Will Leitch

Will Leitch: Turn Back Tuesday

Will-from-fb.jpg

A little more than four years ago, I interviewed journalist Will Leitch to debut my first web site! This week, let’s revisit my conversation with him for two reasons: First, Will offered some great insights. Second, this is the first interview on Dreaming Made Simple.

Dreaming Made Simple is your dream destination for practical strategies and resources to help make your dreams happen!

Sam Miller: What is your dream?

Will Leitch: All I ever wanted to do was write for a living. More accurately, all I ever wanted to do was to write about things that I care about. For me to have the opportunity to write about what I want in a lot of different places, it is a dream. My dream is to be able to keep doing this as long as I can. It’s not so simple as “OK, you made it. You’re all done now.” I have to keep working hard to sustain that.

Sam Miller: When did you realize you were living your dream?

Will Leitch: If you had told me six years ago, “Will, you’re going to be able to do a movie site with your friend Tim [Grierson]; you’re going to be able to write for New York magazine, one of your favorite magazines; and you’re going to be able to write a big story about Michael Vick for GQ,” I would have been like “Holy crap, I’m living the dream.” Once you’re actually doing it, it’s just work, which is good. I think people have a bad connotation with work. They equate work with job. I like to work. That’s what gets me up in the morning.

Sam Miller: What are the steps you’ve taken to get where you are?

Will Leitch: A large percentage of everything that happens for anyone is luck. You make your own luck, don’t get me wrong. Once you are given an opportunity, you have to take advantage of it. As it happened, Hugo Lindgren was a deputy editor at The New York Times Magazine. (He now runs the Magazine.) He stumbled across one thing I had written at The Black Table and was like, “Hey, this is kind of funny. I’ll e-mail this guy and see if he wants to do something.” That was absolute luck. The funny thing was I got assigned a huge story, a big huge story, that to be honest I am not sure I was quite ready for, but I worked my ass off on it. It was luck that he even stumbled across me in the first place. On the one hand, he did come across the story. On the other hand, I also wrote a million other things that he did not just stumble across. People misunderstand luck. They think, “That person’s just lucky.” No, you have to put yourself in a position to be lucky.

The first step was deciding that this was what I was going to do. I don’t know if I had necessarily decided that when I moved to New York. I think I knew it in college, but there is a difference in knowing what you want to do and to be, like “I’d do this forever even if I die.” I remember a lot of people in my journ program or different English programs that wanted to be writers, wanted to be journalists. They’d say, “I’ll give this [career] until I’m 27 or 28, then I’m going to law school.” Well, in my opinion, you’ve already lost when that happens. I remember a conversation that me and [Deadspin editor, A.J. Daulerio] had. I was 26, he was 27, and we were both really struggling. We had a friend of ours who was a lot older than us. He was not doing well with his career. We thought, “He was a failure. Are we willing to be failures?” We both decided yes. We were willing to have it not work because we wanted to do it and believed in it.

I think that’s the most important thing – to be willing to go down with the ship. You can’t look for an escape hatch.

If my wife had met me in 2003, I was the biggest loser you could find. I could barely afford rent, I had a crap job, I was writing for free, I was a mess. But I knew what I wanted to do eventually, so I had to put in the work and hope that I caught a break and, if I did, to take advantage of that break.

Sam Miller: What lessons have you learned?

Will Leitch: The main one is not to get distracted and not to give up. I find a lot of people act like a job is owed to them, or they deserve it, or they’re special. A lot of the people who have a really hard time are people who are not ready to deal with setbacks.

A lot of people want to be writers but they don’t realize that requires a ton of work. I don’t think there’s a mystery to it. I think people want there to be. I know a lot of people who love the vision of themselves as writers, but really, you’re committed to it or you’re not.

You don’t even want to know how many years my parents thought, “Why is he in New York? What is he doing there? We send this kid to college, and he’s working in a doctor’s office. What a waste of time this was.” I was a total failure for a long time.

Sam Miller: What’s next?

Will Leitch: All I want to do is to keep doing this and to make it work with my life. I want to be able to do the things I want to do while making sure it doesn’t take away from the things I need to be as a husband and a father. That’s my next goal, to figure that out.

There’s no point where you hit a finish line. That’s something I didn’t realize when I was 25 or 26. I always thought I’d hit a point where I made it. You never hit it.

Thanks for reading!  Keep watching this space for more interviews like this one and for more about Dreaming Made Simple

Dreams: Sam's Dream Blog Celebrates 100 Inspirations

This is a big week on Sam’s Dream Blog!  Here at SDB, it’s celebration time for 100 posts.  Whether you have read every post, several posts, or maybe you are making your first visit, thank you.    

Here are some highlights from the first 100 posts. Follow the underlined links for the full interviews.

1. Writer Will Leitch graciously helped to kickstart SDB. First and foremost on the journey toward your dreams, Leitch says, "You have to be willing to go down with the ship. You can’t look for an escape hatch."

2. Now that you’re committed to your dream journey, per Will’s advice, Dallas Mavericks owner and business mogul Mark Cuban has this to say: "You have to determine whether or not you are willing to commit to working 20 hours a day, 7 days a week?"

3. While you’re at it, "Learn whatever you can from whoever is going to offer it. Every day you should be learning something new," San Francisco sous chef Adam Nichol says.

4. Of course, maybe your dream pursuit cannot be at the forefront of your life right now, due to other limitations for the time being.  Take heart in what leadership expert John Maxwell says: "When it comes to being an authority on a subject, spend one hour a day, five days a week, for five years. Earl Nightingale says that by doing that, you can become an expert on any subject?"

5. If all that sounds daunting, think back to your childhood, Harvard Business Review contributor and TEDx speaker Whitney Johnson says: "Each experience that we have, the good and especially the things that happen to us that we don’t deserve, shapes our dreams.  For example, one of my biggest dreams, which is to encourage others, came, I think, [because I didn’t hear enough] encouraging words as a child.  I deserved that, and I long for that sometimes. Yet, without that, would I even have felt [compelled] to begin writing about dreams in the first place?"

6.  "Exhaust all opportunities for growth," including volunteering, career expert Alexandra Levit says.

7.  Speaking of opportunities, "It’s important to know you want to do things the right way, no matter if it takes longer to accomplish. I guess it’s just being patient," Hollywood manager and producer Trevor Kaufman says.

8. Drybar’s Alli Webb has this to say about your dream pursuits: "It’s key to identify your target consumer and to make sure the need for your business really exists on a scale large enough to sustain the business for the long haul. Then execution is the next hurdle. Be prepared to work tirelessly to really nurture your idea."

9. Candy connoisseur and Sugarfina co-founder Rosie O’Neill keeps her advice about dreams short and sweet: "Try new things as often as possible, stick with what you like, and don’t waste your time with the things you don’t like? Life’s too short."

10. Finally, remember this advice from Estella’s Brilliant Bus inspiration, Estella Pyfrom:.. "Don’t shy away from your dreams. Don’t listen to negative people that say it’s not going to happen.  If you have a dream and you are willing to work for that to make it happen, it can happen."

If any of these comments particularly resonated with you, let me know below, and share with a friend!

Career Paths with Will Leitch

Will-from-fb.jpg

Career Paths:

Career Paths

Will Leitch is a contributing editor of New York magazine, an editor of The Projector blog on Yahoo and the founder of Deadspin.

Sam's Dream Blog: What is your dream?

Will Leitch: All I ever wanted to do was write for a living. More accurately, all I ever wanted to do was to write about things that I care about. For me to have the opportunity to write about what I want in a lot of different places, it is a dream. My dream is to be able to keep doing this as long as I can. It’s not so simple as ?OK, you made it. You’re all done now.? I have to keep working hard to sustain that.

SDB: When did you realize you were living your dream?

Will Leitch: If you had told me six years ago, ?Will, you’re going to be able to do a movie site with your friend Tim [Grierson]; you’re going to be able to write for New York magazine, one of your favorite magazines; and you’re going to be able to write a big story about Michael Vick for GQ,? I would have been like ?I’m living the dream.? Once you’re actually doing it, it’s just work, which is good. I think people have a bad connotation with work. They equate work with job. I like to work. That’s what gets me up in the morning.

SDB: What are the steps you’ve taken on your career paths to get where you are?

Will Leitch: A large percentage of everything that happens for anyone is luck. You make your own luck, don’t get me wrong. Once you are given an opportunity, you have to take advantage of it. As it happened, Hugo Lindgren was a deputy editor at The New York Times Magazine. (He now runs the Magazine.) He stumbled across one thing I had written at The Black Table and was like, ?Hey, this is kind of funny. I’ll e-mail this guy and see if he wants to do something.? That was absolute luck. The funny thing was I got assigned a huge story, a big huge story, that to be honest I am not sure I was quite ready for, but I worked my ass off on it. It was luck that he even stumbled across me in the first place. On the one hand, he did come across the story. On the other hand, I also wrote a million other things that he did not just stumble across. People misunderstand luck. They think, ?That person’s just lucky.? No, you have to put yourself in a position to be lucky.

The first step was deciding that this was what I was going to do. I don’t know if I had necessarily decided that when I moved to New York. I think I knew it in college, but there is a difference in knowing what you want to do and to be, like ?I’d do this forever even if I die.? I remember a lot of people in my journ program or different English programs that wanted to be writers, wanted to be journalists. They’d say, ?I’ll give this [career search] until I’m 27 or 28, then I’m going to law school.? Well, in my opinion, you’ve already lost when that happens. I remember a conversation that me and [current Deadspin editor, A.J. Daulerio] had. I was 26, he was 27, and we were both really struggling. We had a friend of ours who was a lot older than us. He was not doing well with his career. We thought, ?He was a failure. Are we willing to be failures?? We both decided yes. We were willing to have it not work because we wanted to do it and believed in it.

I think that’s the most important thing ? to be willing to go down with the ship. You can’t look for an escape hatch.

If my wife had met me in 2003, I was the biggest loser you could find. I could barely afford rent, I had a crap job, I was writing for free, I was a mess. But I knew what I wanted to do eventually, so I had to put in the work and hope that I caught a break and, if I did, to take advantage of that break.

SDB: What lessons have you learned?

Will Leitch: The main one is not to get distracted and not to give up. I find a lot of people act like a job is owed to them, or they deserve it, or they’re special. A lot of the people who have a really hard time are people who are not ready to deal with setbacks.

A lot of people want to be writers but they don’t realize that requires a ton of work. I don’t think there’s a mystery to it. I think people want there to be. I know a lot of people who love the vision of themselves as writers, but really, you’re committed to it or you’re not.

You don’t even want to know how many years my parents thought, ?Why is he in New York? What is he doing there? We send this kid to college, and he’s working in a doctor’s office. What a waste of time this was.? I was a total failure for a long time.

SDB: What’s next?

Will Leitch: All I want to do is to keep doing this and to make it work with my life. I want to be able to do the things I want to do while making sure it doesn’t take away from the things I need to be as a husband and a father. That’s my next goal, to figure that out.

There’s no point where you hit a finish line. That’s something I didn’t realize when I was 25 or 26. I always thought I’d hit a point where I made it. You never hit it.

Buy Will's book, "Are We Winning," or any of his other three reads on Amazon.com