Each month I publish two issues of this newsletter. Both have different formats. This format is The Roundup. It features a longer-form essay along with riffs on some good content I’ve been reading lately.
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Here's a rundown on what this issue of The Jungle Gym will cover:
📝 Integrating publishing with your profession
Publishing a newsletter and having a full-time job may seem like activities that are at odds with one another. But, in my experience, doing both at the same time has reaped huge benefits for my job as well as my writing. In this post, I’ll share some of the tensions and synergies that come with integrating publishing into your profession.
Recommendations & Riffs
🌇 How the digital city changes us
🗓 Minimizing career regret
🏡 Testing out co-living
🏛 Seeing like a baby boomer
Integrating publishing with your profession
Giving up screenwriting was one of the worst moments of my career.
At the time, I was a 23-year-old living in LA. Despite a decent first year in the entertainment industry where I was a finalist for NBC’s screenwriting fellowship and shopped a pilot to the networks, I knew screenwriting wasn’t the right path for me. I didn’t like being alone all the time. And alone is something you need to be good at to become a great writer.
It took me some time before I felt ready to incorporate writing back into my career.
Not as my sole job, but still as a part of my profession.
Most writers want to keep their day jobs.
They view writing as a means to refine their thinking, grow their networks, and accelerate their careers. Yet, many have trouble imagining how to incorporate publishing into their professional lives.
They worry about the ramifications. What will their bosses and co-workers think? Could publishing give future employers the wrong impression? What if they share an opinion that they later come to regret? I am familiar with these concerns because I’ve had them too.
There are natural tensions between publishing and work.
Unlike other hobbies, online writing can’t be easily concealed from co-workers. It’s a time-consuming activity. And the audience-building aspects can be uncharitably interpreted as attention-seeking behavior.
That said, there are amazing spillovers to be had from merging writing and work. From skill development to idea generation, writing can create plenty of value for you and your employer. The trick is aligning your publishing with your day job. I’ll share how I’ve gone about that and some great things that have come from it.
How publishing and your profession complement each other
To an outside observer, publishing looks almost indistinguishable from the job of a typical knowledge worker. Both involve browsing the web, writing documents, and sending emails. Of course, with both publishing and work, there’s more going on than meets the eye. But the overlap between these two activities allows them to reinforce a common and valuable skill set.
In my case, writing and work have helped me become a more persuasive communicator. The more I’ve practiced creating compelling collateral and presentations in my job, the better my newsletter has become. Conversely, each issue of the newsletter I publish trains me to better express my ideas at work.
Skill development depends on practice.
While books and online courses can help you build knowledge, that kind of learning has its limits. Getting great at something takes deliberate practice. Fortunately, publishing and work are both activities that naturally facilitate practice.
Both writing and work motivate practice through social incentives.
Personally, I find few things more motivating than the embarrassment of publishing a boring issue of my newsletter or shipping amateur marketing collateral. The drive to avoid that embarrassment is the best motivator I’ve found to help me hone my craft.
Become an idea generation machine
The key to having great ideas is to expose yourself to them. Whether reading the right books, subscribing to interesting newsletters, or cultivating a world-class Twitter feed, inserting yourself in the flow of good ideas is the best way to generate them yourself.
By matching your publication's subject matter with the responsibilities of your role, you’ll be able to use these ideas both at work and in your writing. For example, when I’m studying how creators and media companies craft and promote content, I can apply those learnings to work and writing. When I’m having conversations with co-workers or readers, I often pick up inspiration that benefits both pursuits.
These synergies aren’t entirely accidental. Part of what attracted me to work as a marketer at Guild was the functional and topical overlap with this newsletter. Guild solves problems related to learning and the future of work, which ties in nicely with what I like to write about. Meanwhile, the ideas I encounter as a marketer about audience building and content creation are useful at work and growing the Jungle Gym (I even started a monthly newsletter at Guild about Learning at Work).
Attract your people
It’s often said that who you know is more important than what you know. While this quote contains some wisdom, it misses an important caveat:
Who wants to know you depends on what you know.
People are inherently self-interested and want to affiliate with others who can help them get ahead in life. The best way to signal your value is to share what you know in public spaces.
As you build affinity with your audience, the organizations you affiliate with will benefit.
Trust is, to some extent, transferable.
If your audience trusts you, and you speak well of your employer, your audience will be more inclined to trust your employer. This can be particularly valuable if your audience happens to overlap with a stakeholder group that your company wants to attract.
While the Jungle Gym may not reach many of Guild’s buyers (as far as I know), it does land in the inboxes of a number of talented knowledge workers who want to make an impact with their careers. Whenever I can, I make a point to promote Guild so the company can benefit from my audience (by the way, we're hiring 🙂).
Expand your professional identity
Your identity determines how the world sees you and how you, in turn, view yourself.
In particular, your professional identity defines what kind of opportunities you can access and whether you have the confidence and ability to capitalize on them.
Just as it’s wise to take a portfolio approach to your financial life, diversifying between different asset classes to limit risk, the same principle applies to your professional identity. Rather than allowing your reputation to depend on any single employer or professional track, bifurcating your identity can leave you more resilient to unexpected career shifts.
Over the past six months, The Jungle Gym has shifted from a hobby into a new facet of my professional identity. I’ve noticed it during catch-up calls with friends where the question “how’s the newsletter?” has become almost as common as “how’s work going?” I was even a guest on a podcast where I was introduced by my affiliation with the newsletter rather than my job title.
This new layer of identity has had a big impact on how I view myself.
Newsletter publishers make an implicit commitment to their readers to ship their writing. By living up to this obligation month after month, I’ve started to view myself as “someone who ships work” – a trait that benefits not only Jungle Gym readers but also my colleagues at Guild.
Overcoming Tensions: Principles for making it work
While I’ve been lucky enough to have managers and partners who have supported my writing, that doesn’t mean there isn’t tension between these two pursuits:
Aligning your audience
Building an audience can be an uncomfortable endeavor. It forces you to seek attention for your ideas in public places like Twitter and Linkedin that may overlap with bosses and co-workers. It’s easy to get self-conscious, to worry about how others might judge you.
In some ways, this is anxiety you must be prepared to live with. To create anything valuable requires risk.
If everyone you know is fully onboard with your ideas, you’re likely not saying anything very interesting. However, you can still prime your co-workers to root for the success of your publication.
People tend to endorse things that align with their interests. By targeting an audience that overlaps with your employer's needs, you can make writing a slightly more selfless pursuit. By using your platform to reach people both you and your company seek to influence, you increase the odds of getting the rest of your professional network onboard.
Managing time and its politics
Perhaps the most obvious tension between work and writing is time.
Knowledge workers have a limited number of creative hours in a day, and those that are spent writing can appear as though they are detracting from work.
Time conflicts are both a practical problem as well as one of perception. Thus they demand two different types of solutions.
As to the practical question of how to divide up creative hours, I take my cues from Tobi Lutke, the ever-thoughtful CEO of Shopify, who said:
There are 5 creative hours in everyone's day. All I ask of people at Shopify is that 4 of those are channeled into the company.
In this vein, I devote about 80% of my weekday creative hours to work and spend most of my weekend hours writing. If I’m feeling inspired to write the Jungle Gym on a Friday afternoon, I strike while the iron is hot and make up the time over the weekend.
There is also a perceptual challenge that writers must overcome. Unlike other hobbies, the output of writing is very visible. It’s easy to imagine a manager interpreting a rate of publishing as a lack of dedication from their direct report.
While I haven’t experienced anything like this scenario myself, we’ve all heard horror stories about crappy bosses. Given my goal is to ensure my readers don’t get fired, let me leave you with this advice:
The best way to avoid the perception of laziness is to prove the contrary.
Build a reputation for meeting your commitments, creating value, and shipping high-quality work. If you can manage that, you’ll find yourself hard to fire.
Know when to make tradeoffs
Every now and then, there comes a moment when you truly need to choose between your job and your writing. Whether you're a founder whose business missed a quarter, or a manager with an underperforming team, if things start taking a turn for the worse, it's worth reassessing your priorities.
There’s a difference between signaling your dedication and actually reallocating your time. If you’re trying to signal to others that you’re prioritizing work, consider cutting back on publicly promoting your writing. If you’re actually committed to devoting more focus to your job, you may need to take a hiatus from writing altogether.
While these tradeoffs can be painful to manage, it’s worth remembering that you can’t always get re-hired by your employer, but your newsletter will always take you back.
Live your lives
People sometimes ask if I miss screenwriting. While passions leave traces, for the most part, I’d say my creative cup is full. Publishing allows me to show up at work each day without feeling as though I’m denying who I was meant to be. Meanwhile, my job lets me preserve writing as a joyful activity, rather than a commercial pursuit.
If there’s a part of you that’s itching to create, remember that you don’t need to up-end your whole career to scratch it. By being intentional about aligning your passion with your profession, you can get more out of both domains and build a richer and more fulfilling life.
Recommendations & Riffs
30-minute read from L.M. Sacasas
In recent months, I’ve spent a lot more time than usual connecting with people in digital spaces– friends in messaging apps, co-workers in Slack, readers on Substack. All this time in the digital world has made me wonder if my behavior is changing in the analog world. The question calls to mind a Neil Postman quote referenced in this essay:
“New technologies alter the structure of our interests: the things we think about. They alter the character of our symbols: the things we think with. And they alter the nature of community: the arena in which thoughts develop.”
Writing this newsletter has certainly done all three. It has filtered:
The topics I think and read about to ones that fit the interests of my readers
The structure of my thoughts into ideas that work in a long-form context
The presentation of my thoughts into messages that keep my readers engaged
I’m certain I’m not the only one being shaped by my time in the digital city. Whether these changes are beneficial or not will be one of the fascinating storylines of the coming decade.
7-minute read by Apoorva Govind
Minimizing regret is a worthy goal of any career decision. One particular choice that often yields regret is whether to leave a company and join a new one. Silicon Valley lore is full of examples of people who missed the boat on being early employees at rocketship companies.
Or who departed fast-growing companies too early.
Given the difficulty of making these decisions, it’s worth having a framework to help you make good choices.
The author of this post shares how she evaluates whether she’s worn out her stay with an existing employer:
• Accomplishment: Have I done anything noteworthy these last three months?
• Impact: Would I write a line in my resume about the work I have done over these three months? Would I value this specific work experience if I was hiring for my own company?
• Growth/Future alignment: Have I acquired valuable insights or skills? Are these skills aligned with my future goals?
• Challenge: Have there been days when I was thinking about a work problem in the shower so profoundly that I forgot if I used the soap or not?
• Community: Am I excited and happy to go to work every morning and see my teammates. Do I believe in the mission, vision, and leadership of this team or company?
Whether you’re deciding to stay at your current job or trying to retain the people on your team it’s worth making sure any job adds up on these dimensions.
7-minute read by Gillian Morris
One of the most popular topics that I’ve covered in this newsletter is the concept of co-living. Even before the pandemic, it seemed clear that with millennials waiting longer to get married and have kids, many would be looking for new living arrangements that could help them preserve their adult friendships.
However, group decision making is tricky. Do we build the compound in Montana or Texas? Should we invite Paul even though he’s dating that annoying girl? Questions like these tear groups apart before they even move in together.
One way to overcome these challenges is to test out co-living in a vacation rental. Here’s how it works: coordinate with your friends to rent a house somewhere for a few weeks/months. Not everyone has to live in the same residence. People can always rent places nearby. You may find that a temporary community is enough to satisfy your itch for co-living, or you might get convinced to pull the trigger and make the arrangement permanent.
26-minute read from Tanner Greer
Looking back on the 20th century, it’s tempting to believe that we have a clear picture of the events that transpired and their meaning. But as it is often said– history is written by the victors, and by most measures, the victors of the past century have been the baby boomers.
Their wealth accumulation and tenure in positions of power have meant that they have shaped America’s perception of history and had those narratives reinforced by advertisers who want to win their dollars. Thus, the rest of us see the world through their eyes.
The boomers’ self-image casts a giant shadow over our politics, and it means we are inclined to look backward to find our prime. More liberal-leaning boomers miss the idealism of the flower of their youth, while more conservative ones, as might be expected, are more inclined to miss the stability and confidence of early middle age—so the Left yearns for the 1960s and the Right for the 1980s. But both are telling the same story: a boomer’s story of the America they have known. The trouble is that it is not only the boomers themselves who think this way about America, but all of us, especially in politics. We really have almost no self-understanding of our country in the years since World War II that is not in some fundamental way a baby-boomer narrative.
To forge a better path forward, we will need a new generation to take ownership of the narrative.
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