person and I didn't hate it:
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.
I'm not sure where we're headed, but I hope to meet some curious, generous, and kick-ass people along the way.
If you thought this was interesting, just wait until you read the book!