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.
“Our lives happen between the memorable.” — Jack Gilbert
A year ago today, something funny happened in Springfield, MO:
Jordan and I had a Stry.us booth downtown at the ice rink. This guy came up to us. We hoped he wanted to talk about the project. He didn’t.
“You guys got any jumper cables?” he asked.
Not really what we were there for, but hey, I did have cables. So we went outside and got the car started. The driver thanked me. We made small talk. He said he was from Joplin. I told him that the team was going to Joplin the next day to do some reporting.
He handed me his card. I know the mayor, he said. Give me a call. Maybe we can set something up.
And… he helped. He pointed us in the right direction. And we needed that. I don’t know what we do without that — a chance encounter 100 miles away from where we all wanted to go.
Little things, little connections, little moments — it’s funny how much those matter, and how often we forget.
“Sucking at something is the first step to being sorta good at something.” — Morgan Missen
10 years ago this summer, I started my first internship in journalism. I was 16. That summer, I got an article published in the A section of The Boston Globe, and I thought: This journalism thing is going to be easy. I thought I was going to be a very big deal.
Five years ago this summer, I went to China to cover the Beijing Olympics for the Rocky Mountain News. I was in China, reporting on the biggest sporting event in the world. I was doing good reporting, and my bosses were happy with me. I was convinced: I was going to be a very big deal.
And now it’s five years later, and… well, the words “big deal” probably don’t apply just yet. I’m really happy with where I am in journalism. Thrilled, actually.
But this isn’t what I thought it would be. I had visions of reporting, of telling big feature stories that won big awards, of traveling to tell stories that could change lives. I had huge ambition, and no reason to doubt that everything I wanted would come soon.
I never thought about the work. There was no concept that it was going to take work and time and screw-ups to get somewhere good. Everything came easy: the reporting, the writing, the opportunities. Stuff just seemed to work out.
But I ended up in a pretty great place anyway. I’ve learned about the work. I’ve had leaps forward, and I’ve taken steps back. I have screwed up a lot, and I’m better for it.
Somewhere down the road, I might even get good at whatever it is that I do. I’m 26 now, and I think I’m getting closer. Not close — but definitely closer.
Every once in a while, someone tells me how far along I am. They say I’m doing well — really well for someone this young. They talk about how quickly success has come for me.
And not too far off — maybe a few years down the road, even — there’ll be more of them. They’ll talk about how fast it’s all happened for me. The words “overnight success” might even be used.
And only I will know: I’ll have been an overnight success more than a decade in the making.
“There’s a fire burning deep inside / And it’s as mad as it’s mean / It’s hungry as it’s lean / And it’s as fleeting as a dream.” — John Fullbright
Two separate things that happened this week:
The first: A colleague at BuzzFeed died. His name was Michael Hastings, and I never met him. But when you read about him — and you really should — the thing that comes across is a certain fire for his reporting. People at my office described him as passionate, as forceful, as energetic. What a wonderful thing to bring to your work.
The second: I saw a guy play in concert on Thursday. His name is John Fullbright, and he’s a hugely talented songwriter from Oklahoma. Watching him live, he sang with that same passion. He threw himself at the microphone. He sang loud, and played hard. He’s a guy who actually appears to work on stage — he sweats and screams and aches through his music. What a wonderful thing.
It’s an amazing thing to see people doing work they really care about and believe in. The passion comes through. The fire comes through.
I feel lucky to have witnessed glimpses of it this week. That’s what we’re all shooting for, isn’t it?
“Innovation happens at the crossroads of frustration with the present and blind optimism about the future.” — Aaron Levie
A lot of really great stuff can come from being mad at where you are. You’re pissed about your job or your friends or your place in the world, and you do something bold. That’s where a project like Stry.us came from.
But frustration is just a little bit of fuel. It might jump start you, but it won’t keep you going.
What keeps you going are boring things: Routine, effort, persistence, teamwork. The frustration convinces you to start the work, but the structure lets you do the work every day.
It’s boring stuff, yes, but it’s also what actually makes great work happen.
“You have to learn to be bad at something before you can learn to be good at something.” — John Oliver
If I hear one more talk about the future of my industry, I’m gonna be sick.
The future. Goodness, what the hell do we know about the future?
We have no clue what happens next. None. We are consistently, ridiculously wrong when it comes to predicting the future. We are just bad at it.
Here’s what I’m interested in:
What are we doing now?
What tools are we working with now?
What are we trying to accomplish now?
We shouldn’t stop trying to make our world better, but we have to start now. We know what people are doing now, and how people are reacting now. That’s where we should start.
But we get lost in talking about what’s next.
We are constantly trying to sift through all that’s happening now to predict what’s coming next. That’s where we get lost — trying to follow the thread a little too far into the future. We want to write the story as it’s happening. We all want to feel like we’re a step ahead.
But forget about the future for a second. We chase it too often. We follow it to dead ends.
There is a certain point in your life when you realize that you don’t know anything.
Up until that point, you thought you knew what was up. You thought you’d experienced heartbreak. You thought you’d experienced pain.
And then comes this big breakthrough, and you realize, you don’t know jack. You’re just starting your life, and you’re starting from zero, and everyone else seems to know more than you do.
You feel like a fraud, and a phony. You feel like you don’t have anything to offer this world.
And there’s that expression you’ve heard: Fake it ’til you make it. That’s almost true.
Because there’s a second realization that comes a little later: Nobody else knows anything, either.
Everyone, turns out, is kinda faking it. Nobody is just born an astrophysicist or a banker. (And nobody is born or a social media expert.) We mold ourselves into these people. We see what others are doing, we think about what we like to do, and we make ourselves into the people we want to be.
And once you realize that, you don’t feel like a phony. You don’t know anything, but hell, neither does anybody else. We’re all just trying to make it work in this world.
So just do good work and surround yourself with good people, and you’ll be okay. It’s normal to feel like you don’t know anything.
We all feel that way, and we’re all in this thing together.
“Pirate movies have been bombs for a long time… this is one of those streaks that most producers seem to respect. You have to go back to the 1950’s (and earlier) to find an era when pirate movies were successful and liked. And that, I guess, is why the Pirates of the Caribbean ride was made in the first place, because they didn’t know yet the trend was over.
“….As for a movie with really scary pirates that pulls no punches for the kiddies… don’t be lookin’ ‘ere, arrrrr…”
And the same writer in June 2002, growing a little less skeptical:
“I don’t know whom exactly I thought might be announced as starring in this movie, but I’m pretty sure I wasn’t thinking it would be Johnny Depp.”
And the same writer in April 2003, when the first trailers came out:
“The amazing full trailer for this movie did indeed go up last night…. My anticipation for this movie has been building for some time, but this trailer really locks it in there.
“I think the title of “Pirates of the Caribbean” has had a lot of people scratching their heads (and expecting a dopey movie), but clearly Disney, Bruckheimer, Verbinski, Depp and everyone else involved were not setting out to make *that* sort of PotC movie. They’re apparently totally reinventing the property, separate from what you know about the ride, and from what I can see in this trailer… it looks like it might have worked. Wow.”
But nobody knew that at the start. At the start, it was just a weird idea. There was no director, no stars. Just an idea.
Ideas aren’t worth very much. Some ideas bomb. Some ideas get the right team behind them and become one of the highest-grossing movie franchises in history.
Nothing really matters until you start — especially not what everyone else is saying.
“Awareness is the most precious kind of freedom.” — Joshua Fields Millburn
So we’re at the top of a mountain somewhere near Cold Spring, N.Y., and we’re lost.
And sunburnt. And tired. And out of water.
And there’s this guy at the top, too. He’s hiked here 600 times, he says. Every year for the past 30 years, entire weekends up here.
He seems like a good guy to ask a simple question: How do we get home?
The only way back is the way you came, he says. He points out a long trail home. Could be hours that way.
Not happening.
We thank him. We’re mad. We’re tired.
And then this other group comes to the top from the other side.
There’s a path there?
There is, they say. An easier way down. A better way down.
We thank the heavens and head home.
So what about that other guy? The expert hiker? The one who’d been hiking here for years?
I don’t know. Maybe he’d forgotten the other way home. Maybe he’d just never hiked it.
Whatever the case: There’s almost always another way to get where you need to go. Sometimes figuratively. and sometimes quite literally, up in the hills north of NYC.
I went to the Apollo Theater last night for Amateur Night. I went to watch, not perform. That’s probably for the best.
I have personally stood on some amazing stages, but I’ll never be on anything like the Apollo. For performers there, it’s just you, and this decades-old theater, and a crowd ready to boo you at the first missed note.
If you’re unfamiliar with the Apollo, read that sentence again: Bad performers really do get booed off stage. (They even bring out a guy called “The Executioner” to escort you off.)
But the Apollo is kind of brilliant in that way. Most places, if you’re on stage and you suck, people stay quiet. They clap politely when your performance is done.
At the Apollo? Hell no. If you’re bad, you’re getting booed off stage. You know immediately whether or not what you’re doing is working.
And that’s brilliant. That’s how all our work should be.
“Percentage wise, it is 100% easier not to do things than to do them.” — John Mulaney
Don’t.
Just… don’t.
The work will be hard. It’ll be draining. You’ll be tired all the time. You’ll be working harder than you’ve ever worked.
And the work won’t stop. You’ll go to bed at midnight, having put in a full day of work, and you’ll wake up the next day with just as much — probably even more. It’ll just keep coming at you, work day after work day, and the only way to deal with it will be to keep going, deeper and deeper into work that won’t ever end.
You’ll be an emotional wreck. You won’t be sure that what you’re doing is right, and your friends will probably tell you that you’re crazy. Most days, you’ll agree. You’ll be a bad break away from a nervous breakdown, or a big break away from floating on air, and you’ll never be sure which way the next 90 minutes might take you. You will never feel like you’re standing on solid ground.
You will feel alone, and you will feel helpless, and you will feel scared.
You will want to quit. You will tell yourself that quitting is the way out.
And then you will wake up and do it all again the next day. You will want to quit, but you’ll be even more scared that quitting might take you to an even worse place.
So you’ll keep going, day after day, hour after hour, task after task. You’ll lose the ability to tell the difference between a step forward and a step back. Soon, all you’ll be sure of is that you’re taking steps — but you’re not sure where they lead.
The work will make you question everything. The work will bring you to tears. The work will hurt.
The work. It will take everything you have to keep it from crushing you.
So, just… don’t. Don’t do it. Not doing the work is the easy way out. Not doing it is the sane way out.
Unless you want to do something really great. In which case: You’re going to have to do the work. It is the only way.
And yes, you’re going to be tired, and scared, and totally unsure of yourself.
But you’ll be doing the work, and there won’t be a single thing you’d rather do than that.
