I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing 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.
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That’s a photo I took of Willie and his band on September 12, 2021, in Saratoga Springs, New York.
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.
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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.
There’s this lie that we tell ourselves when things are complicated and hard: “Once I get through this stretch, things are going to get easier.”
I’ve told myself this more times than I can count. Dan, if you can just finish this task… if you can just get through this month… if you can just take care of this deadline — it’s going to get easier from there.
But that’s not really how this works.
It’s OK that things can be hard. Things can be hard because you’re trying to learn new skills or taking on new challenges. Things can be hard because you’re in a new role or a new job. Things can be hard because you’re pushing yourself to get better. Things can be hard because life gets in the way — you’ve got more responsibility or more people to care for than you did when you were younger.
Every so often, I have to remind myself: Things are never going to be quite as easy as they are right now. Work — and life — tends to get more complex over time.
But you’re going to find a way to push through and keep doing the work. You’ve done it before, and you’ll do it again in the months and years to come. Things never get easier, but you’re also getting smarter and savvier, and building the team to help you take on these challenges. You’ll be able to take on tomorrow’s obstacles as they come.
So enjoy this moment, right now. Yes, things seem overwhelming some days. But these challenges and obstacles will beget new ones. One day, you’ll look back on these moments and tell yourself: What I would give to merely have those types of problems today.
It’s not getting easier, but that’s OK. You’ll be able to take these challenges head on anyway.
When I was getting started with Inbox Collective, I made a conscious decision: I wanted to help as many people as I could, which meant I needed to share a lot.
Not a Newsletter remained free — even as others built large, paying-subscriber-only lists — because I knew that keeping it free and open would allow me to help newsrooms, non-profits, and individuals who couldn’t afford to pay.
I launched new resources for readers to download and use, like my list of growth ideas, because I knew it would help them take the next steps with their newsletters.
I gave away time every month for 1-on-1 calls, so I could dig in with my readers and really help them figure out specific challenges.
And I’ll admit: I was worried at times about this! Was I giving away too much? Would people think, “Well, I guess he’s shared everything he knows! No need to listen to this guy anymore!”
But the results are clear: By giving away a lot, it’s brought even more people into the Not a Newsletter audience: New readers, and, yes, many new clients. By sharing tools, resources, and strategies, it’s attracted a larger audience for me to help — whether they’re working with Inbox Collective or not. (And many clients tell me: We’ve learned so much from you already, so we’re excited to hire you and learn even more!)
The ultimate metric of success, for me, isn’t revenue — it’s impact. So I’ll keep sharing, as often as I can, as much as I can. I know there’s more I can do to help.
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.
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I took that photo, in October 2018, of the view of New York, looking north from 1 World Trade Center after a thunderstorm.
When I’m working with a team on a project, one of the first questions I’ll ask is: How do we start as quickly as possible?
Let’s say we’re working on a new design for an email. Instead of hiring someone to do coding — on a concept that may or may not work! — I’ll use an email builder that allows us to build an email that’s pretty close to what we want. Will it be exactly what we want? No, probably not. But we’ll get 80% of what we want in 20% of the time.
Once we’ve got that built, we can test it out, see how it goes, and make additional tweaks and changes. Maybe we’ve got a winning concept, and if that’s the case, that’s when we’ll go to the designers to get it to 100%. Maybe we don’t, and we’ve got to keep testing. The good news is, we won’t have wasted valuable resources on a concept that didn’t work.
There are so many tools out there that allow you to test and iterate quickly. Instead of building your own stuff, or wasting time on ideas that might not work, utilize those tools, and see if you can get something live that allows you to collect feedback, learn, and move forward.
First, just see if it works. You can always keep building from there.
When you take the first step on any big project, you might step in it. You might start off on the wrong path, or make the wrong hire, or ask the wrong questions.
It happens. It happens to all of us.
One misstep doesn’t doom a project to failure. It might shake your confidence, but keep moving. Keep asking questions, keep trying to find your way back. Don’t let a bad first step send you permanently off course.
There’s a tendency at a moment like this — whether you’ve just completed an election, like we did in America this week, or whether you’ve completed a big project at work — to have a sense that things are over. You put in the work, you did the work, and now you’re done.
But the truth is: There’s always more work to do. New doors are going to open, new opportunities are going to become clear. The work is never really done.
Inbox Collective is my second attempt at starting a business — a decade ago, Stry.us was my first. I know more this time around, I’ve better organized a network of supporters around me, and this time, I’ve built an audience to support my work. I learned so much from Stry.us, and it’s put me in a far better place to succeed with Inbox Collective.
But even with all that knowledge, I’ve found that there are still obstacles in my way. I believe that these four obstacles exist for everyone who starts something — no matter how ambitious the project or how prepared the team is behind it:
Time — There’s never enough time to do all the things you want to do. In a business like mine, it’s so hard to strike the right balance between doing the work that pays the bills and building the relationships that will lead to paying work down the road. If there were twice the number of hours in the day, I still don’t think it’d be enough. It means that I need to prioritize certain work and say yes to only the things that are most important to me — even though sometimes, I have to say no to stuff I’d really love to be able to do.
Money — This was the big question when I launched: Would anyone actually pay me to do this? The answer’s been a resounding yes, and I feel so grateful for that. But now there’s pressure to keep this thing going. 2020 changed everything — no work-related travel or talks, but lots of remote projects. Could I keep that up for another year or three if I had to? So many of my 2020 projects came from meeting people at conferences and events back in 2019, and if my business stays remote for the foreseeable future, I wonder if I’ll be able to keep this going. I know I can do it, but that fear is still going to be a small weight on my shoulders. Even when things are going well, I’m always going to be looking ahead and trying to plan for what’s next.
Stress — Anytime time and money get involved, there’s going to be a certain amount of stress, too. Inbox Collective is my work, and mine alone. If it succeeds, if it fails, it’s on me. I like the pressure of it, and I’d gladly take this work — even when it’s stressful — over the frustrations of working within a larger organization. (And that might change down the road — that’s just how I feel today!) But it doesn’t change the fact that this job applies real pressure on my life, and it’s up to me to manage that stress. It’s something I’ll always have to deal with.
Failure — At the end of the day, there’s always the chance that Inbox Collective fails. I might not be able to do the work, I might lose clients, I might have to change careers or fields. Now that things are working, there’s pressure to keep this business going, and to keep learning so I can continue to grow Inbox Collective.
I don’t know what Inbox Collective will look like in a year or five. I certainly have no idea whether it’ll be around in 10 years, or beyond that. But I know that as long as I work on this, those four pressures — time, money, stress, and failure — will weigh on me. That’s just part of the job.
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At top, that’s a photo taken of me giving a talk in 2019.
