The Tortured Entrepreneur

About Me

I'm Joseph I write the tortured entrepreneur, a weekly letter sent every Saturday for those who love mental gymnastics. Subscribe for free below:

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Previous Letters


The Perils of Fundamental Attribution

I came across a term recently that has made me think deeply about how I see others, particularly those with whom I don’t usually agree. If we think about it, we often perceive our own worldview as the correct one. We rarely question our beliefs or ideas about right, wrong, morality, hedonism, etc.I've considered those who disagree with me on fundamental issues like truth, morals, religion, politics, and the like, prompted by one simple question:What if I’m the one who is wrong?...


Running 40 Miles on Broken Feet

It’s 2:20 AM. I’m camping in the Mataqua mountains, and I can’t sleep. I’m going to start the longest run I’ve ever attempted in 10 minutes, and frankly, I have a mix of excitement and worry that I’m not strong enough to finish it.I’ve always wanted to run my age but have never gotten around to it until now. I’m turning 40, and now seems like a better time than any to attempt a straight run until my watch matches my age.After some stretching, I take off, and gratefully it’s a full moon. I’m able to run in the moonlight easily without using my headlamp...


Drinking Poison and Jerk Lobsters

I’ve had a rough few months. I don’t just mean the day-to-day stressors and inconveniences of life, but actual “I want to quit” kind of rough.Lots of things in my life broke down, including finances, family relationships, long-time friends, and my own sense of self-worth.If you are a human reading this (I have a few aliens on my list), you can probably relate to moments or even long-term disasters or a dearth of happiness. This isn’t the first time in my life I’ve struggled, but it is the first time I’ve had a desire to observe myself throughout the process.I’ve been fixated on the thought that we can’t go around, over, or under hardships.The only way out is through.Like drinking poison, it can feel like we would rather it kill us than incapacitate or often disable us for a time...


It's Never a Hell Yeah

I bet you’ve heard:“If it’s not a hell yes, it’s a hell no”.I first heard this 10 years ago from Tim Ferris. The idea is that when you’re investigating a path forward in life/business etc. approach the decision being made based on your feeling of “hell yeah” or “hell no”.It’s not a bad idea right? Who wants to pursue something they aren’t very passionate about. Or even worse something they only are doing for financial gain vs. enjoyment.Here’s the other side of the coin though.Everything worthwhile is usually not a massive “Hell Yeah” (insert your favorite cuss word).Most of the time we timidly work towards something with hopes it pays off but not knowing for sure if it will. ..


9 Things I do to Force a Good Day

Often I hear “It’s been a bad day” Rubbish. Just kidding I know there can be valid bad days but I rarely have them.Why?I’m a big believer in having daily habits that enhance vs. detract from life. More often than not we kind of just let life happen and habits form on a whim. No decisions made or planning just waking up and realizing coffee every morning is a thing and not sure when it even started.I’m not saying coffee every morning is a bad habit but I bet it’s a habit that wasn’t approached with “I’ve decided I’m going to get up at 6am sharp and drink a cup of black coffee every day” type of mentality.Every month I try to take a really hard look at my processes and see what contributes the most to my:HappinessFinancial SuccessExperiencePeaceFirst thing I look at are my daily habits I’ve formed on purpose. So without dragging this out any longer, these are my main habits that have lasted a long time and continue to essentially force every day to be a good one...


Holding it and Neural Pathways

I had to drive north today to drop my daughter off at the family reunion, a few days before I can join everyone. As long car trips go, there were many stops for gas and bathroom breaks.During one particularly long stretch, it was quite a while before we could find another bathroom. Both of us needed to pee, but it was one of those urges where you think,"I can hold it until the next exit."Finally, we reached an exit with a familiar gas station.Have you ever noticed how the closer you get to a bathroom when you really have to go, the stronger the urge gets?Well, that's exactly what happened when we pulled up to the gas station, only to discover it was closed.The problem is, when your bladder's sentinels realize you're close to a toilet, they decide to take their lunch break, leaving nothing but sheer will to hold back the flood.We quickly retreated to the overpass and thankfully found an open gas station on the other side...

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