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.
I saw Willie Nelson perform on Sunday, and here’s something I didn’t realize about Willie until he walked out on stage: He’s 88 years old.
88! And still performing live, currently on a 14-stop tour over two months in 10 states!
Now, at that age, nobody’s expecting Willie Nelson to go out and play a marathon set. But I was impressed by the way Willie still found a way to put on a great show:
• He limited the set list to an hour — he’s played about 11 songs per night on the 2021 tour so far, instead of what had been 17 song sets pre-pandemic, per data on Setlist.fm.
• He loaded the lineup with not one but three openers, stretching what would be a normal concert into a six-hour-long festival.
• He toured with his son, J. Micah Nelson, and let him take lead on a few songs. (Willie’s kids can really play, so fans didn’t mind Willie taking a step out of the spotlight for a few minutes.)
• He didn’t waste much time with banter, saying a few words between songs — or just moving right into the next number.
All in all, it meant a set with a lot of hits and very little filler. I’m sure Willie would love to have the energy of a younger artist, able to go out and play for 2+ hours as a headliner. But he’s 88, and he’s got some limitations — and he still found a way to make it work.
As Willie sang that night: He’s still not dead, and still on the road. Impressive stuff.
———
———
That’s a photo I took of Willie and his band on September 12, 2021, in Saratoga Springs, New York.
It’s the first round of the tournament, and I’m watching Reilly Opelka, a 6’11’’ American with a massive serve. (The fastest I saw him serve: 141 mph.) On one point, he serves just a little wide, and there’s that familiar call from the umpire: “Out!” He hits his second serve (something merely around 105 mph), and a rally ensues. Another ball goes just beyond the baseline. Again, that familiar call: “Out!”
Except that this time, I’m looking around, and can’t figure out where the voice is coming from.
There’s the umpire in their chair, but they’re not in position to make a call like that. There are the ballboys, but they don’t make calls like this. (Some are teenagers! The winner of this match will make $115,000 — there’s no way the U.S. Open would let them make these calls, right?)
It happens again a few minutes later, a male voice yelling “Out!” just after the ball misses the line. But again, I can’t figure out where it’s coming from.
NEW YORK, Sept 3 (Reuters) – Ash Barty, the No. 1 seed at the U.S. Open, watched on match point as her opponent’s backhand sailed long on Thursday, prompting the familiar sound of a linesman yelling, “Out!”
There was no line judge, however. The call was a recording, triggered after an advanced system of cameras known as “Hawk-Eye Live” tracked the ball until it landed out of bounds.
For the first time, the tennis major has installed electronic line-calling on every court, replacing human judges who were responsible for determining whether, say, a serve traveling at 140 mph touched a line the width of a ruler.
At first, it feels a little strange. Tennis has always had these moments of confrontation between the players and umpires. (Go to YouTube and search, “You cannot be serious.”) So to lose that felt initially like losing a little part of the game.
But the more I watched — and I saw matches on Tuesday, and then again Friday — the more I came to appreciate the robot umpires. Some of these balls were hit so hard, and so precisely, that it felt impossible for any human to actually know whether they landed in or out. On Friday, I sat just a few rows up from the baseline,, and couldn’t tell if several shots were in and out — they were simply too close to call.
Things change, and that’s OK. So often, we get used to the manual way of doing things — taking on specific tasks, because it’s the only way to do so, until the moment when we find a way to do things faster and more effectively. It’s hard to embrace change, but I know for me, when I find a way to get faster at my job, I try to take advantage of it. (After all, there are only so many hours in the day, and every hour I waste on manual tasks is one I could be using to help a client.) Sometimes, that means finding a calendar tool the help me speed up the process of booking a meeting. Sometimes, that means using tools like Zapier to automate previously-manual tasks. And in the future, it might mean hiring people to take on work that used to be central to my job.
What are the essential tasks that only we can do, and what are the things that can be automated? At the U.S. Open, I got an answer to that question — and in the end, really liked what I saw.
———
I took that photo at the Angie Kerber-Sloane Stephens match at Louis Armstrong Court.
I went to the U.S. Open yesterday to watch some first-round tennis matches. If you’ve never been to the U.S. Open, you should really try to go if you can — even if you’re not a tennis fan. The Billie Jean King National Tennis Center is an absolutely spectacular place to spend a late-summer day. Sure, you can go to one of the big courts to see big names — Arthur Ashe Stadium seats nearly 24,000, and it’s where you’ll find stars like Novak Djokovic and Naomi Osaka — or you can check out one of the outer courts, where you’ll catch top 100 players playing for just a few hundred fans. (Yesterday, I watched a matchup of two top 75 talents from the second row. Pretty cool.)
But one of the highlights of the day was watching Denis Shapovalov, the tenth-ranked player in the world. He played at Louis Armstrong, the second-largest stadium on the grounds, in the middle of a Tuesday afternoon. His was the third match on that court that day, and many of the fans who’d come for earlier matches had drifted out to other courts. Shapovalov played a stadium that was less than a third full.
Still, Shapovalov’s a star in the tennis world, and a player who could absolutely make the finals in Queens this week. To win the U.S. Open requires a player to win seven matches, and the men’s matches can last up to five rounds (and can sometimes go as long as four or five hours). Shapovalov couldn’t afford to let his match go long. He needed to dispatch his opponent (Federico Delbonis, the 47th-ranked player in the world) as quickly as possible.
Shapovalov did just that, winning in straight sets (and in less than two hours). But what I found fascinating was the way Shapovalov stayed engaged at every moment in the match. In front a sparse crowd that seemed more interested in checking their phones than watching the match, it would’ve been easy for Shapovalov to lose focus. But without the crowd keep him engaged, Shapovalov found his own ways to bring the energy. After every point he won, he gave a little fist pump. After big shots, he looked over at his box, nodding to them and letting them know that he was locked in. After breaking serve or winning a set, he’d let out a little scream, or a “Let’s go!” A few times, he gestured to the crowd to make noise.
This was the sort of match — against a talented and experienced opponent — where Shapovalov could’ve lost focus for a bit and let the match stretch into a fourth or fifth set. But he simply refused to let himself disengage. He was both player and hype man, never letting his attention drift, even when the crowd’s energy dropped.
I spent the subway ride home thinking about ways to try something similar with my own work. It’s easy for my energy to slip, especially at the end of a long day of calls. Maybe I need to find ways to take small breaks: A walk around the block to reset, or even a few jumping jacks in the ten minutes between calls. Maybe I need to start keeping a gratitude journal, so I can use those few minutes to jot down thoughts about the good that’s come from that day.
But seeing Shapovalov play, I was reminded that to be at the top of my game, I have to find ways to maintain that focus throughout the day — especially when the energy isn’t naturally there.
———
I took that photo of a Shapovalov fist pump during yesterday’s match.
But the truth is: I’m still not very good at saying “no.”
It’s hard to turn down work — especially when it involves projects I’m excited about. It’s hard to turn down revenue for the business. It’s hard to say “no” to people I’d love to work with.
I know that saying “no” is often the right move for me. But it’s still hard to do.
Right now, I’m reading “Eat a Peach,” the memoir from chef David Chang, and he talks often about the pressure of working as a chef — one whose success opened up all sorts of exciting new opportunities for him: Opening new restaurants, writing books, even TV. He writes that at times, he felt like he needed to hit rock bottom before he would be willing to change the way he worked.
“The paradox for the workaholic,” he writes, “is that rock bottom is the top of whatever profession they’re in.”
That line’s stuck with me the past few days. I’m not a celebrity chef, but I’ve been lucky to have had some success — and to have gotten a little publicity — the past few years. I’ve gotten all sorts of interesting new opportunities as my business has grown.
And I’m starting to understand what Chang might have experienced himself. I love to do this work, and if I could say “yes” to every potential client, I would.
But that’s not an option.
So I need to keep getting better at saying “no.” I need to do it for my family, for my friends, for my business, for my industry — and for myself. Saying “no” is what I need to do make sure I’m prepared to say “yes” to the right opportunities going forward.
A former BuzzFeed colleague of mine just left a job there for a new role, and we had lunch the other day. She asked me if she should know anything about working at a new job — a real job, where there isn’t a test kitchen and where staff writers don’t wear JNCO jeans as a fashion experiment.
“They’re going to think you have magic beans,” I told her.
She looked at me funny. (And I don’t blame her.) I went on.
“When you leave BuzzFeed for a new company, they’re going to unusually curious about what you’ve learned at BuzzFeed. They might think you know some sort of deep secret of the internet — that someone on the BuzzFeed team, on your first day, gave you the cheat code to unlock all that internet traffic that BuzzFeed gets every day. And they’ll be a little disappointed when they find out that there isn’t a secret to BuzzFeed at all.”
I paused for a second.
“There wasn’t any big secret to BuzzFeed — just a set of lessons that helped us build a platform that readers loved. Remember those lessons: Test out weird ideas. Be willing to look stupid, and be willing to move on when things don’t work. When you get the chance, hire smart, curious people who listen to one another. Make sure you have the tools you need to test out your ideas. Make sure you know what you’re measuring when you do the work.”
She nodded along.
“Just show up and do the work every day,” I reminded her. “I’ll take your work ethic and the lessons you learned from BuzzFeed over a bag of magic beans any day.”
———
That’s a photo of a giant LOL sign that hung at the entrance to the BuzzFeed office on 21st Street in New York.
But this past week, I tried something new: Transparency with a personal touch.
I told people when I’d be back and when they might expect a reply — the usual. But I added a personal flourish, explaining that I was out for a few days to celebrate my anniversary. A few years ago, I wouldn’t have included such a detail, worrying that it might’ve seemed too personal. Do people really care where you are? Don’t they just want their email answered as quickly as possible?
And instead, what I found was that so many people wrote back to my OOO with kind messages, and notes about the urgency (or lack thereof) of their messages. ”Enjoy your time off!” they wrote. “We’ll talk when you’re back.” I still wrote back to many of them, but felt far less pressure to reply while on vacation.
I’m planning on keeping this template: Telling people when I’ll be gone until, how frequently I’ll be checking email, plus a sentence about where I am or what I’m up to while I’m away. (If you’re in a big company, you might want to add a note about who else can help while you’re out of office.) The replies were so friendly, and I’m betting that several clients will ask, “How was the anniversary?” when we chat next.
Friendly, transparent, and a potential conversation starter? I think I’ve found an OOO format to use going forward.
———
Above, that’s the full OOO message, plus one reply from a client.
Just because I have expertise in the email space doesn’t mean I have all the answers. Clients are constantly challenging me with ideas or strategies that I haven’t tried, and I don’t always know how they’ll work when we roll out these concepts in the real world.
These clients are paying me to give them good advice, and that’s easy to do when I’m proposing that they implement email best practices. But how do you advise someone on a strategy you can’t guarantee will work?
I’ve found, over and over again, that the only way forward is to be as transparent as possible. I’ll tell them: “I haven’t tried this strategy yet, but I like the concept, and I think it’s worth testing this out! If it doesn’t work, we’ll quickly move on to the next thing.”
Or: “I tried something similar with another client recently, and it didn’t work out. Now, that’s a different client with a different audience, and if you want to test it out anyway, you should go for it! But there’s no guarantee that this will work.”
Or: “To be honest, I have no idea how this will work! But let’s try it together and see what happens. If it doesn’t work, we’ll stop the test and try something else.”
It’s a good thing to be able to say, “I don’t know.” Be unusually transparent with your teams, and make sure you set the right expectations for any project. If you do, everyone usually goes into it with the right mindset — and even if the idea doesn’t work out, they understand that what they were trying wasn’t a best practice but a test, and tests often fail.
I watched an Olympic sport this morning that I didn’t understand: Freestyle wrestling. The broadcast had suckered me in. They’d done one of those big feature stories on an athlete, Adeline Gray, who wrestles in the 76 kg category, and I was inspired by her story. She’d won five world championships, but at the last Olympics in Rio, she’d been injured and didn’t medal. She fought her way back, and today, had a chance to win gold.
Instead, she came up short — a second-place finish, and a silver medal.
But in the post-match interview, you wouldn’t have known that she was disappointed. She spoke of the challenges she’d faced on the road back. She talked about how excited she was to finally win a medal. She spoke directly to young athletes, and encouraged them to chase their dreams — that they could go back to school for a Master’s degree, or start a family, or win an Olympic medal. That they could have it all, if they wanted.
Our women are breaking all types of stereotypes. Public perception would tell you that after a loss of this magnitude you need to be crushed, cry, and hide. If you’re not angry, you didn’t want it bad enough. Lies. @AdelineGray thank you. Your spirit will inspire generations 🙌🏾🇺🇸
I’m sure Adeline Gray wanted more. I’m sure she’ll be disappointed that she didn’t win gold. But to see her celebrating afterwards, even after a tough defeat, was inspiring.
She’s not the Olympic champion, but she’s an Olympic champion. Congrats, Adeline. Go celebrate. You’ve earned it.
———
That’s a photo of Gray showing off her medal to family via video call after the match.
This weekend, one of my dearest friends, Allison, was in town to visit, and we spent a good chunk of the weekend watching the Olympics. She’s a former swimmer herself — she swam at our alma mater, and was fast enough to swim at the Olympic trials in her home country of Canada. (She finished two seconds away from qualifying for the 2004 Olympics in Athens.)
So I was excited to watch some of the swimming with her. What I didn’t realize is that we’d end up watching completely different races.
While I was yelling about the obvious stuff (“They’re so close to the world record line!”), Allison was noticing all the little details. During a backstroke race, a favorite was behind with 50 meters to go. “Did you see that moment of panic?” she asked me. I had not. We rewound and paused, and sure enough, there was a quarter-second where the swimmer glanced right, realized how far behind he was, and kicked it into high gear. It’s the kind of thing that you’d never notice — unless, of course, like Allison, you’d spent thousands of hours in the pool, competing at some of the highest levels of the sport.
Over the course of the morning, she pointed out tiny details over and over again. When one swimmer suddenly lost his lead coming out of the turn, Allison explained that he’d gone too deep out of his flip turn and lost momentum. When one swimmer was disqualified for an illegal touch on the wall, Allison spotted it seconds before the TV crew.
It’s gotten me thinking about all the other things I wouldn’t spot — and have been completely oblivious to all these years! — that a true expert can see right away. Having that depth of knowledge gives you a superpower: The ability to analyze in real time, at speeds that the rest of us can’t. It’s something that I know I strive for in my work: When someone throws a new problem or challenge at me, do I know enough that I could diagnose the problem — and suggest a solution — right then and there?
I’ll never be able to spot the things in swimming that Allison can spot right away. But it’s fun to know that if I ever have a question, I’ve got just the swimming expert a phone call away.
———
That’s a screenshot from this year’s 100 meter men’s swimming final. To be honest, I watched that clip three times to get the screenshot, and even now, I can’t recall what they were talking about when that swimmer got circled on screen.
I’m on vacation this week, out west visiting my family. I’m doing the stuff you do out here: Spending time at the pool, reading, taking afternoon naps, firing up the grill.
But I’m also working, pretty much every weekday morning, for a few hours.
This isn’t supposed to be some sort of treatise on the importance of hustle, some #nodaysoff mission statement. I’m a unique case: I’m in my 30s, I don’t have kids, and I run a one-person business — one I’ve built to serve a lot of small clients (instead of a few big ones). What I’ve done in the past is the traditional vacation: Shut down the laptop, turn on the out-of-office reply, and then return a week or two later to dive back in.
But with Inbox Collective, I’ve discovered that if I shut down everything for a week or two, here’s what happens:
1.) I return to a million unanswered emails (since there’s no one else clients can redirect their questions to).
2.) The week before vacation and the week after vacation are absolutely stacked with meetings, as clients try to squeeze in time before I leave.
The last time I took a week off, I spend the entire week stressed out about how much work I had the next week. I seemed miserable the entire trip.
So I’m making adjustments. On recent trips, I’ve tried to carve out a little time in the morning — about 2-3 hours — to reply to emails and take calls. I’ve blocked off every afternoon for myself, and I’ve turned on my out-of-office reply so people know I’m not going to write back right away. And it’s working: My inbox is manageable, my schedule when I return from vacation is fairly normal, and once the clock hits about 11 a.m., I shut down the laptop and head out do to something fun.
It seems a little odd to still do some work on my time off. But if this is what I need to do to make sure I actually enjoy the time off — to work 10-15 hours a week, even on vacation — then it’s a trade-off I’m willing to make.
———
That’s a photo of me, on one of my afternoons off, on the golf course. A beautiful day, but a pretty terrible lie for that particular shot.
