He created his own job at a media juggernaut. Here’s his advice for you.

Steve Krakauer is the executive producer of the Megyn Kelly Show and founder of the Fourth Watch podcast and newsletter. He started his career in journalism covering softball for his local New Jersey newspaper, and went on to work at CNN, NBC, and TV Newser. He even did a non-journalism stint in marketing. TLDR: he’s got a seriously robust resume. We are so lucky that he agreed to (virtually) sit down with us for a wide-ranging interview. We talked about his evolving career path (including that time he created his own job at CNN), how moving from NYC to Texas changed his perspective on the media landscape, and his advice for forging your own way.

What follows is a condensed and edited version of our conversation. 

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How do you feel if you look back from your days as covering men's softball in the summer in New Jersey to where you are now, are you surprised by that course that you've taken or do you feel like you were kind of always going to go from point A to point B?

Yes and no. First of all, I've always felt that you really can't hundred percent plan a career in the media business. There's not a linear track. It really zigs and zags and you try to jump on an opportunity that you can't necessarily anticipate or plan for. The one gig, which I think is really integral to my career is CNN. I was covering the industry at the time for TV Newser, and I saw that Piers Morgan was going to get the job at CNN to replace Larry King. And I was just a huge fan of his interviews and felt with what he was about to do, there was an opportunity to really build out a digital presence. And I had a meeting with him under the guise of “Hey, let's have coffee and meet, because I cover the industry.” At the end of that meeting, I said, “Hey, you know, I'd love to work for you and be your digital producer.” 

I think that those are the sort of moments where you're really trying to carve out the path you want. And then, I think you pivot if it's not going the exact way you're looking to go. I mean, I loved 99% of my time at CNN, but there were also some parts that I was kind of missing. I think I've shifted more towards an editorial point of view rather than a marketing one. And so trying to be conscious about how you want to shift your career is really crucial if you want to be able to try to get the most out of what you're doing.

Wait, so let me get this straight. Did you pitch him a job that didn't exist? And then they were like, that's a good idea. Come do this job?

Basically, yes. I said that “Piers Morgan Tonight” is going to be on the air one hour a day. What's going to happen the other 23 hours a day? You know, this is something that you're gonna have tons of content. It's going to be a really shareable videos. We really made it a huge part of the show. In fact, Piers now like never stops tweeting. One of my early claims to fame was that I convinced him to join Twitter because I felt like it was a perfect medium for him. And if he was doing it, it was so much more effective than what I could do from a show account. And if we could do it in partnership, he would grow the show account. 

So that was the pitch. And then ultimately they decided at CNN about a year in I became the senior digital producer and we hired that position at all of the CNN prime programs. 

You left New York City for a job at The Blaze located in Texas, and that then ended within a year. And you took a position that maybe wasn't the best fit for you at the time, or wasn't exactly what you were looking for. Do you have any advice for people who might find themselves in similar situations? 

I think being open-minded is so crucial to work. In some ways I wish I had a job where I work nine to five and I don't think about it, but I also know myself enough to know that that wouldn't be satisfying. I am lucky to have things that I'm super passionate about and interested in with work, but at the same time, it's called work because it's work.

I think in work, there's three things that you try to look for and ideally you have one or two of them. In a perfect world, my job would be interesting, challenging, and important. You know, sometimes it's not going to be challenging or important, but if it's a job, it's steady, and it gets done, great. And not overthinking it is important, too.

Talk to me about what you’re doing now -- the Fourth Watch. What should we know about it? 

I wanted to write about the media business and do some level of media criticism, but I'm someone who loves the media. I'm a media nerd going back to when I used to watch cable news when I was 15, or 16 years old. What I would say is that I'm probably more critical of the media than most people who say they love the media. But I think I approach it from a position of not hating it. I think a lot of criticism veers into territory of like, “these are bad people,” and I don't think that at all. I'm somewhat critical of CNN these days. But I love a lot of people that I worked with there that are still there, and I think they do a great job. The other hook about it is really, I think from my time now being outside of the bubble of what I call the “Acela media.” I used to take the Acela train when I was at CNN all the time from New York to DC and back for election nights and everything. And I would say I had blind spots, and I was not alone in that. And by stepping outside, I think it's opened my eyes more. 

I think that the country is not as divided and people are not as at each other as they are portrayed a lot in the media. I think people are a lot more complicated and messy and nuanced than what is often portrayed on both sides of the media. And so that's kind of the perspective I try to bring to my work now. I'm not trying to pretend I'm like this regular Joe Schmo. I do certainly have that media experience, but I also try to bring something that I can only really have gotten by literally being outside of it. 

If you had words of wisdom to impart to our readers, what would they be?

One thing that I've always believed is if you're able to do something, just try it. No matter what it is. Things that feel like they might be a waste of time, even if they are a waste of time, are good experiences. I felt this way with a lot of the social media platforms that kind of pop up and I don't know if we need a whole strategy, but let's try it. You know, it can't hurt to try it and what's the worst that's going to happen? We waste a few hours or a few days. 

I really do think that's important. I think a lot of times people are afraid of failing. I think there's a sense of people really feeling like something might not work, so it's just better not to try it. And it's just the total opposite of the way I think. With the podcast now, it’s like how we position it on social media and how we do clips and what do we do with YouTube? And I don't know. I'm throwing a bunch of stuff against the wall and trying to learn as we go and look at the analytics, but let's not get set in our ways or be afraid to fail. The media is changing so much that it's just worth just trying stuff. If you've got the bandwidth to do it, give it a try. Fail, try something different.