Two Great Questions: Why Not? And What Else?

There’s a pizza place around the corner from me that’s pretty good. They’ve got a good pepperoni and mushroom slice, and they’ve got this chicken caesar pie, too, if you’re into something kinda different.

But what I like most about this pizza place are the guys behind the counter. There are two guys I see most often working the counter, and they’ve each got a catchphrase.

The first guy waits for you to order, and when you announce your choice of slice, he says, “Why not?”

Order another slice, and you’ll hear, “Why not?”

Hang around the restaurant for 10 minutes and you’ll hear him say it over and over again.

The second guy behind the counter has a different way of responding to each order. Each slice is followed by a simple question: “What else?”

And usually the customer pauses and says, Well, maybe that one? Or that one?

“What else?”

Maybe that one…

I really like this pizza place, because I really like those two questions. I like how, subtly, really good questions can challenge a captive audience. The right questions can force someone to take action that they might not otherwise take.

I’d like more people to ask questions like that when they’re taking on new work. Something too big? Too scary? “Maybe I shouldn’t do this,” you find yourself saying.

Well, why not?

And when you think you’ve hit the end of some work, and you’re trying to figure out if there’s anything left to do:

Well, what else? Is there something more to do?

Those two really good questions could unlock a lot of really good work. Don’t thank me, though. Thank the pizza place on the corner.

———

That photo was taken by Peter Bravo de los Rios for Unsplash.

The Easy Way Out.

“The journey is all. The destination is beside the point.” — Leo Babauta

 
Let me pose a hypothetical to you for a second. Tomorrow, I’m going to give you the chance of a lifetime:

I’m going to make you a lottery winner. You’re going to get $20 million. You’re never going to have to work again.

But there’s a catch: In exchange for that $20 million, you’re also never ALLOWED to work again.

You can take the $20 million, and never work another day in your life — never ever — or you can stay on the path you’re on, grinding it out, trying to make it in this world.

What do you choose? A life without work but lots of money, or a life with a lot of work and whatever money you can make along the way?

If it’s me, I take the latter. Yeah, the $20 million would be nice for a while. A few months on the beach somewhere, swimming and napping and drinking away the day. I could do that.

But after a few months, where would I be? What I’m doing matters to me. I want to make a big contribution to this world, and my work is largely how I make my stamp. Take away that, and what am I?

People say they want the easy way out, but I’m not so sure I buy that. The road ahead is tough. It’s going to suck.

But it’s also really rewarding. There is satisfaction in putting in the work, day in and day out.

So me? I’d reject the money and stick with the road I’m on. I know it’ll be rewarding. I know it’ll be hard. Maybe it’ll make me a little money along the way, or maybe it won’t. But it’ll my road to make.

I probably won’t get the months and months of drinking on the beach on this path, but if I do good work, I might get a few good weekends a year in a sunny place. That’d be alright by me.

Too Late/Too Soon: The Fear.

When do you know that it’s time? The fourth in a month of posts about how I learned to stop worrying, buck up and do the work.

 
The fear caught up to me on the flight to Mississippi. I remember looking out the window as the flight came over Gulfport. I didn’t recognize anything.

I was alone, in a state I’d never seen, in a city where I knew no one. I essentially showed up with nothing more than a dream and a name — and nobody had ever heard of “Oshinsky” or “Stry.us.”

And then I landed, and my cell phone didn’t work for two days. It couldn’t find the satellites.

I felt very, very alone. I was equal parts cocky and terrified.

I remember calling a friend in Kansas City. I was in my hotel room at the IP Casino in Biloxi. I’m moving to Mississippi to do some reporting, I told her. I don’t think she believed me.

I don’t think anyone really believed me at that point, actually. My bosses, my parents, my friends — they all knew that I had the ambition to do something as audacious as Stry.us. But no one knew if I actually had the drive to will something like that into existence.

And to do it solo! That would be a challenge in itself. I knew nothing about business, and only a little about how to report from a foreign place. This was, at best, an unreasonably large challenge for a 23-year-old to take on.

The fear really hit on the drive to Mississippi. I think it happened as I got close to Biloxi, somewhere along I-10. I started to realize: I’m doing this! I’m moving here! This is actually happening!

And scarier still: The only thing between this working and this failing is you. Only you can decide how big this can be.

Hoo boy. That’s a lot for a kid to stare down. And I really was a kid: An ambitious, hungry, dumb kid.

The timing was right, but I was scared. I had a big apartment with an IKEA table and a Target futon — and I never bothered to put the futon together. I just slept on the cushions all summer. I ate peanut butter and jelly and tuna fish all summer. There wasn’t anything stable about my living conditions.

And the reporting was as strange as anything I’ll ever do. I had stories to tell, but no one knew my name. I worried that they wouldn’t talk to me. I worried that they wouldn’t take me seriously.

I think one thing that saved me was the humidity. I was always sweating in Biloxi in that 100+ degree heat. But I would’ve been sweating if it was 15 below — I was so nervous!

The humidity masked the flop sweat, I think.

And after a few introductions to sources, I started to feel confident. When I got the first story up, I felt like I had something. I could show off my work.

Better still: The people in Biloxi were used to being interviewed. They’d all been quoted somewhere or another. But they all felt like they had more stories to tell.

All of that helped keep the fear at bay. It never really left. But I settled down enough to go out and do my job, and keep going. I knew I had three months to do this reporting. Every day I lost was a day I couldn’t get back.

That helped keep me going.

I also didn’t fully realize how insane I was to be living in Mississippi by myself and doing Stry.us. I wasn’t aware of how crazy this thing was.

That helped, too.

Too Late/Too Soon: The Dream.

#dreaming

When do you know that it’s time? The third in a month of posts about how I learned to stop worrying, buck up and do the work.

 
The dream really started sometime in the spring of 2010. I’ve told this story a few too many times: I was working at a TV station. I was frustrated with my place in the journalism world. I decided I wanted to do something about it.

It was time to do big work. I was sure of that.

So I came up with a spinoff on the original de Tocqueville journey. I called it Four Days in America. I’d go to a place for four days. Do some reporting. Package it all into a big story. And then ship off to the next place

I’d see the country, tell some amazing stories and find myself along the way.

Dumb idea, Dad said. You’re going to travel all across the country, by yourself, and move just frequently enough to never make friends? Are you just trying to isolate yourself, Dan?

And he was right. To move from place to place, with no consistency, with no backbone to work off of? It couldn’t work. Four Days in America was a hopeless idea. To even attempt something like this, I needed a support system.

So I went to the backup plan: One place, three months, tons of reporting. Tell one great story. Chase one big thing at a time.

I had a few places in mind, but one stuck out above all else: The Mississippi Gulf Coast. It was five years after Katrina. Oil was leaking out of the Gulf. The economy was terrible.

I didn’t know anyone there, but I decided that if I could put a few pieces in place — a place to stay, a story to cover, a website to publish on — that I might be able to make something of a summer in Biloxi. I knew that having a structure was going to be a game-changer for me.

Best case, I could turn my little reporting enterprise into a business. Worst case, I’d have a nice portfolio of clips to apply for future jobs.

Well, that wasn’t actually the worst case. The worst case was that I’d quit my job, move to Mississippi, and then get scared. I’d back off the story.

I’d quit Stry.us, too. I’d leave Mississippi with nothing.

That really scared me. I couldn’t take two steps back. This was my time to do something big.

I knew I had enough to start. I bought http://stry.us. I put up a Facebook page. I told my bosses that I was going to leave my job in a month and move to Mississippi.

My parents thought I was trying to punish myself. They thought that moving to Mississippi, in July, was a sort of self-inflicted torture.

I thought it was a way forward. I didn’t know what it was leading toward, but I knew that something would come of all this work.

But that’s all it really took to start: A dream, and an uncertain goal, and the knowledge that I had a moment to actually do something big.

It was going to be a big success, or a big mess, but I was going to do it — and do it now.

Photo at top by Jochen Spalding

Too Late/Too Soon: The Call.

phone

When do you know that it’s time? The second in a month of posts about how I learned to stop worrying, buck up and do the work.

 
Long before I ever started Stry.us, I had this dream for a journey across America. A friend called it my De Tocqueville trip, and that was pretty accurate. It was 2007, and everyone was talking about Barack Obama. I’d watched him go from anonymous politician to Presidential candidate.

I wondered: Who else is out there? What local politicians and leaders are out across our nation, ready to take the next step and lead our country? I wanted to go out and interview them.

But I never left on that journey. It was too big. Too scary.

Too much.

I had a lot of ideas like this. My dad would bring them up sometimes. Such good ideas, he’d say. But you’ve got to see one of them through.

And I knew it, too. But I didn’t understand how to make the follow through happen. I wasn’t sure I could learn.

I was going to be a reporter and a writer. I could tell stories. I could interview people. I could take photos.

What else could I do?

What else should I do?

I started to divide the world into categories. There were people who made stuff. And there were people who didn’t.

I wanted to make stuff. But I wasn’t ready to take on projects that failed. I had a shitty attitude. If something didn’t go my way, I got bitchy.

I talked a big game, but I wasn’t willing to do the work to back it up. I was afraid, and I didn’t know how to get unafraid.

It took a dream — a really big dream — to help me find the courage to stand up to the fear.

Photo at top via Nicholas Vigier.

Too Late/Too Soon: An Introduction.

When do you know that it’s time? Introducing a month of posts about how I learned to stop worrying, buck up and do the work.

I’ve had a song stuck in my head for a few weeks now, and it just won’t leave. It’s called “Too Late Too Soon,” and it’s by a Nashville musician, Will Hoge. The song is technically about love lost, but that’s not what I heard when I first heard it.

Hoge sings:

But you say that it’s too late too soon
And your eyes ain’t the only thing blue
I try and I try just to make one thing true
But sometimes it’s just too late too soon

But what I heard was this: You wanted something, and you worked for it, and the timing just never worked out.

There were a handful of points during my adventures with Stry.us where I realized the importance of timing. I’d be doing work that I thought was really great, but then I’d try to get the work out into the world, and I’d get pushback. Sometimes, they weren’t ready for the work I was doing. More often, I wasn’t ready for the work they wanted.

The cycles weren’t lining up, and I was frustrated.

I tried and tried, but you can’t change timing. Sometimes, it really is too late, and sometimes, it really is too soon.

So this month, I’m going to write exclusively here on the blog about the concept of Too Late/Too Soon, and walk you through the entirety of Stry.us. I hope that people out there who want to do great work read these posts and understand: We all go through this. We all struggle with it.

With patience, and hustle, and time, the work can eventually get out there.

Come along this month with me. Learn from my mistakes.

We have much to learn about our work.

The Experts Are Probably Wrong.

“Whatever you believe / You might be wrong.” — Paul Thorn

 
When I was in college, I was part of a small group of journalism students who took classes that were basically about the Internet. This was 2005 or so. Journalism on the Internet wasn’t new, but it was for journalism schools.

Anyway, we spent a lot of time in class talking about things that seem funny now. Was Facebook journalism? Was blogging?

Again: It was 2005.

But one thing was made very clear to me by my professors, and by pretty much every professional person I knew: We had to be careful about what we posted online. If we weren’t vigilant, we’d never get a job in the real journalism world!

Yesterday, my current employer hired a guy whose Twitter handle is @WeedDude.

Really:

And then there’s stuff like this:

And this:

And this:

And this:

And here’s a presentation that the CEO of my company likes to give at conferences. It includes this slide:

And I could go on and on. Just know: All of that comes from respected, professional, important people who make stuff in our world.

Point is: Whatever the experts are telling you, there’s a good chance they’re wrong. Seven years ago, every professional journalist in the world would’ve told you that professionalism came first. That keeping the appearance of seriousness mattered.

It turned out that they were wrong. Newspapers might’ve been built for professional-looking/sounding reporters, but the web is a wonderful place where strange/eccentric/bizarre people flourish. Weirdness is celebrated here.

Anyway, if someone tells you something’s for certain, there’s a good chance they’re wrong. Don’t blindly accept the advice of experts. Question them. Challenge them.

Just FYI.

Seriously, Penny Lane.

“I always tell the girls, never take it seriously. If you never take it seriously, you never get hurt. If you never get hurt, you always have fun.” — Penny Lane

 
With all due respect to the immortal Penny Lane of the immortal film, “Almost Famous”:

That’s a load of crap.

Take your work seriously. Work hard. Throw yourself into what you do.

Overcommit to the work.

Yes, you get hurt doing great work. You get pushback. You run into haters. You struggle.

But if you never get hurt while doing the work, how much were you really putting into it?

You have to take it seriously. You have to get hurt sometimes.

Anything else is just work half-assed.

Finding The Difference.

“When everyone has good players, teaching will be a telling difference.” — John Wooden

 
Assume, for a second, that everyone in your world is smart. That everyone in your world is talented.

So, here’s the question: What’s the difference between you and them?

For legendary UCLA coach John Wooden, it was teaching.

For you, it might be hustle.

Or teamwork.

Or focus.

And if you can’t answer this question — What sets me apart? — then here’s the bad news:

You’re playing on everyone else’s level.

And that’s okay. But if you want to do great work, you’ve got to figure out how to elevate your game.

Now’s your chance.

What Is Long, and What Is Not.

“The NFL isn’t a career — it’s an experience. Most careers last 40-50 years, and people grow old in them.” — Alfred Morris

 
Two things got me thinking:

The first is that quote, at top. It’s from Alfred Morris, the rookie running back for the Washington Redskins. (That’s a photo of him sleeping on the couch. He still sleeps on the couch when he visits his parents.)

NFL players don’t usually have that kind of awareness, but Morris really seems to understand what’s happening in his life. The NFL is something most players have worked for since they hit puberty. It’s all they’ve worked for. The idea that it wouldn’t be forever is…. well, impossible.

Understanding what the NFL is — a job, an experience — and what it is not — a career, a lifestyle — is going to change everything for Morris. It’s going to let him make the most of this incredible opportunity.

But most of us can’t tell the difference between what is big, and what is not. We see a half an inch of water and we tell ourselves we’re going to drown. We hit a bump and think it’s a mountain.

We lack perspective, and that’s one thing we need most to understand the road we’re on and the places we’re headed.

There’s a second thing. I had a Latin teacher in high school, Miss Cherry. One of her quotes comes to mind now: Ars longa, vita brevis.

Art is long, but life is short.

And in high school, I remember thinking: What the hell is that? Art is long?

LONG?!

But that’s exactly what Morris is talking about, too. It’s this idea that some things are forever, and some things fade away.

The memories are long, but the job is short.

The ambitions are long, but the opportunities are short.

We work to build things that are long — but ultimately, the one thing we know is that the chances to make them are short.

Make things now, with the time you have now. To wait is to discover that now is very, very short.

Photo at top of Morris comes via the Washington Post.