Adult "Leaps" & The Ever-Elusive Meaningful Work | #217

Writing again after having a baby

April 1st, 2023: Greetings from Austin! I have been enjoying lots of quality time with Angie and Michelle as well as a month of disconnecting from work. Every time I have leaned into non-work, I am always reminded that writing is the thing I miss and want to come back to. I am excited to be writing again and am hoping to do a little more than I have in the past. We will see how that goes.

In terms of life, I don’t have strong convictions or strong plans but it is quite clear to me that spending meaningful time with my daughter is one of the most important things I can do with my time and something I want to build my life around going forward. I’ll be writing about some creative strategies I plan to adopt in the coming months.

Also, thank you so much to the guest posters who all did a wonderful job injecting the spirit of this newsletter into their writing and sharing their own stories. If you missed them: And if you haven’t read the guest essays yet, they’ve been fantastic:

• Jonny Miller
  on nervous systems and recklessness vs. courage,

• Sam Sager
  on intuition, fitness, and uncertain journeys, Alice Lemee on skipping the 9-5 and her freelance writing journey, and

• Michelle Varghoose
  on parental expectations and being a grown woman.

• Alice Lemée on skipping the 9-5 to build a freelance career

• and

  Kris Abdelmessih
  on thinking about life through the lens of a math-loving former trader

While I was gone I also had some pretty epic podcasts that dropped:

• Derek Sivers on moving beyond comfort

• Russ Roberts on why he moved to Israel to “start over” in his 60s

• Steph Smith on how her relationship with money has evolved on her path

• Trungphan2
  on living as an Expat in Vietnam and carving a path as a modern meme-driven writer

• Sam Spurlin
  on getting companies to embrace complexity as a consultant

Without further ado…

---

#1 Working Hard And Liking It?

Intense hard work within a great culture can be one of the greatest things in the world. It’s also damn hard to find.

I’ve experienced three stretches of working in such environments, one of which was my entire two years at McKinsey when I was 23. This experience was the greatest thing for my own skill development but also the worst because every work experience after was disappointing. We like to think that we as individuals can conjure up great work through great effort. But it’s not true. We are only capable of what our environment allows.

Brie Wolfson

shared a fantastic reflection on working at Stripe, a place that pushed her incredibly hard but was also immensely rewarding. For example:

My colleagues chimed in on my work—because I asked them to, and because it made the work better, not because they didn’t trust me. Once, the CFO called me after sending out notes from a “postmortem” I ran to remind me that we should use the word “retrospective” instead (it’s more reflective of what we were doing and a lot less morbid). My work was meticulously but warmly critiqued by my peers and leaders alike, and my work got better and better because of it.

If I never experienced a similar thing at McKinsey, I might write Brie off as delusional. A workaholic. But at McKinsey, I received similar kinds of criticism and by the end of my time there, craved it.

People get critiqued all the time in the workplace but rarely do they get to experience it in a culture of people that actually give a damn about their work. Brie talks about skipping a vacation and not regretting it because of how much people cared at Stripe:

Once, my manager asked me to reconsider the vacation I had been planning because my team needed me. “If you go, who will cover your work?” I looked around at my colleagues who were also regularly working 15-hour days and decided to stay put. I’m proud of that choice. Call me masochistic, but I have to admit that it felt good to care about anything that much. And, to be around people who I know cared that much too.

You might think this is counter to what I write about here on Boundless.

Would I have taken the vacation? Almost definitely. Would I have tried to work less than fifteen hours a day while still doing good work? Also 100% yes. But I also completely understand what Brie is talking about.

When you are around people that give a damn it is infectious.

She puts it better than I can:

It’s more about missing that universal agreement that it’s really, really cool to devote yourself fully to your work. And to expect that from your colleagues in a way that makes you feel that “we’re all really, really, really in this together” kind of way.

In business school, I volunteered as part of the Sloan Sports Analytics Conference. If you know sports you know this conference. I got to work with Daryl Morey and Jessica Gelman who were both volunteering their time outside of demanding jobs working in professional sports.

They set a high bar, supported people, and gave us room to make decisions. They cultivated a culture of support but also excellence. I wasn’t getting paid and I didn’t even have a goal of working in sports but it was one of the things I spent the most time doing during my second year of business school.

All worth it for my pic with Bill Simmons

The feeling of marching toward a finite goal with a collection of amazing people all doing it because they gave a damn was delightful. And for five years after business school, I more or less failed to find that magic again, stumbling from job to job working for various insecure grown men.

These great environments are so hard to find and they get lost in the stupid debate over “hard work.” I think it’s pretty stupid to work long hours when you aren’t being supported and the people around you don’t care. But if you stumble into the magic Brie had at Stripe or I found at McKinsey? Then go all-in - you likely won’t regret it.

In ten years on the default path, I experienced the magic of good hard work for two years at McKinsey, twelve months working on the conference in business school, and three months while at BCG.

This is less than 30% of my time which means that 70% of my time on the default path was time I spent frustrated, constrained, and hyper-aware of my constrained potential.

The biggest upside of working for myself has been that I spent 0% of my time constrained by any sort of crappy culture or manager. That’s worth it mostly for the inner peace that I have most days. Yet working on my own I’ve also been able to embrace some of the same magic of doing great work in teams and applying it to working on my own. I couldn’t have created the book I did without those experiences in high-performing environments.

Like Brie, I’m nostalgic for those magical times when the stars aligned. Maybe I’ll find my way toward working with others again but for now, I’m happy doing my own thing here and trying to create my own high standards on my own terms.

---

#2 Adult “Leaps”

This week I learned about something that babies experience about eight times in their first year: “leaps.” A leap is a period of rapid development, which can be a bit overwhelming. They feel as if they’ve woken up in a new world with heightened senses and when this happens they require a bit more comfort than normal.

Isn’t this what so many of us experience in adulthood too? When I left full-time work I had the feeling that I had entered a new reality. I was disoriented and saw things from a new perspective. Walking around Boston that fall it was as if I had installed a new software upgrade and hadn’t quite gotten the hang of things. I wondered how a simple change in my relationship with work could change everything.

How many people are going through “leaps” in their life right now? When people change jobs, relationships, or move, they enter a new reality. In Life Is In The Transitions. Bruce Feiler argued that this is what life is like - a series of disruptions that we are constantly adapting to. He calls them “disruptors” and estimates that most of us will experience 30-40 throughout our lives.

But many people deny this by failing to notice how much things are shifting all the time. Or by clinging to outdated stories of the linear life path. And this might be an adaptive response because if you’re the one deciding to leap, you may not find many people willing to comfort you. Better to pretend everything is okay than signal that you are on shaky ground.

But what if we looked at adults a little more like oversized babies? Could we stop pretending a little? Could we look at others and wonder how we might help them find their footing on new terrain? Would it potentially help us dream a little bit bigger about leaning into the change that will inevitably join us on our journey?

---

Thanks For Reading!

I am focused on building a life around exploring ideas, connecting and helping people, and writing. I’ve also recently launched a community called Find The Others. There are weekly writing sessions, monthly “find the others” (literally) meetups and general supportive vibes.

• You can join Find The Others if you want to hang with us too

If you’d like to support my journey, the best ways are to:

• Buy or listen to my book, The Pathless Path (or message me if you want to bulk order at a lower price)

• I’m looking for sponsors for 2023 for this newsletter or podcast. Please reach out or book a package here directly.

• Subscribe to my podcast and leave a review

In addition, I recommend all of the following services (affiliate links): Riverside.fm for HD podcasting, Descript for text-based video editing, Transistor for podcast hosting, Podia or Teachable for courses, Skystra for WordPress Hosting, and Circle for running a community

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.