Stuff We've Messed Up (and Learned From)

To wrap Season 3, Eric and Jonathan are doing something different — and a little vulnerable.

In this raw and unfiltered finale, they look back on the leadership decisions, strategic misfires, hiring blunders, and marketing missteps that didn’t go according to plan. No spin. No gloss. Just two founders owning their hardest lessons out loud.

Why end the season like this? Because mistakes aren’t just part of leadership — they are leadership. If we want a social impact sector that embraces failure as fuel for growth, we have to start by telling the truth about what we've gotten wrong.

So here it is.

Episode Highlights:

[00:00] Opening: “Today we're going to talk about all the shit we've messed up.”
Jonathan sets the tone for a candid conversation.

[01:35] Why talk about mistakes at all?
A response to listener feedback—and a call for more honesty in leadership culture.

[02:23] Jonathan’s board breakup
“I disbanded the board completely. Everybody just bandaid style.” And why he’d do it differently today.

[05:34] Eric’s accidental leadership path
“I should probably just share that I am an accidental entrepreneur and leader.”

[08:04] Burnout and showing up as a leader
“The meeting ends and five minutes later you're like, man, I probably could have handled that a lot better.”

[10:26] When design isn’t enough
Eric unpacks why creative excellence without strategy wasn’t cutting it at Cosmic.

[13:28] Strategic blindspots
Jonathan shares a moment that still stings: “You're a B minus strategic thinker.”

[18:17] “I blind copied them.”
A painful HR mistake Jonathan will never forget.

[20:48] Firing with (or without) dignity
Why quick, clear, and kind is better—for everyone involved.

[27:07] Going too wide in marketing
Jonathan: “I tried to do too many things when really the solution was right there.”

[28:53] The cost of not marketing
Eric: “Ironically, the biggest marketing mistake that we've made is not marketing.”

[33:30] When vision stalls
Why coasting on clarity creates future problems—and how to reset.

Notable Quotes:

• “Today we're going to talk about all the shit we've messed up. And so I disbanded the board. I remember this outright. I disbanded the board completely. Everybody just bandaid style.” — Jonathan Hicken [00:00]
• “Going into a conversation or you're in a meeting and the meeting ends and five minutes later you're like, man, I probably could have handled that a lot better. I probably could have been a lot more patient with that one person.” — Eric Ressler [00:12 / 08:04]
• “I was really just hyper-focused on the people and the process. Frankly, rather than the strategy or the results. And looking back, that was a mistake.” — Jonathan Hicken [17:44]
• “Ironically, the biggest marketing mistake that we've made is not marketing.” — Eric Ressler [28:53]

• “At some point in my career, let somebody go and accidentally blind copied them on the email to HR about the decision and saw them open the email.” — Jonathan Hicken [18:17]

   

Resources:

• Podcast - Rethinking Failure in Social Impact
• Podcast - How to Stop Planning and Start Doing - Discussion of MVS framework
• Podcast - Designing a Purpose and Strategy with Eric Ressler
• Article - Test Your Niche to Develop Your Organization’s Superpower
• Article - 8 Key Ingredients to Defining Your Social Impact Niche
• Article - How to Build a Next-level Content Strategy
• Article - A Guide to Social Impact Marketing Through Brand-building

Transcript

Jonathan Hicken [00:00]:

Today we're going to talk about all the shit we've messed up. And so I disbanded the board. I remember this outright. I disbanded the board completely. Everybody just bandaid style

Eric Ressler [00:12]:

Going into a conversation or you're in a meeting and the meeting ends and five minutes later you're like, man, I probably could have handled that a lot better. I probably could have been a lot more patient with that one person.

Jonathan Hicken [00:22]:

I wasn't seeing the trends from the customer side of things and I wasn't positioning the team differently or making sure we had a seat at the table. I was really just hyper-focused on the people and the process. Frankly,

Eric Ressler [00:35]:

Hopefully this is inspiring for people to do this constructively and we can start to build a culture of failure and mistakes being a little bit more normalized, a little less stigmatized. I'm Eric Wrestler. I'm Jonathan, and this is Designing Tomorrow. Jonathan, this one should be interesting. Today we're going to talk about all the shit we've messed up. Where to begin. Exactly. Well, let's talk about why we're doing this. So a couple reasons. One, we talked about in a previous episode wanting nonprofits and social impact organizations to embrace failure to be better about embracing failure and to develop a broader culture of that being more acceptable. And one of the things we talked about was we got to be willing to admit our mistakes to do that. And so some of this is kind of eating our own dog food. The other thing is before we started recording season three, we kind of put out a call to our community and our listeners and said, Hey, here's some episode topics, some of our worst episode topics that we're thinking about.

[01:37]:

Help us come up with some better ones. And this episode was one of those worst episode topics and a number of people said, no, no, you should actually do that episode. So we've got two reasons to do it. So we're going to give it a shot. Listeners, bear with us. Hopefully it'll be at least entertaining if nothing else. And really, I mean we don't even have clear ideas around this, right? We've got some stuff floating around our heads. I'm hoping that the conversation will just develop naturally, but we want to talk about some of the things we've messed up and hopefully what we've learned and even more, hopefully we can help potential listeners maybe not make some of the same mistakes that we did. So I'm going to put you on the spot and I'm going to say, Jonathan, let's talk about some things that you've messed up over the years and let's start with maybe some leadership mistakes.

Jonathan Hicken [02:23]:

One comes to mind immediately.

Eric Ressler [02:25]:

Okay,

Jonathan Hicken [02:26]:

This has to do with the board at the Seymour Center, the organization I run today. And keep in mind, we're actually part of the University of California Santa Cruz, and so we kind of legally sit underneath the foundation arm of the university, meaning we don't actually legally need a board in the same way that most nonprofits do. Nevertheless, we had a board and it was a very dedicated group of people who had done a ton of work, particularly coming through Covid to keep the organization going at a really tough time. And when I started, I had some ideas about what the board needed to be or the work it needed to do, couldn't come to an agreement about what that work should look like. And so I disbanded the board. I remember this outright. I disbanded the board completely. Everybody just Band-Aid style we're done. Looking back on that, I stand behind the decision to sort of shift the purpose and the outcomes that the board needed to be focused on. I really messed up actually how I disbanded the board and damage some relationships that in 2020 hindsight that were not good relationships to damage.

Eric Ressler [03:44]:

I have a feeling this is going to be a theme throughout this episode, which is how you do what you do is often where the mistake really comes from. So even in this case, it sounds like if you had to do over, you probably still would've disbanded the board or really tried to make a big pivot. And so you wouldn't rethink that, but you've learned that maybe you would go about it a little bit differently. Are you willing to share what you might've done differently?

Jonathan Hicken [04:08]:

Yeah, and so the way I did it was just like I said, it was a bandaid. I made 12 calls back to back and it was done within an hour. I think what it would've done is actually involve these people more in sort of the thinking behind some of the changes and invite them to opt in or opt out on particular tasks or particular duties and basically share the power and share agency in this, especially given the amount of work that they did and how dedicated they were. It really was unfair of me to come in and just kind of rip it, just cold, rip it off and be done. I think at the time my feeling was like, I just need this done. It's not a good use of my time. I need to be focused elsewhere. But that was shortsighted because I damaged some relationships that are really important to me.

Eric Ressler [05:02]:

That's a tough one. Sometimes you do just need to do the band-aid rip off, and you could have drug that along for months, years even, and still ended up just kind of having to rip the band-aid off then or still maybe would've ended up parting on not so good terms with some people. So I see why you did it and at the same time, I know you well, I know your intention is never to be unfair to anyone, but sometimes, yeah, hindsight is 2020. Probably another theme that will come up a lot in this episode.

Jonathan Hicken [05:34]:

Alright, your turn. Are

Eric Ressler [05:35]:

We talking about leadership mistakes?

Jonathan Hicken [05:36]:

Yeah, let's stick with leadership

Eric Ressler [05:38]:

Of where to begin. Well, I mean I should probably just share that I am an accidental entrepreneur and leader, so I have no formal leadership training other than running cosmic for the last 15 years. And at this point I feel like I have pretty extensive opinions and perspectives on how to do leadership, but I basically learned all of that through a series of mistakes. And so how do I make this not a completely long-winded story? I would say that the biggest leadership mistakes that I've made over the years that has kind of formed a number of micro mistakes is not understanding that the way that my brain works is the way that most people's brain work. And so for a long time as a leader, I would kind of just sit there and just wonder why aren't people getting this? Why do I have to break these things down?

[06:32]:

Why do I have to explain this thing? It's just so obvious, and I'm not even trying to say this as I know everything and I'm so smart. It's more just like I can see my own vision for where I want things to go, how I want things to go at Cosmic. And I had to learn the hard way in many times that you can't just assume people are going to pick that up organically by even sitting in the same room as you. And how do you take that vision and your approach and your leadership style and be really intentional with it and just learn that people's brains work in different ways. And so I've had to learn a lot of hard lessons because of that. That's led to hiring and firing mistakes, which I'm sure we'll get into. But that's really the big theme for me in terms of leadership is just learning to become a leader.

[07:19]:

And I think one of the other big things I've learned as a leader is that so much of your team culture and how your team reacts and what your team thinks is good and bad and right and wrong is about how you show up every day. And man, I've definitely not shown up at my best at times and even in certain cases for long periods of time. And I think it's probably mostly stress, burnout, other personal things that have happened in my life that have made it. So my intention was not to show up at my worst. I don't think that's ever true, but it's always that hindsight where it's like you go into a conversation or you're in a meeting and the meeting ends and five minutes later you're like, man, I probably could have handled that a lot better. I probably could have said that a lot better.

[08:04]:

I probably could have been a lot more patient with that one person. And so that's something that frankly is still something I struggle with to this day. Now what I've learned is that for me, a lot of that is just my baseline psychology. Am I getting enough sleep, which for a long time with young kids I've not been, am I keeping my exercise routine up? Am I spending time connected with my community? Am I getting out in nature? Am I being creative outside of work? Am I getting my music time in? Those are the things that sets me up to be the best version of myself. And when I'm not doing enough of those things consistently enough, which sometimes happens because life is messy, then I'm not set up to be the best version of myself, and then I can start to set a bad example for the rest of the team about how to show up and how to handle things not going well.

Jonathan Hicken [08:53]:

So it sounds to me like there's actually two things going on in there. There's the one, Hey, how do I communicate vision or priorities or outcomes here more clearly to the team, but also how do I manage myself and my own time to show up healthy? I'm curious, you've outlined your dedication to exercise and creativity outside. What have you done on the communication side to help bridge that gap between as you described, where your head's at and where everybody else is at?

Eric Ressler [09:27]:

So many things over the years, lots of experiments. So for a long time we had no formal internal communication plan other than we had a lot of internal standups. We all worked in the same room, so a lot of it just kind of happened organically. And in the early days, the focus was just so clearly on the work. It was just like the work we want to do, the work, we want to do the work well, which I think is right. In those early days when you're really just cutting your teeth, it's almost just bootcamp and it's just like, we're going to do the work. We're going to focus on doing the best creative work we possibly can. This is actually another mistake in my opinion, in that if as a creative professional and the work that we do, and my background is as a designer and as a creative person, and I think I had to learn the hard lesson that creativity in and of itself is not necessarily going to create business outcomes that our clients are looking for.

[10:26]:

And if you get stuck in that mode of like, well, we're going to just compete on the best creative output possible. First of all, there is a high bar. There are some incredible creative people in the world and incredible agencies doing amazing work with massive resources and usually massive budgets to back up that work in big teams and long timeframes and usually working on bigger brands. And that's not who we serve. We tend to serve small to mid-size nonprofits between two to 50 million a year usually. And they don't have the same budget as Coca-Cola, obviously. With all that to say, I've had to learn, and especially a lesson I've learned in the last five years or so, and even really, really strongly dedicated to this right now, it's like how can we connect and explore how design and creativity and communications have a place and a seat at the table, a proper seat at the table when it comes to moving social impact missions forward?

[11:26]:

And it is kind of a design problem. So it's not out of bounds for me in terms of even the way that I solve problems, but for a long time I was just so focused on the creative side and not how to tie that into the strategic side. So that's like a meta answer to that. And then the communication internally to the team. I mean, I don't even know where to begin there on mistakes that I've made from over-communicating to being too, to not being rigid enough. There's something that kind of happens if you hang onto the same team long enough, which has really been my focus and my focus has really been on that showing up and being my best self, where there is some amount of that that just kind of starts to gel organically in my opinion. Now, I think that's one leadership style.

[12:13]:

I don't think it's the only one. I think it's the one that tends to work best for me. We do some light strategic planning every year, I would say. So we usually open the year up with a vision and some clear KPIs, and we try to break it down to three main objectives for the year, because I've just found that anything more than that and it just doesn't get done starts to get overwhelming. And then we do use the MVS framework that I outlined in episode one of this season to test these new ideas. We do have objectives, we have problems we're trying to solve all the time. And so it's kind of a combination of those two things of having a big clear, simple distilled vision and then testing, testing, testing against that vision and assessing what's working and what's not working.

Jonathan Hicken [13:01]:

Can we move on to business strategy? Because everything that you just described to me is like you're talking about business strategy as much as the idea of design, having a seat at the executive table. To me that is a strategic positioning move for you and cosmic. So I wonder in that realm, what's a mistake in that area that you've made?

Eric Ressler [13:28]:

Well, I think the biggest mistake, and I kind of hinted at this, is that not realizing that early enough and not doing a good enough job knowing what the answer to that question is and making a case for it and approaching our projects from that vantage point. This is something we're good at now, and I think there's still room to improve here. I think part of that is because there is some level of subjectivity with branding and messaging, and it isn't necessarily only a science. And I think if you get too scientific with it, in my opinion, that's the wrong way to look at it. So the mistake I would say is not getting into that soon enough and really not thinking deeply about any kind of coherent business strategy. And this leads into maybe a little bit more on the marketing side, but for the longest time in the early days, we did the work.

[14:21]:

We were born out of a coworking space, so opportunities were coming to us naturally. Everything was referral. It was a hundred percent referral based. And this is pretty common for creative agencies is that it's often largely driven by referral. But I learned pretty quickly that that was a pretty shaky business strategy because referrals are not consistent. They're not guaranteed. You can't predict how they're going to happen. And so you're really operating on a lot of risk and trust and that can work out. And that actually us for quite a while. But we did find that it had a limit for us, and maybe that's my network wasn't as strong as it could have been. If I had a stronger, more connected network, maybe we would be great with just that strategy. But this is actually, frankly what led us to focusing on social impact is one of the things we realized is that we've got to own a niche.

[15:10]:

We've got to have a clear way to differentiate our agency against the 40,000 plus other agencies in America, and then not to mention the world. And we need to build some deeper expertise and some repeatability in our work because we were just doing all kinds of projects early in the days from video production work to branding work, to web design work for all kinds of different organizations. And so we were building some foundational skills, but not enough repeatability to really get super good at any of it. And so the nicheing in helped us understand what are the things that this niche needs the most help with? And even within that, there's still only certain things that we help our clients with, and we have boundaries around that too.

Jonathan Hicken [15:52]:

A mistake I made actually sounds a little similar. This is actually before my time in the social impact space. It was when I was in tech, but similarly, I wasn't putting enough thought into strategy and niche and I was running a customer success team. It was like 50 people, 25 million quota. It was a big team with some big goals. And I remember, so at the end of my time there, I got replaced, replaced. So I was part of this company from when there were less than 10 people, and by the time I left there were 400. So I was there during this early rapid growth phase, but I got replaced by someone who was more seasoned in that next stage of growth. And looking back on it, I totally get it. That person was more suited for the job as it existed at that time. But I remember my exit interview with the CEO and he said something like, Jonathan, you are an A plus team leader. You are an A plus culture guy. You are an A plus sales guy, but you're a B minus strategic thinker and that it's stung. But I heard it. And looking back on that, I was really focused on my team because I knew that that was my strong suit. It was a big team. I really cared about the people and I spent a lot of time with them trying to set them up for success.

[17:22]:

But all the while I wasn't seeing the trends from the customer side of things, and I wasn't positioning the team differently or making sure we had a seat at the table. I was really just hyper-focused on the people and the process, frankly, rather than the strategy or the results. And looking back, that was a mistake.

Eric Ressler [17:44]:

I think that's natural though. And I hear some reflection and some congruency between experiences. And I do think you can have the opposite problem where if you're only focused on theoretical strategy, but you don't understand the customers, you don't understand the people, you don't understand the processes. I mean, we need all of these things to be kind of humming. Should we get into kind of team and hiring mistakes? Yeah, sure. Talking about team. Yeah. Do you want to start or do you want me to start?

Jonathan Hicken [18:17]:

Yeah, I mean, I got to share one particular story. I'm not going to use any names or any identifying information. At some point in my career, let somebody go and accidentally blind copied them on the email to HR about the decision and saw them open the email

Eric Ressler [18:37]:

As, oh, in real life.

Jonathan Hicken [18:39]:

In real life, oh, Jesus watched them open this email. So I mean, literally that one moment was absolutely crushing. I made the worst mistake that any manager can make when they're to make an already difficult decision to let somebody go. But needless to say, I have learned to be extremely careful about the address line in emails, particularly with sensitive information.

Eric Ressler [19:06]:

Yeah, probably just good in general advice,

Jonathan Hicken [19:09]:

But that was just sort of a silly mistake. I would say another mistake was letting somebody go in a way that wasn't dignified and didn't leave them with the feeling of the dignity and respect and mutual admiration. I let somebody go in a way that really hurt them. And I actually think about that a lot to this day. And this happened a long time ago, and that was a big mistake. And I don't want to be that kind of leader. I want to build teams where even when those difficult decisions happen, the baseline level of human respect and partnership still exists, even if we need to part ways. That's what I aspire to and I made a mistake and I hurt somebody. And I look back on that and I feel really bad about it.

Eric Ressler [20:09]:

Yeah, I mean, I can absolutely resonate with that. And I've been lucky that I've only had to let a few people go over the years more than I would like to, but less than I think is usual for a company of our size and length of operations. And I know this may come off as like, oh, the poor founder story, but if you've never had to fire someone, it is awful. It is awful. And if you've never been fired, of course being fired is awful too. Let's be real. And probably if you had to choose one or the other, firing someone is probably the better. I mean, you've been fired and fired people. What do you think?

Jonathan Hicken [20:48]:

Oh, well, very difficult for, I have been fired. I've been fired multiple times. Let's be clear about that. I've also had to fire people. They're both extremely difficult. I think the ramifications of being fired are deeper and broader in terms of life impact than the intense emotional difficulty of letting somebody go. Nevertheless, they're both challenging in their own way.

Eric Ressler [21:14]:

So let's talk a little bit about that process because this is something that I've gone all over the place on. So I'll share just a brief story. The very first person I ever had to fire was one of our very early employees, and he was an awesome guy. He was one of our developers, and he was the most kindhearted, generous, amazing person. Loved him, still loved him to this day, but there came a point where he just was not getting his work done at all, and it just wasn't working. I'm not really sure exactly what was happening. I think there were some challenges with distraction and procrastination, which I struggle with personally, so I completely get that. But at the end of the day, we got to ship product, we've got to ship solutions for our clients. And if that's not happening and we're relying on a team member, that's not a sustainable situation.

[22:04]:

And because this was early in the day for Cosmic, and I'd never fired anyone before I got really deep into, okay, let's work on this together. Let's put a performance improvement plan together. Let's, let's set some really clear guidelines for what that looks like and what we're expecting of you and make sure, hey, are we not doing a good enough job communicating expectations? Is that maybe the problem? And went kind of deep on that that wasn't working, then started to go even deeper and okay, it seems like you've got some issues with procrastination and potentially attention. Let's fund some therapy for you to get through that. Which at the time, looking back, I think that's a pretty intense performance improvement plan that's a little above and beyond what a typical employer will do. And to be clear, we've never done that since, but we were really committed to, we'd love this person, they're a value member of our team, and we want to help them improve.

[23:02]:

And we did that for a while and there was still not improvement after that point. And then we gave them an even longer runway to continue to try. And at the end of this, it had probably been six months of really concerted effort. It was taking a lot of my personal time. It was really bringing the team down. We were missing deadlines for clients. It was a bad situation. We were pretty small. So any one person not performing has a huge impact on a company that's really small. And finally, we had to actually fire this person. And even though we did all of that, I distinctly remember when we had to fire this person, it was raining and I was carrying computers and gear out, and I felt just so horrible about all of this. And looking back, did I make a mistake there? I think I did, but I think the mistake I made is I didn't fire this person quickly enough, which sounds really brutal, and I feel bad about that perspective, but it is actually the one that I've landed on.

[23:57]:

And maybe the way to frame this is, I know we've talked about this before, but a lot of times people use this kind of metaphor of running a team. It's like your family. We're a family here. And I just think that is a really toxic way to think about running a team, even if it's grounded in good intention. And when I think about running cosmic and the teams that I see, they're the most effective. They really think about their team, like a high performance sports team where there's a group of people coming together for a shared mission in the case of sports to win the game. But in the case of business or social impact is to create an impact or to have outcomes that are based on your business. And you're trying to find the very best people in the world to do that together.

[24:36]:

And everyone needs to pull their weight. You want to see everyone within reason, dedicating time, energy, effort, learning, respect for everyone else on the team. And no one's going to show up at their best every day, as we've talked about earlier in this episode. But the overall trend should be as equal as possible. And if any one person on the team is not performing to the needs of the job or in a way that the rest of the team really can see, that is just so bad for culture. So inspired by some different philosophies on this from various sources, I've really kind of come around to, especially with a new employee, if there's not a meaningful fit kind of starting to gel pretty quickly and we have good onboarding to support this, we part ways fast, and we're very generous in how we do that.

[25:28]:

We're clear about that upfront, and we have generous severance packages so that it's not as disruptive. And really it's kind of in lieu of a performance improvement plan. We're not militant on this. We're human. We understand people will make mistakes and we give people the benefit of the doubt, but I've learned over the years that that's actually better for everyone, even the people who end up not being a good fit because it's coming. It's coming anyway. And no one likes being part of this kind of awkward place where everyone knows it's not quite working, but you're trying to work through it. So obviously there's a balance there. But I mean, how do you think about that?

Jonathan Hicken [26:04]:

I agree with that. I've also learned the hard way in that regard. It's one thing for write an executive director and an agency founder and director to talk about this, but it really is true that I have found that the terminations that ended with the most dignity and respect were the ones that happened quickly and swiftly and clearly not the ones that were drug along. It's almost like a relationship. If you're dating someone and you're like, this is not working, and you keep it going, that can be a really painful period. And I think this is not too dissimilar. And so yeah, again, going back to that theme of dignity and respect, that's what I strive for when I have to make a termination. And more often than not, that outcome of dignity and respect can be achieved if it happens quickly and clearly and kindly.

Eric Ressler [26:57]:

Yeah, I think that makes sense. Let's talk about marketing mistakes. I'm going to make you go first on this one and then you can start to prod me.

Jonathan Hicken [27:07]:

Yeah, honestly, I've made so many marketing mistakes because I'm learning every day and the landscape is changing every day. And I think many of us are learning on the fly because our jobs mean we can't put all of our time into thinking about marketing strategy. But I think the single biggest mistake, and I've made this mistake multiple times, is not going all in on a channel that I know is working and looking back and being like that. That was the way to go. And I spread out the resources too thin. I tried to do too many things when really the solution, the best solution was right there. And we could have gone five x on that particular channel and seen better results than we got by spread it kind of going this wide blast method.

Eric Ressler [27:58]:

I would say this is probably one of the most common marketing mistakes.

[28:03]:

I might even say that I think we might be making this mistake right now for our own marketing at Cosmic a little bit. We're looking at what to do. Don't worry, listeners, the podcast is not on the chopping block. But yeah, it is hard to know because marketing in certain ways, doing marketing well is just making a bunch of mistakes and learning from them. And I think that you do have to, and it is always changing. And another big marketing mistake is just finding something that works and just putting it on autopilot and then eventually it stops working usually. So yeah, that's a common one for sure. So I wouldn't feel too bad. I would say, honestly, ironically, the biggest marketing mistake that we've made is not marketing, right? Yeah. I mean, we didn't market cosmic for really at least six, if not seven years, the first six or seven years.

[28:53]:

We were really focused on client relationships, client work, and referrals. And that got us to a certain point, we talked about this already a little bit, but then we realized of course, that marketing is important. And more than marketing, really building a brand and getting brand awareness and having clarity around our niche and all of that. And the thing is though, that until you're forced to market, you might think you have those answers, and then you actually don't until you have to answer questions like, well, who is your actual audience and what channels are they on? And how do you define them from a demographic standpoint or whatever? And okay, what's the ad going to be and what's the message that's going to work better? Because this audience so well, marketing is such a forcing function for business strategy. And so even if you don't think you need to do marketing for some reason, I would challenge that, not just because I believe so fully in marketing, but because it is a forcing function for having to make all these really tough business decisions that have so many other benefits outside of being able to do marketing.

Jonathan Hicken [29:56]:

Well, I'm like sitting here beating myself up over these decisions that I've made on jobs that I had years ago that I've moved on from. But one example that really comes to mind is I was a part of, we worked together on the Museum of Art and History at Santa Cruz Museum of Art and History, and we were getting to launch this new public plaza called Abbott Square, and I was in charge of marketing it. And actually looking back, we did a good job overall, but I realized that we could have done even better. What we realized in hindsight was the person to person word of mouth was really the most powerful way of getting people down. And so we did something. We had, we had hats. We were giving out freebies that sparked conversation between friends and family. I would've actually gone heavier on that hyper centralized marketing in the downtown Santa Cruz area. Physical sort of physical, whether it's billboards or signpost flags or more swag, but really things that got people who are already close to the plaza wanting to take the block, detour to check it out, or next time they were thinking of going downtown, they're like, Hey, we should check out Abbott Square. That really worked for us. And in hindsight, I would've done more of that.

Eric Ressler [31:18]:

That makes sense. And I think, again, 2020, right? Hindsight is always 2020. I want to share another mistake that I've made that I still feel like I make from time to time, and this is, it's like an ebb and flow mistake for me. What tends to happen is we have a big challenge at cosmic, a big growth point. We're changing our services or our niche or whatever. Over the years, we've made these big moves, and in those moments of inventing something new, I'm really energized and activated and engaged because that's tantalizing for me. That's where I really, I think, get the most energized doing this work. And then we roll these things out and they start to work, and they start to get into the operational end of it, taking an idea from the exciting, messy, creative idea space into the operational space. Luckily, I have really solid members on my team who can do operations that I trust to do operations that can help take these crazy ideas and break them down into the necessary logical components.

[32:21]:

But what I've found over the years is that I've kind of let things coast at times where that exciting, messy work is done, and then we get to the point of solving some of the early problems, and then it's kind of working, and then I just kind of sit back. I'm like, it's working. Cool, cool. And I'm in mode, and I think I don't even realize I'm in that mode until a new problem arises and we have to get back in that problem solving mode. And then in reflection, I'm like, oh, I was coasting. I needed to be laying the path for the next stage of the organization. And the longer I've been running cosmic, the more I've realized that amongst all the jobs that I have to do, because we're a small team and we all do multiple jobs, the single most important job for me is to just be crystal clear on vision and always be thinking about that, and always be curious about whether or not are we meeting our vision? Is it the right vision? Do we have the right steps in motion to meet that next kind of block that we need to be building to meet that vision? And basically, as soon as I get out of that mindset, I'm creating a future problem for Cosmic.

Jonathan Hicken [33:30]:

Look, I'm getting excited, imagining being a team member. That's exactly what I would want my boss, the owner of the company to be thinking about. It's easier said than done. It is bringing it back to something you said earlier. It is like you got to take care of yourself and you got to pace yourself. And so there are these times where you're like, okay, there was an accomplishment. I can take a deep breath. We did it. But then that can sometimes stretch out too long.

Eric Ressler [34:02]:

It can stretch too long.

Jonathan Hicken [34:03]:

Yeah.

Eric Ressler [34:04]:

And I mean, it's not always easy to have vision. Sometimes things are murky, the world is changing, or you get pulled into another really important part of the business, especially if you're a smaller organization where, yeah, it'd be nice if all I had to do all day is sit around reading business books and thinking about vision for Cosmic. That would be an awesome job, but I don't have that luxury. I need to also be our creative director and work through internal problems that we're having and having meetings with new potential clients. I have a lot of things that I'm doing. And actually all of that is helpful for building vision. If you're just completely detached, can you even really be strategic if you're not closely tied to the work that's being done? I don't know.

Jonathan Hicken [34:48]:

Yeah, absolutely not. No. I mean, it is a requisite part of the job.

Eric Ressler [34:51]:

So it is hard though, because you can't just sit down every day and say, be visionary. No one can do that. I don't care. And I think a lot of times my biggest strategic achievements and epiphanies have happened when I'm not working, when I'm not, it's in the background or I watch a film and that sparks some idea that has some kind of association, right? This isn't linear work. So I don't know what the answer to that is, but I do know that I've made that mistake of coasting for too long and just losing sight of that important part of what I should be doing every day.

Jonathan Hicken [35:25]:

I'm sitting here smiling, but also dreading talking about the other hundreds of mistakes I've met. Honestly, we could have a three hour episode on mistakes and it would be really interesting, but it's been fun to open up about some of these things with you.

Eric Ressler [35:39]:

Yeah, totally. This has been fun. Hopefully it's fun for listeners to bring it back to the early framing of this episode. I do think being more open about mistakes and doing that respectfully and with good intention, I think is a good thing to do. It's a good exercise. I feel kind of a little bit of weight off my shoulders actually just doing this episode. So hopefully this is inspiring for people to do this constructively, and we can start to build a culture of failure and mistakes being a little bit more normalized, a little less stigmatized, and maybe we'll learn some stuff from each other and that'll help move the entire sector forward. So thank you, Jonathan. This has been fun. Thanks for doing this.

Jonathan Hicken [36:15]:

Yeah, thank you, Eric.