Organizations & Culture

The Ultimate Guide & Reasons To Take A Sabbatical

After I quit my job in 2017 I spent 5 weeks in Europe. It was the longest break from the “real world” I had ever taken and in the second week, I started to feel extremely guilty. I became hyper-aware of the script in my head that said I should be working or that at ... Read more

My Five-Year Journey Creating, Launching, Failing & Succeeding With Online Courses

I created my first online course because I didn’t want to help any more people with resumes. I called this course “Crushing Your Resume.” Little did I know that this small act of creation might lead me down a path where I might not need a resume for the rest of my life. A Bit ... Read more

Accidental Meaning: How The Baby Boomers Misled Us About What Leads To A Happy Life

There was a state of affairs in many places across the world that enabled many to build meaningful lives by following a standard script. Go to school, get a job, have a family, and devote yourself to work and you will be a successful person. In the US we call this the “American Dream” and ... Read more

How I Think About Money & Retirement While Self Employed

The most common question I get from people who are not self-employed is about my level of worry when it comes to money. People wonder if I’m worried about the future. Worried about having “enough” for things like a house, college, and retirement. People are often surprised at two things that emerge from a deeper ... Read more

How Obsession With Work Killed Our Connection With Leisure

More than two thousand years ago, the Roman stoic philosopher Seneca wrote a letter to his friend Paulinus, urging against a certain type of rest: I do not summon you to slothful or idle inaction, or to drown all your native energy in slumbers and the pleasures that are dear to the crowd. That is ... Read more

The Inevitable Decline Of The Elite Full-Time MBA

I want to explore the changing dynamics of how people earn prestige, the new dynamics of credentials and status, and what this might mean for how people navigate work and their careers in the future. I am going to look at this through the lens of the full-time MBA, something I did from 2010 to ... Read more

The Battle For The Soul Of The Creator Economy

The “future of work” is dead or maybe it finally arrived in the form of what we are now calling the “creator economy.” This week Twitter announced that it was going to enable monetization through “super followers” on its platform. It appears to be taking some of the features of Substack, Patreon, and others and ... Read more

What I learned in Ali Abdaal’s YouTube Course

In the last 12 months I had a channel on YouTube go from about 500 subscribers to almost 9,000 subscribers. In that time I became eligible to monetize my channel and made about $2,000 from YouTube ads in 2020. This captured my attention and I became a bit more fascinated with what was happening over ... Read more

150+ Things Worth Reading & Listening To From 2020

This is a compilation of all of the links, essays and podcasts mentioned on the Boundless newsletter. If you’re interested in subscribing you can join here. Favorites From The Year From Nuclear Families to Forged Families (link) Redefining what “prosperity” means for capitalism (link) The Inner Ring by C.S. Lewis (link) Solitude and Leadership – ... Read more

Don’t Follow Your Passion, Work In The Corporate World First

I want to make an argument for spending some time in the corporate world.  I am not arguing that one should devote their life to a corporation or full-time work but I believe that many young people are not taking seriously some of the benefits of pursuing at least some time as a full-time employee ... Read more