There Are No Off Days. (Jean-Ralphio and I Agree On This, Actually.)

Two things caught my attention last night and got me thinking about the work I’m doing right now. The first was this Instagram photo of the rainbow at the end of the road. (More on that photo in a second.)

The second was Jean-Ralphio.

Okay, not actually Jean-Ralphio, one of those strange, lovable TV characters on “Parks and Recreation.” It was actually Ben Schwartz, the actor who plays Jean-Ralphio on “Parks.”

I was just reading an interview with Schwartz from a few months back. He said something I especially loved about his own career so far:

“At the very beginning, I was a page at Letterman, and I freelanced for any place that would let me write any word. I wanted to do this so badly. Then when I got a tiny bit of success, I was petrified that I was going to lose it. I still feel it. House Of Lies finished filming, and I don’t know when I’m doing Parks again. The second that happened, I thought, “Fuck, I have to start writing. I have to keep myself working, because why else did I move to Los Angeles? If everyone else is working 9 to 5 every day, why shouldn’t I?” I wrote those postcard books, I’ll do short films for free, I like to keep myself creative. But there is an essence of “When does it end?” That drives me, and also gives me terrible stomach problems. The anxiety of not knowing what my next gig is keeps me hungry. I’m doing exactly what I’m doing, and I don’t want to fuck this up. There will be days where I’m not writing, but I’ll think back to when I was a page. I’d wake up at 6 in the morning, write monologue jokes as a freelance writer, go work the first page shift, sleep in the security office, work the second page shift so I could get some money, then I’d go take classes from 7 to 10 at UCB, then watch every show I could and take the last train home. I’d get four hours of sleep, and I did that for about two years. That guy would hate me if I took the day off today.”

That’s a hell of a fine reminder that there are no shortcuts. You do the work yourself. You finish what you start.

There is no plateau. There is no easy road. This life is not about a little bit of hard work and then a whole lot of coasting.

I have to keep slamming that into my skull. I’m still just learning how to do the work every single day. It takes discipline and practice, and I’m re-learning those traits, too.

There are no easy days. The work gets done, or it doesn’t. That’s my choice.

Sometimes, I have weeks like this — good weeks. Nothing big has gone wrong this week. I keep doing interviews with potential candidates for these Stry reporting positions, and the response to the project has been overwhelming. People seem to like the project! People seem excited about the idea! People don’t even seem to be insulted by the amount of money I have to offer!

And in a week like this, it feels like maybe, maybe I can just coast for a little. Things are going well. I can relax, right?

Wrong. So, so wrong, Dan.

The work continues. I can enjoy the satisfaction of a week like this, but not for long. The work doesn’t stop. There are new challenges, new opportunities. Shit I didn’t even know would happen is going to happen. I know it will.

There is so much more work to do. Gotta hire the team, gotta train the team, gotta get them out into the world, gotta find great stories, gotta get these live events going, gotta keep my stakeholders happy, gotta build the community.

There’s so much work to do. Either I get it done, or I don’t. There are no off days here.

I know what I’m shooting for. I see that rainbow at the end of the road. That’s what I’m aiming for. But I’m also aware: When I get to that spot at the end of the road, I’m going to find my goals and ambitions and dreams have shifted. The rainbow is a moving target. It’s not as much a destination as an aspiration.

That’s what’s going to keep me hungry. I don’t know what the next thing is for me, but I can’t let up now.

In the meantime, it’s all about staying sane and getting happy along the way. The journey continues. The work must get done.

04/02/201212/02/2018

Good. Better. Done.

There’s a Bruce Springsteen anecdote I really love. By the mid-1970s, he had recorded and released two albums — two really good albums — already. But Springsteen felt the pressure to turn in a breakthrough hit with his third album. He feared that if the third album didn’t go big, he might be finished in the music business.

The first song he stepped into the studio to record for that third album was “Born to Run.” Even if you don’t know anything about Bruce Springsteen, you know that song. It is a legendary, epic rock and roll song, and you won’t find a rock critic or a rock fan who disagrees with that.

Except that at the time, Springsteen himself didn’t think so.

He spent six months — SIX MONTHS! — working on that song. He spent six months working on a song that doesn’t run even five minutes long.

Springsteen, the story goes, became obsessed with the idea of making the perfect rock and roll album. He wanted to make rock and roll clichés seem brand new. He wanted to layer sound upon sound and turn it into something grander than anything that had come before.

“Born to Run” was his first stab at that perfect rock and roll sound. So he worked and worked on the song. He tried to make it perfect.

What he almost ended up doing was smothering a classic.

See, Springsteen lost all connection with how the work is done. Later, he’d tell biographers that he’d been hearing a sound in his head, and he’d become obsessed with it. Problem was, he just couldn’t explain that sound in the studio.

Maybe there really were sounds in Springsteen’s head, but I don’t think so. I like to think that Springsteen was just hearing the voices that all of us who do the work hear — the doubts, the fears, the worries.

The things that kill good work.

All of us who are doing the work — you, me, Rock and Roll Hall of Famer Bruce Springsteen — are all chasing the same thing. We’re all trying to create work that lasts, that has impact and that matters.

But no matter what you’re building or doing, there are only three stages that matter when you’re doing the work:

Good.

Better.

Done.

You start the work. You improve the work. You get the work up to your liking.

And then you decide that it’s done, and you send it out into the world.

I’ll admit that I didn’t always understand this. After all, aren’t we all striving for a certain level of success? Don’t we have personal standards to maintain?

Certainly. And as you do the work, you’ll learn to reconcile “perfect” with “finished.” With time, it’ll make sense.

Just remember for now: You’re not doing the work just for the sake of staying busy, right? You’re doing the work because you want to get it done and get it into the hands of others.

If you keep holding onto the work until it is absolutely perfect, you will be waiting a very long time. Get the work done, and get onto the next thing. You might think that you should hold onto it, that you should chase perfection, but what you’re really doing is keeping yourself from moving onto newer projects and better work.

Imperfect is okay. What isn’t acceptable is idling. When the time comes to decide if the work is done, don’t hesitate.

Stop asking yourself, “Is it ready?”

Start asking, “Is it done?”

Once you start following those rules — Good. Better. Done. — you’ll start creating a lot of work. Some of it will be good, and some of it will not.

But you won’t really know which is which until you get it out into the world.

———

That photo of Bruce Springsteen was taken by Takahiro Kyono and reused here thanks to Flickr and a Creative Commons license.

03/30/201206/11/2012

This One Daydream I Had: Get on I-35 North. Never Look Back.

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.

People are also scared to do. The fear of failure is often stronger than the desire to break away from a job that makes you unhappy.

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.

03/27/201207/25/2012

Help! I’m Sending in an Application For a Job in Journalism!

I posted the job openings for Stry.us on JournalismJobs.com last week, and since then, the apps have been rolling into my inbox. Some are exceptionally good. A few have been exceptionally bad.

Many have left no impression on me whatsoever.

That shouldn’t happen. I’m seeing apps from talented people who just failed to catch my eye. Remember, Future Job Applicants of Tomorrow: The app is your opportunity to sell me on you and your skills. If it’s not eye catching, I’m not hiring.

Some of you guys really need help. So here’s some unsolicited advice for job seekers — specifically, college students and recent grads applying for a reporting job.

There are five questions I’m thinking about when I open your job application email. They are (in this very order):

1. What happens when I Google your name? You should know the answer to this already. I’m hoping to see a portfolio site, some work you’ve done for a news outlet, and maybe a social media profile or three. I will not look past the first page of Google results.

2. Do you have a website? If you’re selling yourself as a modern reporter, you must have an online portfolio. It does not have to be terribly fancy. It can be a blog on WordPress or Tumblr or — and I have seen more than one of these this week — Blogspot. It can be an about.me or a flavors.me page. It must have your contact information, a brief bio, and a list of links to your recent work. It must have been updated in the previous three months.

3. Do you have a LinkedIn page? I want to see where you’ve worked, and I want to see that you’ve actually connected with co-workers. I want to see that it’s been updated in the previous three months.

4. Can you prove any other forms of digital literacy? I want to see that you have an account on any of the following sites: Twitter, Flickr, YouTube, Vimeo, Instagram, Quora. Just having a single account on any of these sites proves that you actually use the Internet, which is good. (One job applicant this week offered to snail mail me a resume and clips. Another sent me a resume in a file format that I’d never seen before. These are equally bad things.) I want to see that you use the Internet.

5. How organized is your resume? Your email to me? This is important. I want to see that you know how to correctly format an email. When you send me a link, I want to know that you know how to use anchor text. I want to see that you can write succinctly, that you can spell my name correctly, and that you use paragraphs when writing. I need to see that you have an understanding of how words, pictures and links should be laid out visually.

If you can do those things — pass a basic Google test, maintain a website, keep a LinkedIn page, prove digital literacy, and keep your email/resume organized — then the chances of me following up for an interview are infinitely higher. I am likely to pass on you — even if you’re an award-winning reporter who does rocket science in your spare time — if you cannot answer these questions.

Because here is the simple truth: If you fail the five questions above, what you’re really telling me is that you don’t know how to do work on the Internet. And this job I’m hiring for — and pretty much any job in journalism today — is Internet-first.

Before you click “send” on that application to me, go through those five questions. If you can’t answer one, then you better get moving on the answer.

I’m going to close the application process for these Stry.us jobs in two weeks. Get going, guys. Wow me with your apps.

03/26/201205/30/2012

When You’re Lost, Don’t Be Afraid to Ask. And Definitely Don’t Be Afraid to Listen.

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.

You shouldn’t.

03/23/201205/16/2012

The ‘Cool Runnings’ Theory of Doing the Work.

I’m going to guess that you’ve seen the movie “Cool Runnings,” simply because I’ve never met anyone who hasn’t seen “Cool Runnings.” It’s one of my favorite films, the based-on-a-true-story tale of four Jamaican guys who somehow qualify for the Olympics as bobsledders. It’s funny, and goofy, and inspiring.

It’s also, it turns out, a really interesting case study in learning how to start doing the work.

Think about the beginning of the movie. We meet our four intrepid bobsledders in unlikely places: Three are trying to qualify for the Summer Olympics in track, and one is a pushcart driver. But when the track thing doesn’t work out, they come together to try to qualify for the Olympics in bobsled, even though they’ve never seen snow, and the Olympics is only a few months away.

And somehow, they qualify for the Games. These four men — through sheer willpower, and also a few classic Disney montages — put in the work needed to learn how to bobsled, and they make the Olympics.

But on the first night of the Games, disaster strikes. They can’t get into the sled fast enough, and the driver, Derice Bannock, has a bad race, and Jamaica finishes the day in last place among all teams.

Then comes the key scene. The whole team is back in their room in the Olympic Village. Derice and his coach, Irv, are talking about what went wrong. Derice suggests that maybe they don’t know enough about the race course. Maybe they don’t know about bobsledding to win.

And that’s when their coach says:

“You know the turns! You know everything there is to know about this sport!”

Think about that for a second, and strip away the fact that this is a Disney movie. Imagine it by itself: An Olympic-caliber coach telling his team, You know everything there is know about the sport, even though you just started learning about it a few months earlier.

That sounds outrageous, and it is. Of course they don’t know everything about the sport! Hell, it’s not even clear that a single member of the team could name someone besides their coach who’d ever competed in an Olympic bobsled event.

But what if I told you that their coach was right? What if I told you that they knew everything they needed to know? — to start, at least.

What do you really need to compete in a four-man bobsled race?

1. A sled
2. A bobsled track
3. Four really big, really strong, really fast men
4. Four helmets
5. Ice

And that’s it. You don’t need fifteen years of bobsled experience to start. You don’t need to know who won the four-man event in the 1984 Sarajevo Winter Games.

All you need is a sled, and a track, and four dudes, and some helmets, and some ice, and you can start racing.

Again, here’s the key concept: That’s what you need to start racing.

Yeah, to win a gold medal, it’s going to take years and years of practice. It’s going to take thousands of hours of work, and then some luck, and Jamaica wasn’t even close to having enough practical experience to win.

But to start, they had everything they need to know.

That’s the idea I want to drill into your heads. If you’re thinking about becoming the world’s best painter, well, yes, it’s going to take some time. You’re going to have spend a lot of time painting, and you’re probably going to spend a lot of time studying other painters.

But to start? All you need is a brush, a canvas, some paint and a little free time.

The world’s best basketball players all started with a ball, sneakers and a court. You think Michael Jordan waited until he’d watched a decade of basketball games before he felt he had enough basketball knowledge to pick up a ball?

Hell no.

The truth is, to start, you don’t need to know all that much. So start before you’re ready, because as Travis Robertson once wrote, you won’t feel ready until long after you’ve already started.

Let me give you another example. I was at a startup event in the fall and heard a guy pitch a lending business. He talked about how he’s been studying the field for five years, reading everything he can about lending, and he’d finally decided that he was ready to start.

The judges asked him what he’d actually done for his business idea in those five years.

Well, he said, I’ve read the books, and I’ve…

No, no, the judges said. What have you done? What actual work do you have to show us?

Nothing, he said.

And where do you think you’d be if, five years ago, you’d started building something instead of just thinking about it?, the judges asked.

The man’s face went blank.

You don’t need to know that much to start. You just need to know that you can do the work, and that you’re passionate about doing the work.

You need to start before you’re really ready to start, because that’s when you’re going to learn the most about what you’re doing. What you’ll read about in books is helpful, and important, but it’s nothing compared to the self-discoveries you’ll make along the way. The most important knowledge is what you’re going to learn during the process of the doing.

If you already know what you want to do, then ask yourself: What are the most basic tools I need to start?

If you have them already, then the only thing truly keeping you from starting is you.

03/19/201203/19/2012

Lovers of #Longreads Wanted: Stry.us is Hiring For Our Next Reporting Project!

I’m hiring four reporters for the summer for stry.us. Send your stuff to [email protected].

I’m looking for lovers of longform for a summer-long reporting experiment in the Midwest. You’ll be working with Stry [pronounced STOHR-ee], a new reporting agency that’s trying to take a snapshot of life in 2012.

I’m looking for reporters who love to listen, who stay persistent on new beats, and who just can’t get enough of stories.

The job is for three months this summer. Money, food and shelter are included. You’ll need to find your way to the Ozarks, too.

If you’re curious, click here and send me three things:

1. Your résumé
2. Your online portfolio
3. Two links to awesome stories you’ve read this month

I don’t care what type of stories you specialize in. If you love stories, and you want to be a part of big experiment in storytelling, I want to see your stuff.

No cover letters, please. If I like you, we’ll talk.

-Dan
[email protected]
@danoshinsky

(FYI: Stry.us is undergoing a facelift right now. I’ll lift the lid on the new site in April. In the meantime, if you’d like to read some old stories from Stry, you can check them out at this link.)

03/17/201203/17/2012

The Difference Between Patience and Persistence.

I remember watching my little brother go fishing once. He was in fourth or fifth grade at the time. You have to understand that my little brother is highly allergic to fish. The kid’s face puffs up if he so much as walks past a Benihana.

But he sat on the banks of that river for three, maybe four hours with a fishing reel. Cast one out, reel it back in. Cast one out, reel it back in. He wasn’t going anywhere until he caught something.

Now, I don’t know what he thought he was going to do when he actually caught something, since he couldn’t actually touch the fish. But he’d deal with that when that time came. First he’d reel something big in, then he’d figure out how to get it onto land.

That’s how my family goes about doing the work. We finish what we start — even in situations where the finish line seems quasi-unreachable. We hang around longer than anyone would reasonably expect us to.

Some people call this trait patience, but that’s not quite it. Patience needs to be paired with something else to be worthwhile. By itself, patience is just the ability to tolerate the passing of time.

Patience is for people who don’t have the balls to get what they want.

What you really want is to pair patience with persistence. Persistence is the ability to push and push and push and push. It’s the ability to be stubborn in the best possible sense of the word. It’s the ability to be tenacious in pursuit of dreams.

I had that in mind when I heard this clip from This American Life’s Ira Glass. He says, and I’m paraphrasing here: When you start working on something, you will not be able to do the work like you want to. You have to spend a very long time building things that suck before you build anything good.

Getting good at something requires patience — yes, you have to understand that things probably will go slow, and be able to tolerate that — but you also have to have persistence — that voice that says that just because I’m telling you it might go slow doesn’t mean it has to.

The difference between patience and persistence is the difference between doing and dreaming. It’s the difference between those who get to the finish line and those who quit before the work really begins.

Be patient. Be persistent.

Do the work.

03/14/201203/13/2012

Want to Know The Secret to the Perfect NCAA Bracket? Pick By Storyline.

It’s that time of year when everyone’s breaking out their brackets. And everyone’s got their methods. Some pick based on reputation. Some turn to the computers for advice. Some pick based on the cuteness of a school’s mascot.

I’ve got a new system this year, and I think it’s a winner:

I pick by storyline.

That’s right. Forget the percentages or the seedings. Who’s got the best story?

Because that’s what it’s been about the last few years. Look at last year’s bracket. We had four great stories in the Final Four:

1. Kemba Walker’s amazing one-man run through the tournament
2. John Calipari — the villain of college basketball — tries to win it all with a team of guns-for-hire
3. Shaka and 11th-seeded VCU shocks the world
4. Butler’s unbelievable repeat Final Four trip

We love great stories in the tournament. Jimmy V’s Wolfpack were a great story. Juan Dixon’s Terps were a great story. George Mason’s Final Four team was a great story.

This year, I’ve made it my motto: If I can’t envision the movie being made about a team’s performance in the NCAA Tournament, I won’t pick them.

So, yeah, I’m picking Missouri. They were left for dead back in the fall, defied all odds, somehow worked their way into a 2-seed, and in the Final Four, they might have to go through Kentucky — future SEC foe — and Kansas — the once-and-forever rival. I’d watch that movie about the underdog Tigers gunning for their first title.

I’m also picking Harvard. The Ivy League team that can actually play? Denzel’s already lining up for his role as Harvard coach Tommy Amaker in this one. Harvard’s been seeded in the East, and that region’s road to the Final Four runs through Boston. I’d pay to see the Spike Lee joint about Harvard, fair Harvard, suddenly playing for keeps in front of a rowdy hometown crowd[1. Spoiler alert for the film: Jeremy Lin comes back to give the team the inspirational speech before their Elite Eight game.].

Or maybe I should pick Purdue. They’ve got Robbie Hummel, a sixth-year senior. Two ACL surgeries later, he’s finally back in the Big Dance. He’s “Rudy” crossed with “Rocky” — a movie just waiting to happen.

Or what about New Mexico? They’ve got Demetrius Walker, who’s already got one hell of a story out about him in print already. Or South Dakota State, the underdog tale of a tiny school in a tiny state taking on a Monstars-sized Baylor team? Or Gonzaga, the former Cinderella who’s become a giant of college hoops?

I’m looking at my bracket, and all I see are great stories: Stories about underdogs, about dreams, about greatness.

The kind of stories that just might help me win an office pool.

03/11/201203/13/2012

How I Got Myself a Bunch of Free Flights to Awesome Places.

At the end of ~~2012~~ 2011, I made a promise to include travel on my list of things for the upcoming year. Except that I’m not sitting on a mountain of disposable income here. If I was going to travel, I was going to do it cheap.

So that’s how I got interested in travel hacking.

Travel hacking is this movement of people who rack up frequent flier miles in all sorts of ways. Most consumers think frequent flier miles are just for those who fly a lot. That’s wrong. These days, you can earn just as many miles on the ground as you can in the air. Buy music on iTunes? You can earn miles. Subscribe to Netflix? You can earn miles. Buying flowers for your girlfriend? Yeah, you earn miles.

Point is: I started tapping into the travel hacking world back in December. Since, I’ve paid attention to how I spend and how it helps me earn miles. I’ve learned way more about how credit works.

This is the especially cool part: I’ve got 200k+ miles sitting in my frequent flier accounts right now. I’m not broke, and my credit doesn’t suck. And best yet: Whenever I find myself the time to take vacation, I’ll be flying for free.

So here’s what I’d suggest for you, Potentially Curious Travel Hacker of Tomorrow:

1. Set your goals

If you could go anywhere in the world, where would you go? I’d really like, in the next 18-24 months, to see New Zealand and Croatia. It’ll take 100k to get to New Zealand, and 40-60k to get to Europe.

If you’re curious about how many miles it’ll take to get to your dream destination, here are the mileage reward charts for the SkyTeam (including Delta, KLM, Air France), Star Alliance (United, USAir, Lufthansa, Swiss Air, Air New Zealand, Air China, Air Canada), and Oneworld alliances (American, British Air, Cathay Pacific, Iberia, Japan Airlines, LAN, Qantas)[1. Independent airlines like Southwest and AirTran have their own frequent flier programs, and they’re both totally different. Check them out for yourself if you fly either of those with frequency.].

2. Sign up for AwardWallet

AwardWallet is this incredible site that keeps track of all your frequent flier miles from all the airlines, hotels, and rental car companies you use.[2. The one catch: American Airlines blocks the site. But everybody else in the universe works on AwardWallet.] They’ll automatically tell you when you’ve earned miles, and they’ll tell you when your miles are about to expire. (And it’s free!)

If you’ve flown at all in the past 24 months, you’ll see miles show up on your statement. Thanks to AwardWallet, I found out, quite accidentally, that I’d already racked up 50,000 miles on United. That’s two free domestic round trip flights. I had no idea I’d been sitting on that gold mine.

3. Start following these guys on Twitter

@MilMileSecrets
@thepointsguy
@boardingarea
@FlyerTalk
@HackMyTrip
@FrequentMiler
@milepoint
@FrugalTravelGuy
@airfarewatchdog

They’re tapped into the world of miles and deals, and they’re blogging about deals and offers. Like, a couple of weeks ago, British Airways had a crazy deal: For every dollar spent, I’d earn 36 miles on BA. I had to grab some gifts anyway for family, so I pulled out the credit card and spent a few hundred bucks. Now I’m sitting on a roundtrip flight on BA[3. To clarify: BA’s miles program is different then most. A short flight — say, NYC to Toronto — starts at 4,500 miles. I’ve got 11,000+ miles on BA now. So it’s a roundtrip, but nothing long-distance.].

That’s what travel hacking is all about: Spending money on things you want/need and getting something else in return: Miles.

To get a free domestic ticket on any of the big American airlines — American, Delta, United — you need about 25,000 miles. That’s what you’re shooting for.

If you’re looking to dive into the deep end with travel hacking, consider joining the Travel Hacking Cartel. I did back in January. It costs a few bucks each month, but they send me a few awesome deals each week[4. 1,000 points for signing up for — and then immediately canceling — text messages from Hilton? Thanks, Travel Hacking Cartel!]. They’ve also got all sorts of tutorials about how to redeem miles.

4. Start spending… small

You can get miles for everything these days. All it takes is a handful of small purchases. Like:

A. Airline dining programs

Airlines have deals with some restaurants and bars. You register your credit/debit card with the program, and when you use it to buy food/drink, you automatically earn miles.

For example, I’m a member of United’s dining program, and at certain places here in Columbia, MO, I get 3 miles for every dollar spent. When I buy a sandwich at Which Wich, I earn miles. Same if I buy a beer at Room 38. Or Quintons. Or Bleu. Or Boone Tavern.

American Airlines, Delta, Southwest and US Airways all have dining programs, too.

If you’re in a different city, pull out the credit card. Last month, I bought some drinks[5. Okay, “some” might be an understatement here.] at a bar in NYC. I got an email later that week that the place was a United dining partner, and I’d been credited with 200 miles. Sweet!

This alone won’t get you that flight to Tahiti. But it’s an easy way to earn miles on things you’re already buying.

B. Shopping online

Same goes for online purchases. You can get 1 mile per every dollar spent on Apple products, and 3 miles for every dollar spent on iTunes. Like J. Crew? On American, you can get 5 miles per every dollar spent on that new sweater. Sign up for Netflix, and United will give you 1,000 miles. Buy flowers on FTD, and you’ll get anywhere from 20 to 36 miles per dollar spent.

Don’t believe me? Search here for your favorite retailer. All you have to do is log into the specific airline’s shopping store before going to, say, JCrew.com, and you’ll earn the miles.

5. Sign up for a credit card (if you can)

Here’s the precursor to this: If used incorrectly, credit cards can cause you trouble. Credit card debt can keep you from doing things like buying a home, or a car, or pretty much anything where real money is at stake.

So here’s my brief advice: If you don’t have money to spend, don’t go getting credit cards. You will spend money you don’t have, and you will end up in debt.

But if you have money to spend, credit cards are an excellent way to rack up miles. Some cards come with a big sign-up bonus. Some give you a bonus after a minimum spend. Some give you perks — free airline lounge access, free checked bags.

This site has more advice on which cards are right for you. You’ll want to pick one (or three) that fit your travel needs/wants/dreams.

What Now?

Maybe travel hacking isn’t for you. Maybe you’ve got a cash-back debit card, and you’re happy with it. Nothing wrong with that.

But if you love to travel, I’m telling you that there’s a way to make it happen. Like Ferris once said:

If you have the means, I highly recommend checking it out.