Boomer vs. Millennial Career Advice, Embracing the Grind and The Great Online Game

💌 Roundup // 025

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The next time you hear from me, I’ll likely be a dad. That’s just wild.

To prepare for this transition, I’ve been reading Hunt, Gather, Parent. While I haven’t read many parenting books (yet), I think this one will be tough to top. The book explores the downsides of Western parenting and what indigenous cultures in Mexico, Canada and Tanzania can teach us about raising “happy and helpful little humans.”

While there were a lot of great takeaways from the book, my biggest one was: instead of planning life around your child, insert him into yours. That means letting him help cook breakfast and do the dishes even if he makes the work slower. This nurtures kids’ innate desire to help. Highly recommend this book to all the parents out there.

Okay, let’s get into it. In this issue of the Roundup, I’ll be riffing on:

  • 🕹 The great online game

  • 🔧 Creating a career path for inventors

  • 👨‍👩‍👧 Boomer vs. Millennial career advice

  • 💞 Why we play hard to get

  • 😥 Embracing the grind

Riffs & Recommendations

Some reflections on the best content I’ve been consuming lately.

🕹 The Great Online Game

18-minute read from Packy McCormick

In case you haven’t heard, America is in the midst of a serious labor shortage. While retiring baby boomers are partially to blame, demographics can’t fully explain why this country’s labor participation rate is lingering at 1970s-era lows (61%).

After reading Packy’s post, I’m beginning to suspect the internet may have something to do with it. Over the past year, many have become engrossed in what Packy calls The Great Online Game.

We now live in a world in which, by typing things into your phone or your keyboard, or saying things into a microphone, or snapping pictures or videos, you can marshall resources, support, and opportunities.

Anyone can play. You can choose how to play given your resources and skills at the current moment. You can level up fast. Financial and social capital are no longer tied so tightly to where you went, who you know, or what your boss thinks of you. This game has different physics and wormholes through which to jump. It’s exponential instead of linear.

From sharing content on creator economy platforms to pursuing speculative crypto investments, The Great Online Game has provided many with friendship, income, and a sense of purpose.

What does this have to do with the labor shortage? While some workers are staying home to take care of kids and others may indeed be content playing video games, I suspect that a growing number of people are using the internet to forge a new type of career path, playing a game that will only get more popular in the years to come.

🔧 We need a career path for invention

5 minute read from Jason Crawford

Why isn’t “inventor” a more popular career path?

One reason may have to do with the social support structures surrounding the role. While a failed entrepreneur can often find a soft landing as a product manager at a big tech company, inventors do not have an easy fallback. This makes the role much riskier and likely dissuades talented people from doing the tinkering that’s necessary for large breakthroughs.

👨‍👩‍👧 Advice My Parents Gave Me Versus Advice I Will Give My Kids

3 minute read from Danielle Kraese and Irving Ruan

So many of the career-building tactics that worked for baby boomers have outlived their usefulness for younger generations.

For example, if you listen to any baby-boomer explain how they got the “big break,” you’ll likely hear a story about how they pitched a gatekeeper who decided to give them “a shot.”

For Millennials and Gen Z-ers, the dynamic has changed. Rather than a single gatekeeper giving (or keeping us from) our big break, opportunities often come from viral exposure to the masses.

I can only imagine how outdated our tactics will feel for the next generation.

💞 What People Are Really Doing When They Play Hard to Get

7 minute read by Luke Burgis

As a marketer, I’m often thinking about what people want and how to create desire.

If you’ve studied the work of philosopher René Girard, you’ll know that desire is rarely generated in isolation. To determine what we want, we observe what others want.

But not just anybody. We model our desires after people who are both prestigious and similar to us. After all, if someone who is just like us– but better– wants something, it’s probably a good idea for us to want the same.

😥 Embrace the Grind

4 minute read by Jacob Kaplan-Moss

Leverage, many suggest, is the key to building wealth and a successful career.

While I agree with this sentiment, it’s also interesting to see people find success through the opposite strategy of grinding long hours of low-leverage work.

For example, I once joined a team maintaining a system that was drowning in bugs. There were something like two thousand open bug reports. Nothing was tagged, categorized, or prioritized. The team couldn’t agree on which issues to tackle. They were stuck essentially pulling bugs at random, but it was never clear if that issue was important. New bug reports couldn’t be triaged effectively because finding duplicates was nearly impossible. So the open ticket count continued to climb. The team had been stalled for months. I was tasked with solving the problem: get the team unstuck, reverse the trend in the open ticket count, come up with a way to eventually drive it down to zero.

So I used the same trick as the magician, which is no trick at all: I did the work. I printed out all the issues - one page of paper for each issue. I read each page. I took over a huge room and started making piles on the floor. I wrote tags on sticky notes and stuck them to piles. I shuffled pages from one stack to another. I wrote ticket numbers on whiteboards in long columns; I imagined I was Ben Affleck in The Accountant. I spent almost three weeks in that room, and emerged with every bug report reviewed, tagged, categorized, and prioritized.

The trend reversed immediately after that: we were able to close several hundred tickets immediately as duplicates, and triaging new issues now took minutes instead of a day. It took I think a year or more to drive the count to zero, but it was all fairly smooth sailing. People said I did the impossible, but that’s wrong: I merely did something so boring that nobody else had been willing to do it.

I think this offers a good lesson for folks who are early in their career. If you want your company to give you leverage (allow you to hire a team, let you purchase expensive software) you need to first prove that you can be effective without that investment. The best way to prove yourself worthy of leverage is often by temporarily embracing the grind.

Friends of the Newsletter

Some great projects and pieces of writing from friends of the Jungle Gym:

Stuff from me you may have missed

Here’s what I wrote about since the last Roundup:

  • If you had your dream job, would you be happy? asks a seemingly simple question with a complicated answer.

  • Great relationships are not discovered– they are built includes an interview with author and dating coach Logan Ury, who shares some advice for rekindling romance in your life, post-COVID.

  • Work and Let Work is an older post, but one that I’m resurfacing given all of the recent controversies around Basecamp and Apple.

You can always search the back catalog of this newsletter by topic, or find a curated list of the best essays I’ve written.

Thanks for reading. Do you have a friend or a co-worker who would enjoy this issue? I’d be honored if you shared this with them or amplified it on one of your social networks.


Until next time,