WWPD, Quitting, Beliefs, Creators & More | #137

April 17th, 2020: Greetings from Taipei. This “spider tree” outside our apartment has attracted a steady flow of tourists as it is in full bloom. It’s quite the tree and I share it here with you as well.

Greetings to the 40 new subscribers and thanks for becoming a paid supporter JP!

I’m delighted to have you all here. If you are new here, I write this newsletter (most) Saturday’s and it will always be free. I post the occasional paid subscriber-only post, such as the post I did on the cost structure of my businesses this week, but also keep paid subscriptions open as a way for people to support my ongoing writing and journey if they feel inclined. All subscribers will be receiving a free copy of my book when it launches (20k words down!).


#1 BigCorp => BigTech => Startup?

I wanted to share this story from a friend who responded to last weeks newsletter about the inspiration deficit in our economy. He has been a full-time employee for most of his adult life but I think captures the reality of employment for most people - the fact there there are no certain paths.

I may write about self-employment but increasingly the lessons about carving your own path will be the lessons that almost all adults will need to embrace. We saw this more than ever in 2020.

It happens that this friend also appeared in newsletter #33 about being laid off (twice!) by a large corporation in late 2018. A quick refresher from his story he shared with us:

As an amazing example of big corporate bullshit, the new position I was going to accept was then re-orged into oblivion as part of an unrelated org change that wasn't coordinated with the first one - effectively laying me off for a second time in six weeks. From there, the guy who would have been boss kept putting me in touch with internal people who had open positions, which I felt I might as well explore.

Half of those conversations were about mind-numbingly boring jobs or resulted in the hiring manager saying "I've heard great things about you, we had a great conversation and you seemed great to work with, but I need to hire someone with more specific experience here".

Those reactions highlighted that whatever cachet I had as a high-potential general manager was evaporating before my eyes as part of this acquisition of my business unit. Whatever interest I had in staying evaporated along with that realization.

After this he did want many savvy b-school types have done in today’s economy, go to BigTech. He ended up joining a large and still rapidly growing tech company but once again was feeling as if something was off:

Here is how he described his thinking (anonymized to protect the innocent):

The new job is building the US operations team for an a healthcare startup as they look to build a presence here. I decided a while ago that BigTech was not the place for me long term…I was just promoted and in my review my boss listed all of the things where I could continue to develop - and they were all such large company bureaucratic nonsense: building empires, blasting cheery updates into the void of an un-listening audience, navigating politics, pretending the company was empathetic about current events, etc.

The old phrase 'winning a pie eating contest and being rewarded with more pie' came to mind. I looked around at senior people and thought "they've all been here since this was a much smaller company", which is how they ended up in their positions. It was a similar observation I had at BigCorp That Laid Me Off Twice but I figured the fast growth of BigTech could outrun it to some degree.

Wrong. Needless to say, I was not inspired.

While on parental leave, I had two jobs reach out to me and I applied the “What Would Paul Do Framework?” The first was Healthcare Startup whose offer I ultimately accepted, and the second was actually working with portfolio companies of a PE firm. Both would allow me to avoid big company BS, but that's where the path diverged.

I decided the question 'what kind of job would I want if I were a millionaire?' was key for me. I've always thought I would stay somewhere like a BigTech, ideally growing skills until I hit a number and then pursue something that really excited me (the 'fixed point' you mention in last week's note).

I realized, however, that the skills I am building are no longer going to be useful for that hypothetical future role. I then had to think "am I willing to eat shit for long enough to hit my number?" I decided the job with Healthcare Startup was the kind of hypothetical future role I'd want if I was a millionaire: using my skills to actually solve a real problem of sub-optimal health outcomes while getting the chance to work in a less bureaucratic environment.

In the meantime, the salary is solid and I have a lottery ticket with equity if they somehow make money along the way. The PE job would have ultimately been pretty intellectually stimulating, but I could tell it is the kind of thing that would have trapped me in a cycle of eye wateringly high pay but with no clear connection to what I'd want to do after I hit 'my number', and likely still some frustration of working in the PE environment.

It feels very weird to walk away from a giant pay package, but I think I have done enough 'eating my vegetables' in my career with stints in big companies.

Time for the entrée! 

Presenting the “What Would Paul Do?” framework, forcing people to leave money on the table since 2020!


#2 Taking The Leap: Michael Ashcroft

I connected with Michael Ashcroft probably a year ago. This past summer he shared that he was planning to quit his job and I thought it might be fun to interview him along the way. I posted part one (six months before) and part two (three months before) in a podcast this week.

I will likely be recording a third part with him soon after a few months working independently. It will likely become an ongoing series if it gets good feedback.

Check it out => 🎧 Interview With Michael Ashcroft


#3 Ages 18-35 Are When Our Beliefs Form

I stumbled upon this graphic from a friend, Jeremy who writes the Fire Jar, who highlighted the Douglas Adam’s quote:

Anything that is in the world when you’re born is normal and ordinary and is just a natural part of the way the world works. Anything that's invented between when you’re fifteen and thirty-five is new and exciting and revolutionary and you can probably get a career in it. Anything invented after you're thirty-five is against the natural order of things.”

Having turned 36 this year I am not sure how I feel about this. What do you think?

By the way, Jeremy is exploring doing more graphics like this for other creators. Shoot him a message if you might want help bringing an idea to life!


#4 New Perspectives

The magic of the internet is stumbling upon a writer you haven’t read and then diving into their works. I listened to a podcast of Tressie McMillan Cottom and found her energy contagious. She writes across many issues including status, race, wealth and southern culture. I thought readers would enjoy her perspective so I’m linking a few here::

“The Logic Of Stupid, Poor People”

Why do poor people make stupid, illogical decisions to buy status symbols? For the same reason all but only the most wealthy buy status symbols, I suppose. We want to belong. And, not just for the psychic rewards, but belonging to one group at the right time can mean the difference between unemployment and employment, a good job as opposed to a bad job, housing or a shelter, and so on.

“New Money”

New money also comes with a lot of meetings. No one tells you that. But some of these experts want to meet with you all the time. To present a strategy, to discuss a plan and a roadmap. The meetings are so long. I once ran an entire academic program by having 11-minute meetings in the hallway with my colleague and co-conspirator, Tara. But money meetings take hours, half a day sometimes.

The Dolly Moment

Yet over the past five years, it has become verboten to dislike her, much less to critique her. By tacit consensus, Dolly Parton is the one good thing in our empire’s twilight. 


#5 Creator Corner

💵 Jonathan Hillis wrote an interesting five part series on the creator economy. I enjoyed this one on “Decentralized Cities.” It is especially interesting because he’s putting his money where his mouth is and trying to build a “node” for the emerging decentralized, digital economy:

Like any good startup, it's a simple premise with an ambitious goal. For now, it's a place to get together IRL with your internet friends. In the future, I hope it becomes one node in a network of decentralized properties, owned and operated by small groups of independent online creators and entrepreneurs. The density of creative energy of San Francisco or New York, but wherever and whenever you want it to be. If you were designing a 21st century city from scratch, why would you put it all in one place?

🌐 Ben Perrin writes a newsletter in French and recently shared this translated interview with Sari Azout

The number of people that have made a single dollar online is still very minor when you think globally. But that’s going to shift. We would have never thought that teenagers streaming games on Twitch could make a living of it. Or that creators like Jake Butcher would make six-figure revenues by sharing online courses — and more recently selling graphics as NFT. I believe that the young generation will create all kinds of things on the Internet that we cannot even fathom. Then the nature of the job market is going to change dramatically.

💼 I recently connected with Dror Poleg and have found his writing on the emerging creator economy and future of work to be excellent. A couple worth reading:

The Ponzi Career on what the financialization of talent might mean

By letting your fans own a "piece of you," you also incentivize them to support your continued success. If you own an Elon Musk Coin, it will make sense for you to promote Mr. Musk and try to get other people to buy his coins. By increasing demand for the coins you already own, you can become wealthier. And those who buy the coins after you will continue to convince others. And as long as the story is convincing and there are enough new people to convince — the coins will go up in value.

😱 Shon Dass wrote about her realizations during Covid that resonate with my own journey:

It was starting to hit me that the path I was on was not my own. I didn’t have a burning desire to be an attorney, I just needed to make sure my philosophy degree wasn’t useless. Working in banking wasn’t exactly what I had in mind either. To be honest, my journey thus far was fueled by fear: fear of lack, fear of instability and fear of disappointment.

I was running “away from” life rather than towards it.

I started asking myself: What am I doing this for? Who am I doing this for? These questions took me back to my junior year of college (that one semester I took all philosophy courses — I was asking for an existential crisis). Even then, I slowly began to understand the game I was playing:

You get a degree to get a good job. You get a good job to make good money. You make good money so you can support yourself and buy things.

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#6 Inspiration Deficit

I recorded a short video to go along with last week’s essay. If you like the video version of this let me know and I’ll make some more


#7 Tweet of the Week


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