Just Got Back from My 10-Year Business School Reunion | #183
May 28th, 2022: Greetings from Connecticut. I am back in my hometown after being up in Boston for a couple of days for my from my 10-years business school reunion. I wrote about the reunion below but another big update was doing my first DJ "gig” - playing a small set to my enthusiastic family 😂
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#1 My 10-year business school reunion
It was a week after I quit my job. I was nervous but felt like I needed to be there. It was my 5-year business school reunion and as someone that had declared himself a “freelancer” I knew that tapping into my business school network was probably a smart thing to do if I ever wanted to get paid.
Many people secure some client work before they leave their job. I failed to do so despite some attempts. I was a freelancer in name only. The deeper story, one which I didn’t share with anyone at that reunion, was that I was running away. I wanted a vacation from my life. Everything had been right on paper, but everything felt off and in ways I couldn’t quite articulate yet.
Walking out of my office on Park Street in Manhattan that May 26th 2017, there was a small part of me feeling the rush of freedom but the overwhelming emotion was one of relief.
In the US, we are always focused on the next step. Plans. Goals. Ambitions. So when I attended my five-year reunion, I pretended I had them.
“Well, I’m a freelancer now. I want to work on X, Y, and Z. I’m talking to a bunch of companies but still working out the details. Do you have any ideas? I’m available!”
I felt like a fraud, but that’s also what it always feels like when you start working on your own.
I attended my ten-year reunion a few days ago and it was awesome.
I have a deeper sense of who I am. I do some freelance work here and there but it’s not my identity. When people asked what you are up to, I said, “I’m doing a bunch of stuff - writing, creating online, exploring a bunch of fun side hobbies. Most of all I’m really enjoying it all.”
People seemed genuinely curious about what I had to share too. I didn’t feel any judgment and wasn’t embarrassed by the fact that I was probably one of the least financially successful of anyone in the room. I think this was because I really have found a sense of calmness and peace on my new path.
I don’t resent my previous path. I don’t feel like I need to fight against the “default path” and most importantly, I really am enjoying things.
With some of my friends, we went around a table and rated our life satisfaction on a scale of 1-10. Most people were a seven or higher and the highlights were things not related to work. For me, the highlight was meeting Angie.
One interesting experience was finding out that a large number of my friends had read my book already but had not let me know before seeing me in person. I do wonder about the norms around this. Does it feel weird to tell someone you’ve read their stuff? I’m genuinely curious so if you have thoughts, please let me know. I’m the kind of person that has probably messaged hundreds of strangers on the internet that I enjoy their stuff so I probably don’t have a good sense of how most people feel.
Specifically, it was cool to hear how some of my friends were inspired by my reflections in the book. One friend created his own list of six priorities that mattered to him and then assessed how his current work aligned with them. He found out he had 5 of the 6 which was great but the sixth is something he really wants and he’s starting to be more thoughtful about how to make that happen. Another friend revealed her plan to leave work entirely in five years to spend more time with kids and hobbies. She told me I was a role model. That cracked me up.
I think we all want to be loved and as someone on a creative path, it’s often hard to admit we want appreciation and respect from others. It felt really good to hear from some of my closest friends that they genuinely thought my book was great and that it made them more thoughtful about their own paths.
One story that hasn’t really been told in the right way yet is the enormous positive upsides of being able to work remotely, especially for parents. This seems to have led to dramatic life upgrades for some. Even a 20% increase in flexibility, especially when everyone else is doing it, seems to be huge.
Part of me thought that at my ten-year reunion I might find a decent number of people that were successful on paper but didn’t quite enjoy their lives. While many people did admit that they wished they could work a little less, most people seemed happy and content with their lives.
What I really found was that I really missed being around these people – a group of people that I spent nearly every day from 2010 to 2012 only some of which I stayed close with after. During those two years we were more than a “network” of business school classmates and this is what makes questions like “do you regret going to business school?” so tricks. Those relationships were incredible. We got to know each other at a deep level. Met people’s partners and families. Got to know what we were like under pressure and stress. We knew what people really like, not what people claimed to like.
And perhaps that’s why my friends didn’t seem shocked by anything that’s happened in the last five years. Spend enough time around people and it’s hard to hide who you really are. The biggest challenge for me over the past few years was unlearning the stories I had in my head about who I thought I was and who I thought I was supposed to be.
Show up as who you are and it turns out no one will be all that surprised.
#2 🎥Live Curiosity Conversations
Over the last five years, I’ve had 383 curiosity conversations with people from around the world. The reason I started these calls was to lean against the idea that time is money and to immunize myself against the idea that I was some sort of special person that needed to be paid to be accessed.
I kept doing them because they inspired me. I got so many ideas from the people I talked to. Finding ideas through conversation and workshopping existing ideas is a powerful creative engine for me. In addition, people would share things that they didn’t feel comfortable talking about with others. A lot of our personal opinions on work remain taboo. This has given me access to the inner minds of people’s real opinions, not the things they are only willing to say publicly.
Two weeks ago I was a bit fried after doing eight calls in one day and felt like I wasn’t showing up present in these calls either. I decided I wanted to experiment with a new approach and launched a live streaming version of the calls. After two weeks I’m happy to report that they went way better than expected. I plan on keeping these going, so if you want to sign up:
Here is the recording of this week’s call. We talked about non-doing, tacos vs. burritos, worker mode, my current writing practices, and more.
#3 New Podcast Design
With help from Nate Kadlac, a living design genius, I reworked my design themes for both Boundless and StrategyU. In a two hour coaching call, I somehow had my mind blown approximately 73 times.
The things he taught me about color were the most powerful and I’m starting to understand how to apply some basic principles to move beyond my PowerPoint graphic design skills. Here’s the cover I created after our session
Nate’s biggest advice is that “you should feel excited about your colors and fonts, and then everything flows from there.”
I dig it.
#4 Weird Internet Careers
I stumbled upon this essay from Gretchen McCullough on “weird internet careers.”
Weird Internet Careers are the kinds of jobs that are impossible to explain to your parents, people who somehow make a living from the internet, generally involving a changing mix of revenue streams. Weird Internet Career is a term I made up (it had no google results in quotes before I started using it), but once you start noticing them, you’ll see them everywhere.
Weird Internet Careers are weird because there is no one else who does exactly what they do. They’re internet because they rely on the internet as a cornerstone, such as bloggers, webcomics, youtubers, artists, podcasters, writers, developers, subject-matter experts, and other people in very specific niches. And they’re careers because they somehow manage to support themselves, often making money from some combination of ad revenue, t-shirt sales, other merch, ongoing membership/subscription (Patreon, Substack), crowdfunding (Kickstarter, Indiegogo, Ko-Fi), sponsorship deals, conventional book deals, self-published ebooks, selling online courses, selling products or apps or services, public speaking, and consulting.
It’s a seven-part series that I haven’t read yet but I feel seen, thanks, Gretchen!
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