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.
In 2009, I wrote something that I thought was clever.
Turned out I was just being a dick.
I had gone to a concert with my roommate, Nate, at the Blue Fugue in Columbia, MO. There were a couple of bands playing that night, and one of the openers was from Utah. They were called Mad Max & the Wild Ones. They were a family band. (That’s them in the photo at top.)
And that was that. Until, of course, the band’s manager — also, the band’s mom — went home and searched Google. She found my post.
We traded some comments on my blog, and later emails. She was pissed, and understandably so — some asshole on the Internet was writing snarky comments about her kids!
It’s just that in this case, that asshole was me.
The conversation eventually settled down, and I eventually apologized. I never took the blog post down, because I didn’t want to forget the incident. The Internet is written in ink, and this blog is no exception.
What I’m building towards is this: There’s nothing clever about Internet hate. I know a little more now about what it feels like to be on the other side of that hate. Victories are fleeting, but hate stays with you. Especially Internet hate, where it’s often anonymous, and especially vicious. Somebody you’ve never met has just seen something you’ve done and taken the time out of their day to tell you exactly how much they think you suck.
Look, friends: Spread love, or just keep your damn mouth shut. Opening it to spew hate — especially on a blog, or a YouTube comments section — does you no good.
That night at the Blue Fugue, I could’ve just gone up to the band and told them what I thought. I didn’t, because I would’ve been a giant jackass to tell them to their face what I thought. Instead, I went home and wrote the thoughts on a blog, where I figured they’d never read them.
How is that any different?
I traded emails with the band last week. They’re getting older, and getting offers from legit bands to tour. They’re still out on the road, taking their stabs, making it happen. That’s awesome.
They’re coming through Springfield in a few weeks, actually. If I’m here, I’ll go to the show, and apologize in person, and tell them what I could’ve said the first time:
You guys may be young, but hot damn can you play. Don’t let the haters get you down.
Today is my birthday. I haven’t wished for something on my birthday in a long time, but hell, I’m 25, and I’m feeling old. So here’s my wish.
This wish is for you.
Today, I wish that you’ll read this and do something that scares you. You’ll say something out loud that you’ve been afraid to say. You’ll try something that you’ve been afraid to try. You’ll do something a little bit crazy.
On this 25th birthday of mine, I feel so, so very lucky to have the chance to work on Stry.us. This thing scares the absolute crap out of me, but it’s a joy to wake up with that fear. It keeps me going.
I beg you today to experience some of that fear. Please: Go do something that scares you. A little thing or a big thing — it doesn’t matter what it is.
But every good thing in this world starts with action. Forget the fear. Today, you have my birthday permission to ignore it and try something insane.
So it’s Tuesday afternoon, and I’m in an almost empty TV studio in the middle of Springfield. I am sitting next to Leigh Moody, news anchor at the local ABC station. I am the guest for the 4 p.m. news “Close-Up” interview.
And it’s the funniest thing. Because everyone — EVERYONE — wants to know how this thing started. But hardly anyone asks the really big question, which is:
How the hell is this thing still going?
I’ve started plenty of things that never went anywhere. But I’ve never started anything that’s lasted quite like Stry.us.
And that thought was rattling around in my brain when I hopped in the car after Leigh’s interview and turned on the radio. Dylan’s “Like a Rolling Stone” was playing, and Bob was already through the first verse. And he sang:
How does it feel /
To be on your own /
With no direction home
And it all just kind of hit me at once. That’s what this has been — this solo journey, with no discernible course. Some projects are linear. Some have a definite road.
The path for Stry.us has been more of a squiggly.
I didn’t know what this thing was going to become two years ago. In my initial pitch for Stry.us, I talked about filming YouTube videos and wearing sponsored logos — like a NASCAR driver. (Seriously.) I was especially clueless back then. This thing’s gone through so many iterations that I’ve lost track of them all. It’s been a solo operation. A news syndicate. It went through a period of nothing, and then a few periods of serious somethings. And now?
Now it’s taking real shape, because I’ve paired it down to an incredibly simple mission. Stry.us is about two questions:
1. What matters to people?
2. And how do we tell great stories about those things?
It is the simplest thing in the world. And people get it. In my meetings this week in Springfield, I’m seeing that twinkle in the eye when I talk about Stry.us. People love the idea. They get the idea. The love what we’re doing with our reporting.
After two years, I finally got okay with the idea that we’re just a band of reporters in pursuit of really great storytelling, and we don’t need to be anything more. We’re focused, we’re uncomplicated and we’re really starting to go places.
I was at the Stry.us HQ/apartment on Monday night, sitting on the floor, when I looked up and announced to my editor, Jordan:
This is the furthest along this project has ever been.
Stry.us — or versions of it, at least — had been on my mind since 2007 or so. But it really came into fruition almost two years ago to the day, when I worked up a pitch for something I called “Four Days in America.” It would be a story, I decided, about the state of our union, with reporting on who we we are and where we’re going. It evolved pretty quickly to Stry.us. Two months later, I was leaving my job to start this thing.
But right on that floor in Springfield, on Monday? At no point has Stry.us ever been closer to reality than right then.
Right now, we have:
A website that doesn’t suck.
Some fans.
A team.
Some money.
Excitement.
We’re actually on the verge of… something!
And more good things are happening! Like: I’ll be speaking about Stry.us and our new website at the Association of Alternative Newsmedia convention this summer in Detroit. That’s pretty amazing.
And just being down in Springfield, I can sense the excitement. The library team, in particular, is absolutely wired about our project. They’re going to be a fantastic news partner this summer.
But I always find that just when my ego’s getting a little too big, something happens to bring it back to normal size.
On Monday night in Springfield, I slept on a yoga mat on the floor of the Stry.us apartment. I used a hoodie for a pillow. My bed — and bed-related accessories — won’t arrive for a few more days.
Yes, Stry.us is moving along. Yes, we’re making big strides. Yes, after two years, it’s starting to feel like we’re building towards something really big.
Yes, I can even use the word “we,” because there is a we — the Stry.us team I’ve put together.
But you cannot have a big head when you’re going to bed on a yoga mat, with a hoodie for a pillow.
As in the time I brought my cell phone to the AT&T store with a crack in the screen. They asked me, “Did you stab this phone with a knife?” I told them, No! What am I, a maniac?
And then I heard words I would hear many times in the years since:
Oh, well then I guess I’ve never seen anything like that before.
Or the time I was in China, trying to get the right press credential for the Olympics. I was a student and a freelancer and I didn’t live in the same time zone as the newspaper I was writing for. This made the Chinese confused. On a half-dozen occasions, a government employee told me:
Oh, I’ve never seen anything like this before.
Or just this weekend, I was on the phone with the company handling the payroll for Stry.us. Since all my reporters are employees of Stry LLC, we have to go through some fun government hoops to get the team paid. The thing is, the LLC is registered in Maryland. We’re doing business in Missouri. We’re not actually making any money. And my entire team has permanent residences out of state.
So, yeah, you can guess what I heard when I was trying to get the payroll forms filled out:
Oh, I’ve never seen anything like that before.
This is the kind of stuff that happens to me all too often. It happens because I am decidedly weird, and I cause trouble, and I tend to do things that normal people would not do. Stry.us is one giant case study in what not to do.
With Stry.us, I was told:
Don’t quit your well-paying job!
Don’t start your own media company!
Don’t go into a passion project without a safety net!
Don’t start a business if you don’t know anything about business!
And they were right. They were all right. I mean, what I did was stupid. Crazy. Possibly the dumbest thing I could’ve done.
It’s also the single biggest decision I’ve ever made, and the one that’s gotten to me where I am today, and the one that I would make every single time. Even knowing all the crap I would go through, I’d do it again, absolutely.
But I’m also aware that I operate in a world quasi-divorced from reality. There are no cubicles in my world. There is very little normal in my life.
There is — as a friend told me a few days ago — probably something very wrong with me. And maybe that’s a good thing.
I’m someone who tends to make up his own rules, and I know that I will — from time to time — run into a situation where other rules actually apply. And where I will have to obey said rules, because they have consequences.[1. For tax reasons, or because the Chinese could deport me, etc etc.]
I’m always thinking about what I’m aiming for with a crazy new project or idea. I know what I want to accomplish. I know things are going to go wrong along the way.
And I know that I will do things, far too often, that will lead people will tell me that what they’re seeing is something that they’ve never seen before.
For the most part, that probably means I’m doing something right. I’m challenging the system.
There are times when I am flat out wrong. And in those cases, I’ll be the one getting challenged on it. Advisors/friends will tell me, You actually can’t do that! And then they’ll grab me by the collar and tell me again: Dan, you can’t do that. We know you like to push the bar, but for legal/ethical/health-related reasons, you simply cannot attempt this.
Which is good to hear, actually.
“Oh, I’ve never seen anything like that before” is different. When you hear it, it means that you’re trying something very unusual. The person telling you this knows that whatever you’re doing isn’t impossible. But they also haven’t seen anybody stupid enough to attempt it before.
Often, when I hear those words, the person will look up at me and silently ask themselves: Is this guy dumb enough to try this?
And the answer is often: Yes, yes I am.
Weird? Unexpected? Yeah, it happens when you start building a world that you really want to live in.
When I was three years old, I found a red pan in my preschool classroom. I used to walk around with this red pan and pretend to play guitar on it. There is a photo of me that my parents still hang onto. I have big, fat cheeks, and goofy, green overalls, and I’m soloing away at a red, plastic pan.
As I got older, I got rid of the pan, but the air guitaring remained. When I was a kid, I was always pretending to play guitar.
But weirdly, I never actually learned to play. I tried the recorder in third grade. Mom offered to let me play clarinet in fourth grade, but I didn’t even consider that an instrument.
Guitar? I never played guitar.
And then I got to college. Freshman year, there was a kid down the hall named Nate. Nate played guitar. He played in bands. He asked me if I wanted to live in his off-campus house sophomore year.
I agreed on one condition: He had to teach me how to play guitar.
So I bought a Martin guitar that year — dark mahogany, a deep sound. I spent the first three months playing three chords, over and over: C, E minor and D minor. In that order. Over and over.
My roommates grew to hate C, E minor and D minor.
But I kept playing.[1. I kept up my air guitar skills, too, for what it’s worth.] By the end of the year, I had a few songs under my belt. I couldn’t play with rhythm. I messed up often.
But I could finally say I could play guitar.
I kept going. Junior year, I started to gain rhythm. Senior year, I actually figured out how to use a capo and play different sounds.[2. Some of my friends didn’t realize I had learned guitar until much later. One friend saw a guitar case at my apartment and asked if I had, as a joke, purchased a case for my air guitar.]
My first year out of college, I accidentally discovered how to correctly play bar chords. That took me a year or so to master.
By the time this year came around, I wasn’t all that bad. I could play harmonics. I could play semi-complex rhythms. You could yell the words “Free Bird” at me and I could sing the guitar solo while simultaneously playing the rhythm.
But as far as my live guitar playing experiences were concerned, it was still pretty much limited to a lot of me, in front of the bathroom mirror, belting out Springsteen[3. The acoustics are always excellent in bathrooms.], and occasional fireside guitar sessions at the beach.
Here’s the thing: I love TED talks. They’re inspiring, and they’re right on that line between entertaining and informative. That’s the line I’m always trying to toe.
And I’ve always wanted to play guitar in front of a large group of people. I’m not a musician. I don’t play in a band. I don’t get a lot of moments to feel like a rockstar.
So a TED talk about U2 in which I play guitar and lead a sing-along? Hell yeah! Let’s do this thing! No sense in getting in the ring if you’re not going to throw your weight around, right?
I mean, I asked myself: Did I care enough to put myself behind something I’m really passionate about?
I love playing guitar. I’ve always loved it. I was obsessed with it long before I actually started playing.
And here came a crazy opportunity.
So I stepped up to the plate.[4. I know, I’m mixing all my sports metaphors together, but just roll with it.] I was going to speak at TEDxMU — the independent TED event being held at the University of Missouri — and we figured out the logistics. We asked: How long would a sing-along take? What happened if the crowd didn’t sing? What happened if my guitar strings broke? What happened if the crowd watching the live stream at home couldn’t hear? What if I tripped over my guitar cable?
I was worried about everything that could go wrong. So was the TEDx team.
But I started thinking about what’s come before. Life’s always been a series of escapes for me, one larger than the last. Every few months, I do something stupid, get myself into trouble, and then figure out how to get out of it.
And slowly, I started to learn that I was just dumb enough to consistently put myself into strange situations, but I was also just smart enough to come out of them okay. That time my sister and I walked across the Moroccan border? We ended up having an amazing trip. That time I went to China with the wrong visa? I fixed it and got to experience the Olympics.
That time I my Ford Explorer nearly caught fire on I-70? I still made it to the game.
So I know: Whatever I get myself into, I can get myself out of. I try to stay in over my head at all times, but I always go into it knowing that I have a history of surviving whatever goes wrong.
Then TEDxMU came around. I had the guitar tuned. I had the thing mic-ed. I was ready for disaster.
It never came. I started singing. The crowd started singing. I started playing.
I don’t know how I pulled it off. But I knew going in that I would. I believed fully that somehow, on stage, I would do what I had to do to survive the talk.
That was all I really needed to get up there and give a crazy thing a try.
Tomorrow, I will speak at TEDxMU, the TED-approved event happening here at Mizzou. I’m enormously excited to be a part of the speaking list. Astronauts, businessmen, leaders and thinkers will be speaking.
And me, somehow.
Of course, I’m not content giving just any speech. I decided that if I was going to give a TED talk, I was going to make it big.
This is a common theme among my talks. Last summer, I spoke at an event called Disruptathon about a man named Skeet. I had a speaking coach tell me that my speech didn’t make any sense.
I was named runner-up for best presentation.
I spoke in December at NewsFoo. A friend told me that I was an idiot. You’re getting a chance to speak to a big room of powerful journalism folks, and you’re not going to say a single word about your business? You’re going to spend five minutes talking about your mother? That’s just dumb, Dan.
So tomorrow? Tomorrow I will get up in front of the TEDxMU crowd and give a 13-minute talk about U2. I will play guitar for the crowd and lead a sing-along, even though I’ve never played guitar in front of a hundred people before, and I’ve certainly never lead a sing-along before.
I do not know how it will go. I hope it will go well. I’ve looked back at my lessons from Disruptathon — know your audience, show (don’t tell), and use your time wisely — and I think I’ve got it down for this thing. I’ve also kept in mind all those times that things have gone horribly wrong. Even in those times, things have always eventually worked out okay.
I’ve practiced the speech. I know the chords to “Elevation” as best I can. When I put public speaking on my List of Things for 2012, and I meant it. No backing down now.
The only thing left is to get up, smile big, be confident and give the most ambitious, most absurd talk I can.
Probably around January of 2010, a few months before I left my desk job in San Antonio, I started having these daydreams. I’d be driving along I-35 to a Spurs game, and I’d start fantasizing about just driving beyond, past the city limits, past Austin, past Dallas. I’d started to think that I wasn’t ever going to leave Texas, and then I’d be driving up I-35, and I’d think: Why not now? Why not just leave? What’s stopping you?
And then I’d remember what was stopping me: I had a life in Texas. I had a job. I had an apartment. I had stuff.
I wasn’t just going to bail.
But the fantasies never stopped. They kept nagging at me. I couldn’t shake the truth: I wanted to do something more. I wanted to define my greatness and then go out and make it so.
I’ve learned since that what I felt is common among the American worker. People are unhappy with their jobs. People want more with their lives.
Sometimes, it’s only when the dream keeps coming back that we actually admit that it’s time to do something big. When that dream nags at you, you have to explore it. Maybe it’s just about making time for a side project. Maybe it’s about going wild, quitting your job and chasing a career or a business or a lifestyle that makes you happy.
I had this dream of getting out of Texas. I wanted to do something big: I wanted to start Stry and get into the larger conversation about the future of journalism. But it wasn’t until the twentieth or fiftieth time that I had that day dream — I-35, heading north, just going without looking back — that I admitted that it might actually be time to think about taking action.
I did eventually leave that job in Texas. I did chase the dream I had for Stry.
But when I left, I drove right past the exit for I-35 North.
Turned out that the road I needed to take out of Texas was I-10 East.
Let me take you back to 2009. Newspapers were slashing staff daily. Jobs weren’t plentiful. A young, wide-eyed Dan Oshinsky was about to graduate from college.
And in the midst of all this, a strange thing happened: A big newspaper chain decided that they really liked me. They liked my attitude and my skills. They told me, straight up: We want to hire you. We don’t know what for yet, but we want you.
Over the next few weeks, I had a number of phone conversations with one of the chain’s executives. The chain had just launched a big blog project at one of their papers, and they seemed really excited about the numbers. They had an idea for me: Start a blog for our papers devoted to young people and business. We’ll give you $100k and a small team to start. Give it a few days and come up with some potential topics for us.
Understand this: I was coming out of journalism school like most J-school students. I had great clips and great ambition. I was fully prepared to start working for a newspaper on a city desk or a political beat.
I thought I was totally unprepared to lead an ambitious, new journalism effort.
I didn’t know anything about business. I didn’t read business blogs. I didn’t understand the market for business news.
The next week, I told the executive: I’m flattered, but sorry. I’m not your guy for this project.
Looking back, I’m stunned at how stupid I was. I can’t believe that I said no, and I can’t believe that I failed to even produce a single tangible idea for such a blog.
How could I have been so unresourceful?
Over the course of about 72 hours, I was given the opportunity to pitch something really impressive. I had everything I needed to start such a project: I was ambitious, I had blogging experience, and I had a good sense for how to create a voice that was readable.
Sure, I didn’t know anything about business news. But here’s the thing: I knew plenty of people who did.
I didn’t ask for their help.
I could’ve turned to my network — my friends, my former bosses — and asked for input on ideas. I could’ve generated a really impressive proposal for that blog.
And I didn’t even think to ask.
What I’ve learned since is the importance of a really good conversation. You need people who can advise you, guide you and — most importantly — ask the kind of questions that will help lead to you the right answers. When you have an opportunity, talk about it with smart people. It’s amazing how a good conversation can really open your eyes to your full potential.
I was reminded of that last week. I was down in Springfield, taking meetings for my upcoming reporting experiment with Stry.us. And in the course of a half dozen conversations, I started to notice some new themes popping up. I suppose I had been thinking about these changes for some time, but it wasn’t until I started really talking it through with others that I realized how big these changes were.
I can’t begin to tell you how thankful I am to have smart people on my side, asking good questions and helping guide this project towards an even more awesome future. Stry.us will be be stronger because of their curiosity and wisdom.
When you’re starting something new, you have to keep your eyes open. You have to listen fully.
And for goodness sake: When you’re lost, don’t be afraid to ask. You don’t have to go it alone.
Danielle LaPorte, Internet thinker person, asked a question on her blog today: “What’s one dumb thing that you used to believe in?” As someone who says/does a lot of dumb things, I felt qualified to provide this answer:
¶¶¶
I used to believe in radical, blunt honesty. In speaking without filter. In giving advice even when it wasn’t asked.
This is a really good way to lose friends and alienate people.
It’s also a really good way to completely diminish the power of your relationships. The more open I was with other people, the less open they wanted to be around me.
Because being open with others started out with a simple goal: Tell the truth, always, even when it’s uncomfortable.
But I started to realize that it was devolving into something worse. I wasn’t telling it like it was; I was using the veil of truth to be condescending.
I was turning into a dick.
I still believe in the truth, and telling it. But I’m also buying into the filter. Into giving advice only when it’s asked, and to being honest without needing to disclose everything fucking thing.
Once, I thought it wasn’t okay to stay quiet, even for a moment. You have a voice, Dan. Use it!
That was a dumb thing to believe in. I’ve learned: The people who talk most sometimes get heard least.
So shut up and listen, Dan. When it’s your turn to speak, nobody doubts that you’ll have plenty to say.
