One Antidote to Impostor Syndrome with Ben Callahan

| 32-min read Stay updated

If you’re looking for an antidote to impostor syndrome, this episode is for you.

I talked with my good friend (and 4 time guest on the podcast), Ben Callahan, about so many things, including a different way to think about content marketing that removes the fear and pressure that often comes with "putting yourself out there."

Ben is an agency owner and co-founder of Sparkbox. He is also building his own personal brand through which he’s offering coaching – a popular path these days. Ben and I share a love of collaborative learning and in our conversation, he shared how he went from designing web sites and thinking small to thinking big enough to pursue complex projects for companies like Gap. 

It all has to do with his "mantra" -- on a post it note on his monitor!

So listen here (or below): 

If you like what you hear, there are 3 more episodes with Ben Callahan: 

  1. #359 Content Marketing That Works
  2. #378 How to Build Long Term Relationships
  3. #290 Keeping it Human with Meena Kothandaraman too

We’d love it if you write a review, subscribe here and sign up for Quick Tips from Marketing Mentor.

Read the full transcript of Episode 493, One Antidote to Imposter Syndrome

ilise benun

Hi there. This is ilise benun, your Marketing Mentor, and this is the podcast for you if, and only if, you are ready to leave the feast or famine syndrome behind. And I mean, for good.

If you are looking for an antidote to imposter syndrome, this episode is for you. I talked with my good friend and four-time guest on this podcast, Ben Callahan, about a different way to think about content marketing that removes the fear and pressure that often comes with putting yourself out there.

Ben is an agency owner and co-founder of Sparkbox. He's also building his own personal brand through which he's offering coaching, a popular path these days.

Ben and I share a love of collaborative learning. And in our conversation, he shared how he went from designing websites and thinking small to thinking big enough to pursue complex projects for companies like Gap. So, listen and learn.

All right. So, Ben, welcome back to the podcast.

Ben Callahan

Thank you so much for having me back.

ilise benun

It's lovely to hear you and see you again. And I always ask my guests to begin by introducing themselves. So, who are you today, Ben?

Ben Callahan

Thanks. Yeah. My name is Ben Callahan. I am the founder of a company called Sparkbox, and we help complex organizations do better digital-user-interface work. So, we help with digital products, basically. A lot of that is design system related.

For the last six or seven years, I've also been doing a lot of research around design systems, so interviewing folks. And so, I am starting to call myself a design system researcher. I'm just really curious about the space and all of the implications of that kind of work. So, continue to dig in there.

I have, in the last year, started up a coaching practice for design system folks, as well. I think that's a group of people that are not being supported in the way that they need to be, so there seems to be a bit of a gap there. And so, I'm trying to fill that a little bit just by sharing experiences and insights. So, a coach.

And then also, I kind of lead the design-system consulting part of our business at Sparkbox. So, a consultant in that capacity. So, that's all the work stuff.

I'm also, outside of work, I love to take pictures. I'm an aspiring poet. I love coffee and volleyball and all kinds of other fun things.

ilise benun

Awesome. And for those who don't know what a design system is, let's define that, please.

Ben Callahan

Sure, yeah. There's a lot of definitions out there about what a design system is. I think of it as being made up of three main things.

What a lot of folks think about are the assets that come with a system. So, that's the stuff that a team, an internal team, might use to build digital interfaces. So, components that represent buttons or dropdowns or headers or navigations; all of the pieces and parts of a digital interface, right?

But along with that, I think there's a whole lot of stuff that comes with that, that you can't just have those and succeed. And so, we talk a lot about documentation as being a really key part of that—which is essentially giving a language to the way that you design inside your organization, so you understand each other when you talk about the problems you're trying to solve with design.

And then, also the process—which is sort of how the humans work in and around the system.

And so, all of that together is a design system, and it basically gives organizations a way to be more cohesive in the experiences they're creating, even across brands or across products, across platforms like native iOS and Android, versus something that's showing up on a TV somewhere, versus something that's on a browser or on your phone—Safari on your phone or something, right? So, lots of different product places, screens where those can live. The system allows those experiences to sort of feel like they're from the same family.

And then also, when you do that, you're creating with more efficiency; you're reusing pieces and parts, and so it kind of allows the team to solve new problems instead of focusing on solving the same old problems repeatedly, which is nice. So, that's kind of high level, what it is. I know that's still a lot, but ...

ilise benun

Lest listeners think we're going to talk about design systems, we're not.

Ben Callahan

Yeah. That's another podcast.

ilise benun

Exactly. But I think it's relevant to the extent that, what I want to talk about is two things that I think are interrelated.

One is your personal brand, which you've been developing, and you're positioning, and how your Ben Callahan brand relates to the Sparkbox brand. And just kind of watching your evolution of your brand over the years, as I've known you, has been fascinating to me. So, I want to talk a little bit about that.

And then also, under the umbrella of a topic that I know has been dear to your heart for a long time—and which I'm really just starting to open my eyes to, I think, a little bit more explicitly—which is the idea of collaborative learning: how people learn together.

And I connected in my mind, also, and in my process, to what I call: “just-in-time learning”—where, not only do we learn together, but we learn in the moment when you need to know the new thing; not a month ago or two years ago when you studied it, but have forgotten now when you need it. So ...

Ben Callahan

Yes, that's great.

ilise benun

... Just respond to whatever of what I just said you want to first, and then I'll kind of keep us on track.

Ben Callahan

Yeah. Those two things are very interrelated for me. I think I've learned about myself that ... And I have this written on a sticky note that's stuck on my monitor here. It just says, "Stay in learning mode." Because I want every interaction that I have with somebody, I want to approach that as an opportunity to learn. And I actually think this simple little idea could solve so many problems in the industry.

I just imagine all the struggles that folks have or that our industry has had in terms of welcoming different voices into the conversation ... Imagine how different that would be if we all just thought, "I want that person here because I can learn something from them." Right? That changes the dynamic completely.

ilise benun

From what, though? What stance do you think people are normally taking, then?

Ben Callahan

I think it's easy to get into this space, and you look up to lots of folks who are sharing a lot of the things they're learning; they're thought leaders or content creators or whatever, right? Influencers, maybe, is another word for that.

And I have nothing against that. I share my fair share of writing and videos, and all of that, and I think that's important to do.

But I think it's easy to put those folks up on a pedestal. And I think sometimes that happens when people in those positions start to believe that they're on that pedestal.

And so, I think that's what I'm trying to guard against, right, is like every interaction that I have, as somebody who's for 15 years now spoken at a lot of events ... and I still go to an event and I try to find the person who looks to me like they feel like they don't belong. That's the person I want to connect with. I just want to get to know them. I want to make them feel welcome and I want to learn something from them.

And if we all just had that, I think if we all had that perspective, it would really shift the way things feel in the space instead of there being sort of tension around topics like diversity and inclusivity. I think we could really turn that on its head.

So anyway, that stay-in-learning-mode idea. My coaching and consulting business is called Learning Mode. And I think that, for me, has been really about ... that's my brand, essentially.

And that's early, early days. I haven't actually really announced that other than ... so I'm announcing it right here on your podcast. So there's no website, there's no logo yet, but that is sort of the legal entity. And so I have some plans to think about what that looks like in the coming years.

ilise benun

Interesting. So let's talk a little bit about your personal brand and maybe also connect it to this idea that I often talk about, which is listening to the market as we evolve our brands.

And it seems to me that that's what you've been doing with design systems—because when I knew you originally, and I can't even remember how we first met, maybe you do—but you weren't talking about design systems. I knew Sparkbox as a web design agency, I think, right? Isn't that what it was?

Ben Callahan

That's right. Yeah, that's what we did when we started. And even before Sparkbox was a thing, I had my own little web design business, and I just worked for local clients. The first website I ever did, I charged $500. I mean, that's what it was, you know?

And so over the years, I think we as an organization, Sparkbox, fell in love with the idea of web standards. And so Jeffrey Zeldman wrote this incredible book and he was one of many folks who were really fighting for standardizing how we approach working on the web.

So all of that happened and we have a much more collaborative environment for evolving the standards with which we all code to. So that's really cool to see that that's happened, but that kind of pushed us in the direction of thinking a lot bigger about the web.

And so one of the things that led to is working with much larger clients. And when you shift from working with these small local clients who have a website to working with much larger ones who have many, many websites for many products and many brands ... all of a sudden, the challenges are a little different.

You have scale. You're trying to design at scale for these experiences that there's some overlap in what they're trying to do. There's commonalities there that you have to allow to shine through.

There's also uniqueness about each of these properties. And so how do you let that shine through? And so, I think that complexity kind of pushed us towards thinking more systematically about the work.

And that was about the same time a lot of other folks were coming to those same ideas and trying to put a name to it. And so “design systems” really, it's kind of a terrible name because it incorporates way more than design, but it's just a systematic way of thinking about digital interfaces. That's really what it is.

And so, we've been trying to do that for as long as we've been a company, and I think having that sort of emerge in the industry was just good for us because we were sort of already trying to figure that out.

ilise benun

And actually, that just makes me want to ask about how you market differently when you go from companies who have a website that you're going to design to large organizations who have multiple websites.

And you started as a designer, not a business person, but from what I can tell, you've become a very good business person. So what can you say about any of that?

Ben Callahan

Yeah, I started actually as a developer; I studied computer science. And now I kind of moved into design, and then, now the product that I work on mostly is the business. But I think the transition was interesting for us. I remember when ...

I think to start with, when we had the business, when I had my own business just working locally and when Sparkbox started, that's really what we did too.

I think I believed ... there was something in me that was a limiting belief about what we could do. I guess I just thought, well, we’re in Dayton, Ohio. It's like, what are the companies that are the big companies here—that would be the top of what we could do.

But then I remember a couple of my friends who live in Austin, Texas, three of these guys, they were a company, they went to high school together, they were buddies, and they started a company and they redesigned Microsoft.com working out of their houses.

And I remember that moment, I saw that redesign. It was beautiful, incredible work. They're still a company; they still are doing really cool things. But I remember that moment as a shift mentally for me. I think I realized if three guys sitting in their living rooms can redesign Microsoft.com—

ilise benun

And they were hired to redesign Microsoft.com, right?

Ben Callahan

That's right.

ilise benun

They didn't say, "let's redesign Microsoft.com."

Ben Callahan

Yes, Microsoft hired them.

I remember thinking, if that's the case, we can work for anybody, anywhere in the world, and I need to change my perspective on what's possible for us. And so we just started thinking much bigger at that point. And-

ilise benun

And is it a switch you can just flip like that?

Ben Callahan

I mean, it's not ... I would say that was one piece which made it so that we believed we could do that.

And the other stuff is there's timing.

And then there's: do you have the skill to actually execute? If you get that work, can you deliver and can you deliver repeatedly and put that in your portfolio and let it build? So, there's all of that too.

And we got lucky with timing. We had a local contact that I did some work for way back in the day with that first business, moved into a larger organization, and when he needed help, he thought of us. And so we got called in that way.

And so a lot of our growth has been making somebody inside of a big company, or a small company, look great. Now, they can get hired at a big company, and when they do, they bring us with them.

So that has worked really well for us. And so that's kind of the sort of domino thing that happened for us. And we got hired. I remember that first large contract we got was for our utility here in Dayton. And then, from there, we signed a contract with Gap—and that was a big one for us there. Gap, Banana Republic, Old Navy; all of those brands are under that one organization. And so we worked for them for years.

And having that in your portfolio means you can confidently go to other organizations of the same scale. And so we learned a ton working and doing that work that I think enabled us and gave us confidence to go and work for others in that capacity.

ilise benun

And it seems to me, over the years, the marketing tool that you've used most is content marketing. Would you say that's true?

Ben Callahan

A hundred percent. Yeah. We've tried lots and lots of things. We've done cold calling. We've sent stuff to people randomly. All kinds of stuff. We've done some paid ads and things. But really the thing that has worked for us is just being smart in front of people.

So that's speaking, teaching workshops, training. It's also running surveys and doing research and sharing that with the community.

A lot of when we first started, one of the things that we put in place was that everybody at Sparkbox will write. Everybody will write. And that stemmed from a belief that it's our responsibility to share what we know, because we sort of see it as a chain. It's like there's somebody a little better than you, somebody who's not quite as experienced, and you have to share what you're learning so that everybody can continue to grow. That's sort of the model.

ilise benun

And that connects to ... I'm sorry to keep interrupting you-

Ben Callahan

No, that's okay.

ilise benun

But that connects to stay-in-learning mode, right?

Ben Callahan

Yeah, that's right. Yeah, for sure. Yeah, I think writing for me is probably the way that I learn the best, which feels weird because usually you think I don't write until I've learned something. But a lot of times I write just to learn something. It pushes me to read and research and talk to people. And so it kind of is a source of that for me. Yeah.

ilise benun

Okay. So content marketing, speaking, writing, researching, creating content. I know you've put on events; you've spoken at a lot of events and all of that. I mean, have you ever felt what they call “imposter syndrome,” which seems like the opposite of it's my responsibility to share what I know? If you feel imposter syndrome, that's the opposite of it, from my point of view, right?

Ben Callahan

I'm so glad you brought this up because in my coaching practice, now, every single person that I coach feels imposter syndrome. I feel this. Every person that I know ...

And I don't want to ... I want to be careful, right? Because I think there's a tendency, I think it's part of the human condition, to doubt yourself. I think some folks experience this imposter syndrome in much more extreme ways than others. So I don't want to downplay that sort of spectrum of experience there.

But I think I could say generally that I think almost everybody that I know has some level of doubt in their own ability—especially that moment when you've signed up for your first presentation and you're backstage ready to go. And I mean, that's scary. It's scary.

And I think there's a healthiness to that. It kind of keeps you fresh and on your toes. But I actually, I love the way that you drew the connection, because in my coaching practice, when somebody shares that with me, one of the things that I say in response is, "Think about it like this."

And I give them that example of this sort of chain. It's your job. You have to share what you're learning. And that model kind of takes the pressure off. You don't have to be the smartest person in the room. You just have to be willing to share what you know. And that's a nice way to break that cycle.

ilise benun

I've actually talked recently about a strategy for creating content where you don't share what you already know, you share what you are currently learning.

So if you attend a class or one of my webinars or read The Simplest Marketing Plan, then you can just say, "Here's what I just learned and here's how it might apply to the people in my world or my people." And that also seems to take the pressure off.

Ben Callahan

Yeah. I love that. And some of the best articles that I read are when somebody is at an event, they learn a ton, they take a bunch of notes, they come back and they just write a little write-up of each of the sessions. Because that's such a great ... Oh, go ahead. Sorry. I'll let you jump in.

ilise benun

No, I was just going to say, I mean, one of the things I always remember about being at events with you, Ben, is that you've always created these collaborative-notes documents and said, "Hey y'all, come and share what you're learning here." And my impression was always that very few people actually did it. I don't know if that's the reality from your end, but I'm curious.

Ben Callahan

Yeah. So I have got a folder in my Google Drive, because those were always Google documents, so you could literally ... I would just make it open to the public and Tweet that link, and we would always get about a dozen people who were pretty committed and then everybody else would lurk.

And I think it's hard when you're in there in the real time and everybody's trying to take notes in the same place; it gets chaotic.

But my goal with that was just to say, "Hey ...” I wanted to sort of level the playing field. Right? Like, I'm there, maybe I'm speaking, but I'm also trying to learn. And I want that to be part of what everybody ... you know. We go to events to engage with other people, not just to sit there and learn something. So that's a way to create some engagement. And I've got so many great notes, documents, from those days back when I used to go to events.

ilise benun

So I feel like the value there is also in the process, not necessarily in the artifact of those documents, right?

Ben Callahan

Yeah, I think that's true. I mean, it's a way to sort of see who else is taking notes, who else is sharing things, who else is in the session with me. So it does sort of create an opportunity to kind of see who else is interested in these topics. They did make nice artifacts. A lot of folks would take them back to their companies and they have a nice resource to share with their boss who paid for them to go. So maybe that's nice. But yeah, the process of all of that is really where there's value, for sure.

ilise benun

But it also seems like there's a networking aspect, then, to that process as well, if you wanted to follow up, say, on the people who also took notes.

Ben Callahan

Yeah. And we would always put a space in there to say, if you're willing to have conversations about specific topics, just put your name and your email, and list what topics you're interested in. Things like that. So that's fun.

ilise benun

Interesting. Yeah, I think that's something people could still do. I mean, we are, kind of, going back to events eventually, little by little, right?

Ben Callahan

Yeah. I went to one last night.

ilise benun

Oh really?

Ben Callahan

A local meetup, yeah, so it was fun.

ilise benun

Cool. For some reason, this also connects in my mind to AI. And I'm curious: how are you thinking about AI in your business, in your marketing, in your coaching, in this collaborative learning? That's a big question, but go ahead.

Ben Callahan

I mean, the collaborative learning stuff, I think is probably where I'm using it the most right now. I mean, it's never been something that feels threatening to me. I'm like a science fiction nerd. I love The Matrix and all of this stuff like this where the AI is taking over the world and all of it. I love that stuff. I mean, I don't love it because I want it to happen. I just am fascinated by the concept. And I've read a ton of old writings from folks like Ray Kurzweil, who is somebody who's been writing about AI for decades. And actually, I studied computer science, but my specialization was artificial intelligence. And so back then, that was the thing. It was just like studying how the human brain works and trying to create software that more closely mimicked that.

And so I think I am obsessed with that idea, but I am not somebody who jumps into a fad, and I'm not trying to call AI a fad. I just am saying a lot of the ways that people are excited about using it are ... they feel a little fad-ish to me.

I've found a ton of value in especially analyzing large bodies of text. So as somebody who's constantly asking questions and doing interviews and gathering ... having folks answer a question with just a bunch of paragraphs of text, it takes a lot of work as a human to read through all of that, keep it present in your mind to connect the patterns.

That's actually an area where I can easily put thousands of lines of text into an AI and say, "Give me the patterns. Identify for me what are the common things here? What's the theme? What's a summary of this?"

And so that's an area where I use it quite a bit. I mean, the tools are growing so rapidly. There's folks out there saying that even just designing websites, you can kind of do that with AI today. And so that's fun. Writing your own content ...

I mean, I think I'm somebody who believes that we will definitely have a place in the market. I don't see-

ilise benun

“We,” as humans.

Ben Callahan

As humans. I don't see it sort of replacing us completely in the tech space in the very near future. But long-term, I think every programming language that comes out is an abstraction, a higher level abstraction. All of it's boiling down to zeros and ones.

And so, at one point, we wrote code that was very close to zeros and ones. And then we created an abstraction above that, and then we created one above that. And the more we do that, the more they feel like just talking to the computer. While this number is less than this number, do this thing. And that's English, that's embedded in the language. And so I don't see a reason why that won't continue, and it's already continuing in that way.

ilise benun

Interesting. All right. I have one more question for you. We could obviously talk a long time, over margaritas; we will soon.

Ben Callahan

We'll do that. Yes.

ilise benun

But, I want to ... and then I'll have you tell people where they can find you online, obviously.

But you are doing something that I find really interesting, although I don't know a lot about it at this point, which is The Question thing. And I'm just thinking about how I might be able to adapt it for my own process and I want other people, if you don't mind, to think about how they might adapt it for their own process. What is The Question, then?

Ben Callahan

Yeah, thanks for asking. I mentioned that I love to learn. I'm somebody who's been curious about systems for a long time. One of the things I've been ... and this has been an idea I've had for over a year, and I just didn't do it, and I didn't do it, and I didn't do it. And one weekend I was like, I'm just going to do it.

ilise benun

We all have that thing, right?

Ben Callahan

Yes, I know, right? And it wasn't complex. It was little pieces and parts I had to pull together.

So what it is, structurally, is very simple. Everything takes place between Monday and Thursday, and what I'm looking for is people who are like me, they want to learn. And I want it to cost something. So in order for them to participate in the learning, they also have to share something.

And so the way this works is on Monday, I send a question out. So I have an email list through MailChimp. You can sign up for that. You get an email very early Monday morning so that we're hitting folks in Europe and also all time zones or whatever. And so you have basically forty-eight hours to answer that question.

And if you answer it within forty-eight hours, you get an invitation to a deep-dive conversation of the results of the question. So all the data that we gather, combined and analyzed, and we do that the next day.

So Monday, the question goes out. Wednesday, I close it. You have to have your answer in. If you've answered, you get an invite to the deep dive on Thursday. And so then I take the weekend to write up what I learned and post that on my site. And so it all kind of ...

ilise benun

So wait, what happens on Thursday?

Ben Callahan

So Monday morning, question goes out. Wednesday, at lunch, it closes. Thursday, at lunch, Eastern time, we have a one-hour call. And anybody who's answered gets an invite. So usually we have about 50 to 60 people answer, and then we have 20 to 30 attend the call on Thursday, and it's growing and it changes a little bit each week.

This is about design systems, but you could literally do this about any topic you wanted. So pick whatever your specialization is. You could do the same thing.

One other piece that I've added to this is that I also wanted it to be a chance for us to build some community.

So I invite somebody to be a co-host with me each week. Sometimes it's somebody who's more well-known in the space. Sometimes it's just somebody who's attended a few of our conversations. We've had about eight of them so far. I think this is our ninth one, and I've learned so much. I mean in just a few of those, I've learned more than I would have, by far, just going out and trying to research and find stuff on my own.

So I'm hearing other people's experiences. They're getting to know each other. Over the holidays we had one where we just hung out and just kind of chatted a bit and it was super fun. I'm really excited about it.

ilise benun

I love it. So you're creating community. You're creating content. And you're doing networking. I mean, it kind of has all of the components of The Simplest Marketing Plan also. So I could see listeners who have The Simplest Marketing Plan or know The Simplest Marketing Plan could easily find a way to figure out what their thing is, what their specialty is, what their question idea is, and even start very small. I feel like that could be a nice baby step for listeners.

Ben Callahan

Yeah. My vision for this, long-term, is imagine if I had 5,000 people on a list. There's a problem that I'm trying to solve, and I've got a big list of folks that all may be facing that problem or have already faced it. I can ask that question, and in a matter of a week, get a bunch of really good information back. It's like real-time learning. So I love it for that.

ilise benun

Sounds like a good marketing tool, also.

Ben Callahan

I definitely think it could be that. Yeah, and I'm trying to figure out, I want it to be really authentic in terms of community. So I don't want it to be a lot of sales stuff. I've resisted the urge of ... because I've had some folks reach out from product companies that want to be in there, and at this point it's just practitioners. But I don't know, maybe at some point there's a way to sort of facilitate conversation with those folks because tools are important for the work too. And so maybe that makes sense.

ilise benun

Well, I'm just connecting it back to what you said about being smart in front of people.

Ben Callahan

Yes, absolutely. Yeah. And so yeah, I guess that marketing for myself in terms of, I do offer coaching, and so in the emails that I send out to folks, I remind them, "Hey, if there's a topic or if you're struggling in a certain way, I've got this coaching program. Would love to support you in that way.”

I'm doing a little coaching cohort, which is just a five-week session. It's inexpensive and it's not customized to somebody's needs. It's about how design systems mature. So that's an opportunity for folks to get involved in a very inexpensive way and start to build their own community like that.

So there's lots of ways like that I think that same group ... It's just the same group of people that might be interested in coaching are the ones who have the answers for the question.

ilise benun

Yeah, definitely. I love it. All right, Ben, let's put a bookmark here and tell people where they can find you online.

Ben Callahan

So the easiest thing is just bencallahan.com and there's a Connect link there at the top that you can send me ... can give me feedback. You can just say, “hello.” You can ask a question, you can ... all kinds of stuff there.

You could also sign up for The Question. So if you follow me on LinkedIn or connect on LinkedIn, I'm always posting about it there. It's also on bencallahan.com/the-question, so it's right there. If you see a research link on that site, it'll take you to The Question's page. And so that's a place where you could go. If you answer the question one week, you'll get put on the list. You can put your information in as well when you answer the question, and then you'll get each question the following week. So that would be a way.

My company, Sparkbox, is another, if folks are needing help with digital products, that would be the place to reach out. Sparkbox.com.

ilise benun

Awesome. All right, Ben, so good to see you and talk to you, and “to be continued,” as my mother likes to say.

Ben Callahan

Yes, I love chatting with you, ilise. So anytime you want to talk, just let me know.

ilise benun

Will do.

I love Ben's concept behind The Question. If you want to create content and community, what question would engage your market and your people in a way that allows for collaborative learning and high-quality content development, not to mention putting you in a position of authority and expertise without having to know absolutely everything? Think about it. That's your baby step.

So if you want to build a thriving business on your own terms, the first step is to sign up for my Quick Tips at Marketing-Mentortips.com. Once you're on the site, you'll find lots more resources, including my Simplest Marketing Plan.

So enjoy and I'll see you next time.

 

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