I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about building amazing products and great teams.
A few weeks ago, I noticed that I was spending a lot of time worrying.
I’d look at my calendar at the start of the week and think: Wow, I’ve got a lot to do! Lots of calls, lots of presentations, lots of little tasks. It felt overwhelming, and instead of trying to take on all of this work, what I found is that I’d spend a few hours, walking around my office in circles, worrying the hours away. Then I’d get to the next week, and I’d have even more work to do — since I hadn’t accomplished all that much in the previous few days thanks to all the hours worrying — and the cycle would repeat.
So I’ve been trying a few different things lately. One is that every month, I’ll go ahead and block out some time for focused work, blocking it out well ahead of time so that others can’t grab that time. Another is that I’m giving myself time to worry — but only in certain moments (in the shower, in the car) when I can’t actually be working. And lastly, if I catch myself worrying during the day, I’ll give myself a break, even if it’s just to walk around the block or head to the store, as a way to mentally reset.
Yes, I’ve got a lot going on. But it’s not more than I can handle — as long as I don’t idle away the day worrying about whether or not I can do it all.
Worry when you can, Dan, and then get back to work.
A few weeks at the PGA Championship, I watched as Garrick Higgo — a 22-year-old South African — teed off on Sunday at 7:40 a.m. That’s what happens when you’re eleven shots over par, as Higgo was after three rounds. (For the non-golfers out there: The pros typically shoot several shots under par.) He’d had a tough tournament, and I was mostly watching because, well, it was something to do while eating breakfast on a Sunday. I watched Higgo for a little while, and it was clear that he could play — it just hadn’t been his week. He hit several shots close to the flag, and seemed to play freely without the pressure of having to worry about winning the tournament. The announcers mentioned that Gary Player, a retired South African golfer and winner of nine major championships, was a mentor of his. (Not bad when your mentor’s in the Hall of Fame.) That Sunday was Higgo’s best round of the entire event: He shot a 69, good for three shots under par. The PGA Championship was his first-ever PGA Tour event.
I remember watching and thinking: Here’s a pro golfer — he’d never played on the PGA Tour, but he’d won several events in Europe — who clearly could play. In his previous four pro events, he’d finished in the top ten all four times, and won two of them. But even a pro sometimes can’t seem to find his swing.
Anyone can have a bad day, or a bad weekend, even if you work hard and have all the talent in the world. As a friend from the midwest once put it, folksily: “One day chicken, next day feathers.” Bad days happen.
Still, you keep moving forward. The PGA Championship was Higgo’s first-ever PGA Tour event. But I imagine Gary Player told him after the tournament: Pick up your head, kid. If you do the work, and keep competing, you never know when you’ll break through.
Turns out he didn’t have to wait long. A month ago, in his first PGA Tour event, he finished in 64th place, fourteen shots behind the champion. Today, in his second PGA Tour event, Higgo won the whole thing — and the $1.3 million grand prize that came with it.
I suppose there’s another fowl-friendly quote that my midwestern friend would’ve used for an occasion like this: Winner winner, chicken dinner.
The very first blog post on danoshinsky.com went live this month, 13 years ago. I did some occasional posting over those early years, but the blog didn’t really get going, in its current form, until 2011, when I started writing more regularly. With the exception of 2014, I’ve written something for danoshinsky.com pretty much every week for an entire decade.
This started as a way for me to write — and write as much as possible. That’s all it was, really: An outlet for me to make sure that no matter what I was doing for work, I was always making time to write.
And even as the blog audience has grown, that’s really what it continues to be. The work is far more professional now than it was a decade ago, and I write fewer things here about my mother, but as I approach 950 posts on danoshinsky.com, this is really all I’m trying to do: Making time to write. Some of the posts are good, and many are not, but that’s OK. The important thing is that I make time to practice.
There was a time when “writer” was the first word I would’ve used to describe myself. That wouldn’t be the case today, and I’m not sure if there will ever be a time when it’ll be something I consider myself. But I know that I would hate — absolutely hate — to stop writing, and to wake up one day, years from now, only to find that I couldn’t do it anymore.
There are the things you do for your career, and there are the things you do, just for you. This is the latter. No matter where your career takes you, or how busy you get, you still have to make time for both.
———
That’s a screenshot of this website from 2011. I wasn’t kidding about the “fewer stories about my mom” part.
I’m writing this from an airport, waiting to fly home to New York. I’ll admit: It’s been strange to take flights again. Airlines, hotels, and restaurants are understaffed, and under all sorts of new rules and restrictions. Travelers are often a little tense about flying. I’ve seen a few freak-outs at the check-in counter already.
So if you’re traveling again, just remember: Be patient. Things are different, and more complicated than before. We’re in whatever this new normal is. Everyone’s trying their best under complicated rules. Take your time, and let things happen when they happen.
And if I may offer some advice: If you can, try to maintain a sense of humor about everything. You never know when a joke or little bit of kindness might mean the world to someone working a stressful job.
———
That’s me on a recent flight. I promise, I’m trying to smile underneath the mask!
In it are hundreds of stories of the day — stories, of course, told by the survivors of September 11th, 2001. So many of the stories are ones where a single decision may have saved a life: The chef who stopped in to get his glasses adjusted before heading up to his floor; the salesman who was told that his tie didn’t match his shirt, so he headed back to his desk to get a new one; the woman who was fired from her job on the afternoon of September 10th; the dad, who took the ferry to the office, and lived, while his son, who took the train, did not.
Stephen Blihar, an officer with the NYPD, described thinking back upon the day like this: “It was a day of lefts and rights.”
I can’t stop thinking about that phrase: A day of lefts and rights. There are so many choices we make — in a day, in a career, in a lifetime. We agonize over the big choices, when often the small ones — go left, or go right? — are the ones with the most impact. We make the best choices we have, with the best information we have, but who knows what will come of all of it?
Anyway, read the book. I can’t recommend it enough.
——
I took that photo, in October 2018, of the view of New York, looking north from 1 World Trade Center after a thunderstorm.
So you’ve just graduated — congrats! — and you’re trying to get that first job in journalism. Or you’ve been working in the industry for a while, and you’re hoping to get that next job.
I’ve worked at startups (BuzzFeed), established newsrooms (The New Yorker), and launched two journalism businesses (Stry.us, Inbox Collective). I’ve been lucky enough to hire for my teams, so I’ve got perspective on both sides of the hiring process.
Recently, I got the chance to talk with a class of soon-to-be-grads about how they could think about getting their first job in the field. I shared five key rules for them. I hope these rules will help them — and might help you, too.
1.) Your side project is your ticket in — Launch something! At BuzzFeed, everyone had a side project, and I’ve been a believer in these ever since. It’s never been easier to launch a newsletter, a podcast, a blog, an Instagram, or even a print publication. Show hiring managers what you can do and how you work by launching something of your own.
2.) You don’t need to wait for the traditional gatekeepers. — So many early career journalists only apply to big, established newsrooms. But in some cases, applying to those types of newsrooms might be the wrong approach for you. You might get more experience and more opportunity at a smaller outlet. Project Oasis, for instance, maintains a list of more than 700 local newsrooms, many of which are actively hiring right now. Be willing to start small, and work at a place where you can really grow as a journalist. Don’t worry about the title or the size of the org — find a great team where you can learn a lot and do great work.
3.) Even if they’re not hiring, you can ask if there’s a way to help. — Reach out and see if there’s a way to get involved. Maybe there’s an opportunity to freelance or intern. Maybe they’d be open to bringing you on a role that isn’t listed. Maybe they need additional help on a specific project. Reach out — you never know when you might find an editor or a manager who’s willing to give you a shot.
4.) You’re as good as your ability to stay in touch. — If you do get a chance to chat with someone in a newsroom, even if it’s just for a coffee, follow up and say thank you. Buy stationary and send them an actual thank you note. And stay in touch over the coming years. When you see them publish a great story, shoot them a congratulatory note. So many people never follow up. Don’t be that person!
5.) Your next job might be one you create. — There’s never been a better time to create your own newsroom. There are amazing tools — for publishing (CMS), distribution (email, social media, audio), and monetization — to allow you to create a publication. Many of these tools didn’t exist even a few years ago, but they do now. Maybe your first job isn’t at a traditional newsroom — it’s you and a few friends building your own thing. The tools, training — and in many cases, the funding — is there, if you want to start something new.
Remember: We need people like you to tell these stories, and I hope you’ll pursue a career in journalism. Whatever you choose to do next, I wish you good luck.
Two small milestones happened this week: I turned 34 today, and yesterday, Inbox Collective reached $250,000 in revenue. I didn’t start this business to make a lot of money — I’ve tried to make decisions based on the impact of the work, not the revenue it brings in, and I hope that I always maintain that approach. But still, that revenue number represents something: The relationships I’ve built with clients and readers, and trust that they’ve placed in me to help them grow their businesses. That number represents dozens of projects, calls, conversations, and work over the previous two years.
I feel so lucky to do this work, and to be able to do it at this point in my career. I know I have the chance to build something that can grow for a long time, and I’m so grateful for that opportunity. I hope this is just one of many milestones ahead — if I continue to strive, every day, to serve my clients and readers well, I think it can be.
The New Yorker did an interview with John Swartzwelder, one of the most prolific writers in the history of “The Simpsons,” and a man who is legendary for his privacy. (The New Yorker described him as “reclusive, mysterious, almost mythical.”) The interview’s fascinating and funny, but I particularly enjoyed this part:
How much time and attention did you spend on these scripts? Another “Simpsons” writer once compared your scripts to finely tuned machines—if the wrong person mucked with them, the whole thing could blow up.
All of my time and all of my attention. It’s the only way I know how to write, darn it. But I do have a trick that makes things easier for me. Since writing is very hard and rewriting is comparatively easy and rather fun, I always write my scripts all the way through as fast as I can, the first day, if possible, putting in crap jokes and pattern dialogue—“Homer, I don’t want you to do that.” “Then I won’t do it.” Then the next day, when I get up, the script’s been written. It’s lousy, but it’s a script. The hard part is done. It’s like a crappy little elf has snuck into my office and badly done all my work for me, and then left with a tip of his crappy hat. All I have to do from that point on is fix it. So I’ve taken a very hard job, writing, and turned it into an easy one, rewriting, overnight. I advise all writers to do their scripts and other writing this way. And be sure to send me a small royalty every time you do it.
That’s interesting. So create an imperfect world and then improve it?
That’s the way I do it.
I absolutely love this idea. And the most interesting thing for me is, it’s actually the second time I’ve heard this idea this month!
The other time? On the podcast “Two Writers Slinging Yang,” as shared by award-winning food writer Alan Richman. He told host Jeff Pearlman:
I would sit down with my notes in front of me and whatever’s in my head, and I would write a first draft, and I would make sure it was much longer than the story was going to be. I would write maybe three or four thousand words, just off the top of my head, just spewing it out and typing it, and I knew that was not going to be the story. But that gets everything out of my head. By doing that, I would say, “Oh, this is important.” I would start to see what I had in my head and what would make the story… I always wrote a first draft as fast as I could until I got everything out of my head and on paper. And then I would write the second draft, and that’s when I’d start to write.
Someone once said all writing is re-writing, and that’s what I believe in. I re-write and re-write.
Here are two very different writers: A comedy writer, and a writer of long food feature stories for GQ. But they both know their strengths — they’re good at re-writing! — and have built their creative process around that strength. When you’re a writer, you’re judged on your output, not your process. Who cares how you get there? All that matters is that you get there.
Whatever it is you do, play to your strengths. Figure out what you like doing most, and see if there’s a way to build your process around that.
It’s 11 p.m. on a Monday night, and there’s this one last work thing I have to do.
When I’m on calls with clients, I’m always taking notes. Through two years of Inbox Collective, I’ve filled up a few notebooks with bullet points and to-dos for clients.
When I first started, I didn’t do much with these notes. I’d write them down in the notebook, and that was that. That system worked fine at previous jobs, where I saw my colleagues every day, and where the projects I was working on were often things I had to deal with on a daily — or at least weekly — basis. I took notes, then got to work on whatever tasks I had to do.
But in my new job, I might go a month or more without talking to a client. My old notebook system didn’t work anymore, since I needed to be able to quickly — in those five or ten minutes between calls — refresh my memory of what we might have talked about last. For the money these clients pay, they deserve to talk with a partner who’s ready to dive in and use the time together well.
So I made a change: I created a Google Doc for every client, and at the end of every day, I type my notes from our call into the doc. That way, I’ve got a searchable database. Every Sunday night, I go through my notes to prep for that week’s meetings. I usually check back the morning of my calls, too — things get busy, and by Thursday or Friday, if I don’t write it down, I might forget my own name!
(I still do like taking the initial notes on actual paper — I find that if I’m typing and talking at the same time, I’m usually just transcribing the conversation, not actually paying attention and asking the right question. With the paper notebook, I stay more engaged throughout.)
I wasn’t always great about moving my notes over to the Google Doc. I remember one day, early on in 2019, when I’d gone a few days without typing up my notes. I’d gotten a little lazy about the whole thing. And when I finally got around to typing them up, I probably had 30 pages of notes to deal with. The task took me hours.
So now, no matter what else is happening in my day, I make time at the end of the day to type up my notes. It takes a few minutes, and it’s sometimes a pain, but it gets done — and I know that in a few weeks, when I need to refresh my memory, those notes will be there to make sure I can pick up exactly where I left off with a client.
There was a fascinating story in The Washington Post this week about men’s gymnastics, and how the University of Minnesota — which has had a men’s gymnastics team for 118 years — has decided to cut that sport at year’s end. The move will save the university $750,000 per year.
Minnesota’s decision — combined with Iowa’s plan to drop men’s gymnastics and two other sports — is the latest blow to the dwindling ranks of Division I programs, leaving just five Big Ten schools with men’s teams and 12 in the nation. And it’s part of a larger pattern at Division I colleges and universities across the country, where “nonrevenue” sports are being dropped in the name of fiscal responsibility.
At a university like Minnesota, there are only two sports that make money: Football and men’s basketball. Those sports fund the rest: Softball, hockey, and so on.
What the University of Minnesota — and so many other universities that have cut sports — is doing is making all of their decisions around a single metric: Profit or loss. Sports that make money can stay. Sports that lose money, even a small amount, are expendable.
But there are other ways to measure success for a college athletics program. You can look at the obvious metrics of success: Wins or losses, championships won, or Olympians produced. You could look at the engagement of the community with these sports: Attendance, or tickets sold. You even could look at less obvious downstream metrics of success: How much of an economic impact will these scholarship athletes have on their state over the course of their careers? (A study of previous athletes might help a university understand the long-term return on their investment.)
There’s a lesson here for all of us: If profit is the only goal, then you’re only going to work on things that make money. But there are other ways to measure success. Make sure you have a few metrics in mind so you can optimize for the things that matter — and not just that which produces the highest immediate return.
———
That photo of a gymnast participating at the Singapore 2010 Youth Olympic Games comes via Flickr and is used via a Creative Commons license.
