Defining Success for Creatives

David and Blair take a stab at answering the complicated question of what success looks like for each of them personally, as well as what it means for their clients.



BLAIR ENNS: David, this is the success podcast or the success episode, I think.

DAVID C. BAKER: Isn’t it early to call it the success … Maybe the podcast episode about success, right?

BLAIR: Yeah. This one stems from an earlier one we did where we talked about questions that drive us crazy and we didn't get to this one because it was a big one. It was words that make us wince. One of the things that I had contributed to that list was what does success look like to you. As you and I have been talking, does that question make you wince?

DAVID: It makes me wince for all kinds of reasons and some of them are even … they’re embarrassing actually. Yeah, they do make me wince partly because I don't know, I’m not sure I still do, know how to define it but that’s one of those words, it’s sort of like when you pulled that on me, like how do you define expertise after I've written a book on it.

BLAIR: You're welcome.

DAVID: I’d stammered around a little bit. It’s the same thing here with success. That seems like a word that should be very obvious how to define it, right, but then the more you think about it, you just stumble around on it, so yeah. It makes me uncomfortable because of what it stirs up inside of me as well.

BLAIR: Yeah, me too. When I think back to that episode, words that make us wince, some of them were things that it’s like, “Okay, could we quit having these conversations? These are ridiculous statements or questions,” and others were just like highly personal. I think this is one of those highly … There’s nothing wrong with that question, how do you define the success, but clearly, it’s kind of whipped me into a tizzy we’ve decided it merits some exploration here. Let’s start with this idea of when you hear the word success, what kind of weird ideas get into your head?

DAVID: Well, the first one for me is like okay, making lots of money, or I envision the spotlight on me whether I’m on stage or something like adulation. It’s weird. I don't know if I just inherited those concepts of success from other people or if they're coming from myself, but it’s like standing above the crowd and making more money and being more well-known than other people. Then, it just starts to feel dirty very quickly.

BLAIR: Yeah. Isn’t that interesting? I've talked about this before. I participated for a few years in a coaching program for entrepreneurs and they frequently refer to it as a room full of successful entrepreneurs. I remember the first time the coach said that. I cringed and I thought, “Well, I’m not that successful.” Then, I thought, “Whoa, what is that reaction?” I kind of tried to unpack it a little bit. It’s interesting. I kind of went back and forth on, well, what do you mean you don’t feel successful, Blair?

DAVID: Yeah, what do you mean? How did that protect you by saying, “I don’t feel that successful”? I’m really interested in your reaction there.

BLAIR: Well, I think, and I guess we should come to our definition of success, but I think my reaction was, “Oh, no. I still have all of these goals out in front of me and I haven’t achieved them, but then, by that definition, you only get to measure your success at the end of your life, right?

DAVID: At that point, other people are measuring your success. You're not around. The ultimate measure, I guess, is how many people come to your memorial service. I've thought often about putting a long list of people together so that it’s not empty, right? Julie can just pull it out and-

BLAIR: Who cares, right?

DAVID: Who cares? At that point, I’m not going to care.

BLAIR: Yeah, right. Have you thought about a definition of success?

DAVID: I was thinking about this yesterday. I was on a plane coming back from a photo adventure. I was shooting this, as in photo shooting, this abandoned theater outside Philadelphia and I was thinking, “What would I miss if I died,” which is kind of a ludicrous question because if you die, you're not missing anything, but then it just got me to thinking about this. I realized, okay, I would miss family and friends first, and then I would miss learning, just the process of learning. In fact, the things I do to relax, the hobbies, my consulting practice, what I enjoy writing and so on, to me, I look at those things through the lens of learning. If I flip that around just a little bit and look at a definition of success, to me, it’s learning. It’s always learning.

It’s not as if I reach a certain learned point. Success is a process for me that always involves learning and so I could see myself being successful in my better moments, not the earlier moments like we talked about at the beginning of this podcast. In my better moments, I could see myself being successful as long as I have the opportunity to still be connected with family and friends and also be learning in some way.

BLAIR: Boom. Drop the mic. I think you just wrecked this podcast because I think that’s … Maybe it’s just the two of us agree in this and very few others do but I would agree with that completely. I don't think it’s a ridiculous question of what would you miss after your death. I think I measure progress in my life through learning as well. It’s probably my biggest motivator and, yeah, your connections with family and friends, the connections you make with other people. If we go back to the definition, and I haven’t looked it up on purpose, but when I first started contemplating the question what does success look like, well, you start to think, “Well, what’s the definition of success?”

Success is accomplishing your goals. Therefore, success is very objective by that measurement. I’m going to attempt to climb that mountain. I attempt and I succeed or I fail. Success is just setting out goals and accomplishing the goals. At its very, I think most basic level, success is quite objective, but I think when we talk about this question of success, we’re talking about something that’s almost a mirror opposite of it or the second half of it and that is the feeling of being successful, and the feeling of being successful is entirely subjective. We have these two things, the objective measurement of success. We set a goal and we accomplished it, and then we have the messier sense of feeling like we’re successful in the world. Have you thought about it that way?

DAVID: Well, not exactly but now that you say that, it makes me wonder maybe this is why we’re so confused about this. I don’t remember … We usually set a topic around what the next podcast is going to be about and we don’t usually have to think too much about it. You and I have either connected informally or whatever or we both written about it or something, but this one, it was just full of so much confusion in my mind. What you just said answers a little bit of that for me because objective success, measures of success would be how I would measure success for somebody else.

I don’t have access to their own subjective measure of success and so maybe that’s the tension. Nobody knows how I feel about success but they can look at objective measures of success and make their own determination about that. Then, I get sucked into those more objective determinations of success. When I feel like I've fallen short of those things, it gives me this empty, unsatisfying feeling.

BLAIR: Yeah. Isn’t that interesting? I think it’s just an observation and I might just be projecting or generalizing but people who seem to be haunted by the question are lacking a feeling of success. I wonder if feeling successful isn’t just the same thing as happiness.

DAVID: Yeah, right, or gratitude or something. Maybe more happiness than gratitude exactly, but then is somebody who achieves a lot from an objective external goal sort of standpoint, are those people the ones who are driven by this, they never have that deeper feeling? I want the deeper feeling of success, but I don’t want it to the extent that it stops the drive. That’s the internal tension I feel for myself.

BLAIR: Do you feel successful now?

DAVID: I go back and forth. I feel like a little child playing around on the world stage sometimes. Then, in other times, I feel like I have conquered so much and have so much to be grateful for. I can flip back and forth between those things several times in the same day.

BLAIR: Even your subjective feeling about the objective measures probably changes. Is that true?

DAVID: Yeah, for sure. A lot of it is, I think, chemical in my brain. I've struggled with depression over the years. I think that’s part of it, but I just don’t know how to come to some … I want some more comfortable resolution between those two things, like really believing deep in my heart that success for me is constantly learning and being connected with people, but also somehow understanding that achieving and reaching is still good. That process is still good even if I don’t reach those objective goals. That’s what I have not solved. I haven’t even come close to solving that in my own life.

BLAIR: We did a show earlier on … I forget what the title was, but I was talking about themes versus goals. We’re both talking about that and I don’t remember if I told this story, but I remember being with a couple clients who are both friends of mine. We’re playing pool and it was a little after midnight, and one of the guys said, “Hey, it’s my birthday.” The other guy turned to him and said, “What would old you say to young you?” One of the questions that kind of drives me crazy.

DAVID: Yeah, right. That’s why I’m laughing at it.

BLAIR: I loved his answer and I've thought … This was a few years ago. I've thought about it a lot and I've taken a lot of lessons away from his answer. He said, “I would say the joy is in the struggle,” and we both said, “What do you mean by that?” He said, “When I was younger, I had three goals, three main goals. One was to own my own business. One was to have a million dollars in the bank, and one was to …” Well, I don't want to give away too much. It was a fairly big accomplishment. He said, “The day I accomplished all three of those things, the day I had all three of those things was the most depressing day of my life.”

DAVID: Wow. It was probably pretty early in his career too, right? It didn't take very long.

BLAIR: It was fairly early in his career, and he had set out these three big goals, three big mountains to climb. He climbed them and he couldn’t see the other mountains after that. By that definition, he would be successful, and the moment he achieved all three should have been the pinnacle of his success and he should have felt the subjective part of it. He should have felt very successful, but the opposite thing happened. I wonder, how meaningful is this question? How meaningful is this issue of whether or not somebody is successful or feels successful?

That’s the reason I put this question on the list. It’s not something I think about a lot. I probably think about the issues that are related to everything the way I feel about myself and my contributions to the world, but unless I’m listening to somebody else’s language, I don’t put it into the category of successful. I don't think of myself as successful or unsuccessful until somebody else brings it up, and then depending on, I guess what I’m thinking about, or my mood in the moment or as you’d say, my chemical composition, the things that are running through my brain and my nervous system, my response could be just anything on a spectrum. I could feel very successful one moment, and completely unsuccessful the next moment, but it’s not something I walk around thinking about, “Am I successful?”

DAVID: Yeah. How you respond in that moment has so much to do with the people in the room, which is ridiculous, right? How do we bring this around to our audience, these folks who are creative, entrepreneurial mindset people who are … they may be thinking about this but how do they think about it differently than, say some of our family and friends who may not be in the entrepreneurial creative space?

BLAIR: Well, maybe we should break it down into those two categories of objective success and subjective or feeling successful. Do you think it’s even fair to say … You have so much data after having worked with so many different independent creative firms, but do you think it’s fair to say that these are within your financial performance, culture or your relationships with your people, effectiveness of your client work, or whatever the categories are? I think I got those categories from you. Do you think it’s fair to say these are the thresholds of success?

DAVID: I feel less and less so over the years. I do think we owe it to ourselves to understand those and to see where we fit, but we don’t have to embrace them. For instance, financial performance. I think it’s useful just to know what’s typical out there, but I don't think we have to say that meets my goals. There are firms out there that achieve wildly more, firms that achieve wildly less, and I don’t see any connection at all between their own subjective sense of success and maybe somebody else’s sense of that. It seems irresponsible not to understand those things, but it doesn’t seem responsible necessarily, it doesn’t follow that we should necessarily embrace them.

BLAIR: If you had to lay out some categories where creative entrepreneurs would want to benchmark themselves against others, what would those categories be?

DAVID: Well, financial success for sure. Another would be culture, and there are certainly ways to measure that. That last one has become increasingly important to people. The impact that you're having on your clients would be another one. There are some that used to be true that don’t seem to be as true anymore like even winning awards. That seem to be more important in the past than it is now, which I think is good.

BLAIR: You've got the three main ones of financial, culture, and effectiveness or impact on your clients. Why don’t we start with the first one? I think my observation has been that people who seem haunted by the word success may be keeping material score. We’ve talked about money on these podcasts before a few times. We both agree it’s an interesting topic where we don’t want to be obsessed by money.

I think I’d speak for a lot of people and say we don’t want to be obsessed by money, but there are certain financial tests that you must pass to prove your kind of this very sustainability or viability of your business to get some sort of acknowledgement that the world needs what it is that you do. We can’t ignore financial success, and sometimes, huge financial success is reflective of these other things. It’s the scorecard perhaps of the impact you've had on your clients and perhaps even your own people, but we could go deep down this financial success rabbit hole.

I think if I think back to that room, this person is saying, “Okay, everybody in here is just a successful entrepreneur,” and I thought, “Well, I’m not all that successful,” and I even thought a lot of you aren’t that successful either. The reason that the-

DAVID: You didn't say it.

BLAIR: No, but the reason why the person’s saying it, that coach who was leading the room said it is there’s a certain financial threshold of personal income that you have to have met to be in the room. I’m thinking, well, that’s a pretty rudimentary measure of success. Just because we’ve each hit this personal income level, we’re considered successful? It’s an income level that I don’t even consider to be that high. I think most of the people in the room would think, “Well, we could all shut our businesses down and go get jobs that paid this much money. Would that make us … I don’t see the correlation there, but getting back to the heart of the matter of financial success here, is there a threshold, do you think, of an independent creative entrepreneur where like do you see 100,00 or a million or some number as the threshold of financial success?

DAVID: Well, it’s hard for me to envision somebody in this field who’s, let’s say working by themselves who isn’t regularly making $100,000. It seems like it’s more of a hobby below that. I’m talking about in say the U.S. and other countries like it, but it’s so weird to say that because there are so many really good people doing effective work making less than that, but I can’t think of the last line I worked with making that little and so what they would set for themselves are a bit more in the three to 700 range for themselves. I’m not talking about the people that work with them as employees or the firm itself, the profitability and so on, but I’m in a bubble as well because when people hire me-

BLAIR: Yeah. There’s a selection bias there. If they can’t afford you, then-

DAVID: Yeah, exactly. Right. They're hiring me to help them reach a level of success that they have already defined. They hire me to help them make a lot more money ethically. That’s pretty much the bottom line.


DAVID: Why do they hire you? They hire you and your firm and they enter the training program to make it easier, more effective to do the same thing, to lower the cost of sale and to increase the opportunity in terms of pricing, right?

BLAIR: Yeah, I think you're right. I think they hire me for the same reason they hire you or at least maybe that’s the way you and I think about it. We’re thinking about improved financial performance, but I think you and I would both agree that probably the bigger contributions that we make through our businesses, to our clients’ lives is probably a sense of freedom and empowerment, but that without the financial benchmark might be a little bit hollow.

I've always thought of financial success without learning, without maybe empowerment depending on who you are and these other things as hollow. I’m routinely faced with really interesting business opportunities that I think, “Wow, if I … I should really do this for the money.” I just think, I just can’t bring myself to do it not because it’s unethical. It’s just I can’t get excited about it. I don’t see myself learning from it, and maybe I’m projecting my own personal biases again here.

I think it’s easy to look at somebody who has a lot of financial and material wealth and say that person is successful but there’s zero correlation between that and their own feeling of success, so I think we have to acknowledge that financial success is part of it but as soon as we focus on it, it’s like staring into the eyes of the sun. As soon as we focus on it, we kind of ruin everything. If we were just to pursue financial success, I think we would find that we don’t feel successful.

I’m just thinking out loud here. We’re just riffing on this topic but I wonder if that feeling of success doesn’t come from the other things in the finances, the easily measured kind of objective thing that outsiders can point to and make their own assessment of whether or not you feel successful or not, but I think we probably feel successful based on these other more subjective things. You talked about learning, and I wholly agree. That’s when I feel successful, when I’m always learning, when I’m being challenged, when I’m meeting those challenges.

DAVID: Who in the world gets into the entrepreneurial creative field to get rich? I mean, I don’t. There’s a fairly significant percentage of people that achieve that but I don't know anybody that gets into the field driven primarily by that. It’s a part of what they want to accomplish and they make decisions along the way so that the shape of the business, the direction of the business includes an important enough component on the financial success, but here’s something that’s interesting. I think I see this, I think you see it, and I think our clients see it.

We have this toolbox that all of us come to business arrangements with. The tools in the box help us create success for our clients. I do it, you do it, our clients do it, and over and over again, we’re surprised at how our individual clients define success for themselves. We find ourselves saying, “Wait, wait, wait. I can fix that. I've got a tool. I can fix that for you,” and they don’t care. They care about certain things, or they need to check a box, and it feels like, wow, I’m going to have to relax here. This is going to be easier than I thought. I thought that they were going to ask me to help them scale this massive success mountainside and I know how to do that with them, but the deeper we get into it, I realize that this is not a simple thing for this person, this client that I’m across the table from. They want other things. They're defining success differently and I need to not define this for them.

As I was thinking about recording this podcast this morning, I was working in the kitchen. I was actually just cleaning up after breakfast and I thought to myself, “Have I defined success for my kids?” There was just like piercing in my heart. Did I make that mistake where I said to Jonathan and Nathan like, “This is what success looks like for you,” like, “You need to stay in school,” or, “You need to get this job,” or, “You need to get enough sleep,” or, “You need to have these friends and not these friends.”

It just gets confusing to me and I feel like maybe the process should be more about helping the people around us clarify these decisions in their minds and help them always be in the process of learning and letting that just be a simple satisfying definition of success for them as well and not impose this on other people.

BLAIR: Do you feel like as a consultant, you come to the table and it’s like, “No. These people have questions and I’m showing up with all the answers”?

DAVID: I do, but I feel like over time though, I have fewer and fewer answers, but the answers I have, I feel more certain about but I feel like so many of the things that I thought I had answers for in the past just simply don’t matter or I was way more confident about them than I should have been. The tools in my toolbox are more well-worn. There are fewer tools, and I trust them more, and I’m more comfortable leaving them in the toolbox. I think that’s part of what it means to be in an advisory business.

By that, I mean the folks listening to this podcast are in the advisory business as well. They're helping their clients. They need to bring out the same tools, fewer tools, more well-worn tools and be okay just bringing out a few of them and then moving on to the next one because they're walking into these huge corporations and they're done with the meeting. They walk back out to the car and they look at each other and say, “My God. How in the world did this huge Fortune 500 company get to the point it did? These people are nincompoops. How in the world …”

We all do that when we look inside other people’s businesses and it’s okay. It’s like people want to buy a smaller part of success from us and they want to use their definition, not ours.

BLAIR: Well, I was really struck by your emotional reaction to when you're asking yourself what have I done to my children, and then just extrapolate that to our clients. I don’t mean just me and you but all of the listeners too. How often are we guilty of going into a client engagement and defining success ourselves only to find out later, or maybe not even discover for ourselves that their definition of success, what they were looking for in this engagement was entirely different? I suspect that’s rampant.

DAVID: Yeah. I’ll bet it really is. Absolutely. I find that the question that I get, the big question I get after an engagement … You might find the same thing and my clients find the same thing. The big question you get after an engagement is X and you're thinking to yourself, “Really? That’s the biggest question you have after our engagement?” Usually, it’s some smaller sort of an implementation thing and it allows them to move on and all along, all of us who are on the advisory side of the table, you and me, our clients, are thinking there’s some big things that I can help you solve and you didn't even want to pursue those. It’s pretty clear at that point that success is being defined differently for all of us.

BLAIR: Do you think we should be asking each other professionally, personally, or even should we be trying to measure the success of other people? Is it important for us to be thinking about how successful we are?

DAVID: I think there’s freedom to do that and if a client asks for that, we should have a ready answer, it seems to me. Something that you talk a lot about, desired future state, is something that it’s a simple concept but really stuck with me a lot and it’s this notion of early in a conversation with a prospect, trying to get inside their head, which seems to me like it’s another way of helping them define how they would view success, that desired future state. Yeah, I think it’s very appropriate, but we need to be ready to hear different answers and then pivot the later conversations based on what they say.

BLAIR: Let’s go back to this point I made earlier, which it occurs to me that feeling successful is just a sense of happiness. Can we swap those two definitions out?

DAVID: Happiness and success?

BLAIR: Yeah, so I’m thinking of my own kids and I think I probably have moments when I’m interested in the kind of the external measures of success, but what I’m really interested in is are they happy? Are they fulfilled? I mean, really, the impetus for this show and the question is … I have a friend who has a podcast and he asks everybody that question on his podcast and it’s very clear to me that that question is important to him. He’s looking for the definition of success, and I think he should be looking for the definition of happiness.

DAVID: What would happen if we did swap those definitions for success? What would happen to entrepreneurial achievement?

BLAIR: I think if we really did and we could waive our magic wands and have people pursue happiness and not success, to me, the distinction is we remove the outward signaling of our happiness. If we think of happiness as something entirely personal and we think of success as the signaling power of our ability to signal to others that we are happy, and if we can detach those two things and just have to be happy to be enough, let go of the need to project our sense of happiness to others, maybe that’s enough.

DAVID: You know what, the crazy thing though is like how would that translate to what we say in our websites?

BLAIR: "Hire me. I’m really happy."

DAVID: If so much of what’s on our website is helping them achieve what we think they should to be successful and then all of our own signaling about our own level of success to give us the credibility to help them reach these subjective measures of success, so our world is just wrapped in strange definitions of success. I am far more confused half hour later than I was at the beginning of this thinking but it’s really worth thinking through.

BLAIR: Yeah. I mean, it’s pretty clear from this episode that this isn’t really a podcast. It’s more therapy disguised as a podcast. I’m with you. I’m not any closer to any sense of understanding my own feelings of success or lack of success or even the validity of the pursuit of success or the validity of the pursuit of the definition of success. I wonder if we really just shouldn’t be focused on happiness, but the challenge with happiness, I feel the same way about happiness. I can’t believe I’m saying this because I feel like if you pursue happiness, you're almost certainly going to fail.

DAVID: What are we supposed to pursue?

BLAIR: There’s a great book. It’s called Obliquity, which is a great work coined by the author. The author is the economist John Kay and the subtitle, I believe is Why Our Goals are Best Pursued Indirectly. What he says is the meaning of life is the pursuit of greatness, and so the objective of a tiger, of a person, of a corporation, the goal of all of those three different kind of entities are the same thing, is to be the greatest tiger, person, corporation you can be. If you pursue greatness, then the other things that you desire, happiness, money, fame, et cetera, whatever they are, they will come to you, but if you pursue any of those other things directly, happiness, financial fortune, fame, et cetera, you will find they elude you. What are your thoughts on that?

DAVID: Sounds like a Bible verse. I can’t remember what it was but isn’t there one about that?

BLAIR: You're asking the wrong person.

DAVID: Yeah, right. We’re sounding suspicious at like coaches here instead of consultants.

BLAIR: Yeah. I don't know where we go from this. I think this whole episode has been a bum.

DAVID: All right.

BLAIR: It’s been very unsuccessful.

DAVID: Yeah, that’s right. Don’t do this to me again. After our last episode, you said, “Let’s do another … Let’s do an episode on success.” I’m like, “What am I supposed to say?” I should drop one on you right now. All right, our next episode, Blair, is going to be on how to repair disc brakes.

BLAIR: Good Lord.

DAVID: You have no clue about how to do that.

BLAIR: How to identify disk brakes.

DAVID: You have no idea how to do that and I do, so-

BLAIR: They're on the wheel, right?

DAVID: Yes, right.

BLAIR: All right. Well, this has been our least successful podcast ever. Maybe the challenge is this topic is actually big and meaty and meaningful and we need to sit with a bit more. Maybe there’s something here and maybe we’re out of business after this. I don't know. Thanks for nothing, David.

DAVID: Thank you, Blair.

David Baker