Know thyself
What are you good at and what are you passionate about?
Good morning.
This is going to be a long personal essay and I’m not really sure what it’s about. If you aren’t interested in reading something like that, I completely understand and I’ll see you next time. I’m still getting a few things out of my brain post-vacation.
I
As you may have heard, in August, Emily Sundberg of Feed Me wrote the most popular story in the history of Substack.
The piece was called “The machine in the garden” and it was a well written essay that knew what it was doing and since it was published there has been a lot of conversation about the piece. I’m not really active on any other platforms besides Substack now so I’m not sure how far the piece made it but I see something about the essay basically every day now on Substack itself.
Sundberg’s piece is about a lot of things. It’s about how Substack has changed since it has become more of a social media platform. It’s about how a lot of the writing on Substack has begun to feel the same. It’s about writing and content as a commodity. It’s about platforms. It’s about what you believe is worth paying for and what you don’t believe is worth paying for.
You should read the essay and decide how you feel about it. I read it and immediately connected it to an idea I’ve been thinking about a lot lately. Really, it’s more of a question I ask myself at work and personally.
What are you good at and what are you passionate about?
II
There’s so much writing about Substack already, so I feel a bit stupid writing more about Substack here but Sundberg’s essay was posted on Substack and is about Substack so I’ve got to write some more about Substack on my Substack.
What I find the most interesting about Substack right now is how it really has become a marketplace.
For about six years, Substack was a platform for sending emails that you could ask people to pay money for. It remains that, but now that it has the Notes feed it is also a social network.
And over the last year or so, Substack has been encouraging users to make more video and audio content, so it is on its way to becoming a passive entertainment feed of content (like Instagram or TikTok) as well.
But because of Notes in particular, Substack has brought together all these sellers and buyers of content in a strange way. And the Notes algorithm reminds you of that.
Every day you see someone talking about their subscriber count, or what their conversion rate from followers to subscribers are, or how they don’t care about subscribers and are focused on slow growth, or asking people how to get more subscribers, or trying to sell people on how to get more subscribers. Or, more recently, talking about who their target audiences are.
It gets a little bit old seeing all that stuff, but I don’t blame the people who write Notes like that! There are people trying to make a living here. I’m in a lucky position where I don’t need to make money on my Substack. And I don’t think this Substack is worth paying for right now anyway. But I know plenty of people have different situations.
And, of course, there are people (sellers) who get mad because their content isn’t being made visible enough to people browsing the platform (buyers).
It all sounds like stuff I experienced at Artsy, which is a marketplace for buying and selling works of art. It all sounds like stuff people probably experience on Amazon or Poshmark or Depop. Except what people are (generally) selling here is writing or a content membership plan of some kind.
I say all this because Sundberg’s essay, to me, was basically about what you want to spend money on in a content marketplace and what you don’t want to. And it was about how you’re supposed to value your work in a marketplace. And it was about what your product is and what it isn’t.
And that all made me think about what I am—and what I am not.
III
The best professional advice I ever received came during a job interview in 2015. I was near the end of the hiring process for the job I eventually got as Managing Editor at Artsy. My last step was to do an interview with the COO.
In the interview, the COO asked me the following question: “What are you passionate about and what do you think you’re good at?”
Maybe, for you, that question seems a bit obvious. But, to me, at that time when I was 3 months away from turning 30 years old, making $40,000, and trying to get out of a job that was going nowhere, being asked that question in a job interview represented something of a turning point in my career, if not my life.
That may sound ridiculous, I can recall things somehow slowing down even in the moment; and it occurred to me that answering this question honestly might determine a lot of things for me in my life.
What I told him was something like this: I’m passionate about fiction writing and telling stories and the written word. That’s led me to a path in publishing. Along that path in publishing, I’ve realized that what I’m good at is helping other people do their best work and being in the middle of how things work—being something like a point guard. I like to be a part of teams and want to build something. I’ve realized that I can do the writing I’m passionate about on my own time.
That’s probably not exactly what I said (I definitely said the point guard thing), but I’m trying to be honest in my recollection and that’s pretty close.
At the time, I was completely enamored with Grantland (which was crumbling after its short, glorious run) and at Artsy saw that I might have a chance to build a publication like that in my own career. Even if it was at an art publication and I knew basically nothing about art.
I got the job at Artsy. And that job, I am not overstating this, changed my life completely.
The amount of responsibility I had was greater than anything I’d had before; I got my first real opportunity to be a manager; I picked up skills using data that I never imagined having; I got to build a publication with amazing people; my salary kept increasing; and I met my fiancee.
This sounds like a ringing endorsement of my former employer, I know. Trust me, there were also plenty of co-workers and people I managed who had a different experience and who had to leave, as you do sometimes, in order grow in the ways they wanted to grow and to earn the money they wanted to earn.
But really this is more to show how sometimes you stumble onto an opportunity. And in that opportunity you get put on a path that allows you to grow in ways you never expected—and keep growing.
And maybe what lets you meet that moment is knowing what you are and what you aren’t.
IV
I’m at a point in life where people reach out to me to ask me for advice.
Sometimes these are recent graduates from my alma mater. Sometimes they are people I’ve worked with or managed. Sometimes these are people who just look me up on LinkedIn and think my title or employer sound impressive.
Most of these people are smarter and more focused than I was at 21 or 25 or 31. They ask me a lot of questions about my career and building a career and what things they should know.
And, depending on their situation and what they want to do, I’ll give them advice based on what I’ve seen and experienced. Always with the caveat that I can only explain what’s happened to me and I can’t say what will happen for them.
The one thing I always tell them, though, is to really find the distinction between what they are passionate about and what they are good at. I tell them not to worry if they can’t discern that right now. They may not be able to discern it in a couple of years or ever. But as long as they keep trying to make that distinction, they should generally be pointed in the right direction.
I tell them that because I truly believe that understanding that difference helped shape my life as I entered my thirties.
Because I have learned that what I’m good at (I think) are the following things:
Managing people
Leading teams
Communicating within a company
Collaborating with different teams and facilitating collaboration
Understanding the different angles on data points
Translating data into insights
Creating structures and operations that work for multiple teams and situations.
Being organized at work
And I’ve learned that what I’m passionate about are the following things:
Reading novels
Writing fiction
Creating written content in many forms (blogs, comedy sketches, etc)
Listening to music
Watching movies
Both of those lists are simplified, but I think you get the idea, which is that, for me at least, what I’m passionate about and what I’m good at in a work setting don’t really overlap.
And part of the journey of life is knowing the difference and being OK with that.
Maybe it’s been easier for you, but I found gaining that knowledge to be hard won.
V
My birthday happens every year. This year, it was last week. I turned 39.
By the time I got that job at Artsy, when I was 29 and about to turn 30, this is what my professional career path looked like:
teaching assistant in a summer program at Brewster Academy (really a glorified camp counsellor)
paralegal at a real estate law firm (really a glorified personal assistant)
editorial assistant at Conde Nast (really an assistant for a Managing Editor)
editorial coordinator at Conde Nast (really an assistant for a Managing Editor)
assistant editor at Kirkus Book Reviews (really working in their independent books department, which were reviews self-published authors could pay for)
This is what the path of my personal passions looked like:
1 published short story in a good literary magazine
2 novels without representation
3 pieces published on the Paris Review Blog
3 pieces published on Splitsider
1 Blogspot blog that I kept up for about 7 years that never went anywhere (though I did put on a reading in a bookshop once!)
1 sketch class a Upright Citizens Brigade
2 improv classes at Upright Citizens Brigade (one of the Please Don’t Destroy guys was in one of my classes!)
2 years as a part of a sketch comedy group that performed a live show of new material about every other month
I had entered my twenties thinking I was going to be a novelist. In my senior year of college and the summer after, I finished writing and revising a novel. By the time I was twenty-two I was pitching agents. My pitch? Mainly that I was twenty-two and that I was just getting started.
As you can imagine, that didn’t get me anywhere.
In 2010, I got a job at Conde Nast by chance and mostly because I had experience with contracts (in my interview, I didn’t know that a magazine wasn’t composed entirely of staff writing) and started becoming interested in magazines and digital media. I started my blog and then started writing essays about things I was interested in and sending them to places like the Awl and its network of sites, the Paris Review Daily blog, and other places.
I barely knew about pitching. I didn’t think about an audience. I just knew there were things I wanted to write and that there were people who would probably read them. I saw what Bill Simmons had done and then what he was building at Grantland and felt that, surely, something would work out for me. That I’d get a chance to write long, meandering reported personal essays like Brian Phillips. I had no clue that those kinds of things were exceptions and not the rule.
But it was when I got that job at Artsy and had to build a publication that I realized that I was never going to be a professional writer on the internet. I didn’t have the motor. I didn’t have the ideas day after day or week after week. My pitches weren’t sharp. I didn’t really know what was interesting to other people versus what I was interested in.
That’s because part of my job at Artsy was deciding what we’d cover based on what the data showed our audience wanted. At work, I was starting to become good at identifying what audiences, what people, would respond to. When I was doing it for myself…not so much.
In my job at Artsy, I got to manage a lot of talented people who were just out of college. I remember working with a woman who went on to become a reporter at a major newspaper after her internship at Artsy. I’d observe her in meetings and morning pitch sessions and go, “oh, ok so that’s what a young professional journalist looks like.” She was entirely different from the way I was at 22. She had ideas all day and every day, was ready to jump on the phone in an instant, couldn’t wait to chase down a tip.
I realized that, at work, there was a role for me—and that I was good at—setting up ways of working for and providing information to people like that woman so that they could do the best work possible. And part of that was making sure we had a big enough and valuable enough audience to let the company keep our publication around.
So I could do that during the day and feel good, knowing that on my own time I could pursue my passion, which was always fiction writing anyway, and hopefully over time learn how to be good at it.
VI
In the last 10 years, I have been promoted five times (all at Artsy), my yearly salary has more than quadrupled, my responsibilities have grown, and my titles have become more and more unwieldy and hard to parse.
As that has happened, I’ve continued my writing practice but with less and less notable achievement.
Since I started that job at Artsy, this is what my professional trajectory (in title) has looked like:
Managing Editor (at Artsy)
Associate Director of Operations and Growth (at Artsy)
Director of Operations and Growth (at Artsy)
Editorial Director (at Artsy)
Sr. Director of Content (at Artsy)
Global Director of Audience Development, Social, and Analytics (at Conde Nast)
Since that time, here is what the achievements in my personal passions have looked like:
2 more years as a part of a sketch comedy group before giving it up
1 revised novel without representation
1 new novel without representation
1 personal essay published in the Columbia Journal
2 freelance stories published in The Outline
0 short stories published
Putting those two lists next to each other, I think, shows the difference in how a path of doing something you're good at professionally versus what you’re passionate about can take.
Life, work, and art are all complicated in their own ways. Luck and circumstance each play a major factor in how each of them take shape and work out.
Hard work and skill can make a difference, but there are plenty of instances of people doing average work and giving average effort and managing to advance and certainly there are lots of cases of people failing upward in work and in life. And there are countless examples of people working hard and doing great work and never advancing.
Professionally, I’m where I am in my career based on a mix of luck, skill, and hard work. (If I was going to quantify it, I’d put it at 40%, 20%, and 40%.)
When you look at the list of my professional trajectory over the past 10 years and my creative trajectory, you see very clearly that, through various factors, I’ve been able to make a good life for myself based on what I do each day for work. And that, conversely, in following what I’m passionate about, I have not been able to figure out how to make something creative on my own that is worth paying attention to.
Yet, I continue to follow my passion.
VII
Last month, the literary agent Danielle Bukowski published a very insightful piece titled “What’s the point of publishing?” on her Substack.
In the piece, Bukowski asked some very direct questions that she feels it is important for a writer to answer. Why do you want your book published and what do you want to get out of this experience? Why did you write the book? Why do you want other people to read it? What reaction do you want readers to have? What do you want this book to achieve?
And in exploring the answers to those questions, she lays out some plain facts: “The book publishing industry is a business and as a business it publishes books into a marketplace. Books are consumer goods. The book publishing industry chooses which consumer goods they think will make them a profit, and they acquire and sell those types of books. Your book not being selected by the marketplace does not mean it is bad, or you are a bad writer. It means, simply, that you have not created a consumer good that a corporation believes they can sell for profit.”
And then she gives examples of a few different “types” of writers and the reasons they want to write and publish a book.
“If you, as a writer, answer the [questions I’ve asked] with some aspect of ‘I wrote this book for myself as a craft exercise and my goal was to make it as experimental as possible,’ you are writing into the ‘book as art’ camp. If your answer is something like ‘I wrote this book for myself and I don’t care what anyone else thinks of it,’ then you probably don’t actually want to go through the business of book publishing; that’s fine. If you answer[ed] with something like ‘I wrote this book to become [insert name of hugely successful author of the previous century]’, which is what I suspect a lot of writers actually want deep down, then you are going to be disappointed by the book publishing industry. There are very few household-name authors. There are very few authors who make their living off their book advances and royalty checks. Most authors have day jobs, or their job is writing.”
The author Leigh Stein elaborated on that last point in her own response to Emily Sundberg’s essay. Stein’s piece “writing vs. content” broke down the differences in what she creates as “content” to build a business and market her “writing” and how those things differ in how she approaches them and how she expects to make money off each one.
I’ve been creating both content and writing for some time now.
In my writing, I started off like one of the writers Bukowski identifies as likely to be disappointed. And, I have to admit, some days I am still that misguided young man. But, because of my experience, I’ve become more than aware of the realities of the marketplace of publishing books. Still, that hasn’t stopped me from vacillating between writing as a craft exercise and writing for myself no matter what anyone thinks.
I’m aware of the market, I know how to query, and I understand (as much as anyone can) how the world works. I’m aware of what I’m passionate about versus what I’m good at. I’m passionate about writing, but I’m bad at participating in and joining communities (I’m like the old Groucho Marx joke mixed with what the ghost of Bert Cooper told Don Draper) and I’m bad at marketing myself. These are things that are very useful to helping you sell creative work.
But that hasn’t yet changed my approach. So why would I expect to publish or make any money from my writing?
The content I create here is mainly to help me better articulate my thoughts on the work I do each day—the things, I think, I’m good at. I also throw in things that entertain me, that bring me joy, and that let me clear out the meandering thoughts I have from time to time.
At this point, at least from my assessment, none of that makes a compelling case in the marketplace. I’m not a thought leader, I’m not a tastemaker, I don’t provide original reporting or a unique point-of-view.
So why would I expect to publish or make any money from my content?
VIII
This piece has largely been about my experience, but I swear this connects to things beyond me.
Sarah Fay runs the Substack Writers@Work publication and community on Substack. Last week, she published a piece called “The Gentle Art of Paywalling.”
This piece wasn’t in response to Emily Sundberg’s essay but it felt connected somehow because it addressed the many different ways one can approach building an audience and a business through their content and their writing. As Fay lays out, you can keep your articles free and paywall your chats, you can keep some articles free and gate others, you can gate only a portion of a post. It all depends on what you see as the most valuable thing you offer to people as a writer or thinker or content creator.
Because Substack is a marketplace, not everyone’s content and not everyone’s writing is going to command a market or have demand. That’s just the way the world works. The supply is too great.
I think a lot about this at work and when I look at the media landscape. In order to diversify revenue streams, so many media organizations have moved to paywalls. I work for a brand that has a paywall. And the company I work within has several brands with paywalls. It’s not clear if all of them should have one. Or, at least, if all of them should have them in very similar or the same exact ways.
Time put a paywall on their site but took it down last year. They asked themselves what they were good at and what value they offered. And the answer was that, probably, the content was not premium enough for people to pay for. But you know what they thought was worth paying for? The Time logo and brand recognition for events, licensing, and advertising. And that’s the path they seem to more directly be pursuing.
That’s not going to be easy. Time just laid off 22 staff members last month. But that may be the cost for them to focus on doing what they’re actually good at.
Dotdash Meredith knows they are good at SEO and they know that if they rank highly for as many keywords as possible that they don’t have to load their pages (including pages meant to drive affiliate revenue) with ads.
Instead, they make the pages easy to navigate, put ads where they need to be, and hope that the helpful user experience continues to keep them in the good graces of Google and high intent browsers. Maybe it won’t work forever, but it seems to be working now.
Media companies are passionate about a lot of things. Namely, because they are companies, making money. But they also come with a lot of distractions. We need events, and a membership tier, and merch, and licensed products, and we need to make our own product lines, and also affiliate, and also we need to be in games, and don’t forget video, and we should have a store in airports as well.
All those distractions can make it easy to overlook what you’re actually good at and where there may be a demand for your services and what you offer to people.
There is already subscription fatigue and more and more individuals or small operations are spinning up new subscription offerings. What a media company actually is will continue to evolve. Depending on who you are and what you’re good at, you may not even need a traditional website or “home” page.
In this moment, any larger media organization needs to truly ask what it’s good at and where it adds value for actual people and not just the “audiences” talked about in meetings, presentations, and industry interviews.
IX
Back in 2010, when I was starting as an editorial assistant at Conde Nast, I would often have a good amount of downtime in my cubicle outside the managing editor’s office. I spent a lot of that time scrolling Twitter and finding out about new writers and publications I’d never heard of.
If I’d been serious about a career in digital media or as a writer on the internet, I’d have heard of sites like The Awl or Gawker or Deadspin and lots of other places much sooner. But there I was, sitting at my desk and catching up to all the great writing on the internet I’d been oblivious to.
Today, every time I open the Substack app, I usually find a new piece of writing that I enjoy. Emily Sundberg’s essay itself is an example of why I love Substack—and so were the responses to her piece. Over the last month, I’ve read thoughtful pieces and perspectives by people I’d never have found otherwise.
I pay for things like Feed Me and Read Max and Just Reading All Day but I don’t pay for or read Maybe Baby. But my fiancee does. And so do plenty of other people. I don’t find value in that product, but I live with someone who does.
I can’t pay for everything that’s out there and neither, I imagine, can most of you. What you pay all depends on how good you think a product is and how much value you place on what a piece of content or writing in the marketplace brings to you as a person.
The old system of needing to pitch to outlets and hope that your work is accepted and deemed publishable is starting to become less meaningful as it once was. Oh, it will always exist and bylines in certain places will always mean something and help for subscriber acquisition, but it isn’t the same as it was even five years ago, let alone 10.
New writers are coming along every day and many of them are starting Substacks and putting them behind paywalls. Some of them may be successful and others may wonder why they’re not. And it may come down to a matter of whether they are being led by what they are passionate about versus what they are good at.
And I know those things aren’t mutually exclusive. There are plenty of stories across so many fields where that isn’t the case. In those instances, most of the time you need luck and the chance to be put in a position where you can show that you can be good at your passion. Or, you catch lightning in a bottle.
But I am an example of a person who carries a passion even if the recognizable indicators of if they are good at it are few and far between. And, through my experience, I have learned the value in periodically measuring those two characteristics against each other in order to make sure I’m being honest with myself so that I can better know just where I stand and what direction I’m pointed in for the next ten years.
This is really interesting, Matt! Miss your insights and would LOVE to talk substack strat with you some time.