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.
By the end of January, I had my calendar for the entire year pretty much set.
I knew where I was going to give talks this year, and had the flights planned out. I knew which weddings I’d be going to. I had some vacation days penciled in.
Then Covid-19 hit here in the U.S., and all of that changed.
I used to have a nice balance of remote work and in-person work. Now, like everyone else, my work’s shifted entirely online. I’m not sure when I’ll fly next or when I’ll travel again for work.
And that’s OK! I’m lucky to be the position that I’m in. Inbox Collective is doing well, and I’ve got my hands full with work. I feel incredibly grateful for the opportunities that I have.
Still, I’m realizing how much I miss being able to look forward to the next thing: The next trip, the next birthday party, the next night out. Zoom is such a useful app, but it’s not the same as being there with friends or clients.
Here’s the closest thing I’ve found to life before Covid-19: This past weekend, my wife and I decided to get out of town for a few days. We rented a car and drove upstate. We didn’t do much — we ate, we drank, and we saw a few friends from a distance — but just knowing that we had something like that on the calendar lifted both of our moods for an entire week.
Going forward, I’m going to try to keep putting something on the calendar to look forward to. It could be small (setting aside some time to meet a friend in the park) or big (a road trip somewhere). I’m not going back to the pace I had a year ago, and that’s alright by me. Just knowing that something’s coming up is enough to keep me moving forward.
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That’s a screenshot of Flighty, the app I use to track my travel. That’s what my travel schedule looked like from March through June. (Obviously, it all changed.)
No one knows what happens next. We don’t know what things will look like in two weeks, two months, or two years. We don’t know if we’ll be working in offices again, traveling to conferences, or even sitting down at the table with loved ones. Sure, you can make a prediction about the future — but your prediction is little better than a guess.
Historically, pandemics have forced humans to break with the past and imagine their world anew. This one is no different. It is a portal, a gateway between one world and the next.
So how should you approach making a tough choice about an uncertain future? Try to think through two big questions:
What do you know right now? — Do your research. Read a lot. Talk with people you trust, and listen to what they have to say. Try to collect all the information you can about the situation.
What do you believe right now? — Trust your instincts. Think about what you need at this moment. Put all the options on the table, and make the best choice you can with the information you have.
You may not end up making the perfect choice in the long run. Again: To make the perfect choice for whatever’s next, you’re going to need to get a little bit lucky. But you do have the power to look at the current situation, ask the questions you need to ask, think through the options in front of you, and make the right choice for right now.
My mother used to have this expression: “Hurry up and wait.” I remember when we used to go to the beach, and there was this one part of the trip that required us to get on a ferry. The ferry captain would announce that we’d be docking in 20 minutes, and people would rush to the exits, even though they weren’t going to be able to get off the boat for another 20 minutes. Mom always laughed at the idea of rushing to get to the exits before you could exit. We’d sit on the top deck of the boat instead, enjoying the final minutes of the ride into the dock. “Everyone else is just hurrying up to wait,” she’d tell us.
Right now, at this moment, we’re all dealing with the COVID-19 pandemic. We’re calling airlines to ask for refunds on upcoming travel. We’re on hold with the doctor’s office. We’re waiting to check out at — or just to get in to — the grocery store.
We’re all going through this together, and not nearly as quickly as we want. The whole world, it seems, is in hurry up and wait mode.
These next few weeks — and months, if we’re being honest with ourselves — things aren’t going to be normal. Our lives are being disrupted, and things are going to change.
What I’m trying to remind myself is: Things will get moving again, and life will go on, even though we’re not entirely sure when. Things will happen when they happen.
In the meantime: Be kind to one another, and be patient with one another. These are stressful times. The least we can do is show kindness and patience in this moment.
This morning, I had an idea for a friend, but I wasn’t sure how to tell them. I started thinking about how I’d present the idea to them. In my head, I started writing the email to them — how I’d say hi, maybe share a story or two from the weekend, then get into the idea, couch the idea with a few different caveats just in case they didn’t like it, and then close with a “lemme know!” kind of thing at the end. I spent the better part of breakfast thinking about that email, writing and rewriting it in my head.
I can overthink things sometimes, and this was one case. It was a simple idea, not all that controversial. It didn’t need a whole email. In fact, I realized, it didn’t need an email at all — a text would do the trick.
So that got me out of the rut. I picked up my phone, and fired off the text. Two sentences, and it was done. If my friend wants to follow up, they can. If they want to talk about it on the phone, they can. But I spent 20 minutes this morning overthinking an email I didn’t even send, and then 20 seconds sending a text instead. I wish I could have those other 19 minutes and 40 seconds back.
Send the email, send the text, make the decision — and move on. You’re too busy to waste time overthinking something as small as this.
You don’t have to write a check to go the extra mile.
You don’t have to go to school to learn a new skill.
Connecting with an old friend costs nothing, and might mean a lot to both of you.
You can’t put a dollar value on hard work.
You can always make time for a good conversation, to offer advice, or to just listen.
There are certain things in life that are available to all of us. They don’t cost a thing, and they don’t require a fancy degree — just time, or kindness, or a little bit of effort. Make time for those things. Be good to others. Listen carefully. Challenge yourself. Work hard. Some of the best things in life are free — and entirely up to you.
A few years ago, my friend Leslie’s dad died, and she wrote a wonderful piece about him. This one part of her story really stuck with me: Every year, Leslie’s dad would call family, friends, and co-workers on their birthdays and sing “Happy Birthday”:
“The dude had a goddamn calendar full of people he would call on their birthdays. From what I’ve learned in the past couple of months, it numbered in the hundreds. If he knew your birthday, he would call you on it and sing happy birthday. He had what I would call a church choir voice. Which is to say, not great, but he would belt it out nonetheless. If you picked up, he’d sing your ear off. If you screened, he’d sing it to your voicemail.”
And it wasn’t until after he died that Leslie realized how much of an impact those yearly birthday calls had made on everyone who was on the receiving end:
“In the past three months, I’ve had untold numbers of people approach me and tell me they had messages from my dad on their phones singing them happy birthday. Happy birthday to Mark! Happy birthday to Suzanne! Happy birthday to Margaret! Happy birthday to family and friends and to people I don’t know from Adam!”
I loved the idea that one little gesture could matter so much to so many people. I’m not much for singing loudly, so Sally and I made a resolution to try something new in 2017: Sending birthday cards.
We made a calendar of people we love, we got their addresses, and we started sending cards to them. This year, we’ve sent about 75 cards — next year, I hope, we’ll send more.[1. Etsy, I’ve learned, is a great place to buy birthday cards. I love stores like HenPenPaperCo, YeaOhGreetings, hellosmallworld, and lafamiliagreen for original cards.]
This has been a strange, stressful year for all of us, but sitting down and writing a birthday note to friends and family reminded us how lucky we are to have such great people in our lives. No matter what’s happening in the world, we have these relationships, and we’re so grateful for them. And every birthday is a reminder that there are always great reasons to celebrate with the people we love.
Here’s to getting older — and many more years of happy birthdays (and birthday cards) to come.
Since I announced that I was leaving BuzzFeed, a lot of people have been asking: How did you know it was the right time to leave?
I hadn’t been applying to jobs elsewhere when the New Yorker opportunity came around. So to make sure it was the right time for me to leave, I made a list of six questions, and thought carefully through each:
1) Am I still being challenged in my current role?
2) Am I still learning new things?
3) Am I part of the decision-making process at my office? Do I have a seat at the table where big decisions are made?
4) Is there a path for me to grow at this company?
5) Do I have the right people on my team?
6) Do I have what I need to do my best work?
If the answer to one or two of these is “no”, you might be unhappy at your job, but it’s probably not time to leave. Have a conversation with your boss about your role — maybe there’s an opportunity for them to give you the support/training/help you need to fix those issues.
But if you’re answering “no” to more than that, it’s time to make a change. You deserve to be at a place where you’re surrounded by the best team, working on projects that challenge you, and supported with the resources you need to do great work.
One more thing: You’ll notice that money’s missing from this list. I’m lucky in that at this point in my career, I didn’t have to make a move based on financial needs. But if you’re at a different stage in your career, that should absolutely play a role. Don’t stay at a job that pays you less than you’re worth — otherwise, you’ll miss out on the opportunity to make a significant salary leap.
I stumbled across this quick video featuring career advice from Carla Harris, a vice chairman at Morgan Stanley, and I had to share it. If you’re in your 20s or 30s, take two minutes and listen to her advice.
Her three big points:
1) “You will have the opportunity to have four to five careers — not jobs — over the course of your professional journey.” Which means that every few years, you should be evaluating where you are in your career, and whether or not it’s time to switch fields — or merely switch roles.
2) “There is no substitute for the power of relationships.” About this, she’s 100% right — building relationships is the key to helping you move up in your field.
3) “The way you differentiate yourself in any environment is to show that you’re comfortable taking risks, because it says to the marketplace that you’re comfortable with change.” Everyone is going to experience change in their jobs — so prove now to your bosses that you’re willing to lead your team into and through those changes.
Watch the whole video — it’ll be the best two minutes of your day.
Ladies and gentlemen, faculty and staff, distinguished guests, graduating students from the class of 2017: I’d like to tell you a story about a simpler, more honest time in American history.
The year was 2005.
I remember it like it was… well, about 12 years ago. Was it really only 12 years ago? It feels like longer.
I want you to imagine a young Dan Oshinsky. He’s a senior at a suburban high school outside Washington, D.C. He’s heading soon to journalism school — one day, he’ll write for newspapers! He’s yet to discover hair product. He’s driving his maroon Oldsmobile Eighty-Eight down the highway.
When a song comes on the radio. (Again, it’s 2005.) It’s a song that he knows, and loves.
He can’t remember the name of the song.
But he loves the riff. It goes: Dah-NUH duh duh duh duh dah-NUH nuh nuh.
The song ends, but the radio DJ does not say the same of the song.
So young Dan drives down the highway in his Oldsmobile, singing the riff over and over again, trying to remember the name of the song. He sings: Dah-NUH duh duh duh duh dah-NUH nuh nuh.
But he cannot, for the life of him, remember the name of the song.
He gets home, and he finds his mother, who grew up loving rock music in the ‘70s and ‘80s. Surely, he hopes, she’ll know the name of the song.
Dah-NUH duh duh duh duh dah-NUH nuh nuh, he sings.
And she recognizes the riff immediately… but fails remember the name of the song.
So they call their neighbor, Matt. Matt grew up in rock bands. Still plays in one, in fact. Plays guitar, knows everything there is to know about rock music.
They get Matt on the phone — on his house line, naturally. (Again, the year was 2005.)
Matt, they say, we heard this riff on the radio but can’t remember the name of the song. Do you know it?
And loudly, on speakerphone, they begin to shout: Dah-NUH duh duh duh duh dah-NUH nuh nuh.
And Matt says: Yeah, I know that song! That’s “La Grange”, by ZZ Top.
Matt was right:
I tell you this story tonight, Class of 2017, for a simple reason: That story, from 12 years ago, makes 2005 feel as far away as the the 1980s. It feels like a story from an entirely different era.
In 2005, I was driving around in an Oldsmobile — a car company that no longer exists — with a tape deck — a technology that barely exists — with a flip phone — a product I haven’t used in years. The iPhone wouldn’t exist for another two years, and I wouldn’t discover a music discovery app called Shazam for another five. At that point in my life, I’d never owned an iPod, and the idea of high-speed data being transmitted to cell phones was years away.
So if you would have told me in 2005 that one day, there would be a magical, mobile device that could listen to and identify songs on the radio, I would have been amazed. That was something that could only happen… in the future!
The future, it turns out, is happening right now. In the dozen years since I couldn’t remember the name of a ZZ Top song, nearly everything that exists in our day-to-day lives has changed. The technology, the tools, the resources — it’s all changed.
In just a dozen years.
And I cannot imagine what we’ll have at our fingertips in the year 2029. The changes, I’m sure, will astound all of us.
But there’s the flip side to all this change: Just thinking about the unknown ahead of us can be frightening. How do you prepare yourself for a future you don’t recognize? What are the right careers for such a future? What are the right choices?
I wish I had the answer for you — but I don’t.
Instead, Class of 2017, I have a challenge: No matter what happens in the years ahead, invest in yourselves. College may be over, but push yourself to keep learning. Read a lot. Try new products. Learn new skills. If you work at an office that has a Learning & Development team, take their classes. Don’t be afraid to keep growing your skill set.
In the dozen years ahead, everything in our lives will change again. So don’t be afraid to keep learning — it’s the only way to change with whatever the world throws at us next.
Congrats, Class of 2017, and in the words of ZZ Top: Have mercy.
I’ve written lovingly about Warren Buffett many times before. (See here, here, here and here.) I’m a fan. And any follower of Buffett’s will tell you that they’re also a fan of his right-hand man, Charlie Munger. Munger has been as important to the rise of Berkshire Hathaway as Buffett himself. And he might be an even better quote than Buffett.
A friend sent me one the other day, from Munger’s 1989 letter to shareholders of the Wesco Financial Corporation. (Berkshire owned them, though Munger served as CEO and Chairman of the board.) In it, Munger dove into the idea of taking risk. He said that taking big risks for short-term gains — particularly by acquiring other companies — is a foolish move:
“Wesco continues to try more to profit from always remembering the obvious than grasping the esoteric. It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
That’s not to say Munger wouldn’t ever take risks. He wrote:
“Wesco would cheerfully invest $75 million tomorrow, with a 60% chance of total loss, provided the pay-off for winning was large enough to cause statistical expectation to provide a handsome return.”
So what’s the lesson here? Understand who you are and what you do best, and manage risk. It’s okay to bet big sometimes — as long as you understand the size of the opportunity and the amount of risk involved.
Otherwise, Munger’s advice was simple: Try not to be stupid! Yes, he wrote, it’s a strategy that “is bound to encounter periods of dullness.” But it also works in the long-term.
