How His Mistake Chained Him to the Wrong Job for Three Wasted Years | Robert Rose, The Content Advisory

Ashley Stryker [00:00:06] Welcome to the Professional Confessional: How the biggest mistakes we've ever made fundamentally changed our work, our careers, and our approach forever. Gain wisdom and perspective through these audio absolutions. 

Ashley Stryker [00:00:20] Today's guest is Robert Rose: A content marketing champion, master consultant to the Fortune 100 -- and a man whose private insecurities change him to a position he never fit for three years. 

Robert Rose [00:00:33] I was working at a startup company and that startup company was in the enterprise software space, and I was their head of marketing CMO, if you like that title. One of the things that I was discovering was my own confidence in who I was as a professional and the company itself was doing fine. And when I say fine, I mean fine: Not growing exponentially, not horribly sinking the ship, not... There was no drama here. 

Robert Rose [00:01:05] And so in 2006, I was not a happy camper. I was miserable in my job, not getting along with my boss, who was the CEO at a time, who was a friend, quite frankly, from a previous job. And it was one of those things where it was literally, "the husband and wife are together for the kids" kind of thing. 

Robert Rose [00:01:28] I should have left, I should have left, and I should have gone out on my own because I had wanted to. Since I had joined the company in 2001, I had wanted to be out on my own. I wanted to run my own business. I had recognized that one of my gifts, one of my strengths was actually helping people through short term projects and not long term things. And I was here, in this long term thing, and I realized that it was a mistake early on. 

Robert Rose [00:01:55] But my confidence level in myself in terms of what I could do and also a bit of shame I had around myself around never finishing things. And we can go all the way back and talk about other mistakes, like the fact that my inability to finish college in the right way and my inability to do a lot of things and finish things kept me in this sort of status where I was in this job with people in a, "let's make the donuts every day," kind of groove. And I hated it and I stayed. 

Robert Rose [00:02:30] And the only reason I stayed was because I said to myself every day as I was driving home, "You got to finish this. You got to finish this. If you don't finish this, you're going to miss out. You're going to fail. You were going to not be a successful person." 

Robert Rose [00:02:45] And it took me three years to finally get up the courage and the gumption and ultimately meeting this guy who would ultimately become one of my closest friends, Joe Pulizzi, in order to pull me out. And so the mistake, to the extent that there is even a sort of ground zero for that, goes all the way back to 2006 when I used to drive home every day for that year, basically saying, "Why? Why am I not doing this? Why am I not doing this? Why am I not doing this and not doing it?"

Ashley Stryker [00:03:14] Why did you think that not finishing something is a failure? 

Robert Rose [00:03:18] Because I had in my life as a teenager and more sort of recent history to much of my career, if you want to look at that way from school for college onward, hadn't... I had walked out the door I had with college, it was I didn't finish in the right way. I didn't finish even. I finished with enough things, but I didn't graduate. I looked at my... 

Robert Rose [00:03:45] I got in my car and I drove out to Los Angeles. And my goal was to be a rock and roll star, ultimately. And I did. And I did that for twenty five minutes until I decided I wasn't good enough to do it. 

Robert Rose [00:03:58] And so I said, OK, I'm going to be a writer. And so I started doing playwriting and screenwriting and then ultimately discovered I'm not good enough. And I quit that and didn't continue it. 

Robert Rose [00:04:09] And I joined a company and I got a job in marketing this television network, Showtime Networks, and was very quickly climbing up the corporate ladder there. I was doing well, but I got all scared with, "This was going to be my life now?" I was no longer going to be in the arts and I was going to be a corporate guy --and I quit that job. 

Robert Rose [00:04:27] So I kept walking out of situations where I had gotten in and found something I liked about it, but then found something I disliked about and ultimately left because I was scared that I wasn't going to be good enough. I wasn't going to be competent enough. It all feeds on each other. 

Robert Rose [00:04:47] So when you get to this point where I'm 26, I'm in this job, it's, "No, goddammit, you're going to stick this through, you're going to you're going to see this through before we sell this company. And if you don't see the exit of this startup, you will have failed." And what I failed to realize -- my mistake -- was none of that mattered. None of that actually mattered. 

Ashley Stryker [00:05:09] What did matter? 

Robert Rose [00:05:10] What mattered was my happiness. This is something I've just learned. I was never going to be successful if I was unhappy. 

Robert Rose [00:05:17] There's that great Jim Carrey quote that he gave at the graduation speech when he talked about his dad, and how his dad worked at a job for 60 years and hated the job, and ultimately got laid off from it. And he said, "You can fail at things that you stick with, too, right? So you might as well do what you love. Right, because if you're going to fail, you should fail at doing something that you love rather than something that you hate." 

Robert Rose [00:05:39] And so that to me was a huge motivator for me. But I didn't listen to that. I wasn't listening to any of that. 

Ashley Stryker [00:05:47] What had to change for you to be willing to listen to them? How unhappy did you have to be? 

Robert Rose [00:05:54] Man, that's the magic question of life, isn't it? What had to change was me, right? Ultimately, the problem lied within me. 

Robert Rose [00:06:03] And this has happened, by the way, just recently as well, with another large sort of forced universe looking in on me and going, no, you need to pivot, you need to change. 

Robert Rose [00:06:13] And so what it was, then, was the financial of 2008, because what ended up happening was three years after I made this sort of judgment on myself, I stayed there for another three years 'til twenty nine. It was in 2008 that I actually met Joe and the financial crash. 

Robert Rose [00:06:34] I don't know if you remember, but 2008, 2009, we were literally putting money in our mattress. It was the worst time -- it was the absolute... Like, if you said, "Pick the worst time to quit your job and go out on your own," it would be 2008, 2009. 

Robert Rose [00:06:47] It came down to a bunch of my mentors and one guy in particular who I spoke with. I went to dinner with him. I'll never forget. The question on the table was, "Should I just should I finally go out on my own? Should I finally just strike out on my own?"

Robert Rose [00:07:01] And he looked at me and he said, "Dude, could you get a job?"

Robert Rose [00:07:05] I said, "What do you mean?"

Robert Rose [00:07:06] He said, "Can you get can you go flip burgers or can you go manage a restaurant and can you pay rent?"

Robert Rose [00:07:11] I said, "Yeah, of course I can do that. I'm smart enough. I'm talented enough to go get a job."

Robert Rose [00:07:16] And he said, "Then what are you waiting for?"

Robert Rose [00:07:18] He said, "The only thing you're thinking, the only thing you're then worrying about is whether you're going to fail at what you want to do."

Robert Rose [00:07:23] "If you fail at what you want to do," he said, "then you will have failed in the best way and go figure something else out and figure something else out."

Robert Rose [00:07:31] "That's the only thing you're waiting on," he said. "So if you don't have confidence in yourself, have confidence in the fact that you will at least fail at something you desired."

Robert Rose [00:07:39] That was what it took for me. That was what it took for me to change. 

Ashley Stryker [00:07:42] Can I have your mentor? That struck a chord. Damn. All right. Yeah. OK, then. So then you make the decision. How do you go to your CEO and say, "Hey, I no longer want to stay together for the kids?"

Robert Rose [00:07:53] That was an interesting conversation. And we're, by the way, friends to this day. 

Robert Rose [00:07:56] So it was a very hard conversation at the time, but it was one of those things where I made it in my mind way more dramatic when you play it. Of course, you play it out, you play it out fourteen million ways. He's going to say this and then I'm going to say that. And then I'm going to say this and he's going to say that. And of course, none of that takes place. That's always way different than you think it's going to be. 

Robert Rose [00:08:20] When I go to him and have this conversation, he said, "Oh, my God, I've been wanting to have this conversation for two years with you." 

Ashley Stryker [00:08:26] Oh, God. 

Robert Rose [00:08:28] And then you go and you start lamenting the two years that you you start reflecting on this as a huge mistake. "Why did I not do this two years ago?"

Robert Rose [00:08:36] He was lovely about it. And we had a wonderful conversation, and we ended up walking out of there and going and having a beer. And it was great, that we mutually agreed that it was not working for either of us. And ultimately, he would go on to do great things and I would go on to do some good things. 

Robert Rose [00:08:55] And it was-- and that's why I look at it as a mistake. The mistake was not doing it earlier, not actually looking through an honest lens and having confidence in myself to be able to say "Go!" Because it would have been exactly the same, only I would have been I had two more years doing what I do now, which I'm thrilled with how my life is. 

Ashley Stryker [00:09:18] Have there ever been moments where it's come back? Where you've said, "Boy, I'm a commitment phobe, I still can't finish anything I start"? Or, has the embracing of something you've wanted to do helped solve some of that problem?

Robert Rose [00:09:31] Oh, my God. It's still something I deal with every day. What I have now is a bit more perspective, but I didn't solve it. It's still something I struggle with every year. 

Robert Rose [00:09:40] I tend to do a lot more spiritual work these days and I tend to do a lot more journaling and I tend to do a lot more reflection every year, which I've been doing for the last ten years and getting better at it. 

Robert Rose [00:09:53] But it every single year, I think to myself, am I still am I still fooling myself? Am I still over rationalizing? I would say there's no such thing as a perfect treasure chest at the end of the rainbow here. It's a constant struggle and you just... What you hope to do is get better at it over time. 

Ashley Stryker [00:10:11] So you mentioned journaling and reflection. Are there other ways in which you try to cope with the feeling of... I'm going to say the feeling in society or your own self-imposed limitations when you mentally know that's not right? How do you deal with that? 

Robert Rose [00:10:27] I look at the work, in all honesty. One of the things that I realized after I went out on my own and after I started doing the work, there was a whole new "mind of the student" that I took on, because what I started to realize was that I found comfort in the idea that I don't know all the answers. And so I found comfort in going and just putting on my student hat and learning and learning and learning. 

Robert Rose [00:10:55] And what that does is, whenever I'm feeling in a way that says, "Hey, you're either you don't have the confidence or you stayed someplace too long or you don't know what you're doing" -- or any of those things! What I do is I put on my student hat, and I go learn something. 

Robert Rose [00:11:10] There's an interview with Steve Jobs where he talks about his and it's a full-on '70s porno star, Steve Jobs with the beard. In the morning he goes, he says to the camera, the interview camera, "Look, one of the biggest secrets about life that I've learned is that if you look around and all of the amazing, interesting things that you see when you look around, if you just realized they were invented by people who are no smarter than you are. And if you realize that and you realize that, I can go out and do those things, too, if I just know how, then you can really move yourself forward."

Robert Rose [00:11:46] And that, to me, is the sort of way that I move myself forward. If I go learn something that I didn't know before, then I can always move forward. 

Ashley Stryker [00:11:55] So what are your favorite ways to proactively seek out something new to learn? 

Robert Rose [00:12:00] I read a lot. I read a lot. And I try and read things that have nothing to do with the vacuum that I find myself in. In other words, it's very easy to get caught up in our own sort of, as Austin Powers might say, our "own particular brand." And I try and find things that are completely outside the industry that might be reading spiritual books. It might mean reading physics books, it might be reading things, fiction, it might be going to see and listening to music that I've not heard of before. And usually, those things are gateways to paths that you can go learn about something. 

Robert Rose [00:12:39] When I find myself finding that sort of, "Wow, I never knew this thing existed before!" And you go look. And, you can start to bring your own experiences to it, and your own lens to it -- that starts to bring in, "This is how that could or does not at all apply to what I'm doing with clients or what I'm doing in my business or what I'm doing in my life or what I'm doing here." 

Robert Rose [00:13:02] And you can bring those metaphors, those life metaphors to bear. And it just it makes the work better. And that's ultimately where I'm getting to, is that to me, it's all about the work. If I'm continually producing good work, it doesn't matter where I am in the scheme of visibility or how many people know me or how many followers are I have or anything like that. If the work is good and the people I do the work for, I think it's good, then I'm happy. I'm a happy guy and if I'm a happy guy, then I'm truly... I've learned the lesson of that mistake.

Ashley Stryker [00:13:36] For the record, because of the work that you and Joe and everybody did, I'm the professional that I am today, as moderately unsuccessful as I am. It's... It elevated what I did from just following orders to understanding the why. Everything happened because my coworkers back couldn't take a flight to Cleveland-- when he takes a yearly vacation to Hawaii! He gave me his conference ticket, and everything changed. 

Robert Rose [00:14:03] Nice. So I love this. 

Ashley Stryker [00:14:04] Just... for the record. 

Robert Rose [00:14:06] And I love that. I love that. 

Ashley Stryker [00:14:08] So Robert's big mistake was waiting so long to leave his corporate gig-- but more than that, it was believing that inner voice that said he'd always be a failure because he couldn't finish what he started. That insecurity, rooted in his failure to finish college, only dislodged after his mentors reframed the question from "What if?" to "Why not?"

Ashley Stryker [00:14:32] To compensate for that lingering insecurity, despite his recent successes, Robert proactively seeks out new information by putting on his student hat to seek out new opportunities outside of his area of expertise. Ultimately, this process improves his limited scope professional projects and makes him happy. And it's that happiness that drives his success, not a self-defeating adoption of someone else's expectations onto his own career. 

Ashley Stryker [00:15:00] Today, Robert Rose as a consultant, keynote speaker, author, podcast host and creator of content marketing strategy firm The Content Advisory, founded in 2010. (The date should sound suspiciously close to previous years we've mentioned in this episode.)

Ashley Stryker [00:15:17] Personally, I would highly recommend picking up a copy of his killing marketing book for a truly revolutionary look at what marketing could be, if internal leaders are brave enough. You can learn more about Robert at PC-Podcast.com/RobertR, or register for his Content Marketing World keynote, scheduled for Wednesday, September 29th at 8:30 AM. (Sorry to my future listeners who missed it -- I'm sure there will be more opportunities!)

Ashley Stryker [00:15:49] And you can find this and other episodes of the Professional Confessional podcast at PC-Podcast.com, or on your podcasting platform of choice.

Ashley Stryker [00:15:59] Would you like to listen to the whole conversation and not just this story edit? Go to PC-Podcast.com/Support and subscribe for full recordings and early episodes. That's PC-Podcast.com/Support.

Ashley Stryker [00:16:16] In the meantime, please share this episode with someone who you think needs to hear it today. That's all for this Professional Confessional. I'm Ashley Stryker. Thanks again for tuning in, and I hope you'll join us next Sunday at 7 PM Eastern. Talk soon!.