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The Jungle Gym - February 2019

Friends– Over the past few years, I've spent a lot of time talking to people about their careers. In
The Jungle Gym
The Jungle Gym - February 2019
By Nick deWilde • Issue #1 • View online
Friends–
Over the past few years, I’ve spent a lot of time talking to people about their careers. In that time, I’ve noticed that even some of the most savvy individuals lack a good blueprint for dealing with career inflection points.
While I’ve shared some of my learnings before, there are a lot more topics I’d like to write about in a slightly less public forum. So, consider this the first in a series of monthly notes I’m planning to share on the topic of careers.
As you may have noticed, my working title for this is “The Jungle Gym.” The name comes from a phrase that an investor used to describe the career opportunities at a fast growing portfolio company. No longer a flat organization, but not yet ladder. More like a jungle gym. This feels like a good metaphor for modern career progression and also suggest a spaces to play with ideas. So let’s go with it.
If you’re reading this it means that you’re someone who I’d like to keep in closer touch with. That said, I realize your inbox is probably a busy place, and the last thing I want to do is clog it up with emails that aren’t useful. So, if you’d like to opt-in to future emails like this, just fill out this form, and you’ll be officially on the list.
Consider the rest of this email a preview of what you’re signing up for.

How Job Skills Develop and Degrade
There’s a framework we use at Tradecraft to help people think through career transitions. I originally heard it from, our founder, Russ. I believe he got bits and pieces of it from other people, then made some improvements of his own. I think you’ll find it to be a valuable lens to view decisions about your own career as well as the careers of those you manage.
One way to look at your job is as a list of responsibilities. Some of those responsibilities fall into the category of “stuff you’re good at,” and all the rest are “stuff you’re bad at.”
You can divide that same list into “stuff you like to do,” and “stuff you don’t like to do.” Put it into a 2x2 matrix and it would look something like this:
Hopefully, the stuff in the upper left-hand box is a majority of your job since it represents work that is both helpful for the company, and beneficial to you.
The stuff in the upper right-hand box, while not particularly profitable for your company, tends to be work that you really enjoy, since it allows you to challenge yourself and build new skills.
The stuff in the lower left-hand box represents work that you may be good at, but now find annoying (think cold calling for salespeople). Any time you’re doing this work you, and hopefully your boss, view it as you “taking one for the team.”
Finally, you shouldn’t be doing much of anything in the lower right-hand box, since it’s not helpful for you, or your company.
A fulfilling job will mostly consist of responsibilities in the top-left box and almost nothing in the bottom-right. It’s also fair to expect that for however much time you spend doing things in the bottom-left box, you’ll get to spend an equal amount of time in the top-right box. Taking our cues from Google’s 20% time (top-right box), we can fill in a rough breakdown of how you might spend your time in a role like this.
Here’s where things get interesting.
With enough practice, the stuff that you’re doing in the top-right box should shift towards the top left box. Meanwhile, the stuff you’re doing in the top-left box will eventually grow tiresome and sink into the bottom-left box. As you continue to dislike the stuff you’re good at, you’ll inevitably get sloppy. You’ll stop paying attention to best practices and that stuff will drift into the dreaded bottom-right box. The choreography looks something like this:
So what does this mean for you?
If you’re building a team, it’s easy to get tempted by a candidate who’s had the exact same role at a similar company. While the candidate may be able to hit the ground running, how long will they last as the tasks they once enjoyed migrate into the bottom half of the matrix? When I’m sourcing candidates for a new role, I tend to look for people who see this role as a big step up. I’ve found that usually if they’re a good self learner, their motivation will help them quickly close any skill gap.
As a manager, be wary of leaving one of your team-members in the same role for too long. If you want to retain them, make sure you understand the next role they want and what skills they need to land it. To facilitate skill-building, put them on projects where they can work alongside colleagues who are subject matter experts. If that expertise doesn’t exist at the company, find non-mission-critical projects, that they can use to try out new skills in a risk-free setting.
If you find yourself in a job where you’re starting to feel unhappy, it may be worth bucketing your responsibilities like this so that you can go to your manager with some concrete proposals for improvement. And if things don’t change, this framework can also help you evaluate new offers.
Sometime in the next few months I’m planning to write a guide for getting promoted at fast growing startups. If you have any related stories to share I’d love to hear them.
Also, if there are any career-related topics you’d like me to cover in the future, feel free to drop me a note.
Recommendations
Each month I’ll include a few recommendations for some great resources I’ve come across. These will tough a grab bag of topics, but will hopefully will leave you feeling smarter.
In most offices there exists strong incentives to signal business and productivity. Taking on more work signals that we’re valuable members of the team who are deserving of our title and compensation. But what if that drive from each individual to take on more is actually bringing down the performance of the team as a whole?
Tiago’s series of posts elegantly explains the Theory of Constraints. For me, it represented a new way of thinking about managing individuals to optimize team performance. Also, I highly recommend the rest of the author’s work on productivity and performance. It’s some of the best I’ve read.
I don’t know about you, but over the past 3 years, I feel like my political beliefs have gotten completely blown up.
As the left and right have moved towards the extremes, I’ve found myself timidly exploring the wreckage left behind. From the establishment conservatives trying to defend conservative principles in the age of Trump, to the misfits of the Intellectual Dark Web duking it out with progressives over the merits of free speech, to the rationalists who can’t seem to understand why we’re all getting so emotional about this stuff.
For those of you who’ve been in a similarly experimental stage with your beliefs, I recommend giving this article a read. At 39 minutes it’s kind of a beast. But it’s the most clarifying thing I’ve read on what’s been happening in our culture and politics.
Why did humans evolve to adopt beliefs that don’t provide an accurate model of the world? Shouldn’t this tendency have been selected out of the gene pool? Kevin Simler chronicles what kind of social incentives may be driving us to adopt and retain these crony beliefs.
If you find this topic to be as fascinating as I do, I’d recommend you check out his book The Elephant in the Brain as well as Jonathan Haidt’s book, The Righteous Mind.
Offers
One of my goals for this monthly email is to find an excuse to check in more frequently with the people I care about and see how I can help. To that end, here are a couple of offers:
If you’re hiring…
At any given time, I’m usually advising a bunch of talented people who are looking for their next thing. If you share some info about what role you’re hiring for, I’ll try to pass it along to the right people.
If you’re looking for your next thing…
If you, or someone you’d vouch for, is on the job hunt, I’m happy to help however I can. Tell me a bit about what you’re looking for and I’ll keep my eyes peeled for interesting opportunities.
Okay, so that’s the basic gist of what you’ll be getting on a monthly basis. If that sounds exciting drop your details here (if haven’t already).
Until next time,
Nick

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Nick deWilde

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