Boundless #61: Broken Ideas Of Success
Endless Optionality | School Engagement Crisis | Reader Corner
August 10th, 2019: Greetings from Taipei! Experienced a 30-seconds of whole-apartment-shaking earthquake this week and then my first “typhoon day” for a typhoon that ended up missing the island. How was your week?
A quote I’m thinking about this week:
Nearly all creators of Utopia have resembled the man who has toothache, and therefore thinks that happiness consists in not having toothache. - George Orwell
✍ New longform: Where do your work beliefs come from? (3700+ words, ~18 minutes reading time): I expanded on one of the issues around “schools of work” from several weeks ago. If you want to explore the catholic, protestant, hustle, gift, meaningful work and gospel of wealth schools of work emerged, you’ll want to read the essay here.
#1 Belief 2: I believe unreasonable ideas of success prevent us from taking action
Here is belief #2 from my workshop a couple weeks ago. This is going to be part of my course which currently has 25 modules. Share your feedback here to get access to the course progress and early preview of the course.
Everyone has seen an article like this. It exists (and works) because it taps into our deepest insecurities about money, status and power. This is great for the person or company that publishes it in terms of clicks, but this line of thinking convinces us that were not good enough, we cant’t “make it.”
Over the past 2+ years I’ve fielded countless questions about my plans for hiring employees and growing. The assumption is that everyone is an entrepreneur and that everyone must always want more. This assumption is so strong that it convinces countless people to continue going for more even though deep down they know they have enough.
Paul Jarvis, who wrote a book called Company of One, once wrote about a new business venture he joined with two other people:
“If this company needs business growth beyond the three of us, I’m out.”
…Not because I’m afraid of success, but because “success” to me means being able to get what needs done, done without having to hire a team
When I was thinking about launching a podcast, someone asked me how I was going to monetize it. I told him that wasn’t my goal. I just wanted to try something new and see if I had fun doing it. It only cost me about $75 for a microphone and I got started. It was pretty cheap way to find out.
I talk to many people who have been stuck for years. They want to explore pursuing a solopreneur path or something similar but feel that they will be a failure. If they are a consultant worried about competing with McKinsey that will happen, if they are starting a podcast thinking about competing with NPR that will happen too.
This is a screenshot of my podcast in Apple’s mediocre podcast app:
When we look at this, it seems like we are in direct competition with each other. I would even argue I have the cooler cover. Right?
This American Life is only one of NPR’s many podcasts. They have a whole damn team working on just this podcast. Let’s take a look at their team compared to mine and the number of listeners.
If I’m comparing to NPR, I’m an absolute failure. Yet those 200+ people that listen to my episodes? Some of them include you and I think you are some of my favorite people in the world. I’ll take my people any day of the week.
People think the challenge is making a lot of money and being successful. In practice that typically means earn as much money as possible and keep pursuing a vague definition of success that’s never been defined. Instead, people should think about finding their people and its often not that many they need to find.
As of this year, there are 3.8 billion people connected to the internet. Even if you run a local business, most people would agree that it would be crazy to ignore the web. This means that you have access to an incredible amount of people.
If you squint, you can find your relevant speck of the universe you need to tap into. If you are working as a freelance consultant, you likely need no more than 5-10 steady clients to support your life for the next 5-10 years. If you are selling a course for $200 and want to earn $100,000 a year, you only need to worry about finding 500 people who are excited about what you are creating.
That idea could be anything and you’re probably not thinking weird enough. For Marielle Chartier Hénault. In 2015 she started a Mermaid School and now has 10 schools across Canada and the US. She supports her life with this:
She likely started the business to find out if there were other people that shared her same interests. The same driving force led me to start my podcast, keep this newsletter rolling and keep experimenting and trying new things. She found a bunch of people that wanted to go on a journey with her and I’ve found a bunch of people that keep e-mailing me or having curiosity conversations with that say “keep going.”
Along the way of course I’m trying to figure out how to make a living. But I don’t want to scale. I don’t want to create another job. I might be going a little slower than most, but I want to build a life that’s sustainable and built around curiosity and creation. I want to keep the journey going.
Maximizing for wealth and size are only two options among many more. The internet has enabled even more options for sustaining a life than ever before.
My question to you is: if you don’t have to be a traditional success, what might you want to work on? Let me know how I can help.
#2 The Founder of Stripe (from Ireland) on the US
If you're in the US and go to a good school, there are a lot of forces that will push you towards following traintracks laid by others rather than charting a course yourself. Make sure that the things you're pursuing are weird things that you want to pursue, not whatever the standard path is. Heuristic: do your friends at school think your path is a bit strange? If not, maybe it's too normal.
#3 Optionality: Good Or Bad?
I used to play the options game.
The options game is when you make choices in a career path that close the least amount of doors. This is the same mindset that says you should be nice to anyone you ever meet in the professional world in case you cross paths or they have an opportunity for you in the future.
Here is Harvard Professor Mihir Desai on the topic:
The Yale undergraduate goes to work at McKinsey for two years, then comes to Harvard Business School, then graduates and goes to work Goldman Sachs and leaves after several years to work at Blackstone. Optionality abounds!
This individual has merely acquired stamps of approval and has acquired safety net upon safety net. These safety nets don’t end up enabling big risk-taking—individuals just become habitual acquirers of safety nets.
If you dig into his bio, you find that Mihir worked in investment banking, strategy consulting and then went on to attend Harvard Business School and Harvard Law School. It seems bizarre that he would give this advice, but perhaps he is harboring some regret about not taking more risk in his career.
For me, the optionality cover story was great. Often these high-option jobs are well-paid and good places to work. While externally I projected the image of someone that was “successful,” I never really quite fit in the corporate world and knew I wanted to take a different path. The high-option career path was a comfortable place to avoid the fact that I was scared to take a leap.
While Mithir may not be the best role model (perhaps he is just channeling his regret) , I think his takeaway is right:
If your dreams are apparent to you, pursue them. Creating optionality and buying lottery tickets are not way stations on the road to pursuing your dreamy outcomes. They are dangerous diversions that will change you.
I talk to many college students that tell me they want to work “on their own” one day and wonder if strategy consulting experience or insert other prestigious job is good experience for their path.
In most cases it is, except as Mithir says, eventually you become the path. I’ve had a lot of conversations with business school classmates in their mid-30s who are waking up to this and saying “wait a minute, I just kept going after the “right” next job, I still have no idea what the hell I actually want to work on!”
With so many options, people can spend a lifetime preparing and acquiring skills. Eventually, there is no goal other than to keep going on the path. When I left the corporate world, I was surprised at how little my previous jobs prepared me for working on my own. The only experience for doing the thing is actually doing the thing.
#3 Chart Corner: This doesn’t look good (Gallup)
#4 Reader Corner
Reflections on one year of solopreneurship from Solopreneur Shift grad Luke:
You hear some interesting responses when you tell your colleagues, family, and friends that you’re making a career move that involves less money, less stability, less prestige, and worse (read: no) benefits.
Admittedly, some people are amped for you. Others, however, are confused. They respond — with a type of sympathy — in a way that justifies the career move for you or that tags your decision with a recognizable piece of logic that allows them to digest it themselves.
Have something to share? Something your selling? Something to brag about? A question for the audience? E-mail me and I’ll include it!
#5 Misc 🎊
I moved my Boundless Reads newsletter over to substack as well. Follow along here.
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