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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.

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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.

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The March Edition Of The Awesome File.

Every month, I put together a list of 10 things to inspire you to do more awesome work. (Work results may vary.)

Let’s get into it:

1. That Awesome Photo (at top)

DC in the morning after a full moon. Amazing shot.

2. This Awesome Letter


This is the letter Tim Burton sent to Disney when he was 18, trying to get advice about a cartoon he’d done. It’s an awesome moment from an artist who was about to do big things.

3. This Awesome Desk


This is the desk everyone is going to be asking for in 2013.

4. This Amazing Old Subway Poster


It was part of a series of awesome posters for the London Underground.

5. This Awesome Rap Song

Never change, Megan Mullally and Nick Offerman.

6. This Awesome Reddit Thread.

A worthy, awesome question: If someone gave you the entirety of Wikipedia from 100 years in the future for only 10 minutes, what would you read?

7. This Awesome Taylor Swift Remix


The Internet is awesome, sometimes.

8. This Awesome Moment


These Atlantic City firemen got sworn in on an iPad. It’s the future.

9. This Awesome Lessons

Here’s 14 lessons from a Wall Street guy’s 80 years on this planet. Really good stuff.

10. This Awesome James Bond Remix


50 years of Bond in 4 minutes. AWESOME.

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Too Late/Too Soon: The End.

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

 
So if you’re ever trying to decide whether or not to end a project you’ve been working on for the previous 30 months, here’s a recommendation:

Drive across Kansas.

Take a few hours to drink something strong. Sleep it off.

Then drive across Wyoming.

After Springfield, the team shipped off to various parts. The rest of the team got jobs. I headed west for a few days, to visit friends, and to think.

I’ve always found that my best thinking happens when I’m moving. Sometimes, it’s when I’m actually running. Sometimes, it’s when I’m just traveling long distances.

It sounds dopey to say it aloud, but I find that the literal act of heading toward a fixed destination makes me think about where I’m going in my own life.

Some 25 hours in the car across the Midwest and the West gave me time to reconsider where Stry.us had taken me. It had given me amazing opportunities. It had taught me far more than I could have ever imagined about business, and about working with teams, and about learning how to screw up royally and then get up off the mat. It showed me what I could do when I put the right parts in place, and it showed me that I wasn’t going to be able to go back to some desk job.

It humbled me.

But I also started to think about whether or not I wanted to keep it going. It felt like Stry.us was just starting to grow and get moving. Was now the time to put it aside to go work on something else?

I thought about what I had at my disposal with Stry.us. I had a really great website. I had a little bit of attention for the project. I had plenty of time.

But I also thought about the timing for me. I had some momentum, personally. I had a lot of new things I wanted to learn.

And with Stry.us, it had been 2.5 years. Either it had to make money, or I had to.

In the end, it was time to face a hard truth: I was ready for something new, and that meant that Stry.us had to step aside.

It was hard putting the project behind me. It felt like I was breaking up with a longtime girlfriend. I wasn’t really sure who I was if I didn’t have “Stry.us” attached to my name.

But in time, I started to recognize it for what it was: An amazing experience, and an amazing opportunity. It carried me so far, and I’m not really sure how. But I’m sure thankful for it. I got to speak at conferences because of Stry.us. I got to travel all over the country for it — to Biloxi and Boston and St. Pete and Phoenix. I got to tell stories because of it.

It was a big break for me, and it really sucked letting it go.

It’s been months now since I’ve done work for Stry.us. But something funny happened last week. I was at a party here in New York. A buddy introduced me to his friend. “This is Dan from Stry.us,” he said.

His friend looked at me. “Stry.us? Big fan.”

I still haven’t stopped blushing over that. It was a hell of a lot of work to make all of Stry.us happen. It’s nice to know that someone noticed.

I wish it wasn’t over. Maybe Stry.us will continue in some other form — the lessons from it sure will.

But for now, it’s been left behind, somewhere in the Ozarks. For me, for my team, for everyone who supported us, it’s onto the next thing.

Sometimes, you have to know when it’s time to move onto the next. I think I made the right choice this time. I hope I did.

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Too Late/Too Soon: The Team.

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

 
A year ago this month, I called up Jordan Hickey and told him I wanted him to be my editor at Stry.us. It was a strange conversation. It came a little out of the blue.

But I knew I wanted it to be Jordan. We’d known each other going back to our freshman year at college. I knew he was the guy for this project.

Here’s the conversation we’d had in March 2011, when I was stuck with Stry.us:

Jordan: how about you? — grant proposals coming along?
me: meh, kind of mired in the dip right now
me: that point where i’m getting frustrated and considering the ‘what if this doesnt work out’ part
Jordan: have you heard back from any places?
me: i mean, i’ve been rejected plenty
me: that doesnt really bother me
me: the funny thing is, im getting plenty of positive feedback from reporters and journalism people
me: i just need a bit more success with the foundations and such
Jordan: hmm
Jordan: i really do hope you keep with it, man — i was always really impressed by everything stry did
me: thanks, man
me: appreciated
me: i mean, im still here working on it
me: i still think it has a ton of potential
me: so we’ll see what happens

Jordan had stuck with the project since the beginning. That meant a lot to me.

And it meant even more when he decided to quit his job and come work with me in Springfield, MO.

And with Jordan on board, the team really started to fill out. Sarah signed on, then Roman, then Zach, then Bari. And some amazing people agreed to help us: The Library in Springfield, MO; Dave and his newspapers in the Ozarks; Jason and his political website in St. Louis. And the guys at Sparkbox in Dayton.

Stry.us had always been a project built for a larger team.

It just took two years to actually put together the team.

But with them, it’s amazing what we got done in a summer. We launched an amazing website. We told amazing stories. We put on a live town hall. We pumped out some eBooks.

Something as big as Stry.us demanded an awesome team. I needed them, and I’m so thankful for them. They made that Springfield project something fantastic. I could not have done that alone, and I would not want to try something that big without a team just as great as them.

I cannot believe, looking back, that I had the nerve to even try it alone. I can’t believe I was that dumb. I can’t believe I made it as far as I did alone.

I wouldn’t do it alone again. Something like Stry.us is better shared.

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Too Late/Too Soon: The Break.

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

 
The big break probably came in April 2011, when the University of Missouri decided to award me a fellowship to work on Stry.us. They gave me money to keep working on it, and they gave me time to work on it.

Finally, I felt like I had permission again to work on this big thing. I had the money, I had the time. I had new resources at my disposal. I had no excuses.

The problem, of course, was that I still had no idea what Stry.us was, or what I wanted out of it. Money? Experience? An opportunity to lead?

So the real break came later, when months of idling had brought me to a better realization: I had the time to do whatever I wanted, but I wasn’t going to do it alone. I wasn’t ready to do it alone.

Looking back, I’m amazed that I went so long without help. I can’t believe I tried to do it alone like that. I can’t believe I was crazy enough to try.

I just didn’t know any better, and I was stubborn enough to believe that I could pull it off by myself.

But eventually, time showed me that I had to have others onboard with Stry.us. If I really wanted to do the work, I had to bring other people on board and chase a single goal.

That realization was a huge, huge break.

I’m so thankful for what happened next. Without my team, I’m not sure where the heck I end up. Not here, I’d bet.

Photo of those two paths comes via.

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Too Late/Too Soon: The Wandering.

Ramas

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

 
After I left Mississippi, I went through a long period of… well, nothing. I wanted to belong to something. I wanted to be part of something. I wanted identity.

Instead, I had these stories from Mississippi, and some business cards, and that was it.

What came next was this period where I couldn’t really tell people what I was doing, because I wasn’t doing anything. I could tell them what I’d done. Or what I wanted to do in the future.

But in the present? I had nothing. I was lost.

Part of the problem with doing the work is that you’re never really sure that the time is right for your work. And you use that as an excuse to avoid doing the work right now.

I know I did, sometimes.

But this period of wandering — and it lasted a few months — was really good for me. It showed me all the things I needed to do. It showed me what happened when I didn’t put in the hours.

It showed me that the difference between failure and success hinged entirely on my commitment to this work.

Without the wandering, I didn’t have anything to compare my successes to. I didn’t know how low I could go, and how quickly I could get there.

I’m not glad I went to that point. I’m mad I lost so much time there.

But because of it, I understand now. The time I had was the time I had. The work had to happen, now, and it had to be done, now, and if I didn’t do it, now, I was going to have to get myself a job at Arby’s or something — soon.

The time had come to stop wandering, and to start working harder than I’d ever done before.

Of course, I still needed a sign that the work was worthy.

Then came the break.

That photo of being lost in the trees comes via Yulen Zoom.

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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.

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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

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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.

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