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The Jungle Gym - July 2019

Ciao amici, Ash and I are on the second week of our unseasonably warm European honeymoon. So far we'v
The Jungle Gym
The Jungle Gym - July 2019
By Nick deWilde • Issue #6 • View online
Ciao amici,
Ash and I are on the second week of our unseasonably warm European honeymoon. So far we’ve eaten our way through Paris, Florence, Cinque Terra and Rome. Today we’re off to the Amalfi coast, where we’ll spend the rest of the trip working on our tans and adding to our waistlines.
If this is the first issue you’re reading, welcome to The Jungle Gym, my monthly newsletter that (loosely) covers the topic of careers. To get a sense of what this is all about, check out the previous edition here.
If you like what you’re reading, please feel free to forward this email along to a friend or colleague who might enjoy it. If you’d like to stop getting these emails, just click unsubscribe button at the bottom of the email.
This month I’ll be sharing some ways to figure out if it’s time to leave your job and thoughts on the downsides of cultural preservation, as well as a few recommended links.
With that out of the way, let’s get to the good stuff.

Is it a bad job or just a bad day?
There it is again– that nagging feeling that something’s wrong at work. Staring at the three-sentence email you’ve been writing for twenty minutes, you wonder if it’s finally time to hand in your two-weeks notice.
But doesn’t everyone have bad days at work? And what about all the good parts? You don’t want to quit reactively and regret it. So, how can you know if today is just a bad day or if you’re truly in the wrong job?
At Tradecraft, we often have conversations like these with our alumni. Whether they’re in their first job out of the program or their third, the decision to leave is never easy. If you find yourself in a similar situation, here are five practical lenses you can use to examine whether you’re in the wrong job or just having a bad day.
🧩 The Future Alignment Lens
A good job is one that prepares you for the job you want next. To figure out if this role is aligned with your career goals, try asking yourself the following questions:
  1. Am I helping the type of customer (individual, businesses, governments, etc.) I care about?
  2. Am I solving problems (access to information, transportation, health, etc.) that fascinate me?
  3. Does the type of solution we provide (software, hardware, services, etc.) interest me?
  4. Am I spending my time on activities (coding, designing, selling, etc) that I want to master?
Ideally, you’d want a role where you’re gaining expertise in all of these areas. If you find you’re lacking alignment in one or more of them, it might be time to think about a more serious career change.
If you aren’t sure what your career goals are, that’s okay. You can still confirm whether you want to continue down the path you’re currently on.
As a thought exercise, imagine getting a promotion.
Your boss pulls you into a conference room to share what a great job you’ve been doing lately. She’s been talking with her boss, and everyone agrees you’re ready for more responsibility and a title bump to go with it.
What’s your gut reaction?
Are you excited for the new challenge or dreading the thought of increasing your commitment? If a promotion sounds invigorating, it’s a sign that you’re on the right path. If you have no desire to take on extra responsibility, it means you’re either at the wrong company or on the wrong career path. To test which is the issue, picture yourself getting poached by the hottest employer in your industry.
How do you feel– excitement or dread?
Don’t worry if you don’t have immediate clarity on these questions. Replay them over the course of the next week and try to identify the emotions that are surfaced. These responses can you clarify your desires and goals before your rational mind catches up.
📈 The Progress Lens
Let’s assume this job is aligned with your future goals. A good job is also one that allows you to make progress toward those objectives. One way to measure this progress is through rate-of-learning. The question to ask is: are you building new skills and knowledge fast enough to justify staying?
To know whether you’re progressing at an appropriate rate, look at your calendar over the past month. What percent of your working hours were devoted to practicing and learning things that will be useful for the role you want next? 50%? 25%? 10%? Anything less than 15% should lead you to wonder if this job is the best use of your time.
Time-spend isn’t your only indicator of progress. Who you work with also has an impact on your professional growth. Returning to your calendar, consider the five people you spend the most time with at work. Are they strong in areas where you want to grow? Does their feedback help you improve? If you constantly find that you’re the smartest person in the room, it’s a good indicator that you should find a smarter room.
🌅 The Potential Lens
Beyond making progress toward your career goals, a good job is one that will continue offering opportunities for advancement. Here are ways to think about the potential of your current job:
  1. Is my company growing? — A growing company presents all sorts of opportunities to step up and try new things. Conversely, when your company is stagnant or shrinking in growth, you will likely need to spend the majority of your time doing the things you’re already good at (since these are the most profitable activities for the organization itself).
  2. Is my team valued? — Most companies have certain functions and departments that get favorable treatment. This can materialize in the form of increased budget allotment, better leadership, or opportunities for advancement. If you are on a team that isn’t valued, you may experience more resource constraints and limitations to your growth and influence at the company.
  3. Does my manager care about my advancement? — In order for you to grow within your company, you need a manager that is committed to your success. If you are in a situation where your relationship with your manager is tenuous, you have two options. One is to try to improve the relationship through feedback and communication. Alternatively, if the relationship has reached a dead end, you can try to switch teams or managers, though this can be challenging without support from senior leadership.
If you’re concerned about a lack of opportunities at your current company, start thinking about what you will need in order to advance at a faster pace, in the future.
👪 The Personal Lens
A good job is one that also aligns with your personal goals. While many employees have demanding jobs, these stresses, if taken to the extreme for too long, can have a deleterious impact on their health, wealth, and personal relationships. To uncover whether your job is responsible for unhappiness in your personal life, look out for these warning signs:
  • Your job is harming your relationship with your significant other
  • You don’t have time to devote to maintaining relationships with people who are important to you (children, parents, close friends, etc.)
  • Your job negatively impacts your health through loss of sleep or engagement in unhealthy habits
  • You come home from work with no energy
Sometimes the sources of these stresses are temporary and can be remedied. If your anxiety is the product of a specific coworker or your manager, you may be able to address the issue with a simple conversation. However, if you find that your stress is inherent to your role or aspects of your company culture, consider whether you’re getting enough benefit from the job to outweigh the toll it’s taking on your life.
⚖️ The Ethics Lens
A good job is one that empowers you to work within your own value system. If your success at work depends on your willingness to violate your own ethical principles, it’s not a good fit.
How do you know if you’re violating your own principles?
Try asking yourself how you would feel if your activities at work were explained to your parents, children, or published on the front page of the New York Times. While occasional violations may be easy to justify for the greater mission you’re on, repeated transgressions will impact how you view yourself and your ability to maintain relationships with others.
Before you turn in your two weeks notice…
Remember, it’s not always about you. You’re part of a larger organization that ebbs and flows. Some days you’ll need to take one for the team and absorb the stress of the company.
If you do decide that it’s time for a change, give yourself time to plan out your transition while you’re taking home a salary. By defining your career goals up front you will save yourself time and money in your job search and be better equipped to make informed decisions about the right role to take next.
A permalink for this post can be found here.
The Price of Preservation
Epistemic Effort: Been mulling this over for the past few days. Wanted to gather more data, but prioritizing the honeymoon instead. I’m not confident I’m right on everything, but, it still seemed interesting enough to share.
When Ash and I travel, we often bypass celebrated museums and historical monuments in favor of modern cultural attractions, like street art and new restaurants. While this strategy can sometimes lead to disappointment, it often helps us get the pulse of whatever destination we’re visiting.
Strolling the cobblestone streets of Florence beneath soaring archways and white marble statues, we’ve been discussing what it’s like to be a modern resident of this city. While citizens must feel a great deal of pride surrounded by so many artifacts of their cultural heritage, might their surroundings also feel stifling? By prioritizing the preservation of its historical art and architecture, might Florentines be getting the message that their culture’s best days are in the past?
This feeling of, as one Florentine put it, “living in a museum” seems to be linked to a complacency among Florence’s citizens. Most natives we’ve encountered (during our four days spent mostly in the tourist district) seemed content working in the service sector, preserving the past for tourists, rather than creating new cultural works. While our visit was limited, we found it challenging to find examples of notable works of art or architecture from the past one hundred years.
This all leads me to wonder to what extent preservation is stifling the city’s dynamism. Why erect a new building if it’s certain to be less impressive than the one it’s replacing? Why create a new artistic movement when you’ve already inherited have such a rich artistic tradition?
Florence isn’t the only city sending this message to its citizens. Europe boasts over 40% of all the UNESCO World Heritage Sites on the Globe. While these beautiful sites are a gift to visitors, and businesses that serve them, I wonder how this bias toward preservation impacts Europe’s cultural mindset.
I’m certainly not suggesting that the world would be better off leaving these beautiful places unprotected. Are we moderns even capable of improving upon them? I can only imagine how disheartening it would be to watch Giotto’s Campanile be replaced by something like Salesforce Tower or the Vessel. Given modern architecture’s uninspiring track record, I certainly wouldn’t want to take that chance.
I wonder what a young Antoni Gaudí would have accomplished, had he been born in Florence today. He certainly would have been inspired by the masterful works of Renaissance architecture surrounding him. But would he have been motivated to try and top them? Would he have attempted his Sagrada Familia or simply contented himself curating a museum dedicated to great architectural works?
Dynamism, whether on an individual or societal level requires a certain appetite for risk. Releasing a new piece of work may cause your fans to turn on you. A new startup may upend a business model of a sector of the economy that employs millions. These risks are real and in some cases can lead to catastrophe (see Taleb). But, preservation has its own risks.
Cling too tightly to the past and you become stagnant. This means watching others pass you by and losing the ability to respond in creative ways to new challenges. Healthy individuals and societies alike must learn to balance appreciation for what they’ve inherited from their ancestors and ambition to leave their own offspring something better.
Let me reiterate, I haven’t spent enough time researching to feel fully confident in these ideas. If you have thoughts that either support or challenge these claims, I’d love to hear more.
Recommended Content
Lately I’ve been on something of a self-improvement kick, but rather than trying to improve my habits around health, wealth, or productivity I’ve been trying to upgrade aspects of how I view myself, others, and the world around me.
Unlike with habit formation, where there seems to be no end of accessible advice, it’s been challenging to find guidance on this topic. That’s why I was excited to discover Robert Kegan’s five-stage model of adult development.
I found the differences between stage three and four particularly interesting. In reaching stage three you move beyond the self-interested motives of stage two and begin defining yourself based on your relationships. This seemed like an enlightened state until it became clear what was missing:
Stage 3’s limitation is that it cannot resolve conflicts between responsibilities to different relationships. If one person wants you to do something, and another person wants you to do something different, there is no good basis for decision, because relationships have no internal structure; they consist simply of sharing experience.
The key to growing beyond this is to develop a self-authored identity. This allows you to make decisions about which relationships to prioritize based on your own principles, rather than who has the stronger emotions.
The progression to stage five is defined by an openness to cultivating multiple identities.
You are no longer defined as a system of principles, projects, and commitments. You have several such systems, “multiple selves,” none of them entirely coherent, and which have different values—and this is no longer a problem, because you respect all of them.
Examining my own progress, I’m not sure which stage I fall into. Observing myself on a given day, I’m sure I could find evidence for any of them. I’ve found Kegan’s model valuable as a map that indicates which direction I should be progressing.
When advising newly employed Tradecraft grads, I’m struck by how often their issues are linked to some form of uncertainty. How will my manager react if I ask for a more substantial assignment? Do I have the information I need to make this decision?
This article which summarizes Gary Klein’s book The Power of Intuition, lists five sources for this type of uncertainty:
1. Missing information. We can be uncertain because we are missing important information. We may not have it, or we may not be able to locate it if it is buried in information overload. Either way, we cannot access the information when we need it.
2. Unreliable information. We can be uncertain because we aren’t able to trust the information, even if we have it. We may suspect it is erroneous, or outdated, or that we are receiving the same report from several different sources. Even if it turns out to be accurate, this distrust will affect our decision making.
3. Conflicting information. We may have the information and trust it, but it might be inconsistent with other information we have and trust. If this is the case, we are facing an anomaly.
4. Noisy information. We may have to sift through a lot of irrelevant information — noise — but if we can’t be sure if it really is noise, we have to take it seriously and that adds to our uncertainty.
5. Confusing information. We may have all the information we need, trust all of it, find that it is all consistent, find that it is all relevant, but we could still be uncertain if we cannot interpret it. This happens if the data were so complex we couldn’t build a coherent story for purposes of explanation. Or the data could allow more than one reasonable interpretation.
The post chronicles Klein’s methods for dealing with uncertainty including delaying, shaking the tree and preparing for the worst. If you’ve got something you’re uncertain about, I bet you’ll find a strategy that will help you gain some clarity.
“Go into a room and subtract out all the screens. How do you then know you’re not in 1973?”
While it can feel as if technology is changing society at a dizzying pace, it’s certainly hard to find evidence of this in the world of atoms. At least that’s the contention that Peter Thiel and Eric Weinstein discuss in the first episode of Weinstien’s new podcast, The Portal.
Whatever you think of Thiel and his politics, you owe it to yourself to listen to what he has to say. In particular, I think he’s right about the extent to which our higher education system has become a ponzi scheme that wastes the time, money, and brainpower of our country’s brightest minds. Rather than producing polymaths who can make connections between disparate subjects we reward rigid specialization.
Weinstein is a courageous thinker and I’m excited to see what he does next with this podcast. To whet your appetite, watch this short video of him explaining the purpose of the podcast.
Until next time,
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Nick deWilde

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