Productivity Addiction and the Flawed Search for Mentorship

💌 Roundup // 031

👋 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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It’s been two months since I strapped on a jetpack and went independent, so I thought I’d share a quick update about what I’ve been doing and how it’s going.

What I’ve been doing:

  • Incubating a company to solve skilled labor shortages

  • Helping with the marketing launch of an online enrichment program for kids

  • Launching a web3 education project

  • Managing the talent collective

  • Angel investing & advising

  • Writing this newsletter

What needs improvement

While I’m enjoying each of these projects, and they are all going well, this doesn’t feel like a sustainable way to operate. I’m working a ton of hours and always have a nagging feeling that I’m dropping a ball somewhere.

I’ve noticed that I tend to give top priority on my time to consulting work out of a drive to deliver value to clients. While I think that’s the right mindset to be a good consultant, it’s probably not the best strategy if I want to build something of my own or maximize my day-to-day energy.

Since this web3 education project is giving me tons of energy, I’d like to free up more time to focus on it. That probably means trimming down to one main consulting engagement at some point.

What’s going well

With all that said, I’ve been loving this new way of working.

Every project I’m on is intellectually engaging. That seems to be a function of the:

  • Subject matter of each domain

  • Skills I’m exercising

  • People I’m engaging with on a daily basis

While the cognitive load of switching projects can sometimes feel taxing, the variety is really energizing. I think that no matter what allocation I settle on, I will keep taking a portfolio approach to my career.

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

  • ⚙️ Productivity addiction

  • 🤫 The gifts of awkward silence

  • 🔍 The flawed search for mentorship

  • 🎊 How to find friends online

  • 📝 What writer’s block actually means

Riffs & Recommendations

Reflections on some of the best content I’ve been consuming lately.

⚙️ Breaking Free From Productivity Addiction

6-minute read by Alex Olshonsky

One challenge of independence is that you’re under constant surveillance from your boss (a.k.a yourself). My boss not only knows how productive I’m being, he actually knows how productive I could have been if I had stuck to my schedule. He sees the inefficient way I do certain tasks and judges me without offering any advice for improvement.

Ultimately, my goal isn’t to play the productivity game. I’m not trying to maximize the output of each hour. Instead, I’m aiming to do high-leverage work that generates a lot of value so that I can use the rest of my time as I see fit.

Turns out, it’s still hard to break the habits of productivity theater, even when you’re only performing for yourself.

🤫 The many gifts of awkward SILENCE.

3-minute read by Jessica Hagy

Loved these ten gifts of awkward silence:

  1. It’s the ideal deflect for verbal attacks

  2. You say nothing that can be used against you

  3. You seem smarter than you are

  4. It exposes the absurdity of a bad question

  5. Helps you avoid dumb arguments

  6. Gives you time to think

  7. It’s more memorable than anything you could say

  8. The discomfort reveals a lot about the other person

  9. Gives you the position of power

  10. You get to choose your own fate

🔍 Stop Looking For Mentors

2-minute read by Stay SaaSy

Looking for a mentor is a lot like looking for a husband or wife while you’re single. Eventually, someone you date may become a suitable candidate, but the people you meet on Tinder rarely start out that way.

Rather than trying to find someone who will agree to mentor you:

Just find somebody who can answer some questions you have. Then, if you think they can answer some more, ask them again. In reality, a mentor is mostly just somebody that answers questions more than once. That’s it. It’s not cinematic.

🎊 The 1/10/100/1000 rule of finding friends online

6-minute read by Lesley

Over the past couple of years, I’ve gotten pretty good at making friends online. As evidence, I talk to a bunch of people on a monthly basis who I’ve never actually met in person.

In reality, it’s a numbers game. By spending time in the right online communities you surround yourself with lots of potential friends. By direct messaging a portion of those people, you’ll end up taking some friendly Zoom calls. While most of those calls will be one-time events, a few may build the foundation for a relationship. Pretty soon one of those people will start looking a lot like a friend.

📝 If You Have Writer's Block, Maybe You Should Stop Lying

5-minute read by Sasha Chapin

Perhaps you’ve complained before that you don’t have anything to write about. That your “mind has gone blank,” that you don’t have any ideas. 

I don’t believe you. I know that you have mental contents, right? Your mind is constantly moving. You’re always producing judgments, attitudes, opinions, emotions, melancholy, malaise, anger, and so on. You have things to write about. What you do is just put the things in your head on the page, in basically the order they naturally occur. Flip over the rock in your mind, type about the beetles.

If you don’t want to do that, it’s because you’re not comfortable with the notion that these are the things that you actually think.

Friends of the Newsletter

Some of the exciting work from friends of the Jungle Gym:

Shameless Plugs

  • That web3 education project I mentioned is getting some early signs of traction. We’re planning a couple of cool opportunities for our early believers. If you’re interested in jumping in before the public launch, sign up here.

  • The talent collective is accepting new candidates. If you’re tired of filling out applications and waiting for responses sign up here and get intro requests from fast-growing startups delivered to your inbox. (If you’re a company that’s looking for talent feel free to drop me a note as well.)

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.

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Until next time,