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How Creative Rock Stars Thrive on Creative Friction
November 17, 2021 Career Growth Leadership
Guest Speaker

Jason Sperling

Global Executive Creative Director, Reality Labs at Meta

Jason Sperling has spent over two decades creating smart, strategic, breakthrough work for global brands including Reality Labs at Meta, Apple, Honda, TikTok, and Disney Pixar. His work has won several awards, such as a Grand Effie for ad effectiveness, several Cannes Gold Lions, multiple One Show Gold Pencils, and an Emmy nomination. One of Jason’s most recognizable projects is Apple’s “Mac vs PC” campaign, declared a Top 10 Campaign of the Century by AdAge. His latest book is Creative Directions: Mastering the Transition from Talent to Leader.

A real creative rock star leans into creative friction.

Decorated creative director and author Jason Sperling wasn’t always receiving awards for his amazing work. He used the built-in friction of the creative process to thrive, and now he leads his teams at Reality Labs at Meta through the same growing pains he dealt with.

In this episode of Real Creative Leadership, Jason shares how harder times paved his path to creative rockstardom — and how you can use your own creative friction to spark growth.

Watch this episode to discover:

  • One key way to provide a safe work environment for your creative team
  • How to deal with self-criticism, and why it’s important
  • Insights from Jason’s book, “Creative Directions: Mastering the Transition from Talent to Leader”
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mentioned in this show:
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Adam Morgan
Creative Leader and RCL Host
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The Stoke Group
Digital Marketing and Full-Service Content Agency
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Transcript

Adam: We’ve all experienced a ton of change over the past few years, and creativity is always about making something great, but sometimes we have to do that even when we’re constrained or there’s built-in friction in the process. Today, we’re going to be talking with Jason Sperling to learn how he’s creatively adapted in his career and grown his creative leadership — even when it’s challenging. We were talking earlier, and I like this idea of being “at odds.” So things that are “at odds,” and that’s definitely where we’re going to be going with this session — how do you find that creativity and the positivity, even when there are things that normally seem like they’re not positive, they’re not great?

Jason is currently the Global Executive Creative Director at Facebook Reality Labs. He’s worked in advertising and marketing over the past two decades, developing great work that includes work for Apple, Honda, TikTok, Amazon, Disney, Pixar, and UNICEF Worldwide. What a great lineup. And among his most notable achievements are Apple’s “Mac versus PC” campaign, which totally impacted my career. I loved it, loved it, loved it, loved it. So I’m super excited to talk to Jason about that. And we’ll get into that later. But he also had five Superbowl ads that have appeared on the all-time best list. So we’re excited to talk about that a little bit. And then finally, Jason has written a book recently about creative leadership, and that’s why we’re here on Real Creative Leadership, because that’s an important aspect of what he’s written on, which is making that leap from a senior creative into a management position. So we’d like to welcome Jason to the show, Real Creative Leadership. Glad to have you.

Jason: Thanks, Adam. Appreciate it. And happy to be here.

Adam: Excellent. Well, let’s just jump right in. Let’s talk about your career first. It’s nice to have a little bit of background from you of what you’ve done and where you’ve come from. And how you’ve come up with all these great ideas. So we’d love to hear a little bit more about your journey, whether that’s the early stuff, the later stuff. Just give us a little bit of context of who you are.

Jason: I didn’t necessarily know I was inherently creative coming up to college. And to be honest, I didn’t know what commercial creativity was either, that it was an actual career path. It was right around the time that “Thirtysomething” was a show on TV. And they were two guys in advertising who had a basketball hoop in the office, and they made it seem like it was a fun career. I had written on the high school paper, and I had written on the college paper. But I still didn’t really know what I wanted to do. And I ended up, oh God, I can’t believe this is the start of the show.

Adam: Do it, date it. Date.

Jason: At UCLA, there was a job board and there was an ad for a job that was marketing and selling condoms. And I thought, well, seems lucrative for a college student. So I called it and it ended up being the right contact at the wrong job. It was for a creative intern job at a newspaper in LA. And so I ended up going in, taking the job, and really learning about the creative aspects in publishing but making ads and understanding more about design. And so, I realized that, okay, there is indeed a path here, went into, tried getting into art schools with a very limited portfolio, and ultimately I got into one called the Academy of Art in San Francisco. And they immediately, what I came to learn in that school was that it’s really what you put in. It is not full of standouts, there were people that were incredibly driven that did incredible things.

And so I went there, probably stressed more than any other student at that school about, “Am I going to have a job coming out of this? Are my parents going to see this as a complete waste of money?” Because it was still art school, which in my family, carried a stigma.

Adam: It’s like getting an English degree right? Where it’s like, what are you going to actually do?

Jason: Yeah. But, that’s still a BFA or —this was less of an applicable, well-paying job. I think they thought I was going to be smoking cigarettes in the back of a coffee house, just typing, typing away.

And after school ended, I ended up getting a job at a small agency in San Francisco. That was my introduction to advertising. And I should say, I went into advertising, went in with a copywriter background. Because my first class, they told me, “Your art direction is killing you, but your copy is okay.” And I should note too that I actually had one teacher as well. It was definitely, they ground you down and wanted to get you ready for the real world. And I had one teacher, we were presenting work, and he actually went to my piece specifically and said, “How many of you like this?” And nobody besides one merciful person in the class raised their hand. And he said, “No, it’s horrible. It’s shit.” And he actually lit it on fire and put it in a trash can.

So that was sort of the training ground. Then my first job, I worked for this absolute madman of an agency owner, who would basically patrol the hallways with a joint in his mouth, invite people to get high at the end of every day, dress people down pretty constantly, telling people if you didn’t want to get high with them, don’t be bitch. It was an insane experience, drug dealers coming by selling him drugs and him coming in late at night with people that weren’t his wife and it was just wild.

Adam: Oh, that’s the era — the 80s and 90s that are not going to happen ever again.

MAKE YOUR OWN OPPORTUNITIES

Jason: No. I mean who the hell knows? But I hope not because that was a really odd training ground. But it does actually, you form some tight bonds with your coworkers just because you’re all sort of in this together in the trenches. So after that it was small agencies, and fear started to set in that I wouldn’t be able to actually reach, sort of the plateaus that I had dreamed up in school. when I was looking through all of the award books of the best work and all those agencies, I was sort of dreaming to go. I just didn’t have the portfolio that would get me there. I just wasn’t getting the opportunities. 

Adam: I think there are so many people who wonder if they’re ever going to make it. I mean, when we see a rock star, like you in the industry, who’s created some iconic campaigns and things — it’s just really interesting to hear that we all start in the same spot. We all started out of school doing condom ads — maybe not all of us. But it’s the trajectory that you have to put in your stripes to learn and work with some crazy people. 

Jason: Yeah. It dawned on me that I would have to really make my own opportunities if I was to reach that next level. So, I actually started doing a lot of spec ads, and I would reach out to production companies and say “Hey, do you need a great script for a young director?” And surprisingly, there were quite a few that would reach out and say, “Sure, we’ll fund it. We’ll direct it. If we like your script.” And so I ended up doing a few of those, and that’s really what got me the attention of some of these firms I dreamed of going to. And it was one very fortunate day where I was in the lobby of Chiat/Day — one of the agencies I had dreamed of — the person that I was hoping to see for an informational interview did not show up.

And someone I had worked with actually did. She saw me and said, “Before you take that job—” (working on an account, that really wasn’t a great account there.) And she didn’t realize that I was just there for an informational interview. She said, “I want you to meet the creative directors who run Apple.” Which taught me the important lesson of be kind with coworkers, no matter how frustrating things get, because she was someone I worked with, and it was the difficult account. And we managed to maintain a friendly atmosphere, so that down the road. She really thought of me and created this opportunity for me.

So went in, it was an interesting, I always like to tell this story because when I went in there, there were two writers.They were interested in one, who happened to be coming from Wieden Kennedy, Singapore and myself, a guy who was coming from an agency that probably the two creative directors hadn’t heard of. And they flew in the guy from Singapore and his girlfriend. They took him out to dinner, took him on bike rides on the beach, wined and dined. And I had this, I don’t even think the lights were in this broom closet of a meeting room and the managing director comes in and he goes. How do you feel about writing body copy, and body copy being the copy that goes to the bottom of an ad, print ad at the time. And I just said, “I will write the best and body copy you’ve ever seen.” And five minutes later, our interview was over. I thought, there’s no way I’m getting this job. And, they called me and gave it to me. And, they also gave it to the person that they were wining and dining. So, the two of us got the job. And that was the sort of end of it. Or I should say the beginning of what became a pretty, had some notable highlights after that.

Adam: That’s excellent. Well, let’s talk a little bit about this because you brought up some just in that story, it brings up the point of friction, and that in our creative worlds, there are a lot of good, I think there’s a great TED talk I listened to once about how like “the box” is important, like living within a box to have constraints before you can make something great is critical. And so, having some of these moments in your career, a friction where you had to scratch your way up to the top. You had to scratch your way, to get into the right agencies or get the right work. Talk to me about how does friction help us grow creatively, in your perspective?

THINK OF FRICTION AS A FORCING FUNCTION

Jason: Well, I mean, those struggles, they force you to be really innovative or tenacious, more so than you probably would have to. I feel like that type of friction is ultimately at play here when we’re, especially in marketing where we’re in a culture where we’re easily ignored, we’re easily opted out of, and it really forces us to be, becomes a forcing function to be more ingenious and to figure out ways to, in essence, not do what we do, to eliminate the tropes and the conceits that we’ve all learned and, find other ways, other points of connection.

Adam: And now, obviously in your career, you’ve gone from those early friction moments and gone on to do some great work. But the other thing that I want to just transition to right now is your book, because I think there’s a lot to learn from that as well. Many of us in the industry had to go through that whole passage. “I’ve been doing really good at the craft. I’m getting recognition, people are seeing me as a great writer or designer, videographer,” whatever that may be. But then you look up to management, and there’s this huge chasm. And I think at least for me, early on, I didn’t understand how big of a gap there was there. And so, there were some painful moments in realizing that I wasn’t ready for it, even though, everyone thinks, “Oh, I’m the creative director. I can call the shots. I know what I’m doing.”

So, I’m really interested to hear. Let’s talk more about your book because there’s some creative friction in there of trying to make that jump. So what are some of the notable takeaways? Why did you write it? What were you, what motivated you to help share that with the world? And then what can we, what are some insights in the book that we can share?

Jason: Well, one of the insights is actually the sort of principal insight, which is, if making things makes you happy, then keep making things when you become a leader. And that’s actually a really healthy thing to do when you still have that itch to be making things. But, you’re now at a stage of your career where you’re supposed to be championing others and letting them do the bulk of the work. And so, it was something that I felt like I needed to be doing something. I had noticed — it was sort of obvious, it was sort of right in front of my nose — the obvious sort of chasm of, we are artists, we’re wired differently than the sort of more business-focused.

It was obvious to me that we are wired differently. We’re not your typical sort of corporate person. And that we’re suddenly at that point in our career, when we had success doing basically our art that we’re raised up to a level where we’re doing something completely different, or we’re leading, which is a completely different skill set. And it’s something that’s not necessarily innate to us. In marketing creative people, we often spend time locked in a room, thinking of ideas. We’re not necessarily involved in the broader corporate culture. And we’re suddenly thrust into a management position where we’re part of a leadership culture. We’ve made it a point in our careers to really point the spotlight on ourselves, because that is essentially how you get ahead in creativity and creative careers.

And then suddenly we’re asked to now put the spotlight on others, which is a really, really hard thing to do because so much of our ego and self identity is wrapped up in our talent, in our art. We go through dark periods of when we’re making things filled with self doubt that ultimately once we’re like, “Solved it,” it’s like, “Aha!” And, suddenly you go through a period of, I’m amazing. I’m way better than I thought I was. So anyway, it was a combination of this sort of this need for something that wasn’t there.

LEARN TO MANAGE AND BE CREATIVE

There’s a million management books out there, but none really skewed towards the creative mind. And it just felt like based on our skills, based on our wiring, based on the fact that, we’re coming at this from a disadvantage from on our back foot because we haven’t gone to business school.

We haven’t been, what we’ve been doing, the skills we’ve been learning, haven’t been leading up to this, they’ve been wholly separate. It’s just a natural thing to do. And I was at a conference when it sort of dawned on me, there was a panel there and on the panel, someone made the, what did they say? They made the connection that you get better training for a management position in a fast food restaurant then you do in an advertising agency. And that really resonated because having come up at some point in my career, they just said, you’re going to become a creative director. Great, well deserved. And there was no training that went along with it, there was really do what you do. And, it was a totally different job. And so that’s when the light bulb went off that, huh? I think this is possibly a worthwhile thing.

And then the thing that I wanted to make sure that I did with it is not necessarily reduce it down to my field of vision. Marketing is one of many, many commercial creative careers, there’s production, and design of any number of design industrial and architecture, and a number of creative careers that this is applicable to. And so I felt like in order to widen that aperture, and for people to see how it connected back to them was to bring in other voices. And so, I was able to bring in some really amazing people — idols of mine. Some of them were directors like Ava Duvernay and Joe Russo, who directed adventure movies; people from Apple, Google, Disney; huge leaders from marketing; people from TV production as well. It’s really interesting hearing their perspectives.

The head of the executive producer on Rick and Morty shared stories about basically in his position, he’s got to run a writer’s room where he puts it, it’s basically an entire room filled with the people who are voted class clown in their high school, and you have to wrangle some pretty fragile egos as they’re throwing jokes out — some land with a thud and really you have to figure out how do you lift people up when it’s not working in that boiler room kind of environment.

And, I guess you said like some highlights from it. A lot of it’s separated into a few chunks, which is how do you be, how do you manage people, right? Because this is something fairly new and, really the basics of how do you manage a lot of different personalities, some of which want high touch, some of which want low touch, how do you handle the process of killing ideas? How do you maintain an approach where you’re not necessarily doing the work for them?

One of the more controversial thoughts with some people were — I don’t necessarily agree with it — if you have a bull in a China shop, then you should move the China and create an environment where people who gel with the sort of culture, who are really, really driven. How do you make sure one, that you’re still creating a healthy environment, but then how do you create an environment where they can thrive? And part of it is just move things out of their way and let them go, but also teach them along the way. How do you do it without hurting the people around them and impacting the larger culture?

Adam: You’ve gone through so many different things that I want to unpack a little bit, but first I have to say the hilarious part is, and we talked about this earlier, that same conference where you heard the comment about you get better training at a fast food joint than at an ad agency, I was at that same conference with you. And I think it’s no surprise that where Real Creative Leadership has come from — not just that, but it had been something that was on my mind as well — that we struggle in this industry, that we don’t have good guidance. We don’t have a user manual of how to jump into a leadership position, so I appreciate that. And I feel like there are probably more out there that are having the same thoughts as you and I, that there has got to be some more guidance.

And so taking the time to write a book or create a show I think is awesome for us to get engaged with other people out there, because it is a major problem. You start with all those soft skills, call them the creative cave. Your career gets better by you focusing in that flow state, and you just really focusing on the art or the writing in your quiet moments. And then all of a sudden you hit that moment where it’s like, that’s not what’s going to push you forward, you have to do other things, like the leadership, the soft skills, all of those things. So it’s challenging. It’s challenging, so I think this is a real good discussion from your perspective as you went out and interviewed all these other people in other industries of how they do it? How do you lead teams? How do you manage to the individual rather than to a big group? I think those are all awesome things.

CREATE AN INTENTIONAL LEADERSHIP ENVIRONMENT

Adam: Well, tell me a little bit more about that, let’s talk about how do you create some of that in your team right now? At Facebook, how are you creating the right environment? Just tell us about some of the things that you do today to help encourage people on your team to grow and get to that point. That would be awesome to hear.

Jason: It’s an interesting transition having been in agency culture and going into more of a corporate culture. It’s the tech space, but this is a really mature tech company, and they have a lot of policy and training. And one thing that actually is really healthy about it — and I continue to grow too and understand — they have a huge feedback program where there’s a lot of feedback given both ways. This is very reflective and it happens on a regular basis so that you’re really getting a sense of their satisfaction, their state of mind and where they feel like they are and where they want to be, and just a better understanding. It was a little more fast and loose in my agency days; here it really is taken pretty seriously.

This place is, what I found too, is it’s a very democratic culture, more so than I’ve ever experienced. It’s democratic in the sense that a lot of people are given the chance to really give their input, share their thoughts, and we as leaders, entertain thoughts from a much wider swath of people. And it might just be more the culture and not necessarily myself, where it’s like you want to hear what people have to say. And even though creative isn’t in their title, you want to hear, because there’s so many cross-functional partners.

I mean, one thing that’s really interesting about this job is that whereas being at an agency, or being at a design firm, or being at a production company, I guess, you are primarily doing your art, your craft, and you’re working with clients.

And now going into the client side, you primarily are a product company with a marketing arm. So you really become a specialist, but not necessarily the all-star. The all-stars are the ones who are coding for the apps, or who are making the incredible VR technology that goes into Quest. So you’re there doing your thing, but you’re not necessarily that standout, so there’s a little bit more humility in it. And it means that there’s just a lot more partners and voices that you have to listen to and take note of.

Having been a leader where I really have always wanted to hear from people, have wanted to hear dissenting views just as much as I want to hear agreement. I love a culture like this.

I just think at the end of the day, what’s so key is while we have a really democratic way of doing things you want, at the end of the day, a benevolent dictatorship, where it’s like someone is going to come in and be a strong, decisive decision maker. Because ultimately, if you don’t, I just feel like it just leads to swirl and chaos.

Adam: I mean, I find it fascinating that it’s almost a sign of a more mature creative company when they allow people to mingle into areas that are not normally their specialty. Meaning we’re here trying to tell creatives, “Step it up, become a better creative leader,” and you do that by learning to speak business and learning to understand other aspects, soft skills like we’ve talked about, and make that jump to a creative leader, you’ve got to have some of those skills. And yet there’s this inclination from some creative people to be like, “Oh, you’re not a creative. Don’t get in my business.” You may be a marketer or a whatever, financial person.

But you’re saying that democracy is really good because ideas can come from everywhere and you have to be really, truly open to that, and not just in theory, but in practicality. And I think that’s really nice, because they have to be able to welcome us to the business side. We need to welcome them to the creative side, and that shows the maturity of an organization.

Jason: Yeah. And it can be a little frustrating to creative people. We’re all at home working. It can be frustrating at times to a creative person who doesn’t necessarily want a ton of voices changing ideas or diluting ideas, which is totally understandable. And so it makes my role even I think more important where you’re really trying to… You have to build a lot more advocacy and you have to clear a path so that those ideas, in an environment like this, don’t get tainted or turned into a lowest common denominator thing because you’re entertaining every single piece of feedback you get.

Ultimately, it would be great to be able to teach everyone the value of creative and understand that there are things that are — and I should say too, this is a huge generalization, because we know that there’s some creative that’s going to be big and buzzworthy and hyper- creative in its execution. And there’s other stuff that’s going to be harder working and is more data driven or about reach. And so helping people on our team understand that. And we have regular creative presentations where we show people work that’s had huge breakthrough or success — helping people understand that this type of work is good, necessary, beneficial.

STORYTELLING, CREATIVITY, AND DATA-DRIVEN MARKETING

Adam: Yeah. Well, that’s another element that’s at odds. Data driven versus creative. For so long, it was like, “We don’t even need to worry about that data stuff. We’re changing the world with creativity.” There really is a balance there. So talk to me more about that. I think that’s another thing that’s at odds: data-driven marketing and creativity, and how do they work together?

Jason: Yeah. I mean, I think they work hand in hand. I mean, the opportunities of guaranteed breakthrough are fewer and far between. I mean, where do I go down this rabbit hole? I think both have real value, because one is really just more intuitive advertising, allows you to reach people right time, right moment, right head space. I mean, if it’s done brilliantly, it works brilliantly.

Breakthrough ideas, things that don’t follow best practices, things that disrupt a media platform, those have the power for exponential reach, where you’re breaking through and getting PR or getting shared in ways that something that tells you that that shirt that you love, that you were shopping for is now $5 less, or whatever it is. I just think there’s a place in our world for both of them. I don’t think you can necessarily do one without the other, and I think they do need to work in harmony if they’re going to work.

But as a creative person, I think it’s, at this stage of the game, it’s really necessary doing embrace both along with whatever else is coming down the pike, or is out there. I mean, knowledge of the entire ecosystem and not being scared of what’s on the horizon is so extremely important. And you know it just as well as I do. We’ve seen the evolution, we’ve gone through a couple waves of massive changes. And we know that in order to still be here, you need to embrace it wholeheartedly and go with it. I do feel, though, that what we’ve created in terms of in the advertising world, where we’ve got a situation where people want to avoid advertising at all costs. I think that a lot out of this is a self-fulfilling prophecy, and I think we brought it on ourselves as an industry.

I wrote a piece not long ago about learning something from the way that Netflix does their intros and how important that is to the way that we structure our ads. The death of the commercial and the forcing us to move from 30 seconds to 15 now to six, a lot of it has to do with ourselves and the fact that pre-roll, the advent of pre-roll, the way you got out of an ad is you had to watch the first few seconds and then it was skip ad. And I feel like that’s entirely wrong. I feel like what we should have done is done what Netflix does, which is skip to end.

Because if you look at the way storytelling, the best storytelling, right? Some of the best ads ever done, if you ever saw the mini-Darth ad — the Super Bowl ad — one of the best ones of all time. It was a kid going around the house, and he was trying to do the force on all the objects. And then ultimately the Volkswagen comes into the driveway and dad pretends that he’s done the force successfully on it. That ad would never actually work with the functionality that we have, because storytelling, you need that ability to gradually tell a story. And what we’ve done is we’ve really increased the importance of the first few seconds and getting branding in and getting product mentioned, and certain things that aren’t necessarily organic to a story.

And it there’s nothing wrong with the CMOs who have said, “I want more product at the front, because if people skip it, they at least get to see it.” They’re just trying to get that attribution. “I want our logo at the top and not just at the end, because now we’re forced to do that.” Had we done this thing where Netflix, if you’re watching a show and you say, “Skip to the end,” you get the director, the whatever, the name of the show, and you’re out. If we had done that — and totally more natural to the way we advertise — if you said, “Skip to end,” you would get the logo, you would get the offer if there was an offer, you would get all the “Go to this location,” whatever it was. All the essentials that you would normally back into a story.

But we changed it, it made the advertising worse, and then self-fulfilling prophecy. People said, “I hate the advertising even more,” so we shortened the ads and now we’re continuing to shorten it and make ourselves more irrelevant. We’re continuing to try and disguise our ads even more because people are so turned off, and we’re going to influencers and we’re making everything look like it was shot on an iPhone because that doesn’t feel like an ad. I know I’m rambling, but it’s a passion point.

Adam: Good. Well, and I’ve thought about those same things too, it’s not just… I like your idea of skip to the end, but it’s also refocusing on what matters most, which is what is the value from that experience? And if you’re just showing your logo at the top, you’re giving no value or your product. So giving something that has… If it’s interesting and entertaining and exciting, people will continue to watch it rather than skip.

Jason: Hundred percent, yeah.

Adam: Versus if you give them something that’s not fun because you thought it’s all about a time constraint.

LEVELING OUT THE CREATIVE EGO

There’s one other area I want to talk about, and you touched on this early on, which is a little bit about the ego of a creative. And they’re moving from one world to the next and it’s like, “I’m so great today because I did this awesome ad,” and then the next two weeks later, you’re like, “I’m the worst in the planet because what have I done lately?” But I’d love to talk a little bit more about, so how do we deal with that psychology of as you grow in your career, we all do it. We all do it. You think you’re the best, you think you’re the worst. How do we level that out a little bit more? What are some of the things or the tips that you can give our listeners to help them think, “Okay. I still have value regardless of these up and downs that I get with the creative work.”

Jason: I mean, I think a few things. One is it’s absolutely learned. I think that you can’t necessarily teach it out of someone. You have to give permission for those feelings, and it’s feelings that we all have. And it’s natural and in some ways, it’s a driver. I mean, we’ve all had that, at the 11th hour haven’t gotten anything and you’re pushing yourself so hard, and you have that stroke of genius. So it’s not all bad, but I feel like as a leader, what you want to do is minimize exacerbating it. You want to find ways to mitigate it, in my personal opinion. And I see so much in a lot of creative environments that there is this atmosphere of, if you don’t get it right, if you don’t have any value, then you can be replaced.

I’ve had a lot of creative leaders who push you through fear and driving anxiety and pitting you against other other people. And if you win, you win. If you don’t, you’re thought of as a loser. And that’s an ego killer, that is crushing. And I’ve always wanted to try and eliminate as much of that as possible because we’ve already got that. It’s innate to who we are. And so my goal is to try and take as much of that off the table, of fear of losing my job, fear of being irrelevant, fear of someone else winning the pitch versus me, fear of not being the favorite. Take that off the table and just be creative. And hopefully you’ve got people who are innately driven to want to do this stuff that it doesn’t take a huge push. And I try and be as supportive as I can be. I try and acknowledge feelings, for sure. Some days are rough and when it doesn’t go someone’s way, to be there for them versus punish them for it.

Adam: I love this. I just want to jump in a minute because there are a few stories that we can quickly share. For me starting out, I was working on the Intel account, and it was working on TV spots, and there would be 10 teams all battling it out in this huge battle royale, to see who got the best spot approved by the client. But there were a lot of those feelings of, yeah, people would hide work from each other, they weren’t open. There was a lot of internal competition that was just going too far.

And I think later on now, as I’m running teams, I have those same feelings of like, I want to give some ownership to each of the teams so they don’t feel like they have to scrap it out to get some recognition, otherwise they’re worthless and then they didn’t win, and so they’re lame. But I think there were some stories I read from you doing the same thing during just the round after round after round of going through those Mac versus PC ads. Sure there were great things that came out of it, but the process of getting there is pretty rough.

Jason: Yeah. That place had no problem. I shouldn’t say that place because I don’t want to necessarily trash an agency, but I do think the way that things were run back then, it was a little bit more of a “we’re going to push you to the brink.” And because in some ways we were mirroring the culture of Apple, and mirroring in some ways the Steve Jobs mentality of, get it right. If you don’t, I don’t need you. It was a little bit of that, and somewhat cruel, but I can’t help but acknowledge the man’s genius. The hope was to sort of bring that environment to the team.

And because of the way things were run and there was no big strategy machine on the Apple side, there was Steve with, “Here’s my proclamation. Here’s what I want. Go make it.” You were creative. People were carrying the burden of helping him arrive at strategy. So you would go round after round with, “Here’s the work,” and he would go, “None of that works, but now I know it’s not that, which is great.”

Adam: I know it when I see it.

Jason: So happy to help. But there was a cadence to what we did. It was every Wednesday we’d bring stuff up the mountain and then bring it back down with the decree of, he liked it, he hated it, this is on life support, everything else is dead. And people over the course of months were just getting worn out, losing hope. Because we brought in a lot of work, and sometimes you knew right away that this was the favorite. And so you felt like, all right, well I’m going to be working all weekend and well into the night, so it’s worth it. And other times you felt like, I don’t know if anybody really loves it, and I’m going to keep going on it because I’m being asked to, but you just felt like you were just were doing that every single week. And if you felt like this really doesn’t have a chance. It was brutal, because it wasn’t like death. It was like, you’re still doing it knowing that there’s no chance. It’s the work without the reward, I guess.

And routinely I’d have people in my office breaking down in tears, saying, I can’t do this anymore. It definitely became part work, part therapy, going into the later rounds of whether we were launching Mac and PC or whether we were launching the first iPhone or the first iPad, it was just like, there was so much lead up, and rightfully so to a certain extent from Apple’s perspective, these are big products. You have big industry-changing things that require —you’re carrying on a company’s legacy of incredible ads that drive culture and drive sales and everything, whatever you did had to live up to that, but it was not healthy.

Adam: No, that’s fair. And lessons going forward; it’s not that we just complain about the golden days. I like your advice of just trying to understand the situation of the individual and try and help create the right environment so that you can still have great ideas and we can still thrive without having to have all the negative battling it out over concepts and things that we went through in the past. I think that’s super valuable.

Any other last advice on how to become a better creative leader, whether it’s a tip from your book or just things in general? We’ve talked about environment and understanding the person, we’ve talked about how to get past ego, but anything else?

GIVE YOURSELF PERMISSION TO NOT BECOME A LEADER

Jason: I think we need to give more permission to not become a leader. I think that too often I think people feel like the necessary route they have to take is through leadership in order to survive, in order to make more money, in order to just last. And I think we need to give more permission to people to find an alternate route, to keep creating if that’s where their heart is. And so I think that’s one part of it that I feel is necessary.

Adam: Well, that’s awesome. I think you brought that up early in the beginning and I was going to respond to that, that it’s like, I’ve had that conversation with so many people, where they’re like, I see everyone else becoming an ECD, and I guess I need to do that, or it’s my turn to do that. What do I do? And it’s not necessarily the right answer. It’s so funny, the lesson I learned once from a group of developers. I was at a conference, and it was a room full of developers, and a woman got up at the front and said, all right, who wants to be a manager? And one hand in the entire audience went up. What’s going on here? Because if I were in a creative group, it’s like, who wants to be the creative director? Every hand is going to go up like me, me, me, me. I want to be in charge, right?

And so there is some truth to that. We actually did a survey with creative leaders this last fall. And it’s interesting to see how a third of them after they reach ECD, just finally realize they want to go back and just do the craft, and so they go back and just do freelance. So it’s totally fine. I think there are more and more career paths now that you can still stay a senior creative and get paid great and have a great career and not have to go into management and be a creative director. I think that’s totally viable.

Jason: Yeah, wholeheartedly agree. It’s still a difficult discussion to have with someone who doesn’t quite know what they don’t know. And in fact, I’m having that conversation with a friend right now who is really feeling like he is at a CD level and he’s getting offers to become an ECD, and with executive creative director, and I’m trying to tell him about, you really have to embrace all facets of this, a lot more management and a lot more of that side of things. A lot of dealing with leadership across different groups, really getting into the company culture, and you have to embrace that.

And he’s someone that spent a long time being a freelance person, where the life of a freelancer is, is you don’t have to be in a company culture and you don’t have to do any of the more bureaucratic stuff. You really just get to do your craft. You slide it under the door and you’re done, and it’s onto the next thing. And it’s so different. And I’m probably over-concerned that he does the right thing for him, and of course the instincts, he’s concerned about the money and that title doesn’t come around very often.

Adam: You’re right, though, there’s more to it than just title and sometimes money. I don’t think that’s always true, but it’s your happiness, your quality of life. I remember talking with this one person who was thinking that he needed to make that jump. And I just said, let me talk about the real life of a creative director or creative leader. I’m dealing with finance all the time, I’m in meetings all day. That’s all I do, are just meetings. And it’s talking through all those things. You talk about the bureaucracy, the culture, the hiring, all this other stuff that’s not the craft. So if you love, love, love the craft, don’t give that up, if that’s what drives you and makes you happy.

Well, okay. That’s a good thing to end on. Give yourself space, go for what you love, go for what you’re passionate about. Life is too short. I think the lessons we also learned from that research is that so many creative leaders, and I say this out of both sides of my mouth, because I want more people to become creative leaders, I want more people to push to the top, I want more people to make an impact on our industry and to drive it in new ways, absolutely. But there are a lot of them that realize they’ve just chosen the wrong thing and they get burned out and are unhappy.

So pick what’s right for you. If that’s being a creative freelancer, awesome. Learn to make the right amount of money and make a good living out of it and be happy. I think that’s an awesome choice.

Well, thank you. Thank you, Jason. This has been a wonderful conversation. I definitely am more pumped about just really considering my own personal career or my highs and lows and my egos and some of the great advice you’ve given us. So thank you. Thank you for being on the show here with us today.

Jason: Thank you, Adam. Appreciate it. Thank you for having me on and letting me talk your ear off.

Adam: Oh, you bet. Well, thank you everyone else also for listening to us. As always, you can find us here at realcreativeleadership.com. We’ve got a full catalog of past shows that you can check out. Also, if you like this, there are other shows on YouTube. We’ve been posting them all there, and there’s a great following on YouTube. So feel free to join us. You can also email the site, ask a question or for a future topic if you would like to, or follow us on the social channels and get engaged there, we’d really appreciate any involvement that you give us.

As always, you can find me at adamwmorgan.com and you can learn more about The Stoke Group. They’re the ones producing this show at thestokegroup.com. They’re a digital marketing agency. We appreciate their help. And Jason, where can people find you if they want to follow up or just follow your career or ask you a question. What are your locations?

Jason: I think I just changed my Twitter handle to @ThatSperling. And then LinkedIn is my name and the book is on Amazon. It’s called “Creative Directions: Mastering the Transition from Talent to Leader.”

Adam: All right. Well, there you go. Thanks for joining us. The big ask, again, leave a comment, like or share any of the episodes, post a comment or question on social media. We appreciate your engagement and thank all those who have engaged so far. Thanks again, Jason, for being on the show and we’ll see you at our next episode.