The Ladders of Wealth Creation and What If People Don't Want a Career?

💌 Roundup // 029

👋 Welcome to the latest issue of The Jungle Gym – the newsletter that helps you build a more fulfilling career by integrating your work and life.

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One of the best parts of my career has been connecting talented people to fulfilling work. During my time at Tradecraft, I helped hundreds of job seekers board rocketship companies right before takeoff and transition into new functions and industries.

Two pain points I often witness during the recruiting process are:

  • Applying to jobs – Applications take a long time to complete and many companies never respond.

  • Unwanted pressure from recruiters – Talented people get bombarded with conversation requests from recruiters.

To solve these issues I’m teaming up with the folks at Pallet to launch The Jungle Gym Talent Collective, a talent matching service that surfaces interesting opportunities at fast-growing companies.

Here’s how it works:

  1. Fill out your information – Regardless of whether you are actively looking for a job right now, fill out your information (you can choose to remain anonymous).

  2. Get intro requests from companies – Your info will be shared with fast-growing tech companies that can request introductions to you.

  3. Select which companies you want to meet – If a company is interested in having a conversation, you’ll get an intro request which you can choose to accept or ignore.

You can think of The Talent Collective as an always-on talent agent. If you’re happy at your job, just ignore the intro requests. When you are ready to have conversations, you’ll be able to skip the hours of applying and waiting for responses. You pick the conversations you want to have, so you don’t need to waste your time getting pressured to work for companies that don’t interest you.

As an added bonus, anyone who submits their info within the next month and accepts a call with at least one company will get the option to book a free 30-minute career coaching call with me. I’ve had hundreds of conversations like these over the years, and I can typically be helpful at any stage of the job search.

So, if you or someone you know is looking for their next job opportunity, just fill out this form to accelerate your job search and get intro requests from fast-growing companies.

Get Intros to Fast-growing Companies

If you’re interested in participating or have any questions about the process, don’t hesitate to drop me a reply!

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

  • 💰 The Ladders of Wealth Creation

  • 🏝 Why workcations don’t “work”

  • 🚲 Revolt of the Delivery Workers

  • 🗝 Things you're allowed to do

  • 💼 What If People Don’t Want 'A Career?'

Riffs & Recommendations

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

💰 The Ladders of Wealth Creation

26-minute read from Nathan Barry

For most workers, making money is all about optimizing compensation. But salary increases are not necessarily the best way to optimize long-term wealth.

The challenge is that switching to a better strategy can temporarily decrease your take-home pay. The more you make, the harder it is to jump off the trading-time-for-money ladder and grab the bottom rung of another.

While income increases as you move up any one ladder, it often decreases when you jump between ladders. Sometimes that drop may be only for a few months, other times it could be a few years. Let me give you an extreme example.

In 2013 I earned over $250,000 from selling books and courses on design. My income head been steadily increasing for the last few years and I was damn proud of my blog and business. But then I decided to make the leap and switch from selling ebooks to starting a software company—one of the most difficult rungs on the product ladder.

My income immediately and substantially dropped as I focused on ConvertKit. So how long do you think it took to set a new one year income record? A year? Two years?

Nope. I didn’t earn over $250,000 in a year again until…2018. 5 years later!

🏝 Why workcations don’t “work”

4-minute read from Kye Hy

In the age of remote work, it’s easier than ever to do your job from anywhere. It’s also harder than ever to justify taking a real vacation. After all, why waste precious vacation days when you could work from in a cabin in Tahoe after your morning ski run?

While, in theory, workcations sound great, they also represent an easy way for work to weasel its way into precious leisure time. The jury is still out whether mixing work and play just leads to work suffocating play.

🚲 Revolt of the Delivery Workers

34-minute read from Josh Dzieaz

I always had a sense that those delivery workers biking the streets of New York were doing something dangerous. I had no idea they were being forced to mete out vigilante justice to buzz-saw-wielding bike thieves.

What I can’t help but wonder is why so many people keep doing this job when they can make just as much working safer jobs in retail and food service. I suspect that there’s something about the adrenaline of racing around the city, avoiding danger, that may be somewhat intoxicating.

🗝 Things you're allowed to do

6-minute read from Milan Cvitkovic

We all enter adulthood with a set of rules in our heads that define what we can and can’t do with our lives. Most of the successful people I know figured out at some point that a lot of those rules weren’t real.

That’s why I love this list of “things you’re allowed to do.” None of these ideas are illegal they just feel weird due to the invisible scripts we all use to define the boundaries of the game we’re playing.

Here are a few of my favorites:

  • Hire a researcher or expert consultant

  • Host a small conference

  • Arrange your own timeshare with friends

  • Hire a matchmaker

  • Generate your own audiobooks

  • Hire a personal stylist

  • Pay for a convenient parking spot

💼 What if People Don’t Want ‘A Career?’

10-minute read from Charlie Warzel

Common career advice suggests that you should work nights and weekends in your 20s and 30s in order to enjoy time with your family in your 40s and 50s.

What I appriciate about this advice is it protects your financial downside. I suspect that there are few people who worked hard in the early decades of their career and ended up living in poverty during their middle ages.

The problem is, this advice also assumes you can slow down the career treadmill to actually focus on family life. Money and status are two powerful drugs that are hard to deprioritize. I’ve met plenty of people who never actually took the opportunity to reap the fruits of their hard work and let their family lives languish.

Perhaps the more interesting question than how hard you should work to build a successful career is whether your career is the right domain to seek out meaning in the first place.

Friends of the Newsletter

Here are a few great pieces of writing from friends of the Jungle Gym:

If you enjoyed this issue of the newsletter, I'd really appreciate it if you could forward it to a friend, family member, or colleague who you think might like it too.

Or, if you'd like to share it on one of your social networks, that’s always great as well.


Until next time,