Plant bans, London after 9/11, and the art of win-win situations

HappyFunPeople is a series where we talk with HFCers about their life experience, what motivates them, and what it’s like to work at HFC. Nate is a photographer, Midwesterner, dad, and walking example of the HappyFun ethos. He’s currently a Product Designer at HFC.

HappyFunCorp: Nate, thanks for joining us on the show. (laughs) I’m going to pretend like this is a podcast, but it’s totally not.

So you joined us — has it been six months now?

Nate: Yeah? Yeah, it has.

HappyFunCorp: Well, happy six months, or however long it’s actually been.

Nate: Thank you.

HappyFunCorp: It’s a good milestone. I feel like a lot of folks who join us for the first time, it takes like three-ish months to kind of absorb what’s going on. By six months you’re totally immersed. But sometimes you’re dropped in like, “We’re hiring because we have work we need people to do, not because we expect there to be work.” I know you were kind of dropped into that.

Nate: I mean, it was kind of endearing; I felt like probably the onboarding stuff didn’t need to be documented or super-solid because there’s just so much stability. It at least felt like there wasn’t a necessity to onboard a lot of people, because it’s a tight-knit crew that knew what was going on. Whether that was the reality or not, that’s what I gathered from it.

HappyFunCorp: So, I’m looking forward to picking your brain. I’ll probably throw you some questions we don’t normally ask because you’re a little bit newer at HFC.

But before we get into that: If you could just introduce your role at HFC and what you’ve been working on?

Nate: Sure, sure.

So, I’m a product designer and I’ve been working — actually, from the first day — with a company that is taking actual metal assets and, in order to trade them, they’re tokenizing them. Then you can trade those tokens. They’re also using the blockchain to do electronic contracts. It’s a very different world from where I came from, but they’re fun problems to have.

It was an interesting change as well because it’s a team where many of them are in Russia; some are in Connecticut. The other two designers — because I’m embedded in the design team — one’s in Hamburg, Germany and the other is in Tel Aviv. So it’s an interesting standup every morning — or every evening for them.

It’s been super fun to help them figure out not only what their needs are but also how to really come through and deliver what they need.

There’s the content site for GlobeScan, and then I worked with Proclivity for a while to work on some of their more complex negotiation relationships among their different audiences internally. And now I’m working on Mighty.

HappyFunCorp: Which, for folks reading along at home, is a cool kids’ entrepreneurship startup that has a really great vision for getting kids to use e-commerce to learn about business and express themselves creatively. I think that’s a fun one, very on-brand for us.

Nate: I’m really loving it. I’m super into their mission and I really like the direction for their design and what they’re trying to communicate.

On my first day with Mighty, I recorded my daughter going through onboarding: just had her sort of talk out loud and shared that with the rest of the team. As I was looking at the video before I sent it over, my son, who’s 8, came up and he was like, “Dad, can I start a business too?” and I was like, “Yeah. Yeah, let’s get you in here too.”

It’s been fun to not only see it through their eyes and get some good user research, but also encouraging and reassuring that both of my kids saw this and were like, “This is a cool thing that I would actually like to do.” So that’s been an added bonus with them.

HappyFunCorp: Yeah, that’s neat. How old is your daughter?

Nate: My daughter turned twelve yesterday. So: twelve, 8, and 5.

HappyFunCorp: That one might be a little bit too young for Mighty.

Nate: Yeah, but the other two are definitely right in the sweet spot.

HappyFunCorp: That’s great.

So, let’s go all the way back. I like to talk a bit about where people come from: where you grew up, what that experience was like, and how you came to design. Which I’m sure will overlap with some work experience.

Nate: I grew up in Ohio, an hour south of Cleveland and an hour north of Columbus: so just rural fields and farms and things like that. It’s a small town of about 23,000 people.

I went to college just outside of Columbus, Ohio, at a small, private liberal arts school. I studied public relations and photography, and that was just a really wonderful, comfortable experience. It was sort of the idyllic college campus with deciduous trees and a bell tower and all that kind of stuff that you would imagine. I was the photo editor for the newspaper, so I got to do layout and work in all that kind of stuff — so like, Quark and all that.

But then I also was able to study abroad, so I went to London and was able to travel through Europe a little bit. It was kind of interesting because I left for London like a week after 9/11.

HappyFunCorp: Oh, wow.

Nate: Yeah. I was literally packing my suitcase when that was on the news.

It was a really extraordinarily formative time to be out of the country; it was a good lesson in compassion. It was just an amazing time to be elsewhere and see things through a different viewpoint than just being here.

HappyFunCorp: I’m curious to unpack that a little bit: “a lesson in compassion.” I mean, my memory of that is that internationally, especially with US allies, the general sentiment — if you believed the polls at least — was initially people rallying and that sort of thing?

Nate: Yeah. I mean when I got there, I was encouraged to check in at the embassy just to say like, “Hey, I’m here, don’t forget me if you have to evacuate.” Like, it’s London, what’s going to happen?

But yeah, I got there and Grosvenor Square was full of flowers. It was just like, tributes everywhere and such an outpouring of grief and support. And then by the time it was time to come home for the semester it had started to turn, and it was sort of — there was less of a blind following into the military response. I think there was more encouragement to look at things more critically and try to solve problems, not just use the military to reactively fix things.

It was amazing to be there and see how many people were compassionate and so supportive. That was oftentimes one of the first questions, when they heard I was an American: “Are you okay? I’m so sorry.” Mixing that with the ability to sort of see things as an outsider at that point as well was really–it was a pretty foundational experience.

HappyFunCorp: Yeah, being outside the country at that time sounds interesting. Also to sort of see that while we’re still doing our flag-waving and strong rhetoric and all that sort of stuff at home, everyone’s like, “Wait a minute. This is getting a little out of control.”

Have you had a chance to travel back or to live outside the country since?

Nate: I haven’t. Well, I guess my first real job after college was doing international admissions for the university that I attended, so I got to do a tour of Southeast Asia and do recruiting trips, spend a little time that way. But I haven’t been able to live outside of the country for more than six months at a time.

HappyFunCorp: That’s an interesting, very people-centric kind of job: really focused on understanding people. How did that grow into technology? There were lots of twists and turns, or…?

Nate: [laughs] Yeah. I was the international recruiter, but I was also in charge of all the publications and the website as well, so there was still a strong design part of it. But it was also really fun to be able to go other places, listen to people, and create relationships with them. I think that was probably the most informative part of that experience: not only valuing other people’s viewpoints and how they see and experience things, but being able to listen and make sure that you’re actually addressing their concerns — helping them to discover what their questions really are, and answering those.

It actually kind of started right before that, because I did my college internship at the American Craft Museum, which is now the Museum of Arts and Design on Columbus Circle.

HappyFunCorp: In the city?

Nate: In the city, yeah.

HappyFunCorp: I remember when they opened the current location.

Nate: This was when they were on 53rd and Sixth, around there.

HappyFunCorp: Right next to the new MoMa building?

Nate: Yeah, exactly. I was there on a PR internship writing press releases, doing fun stuff like that. But then they were really struggling with the agency they’d hired to build their store website. The manager of the museum store would come into the PR office and complain about it like, “Oh, this isn’t working.” And I was just like: “Do you want to talk about that?”

So I ended up designing their store website and doing some early prototypes in HTML and CSS of what the store could look like and do — and even going through their image catalogue and automating the image processing, because a lot of what was happening was the images were just dull and gross. They just weren’t prepping them to go through the degradation to be web-ready.

I just took my laptop home back to the apartment in the evenings and worked on it a little bit more. That was sort of my first rewarding experience of like, “Wow, this could actually be a future. This is kind of fun.”

It’s good work and people really appreciate it, but also it’s fun to tackle new problems and figure out new things and learn all the time.

HappyFunCorp: I am curious if there’s anything else around–I’m like looking at your background here [on this video call] and I’m like, “Yeah. This guy seems like a designer.” Are there any touchstones in your childhood, when something clicked: “Yeah, I think I like this stuff. I think I care about this.”

Nate: It was just kind of something that always interested me: making art. I’ve never been particularly talented with sketching or painting or anything like that, so being able to have a tool to empower me to make art, I found that very intriguing.

When I was in college and doing photo, of course I did take other art classes as well; I think [it was] mixing some of the basic painting classes with the more composition-based photo classes.

I think the other part of photo that I really enjoyed was being in the actual physical darkroom and that process of creating. It’s not even just that the composition of the image had to obviously be compelling, but then it’s your actual physical craft in the darkroom as you are processing the image and making the print. I just hadn’t even considered before then that photo printmaking was its own art form in addition to capturing an image that looked good. It was that mixing of physical printmaking into the craft of making the final product.

I think how things interacted in space and how light interacted with you physically — just those sorts of relationships. I don’t know how that necessarily clicked into design, but that’s definitely one of the things that impacted me.

HappyFunCorp: That all makes sense. I think I enjoyed the experience of the darkroom partly because it’s like every action is consequential. You have to be really focused; you’re sort of out of your element. It’s like this otherworldly thing; there are dangerous chemicals and like, timing. You’re put in this kind of high-stakes situation, but it’s creative, and that’s kind of exciting.

Nate: It’s just fun. It’s fun to document things, whether it’s being a photojournalist or whether you’re documenting life from an art perspective. It was all just very intriguing.

HappyFunCorp: Now, this will be kind of inside baseball, but do you remember what you were using, tooling-wise, to put the museum site together?

Nate: Yeah, it was definitely Dreamweaver and it was definitely the GUI in Dreamweaver. Basically it was like, lay things out in Dreamweaver and then flip open the code view and see what that did: just slowly picking it up from there until I could transition over eventually to not using the GUI at all.

HappyFunCorp: I feel like there are a lot of folks who cut their teeth either on Dreamweaver or Flash. From that particular wave, anyway.

Nate: Yeah, absolutely.

HappyFunCorp: It’s a great museum.

Nate: Yeah, it’s amazing. The museum was really cool, but I think the board was floating the idea of that building on Columbus Circle then. It was always vacant, or it would have someone and then they would leave. It was this enormous monstrosity sitting on Columbus Circle, and it’s just so beautiful now. I didn’t have any part in the moving or anything like that, but it made me very happy to see them being successful and growing.

HappyFunCorp: That’s cool. So, you spent time in New York?

Nate: Yeah. My brother lived on the Upper West Side for 15 years, so I would come and visit him two or three times a year for a week at a time or so.

HappyFunCorp: So you’re starting to dig into code and design, and getting some exposure to that. I know that immediately prior to working at HFC, you’d spent some time as a product manager.

Nate: When I moved to Chicago with my wife, I was doing a lot of freelance design through different staffing agencies. Those are really impactful experiences because it was — you know, for a few weeks I’d be in a tiny little agency with two other designers, one of whom was the head or the founder of the agency, and we’d be working in a tiny room somewhere. Then the next month I was on the 30th floor of the Aon Center overlooking Millennium Park. It was just wild to see the differences and the different outcomes that were possible in the industry. It made me very excited that it was just kind of wide open.

It was also reassuring to know that you didn’t necessarily have to have an art school degree to be able to do this; it was really more about how curious you are as a person and how willing you are to take risks, learn, and just put yourself out there.

After that I jumped back into higher ed. There’s an amazing art school in Chicago called Columbia College Chicago. I think they’re the largest film school in the country, but they have all of the arts. I worked in their admissions office, ended up being Director of Enrollment Marketing, and really focused on digital stuff.

We had just transitioned to using Salesforce as a CRM. One of the roughest parts of applying to schools and that whole pre-college on-ramp is feeling like, “What’s happening? I applied — did I not apply? Like, what’s happening? I don’t want to have to call all the time.” So, one of the projects that we really focused on was taking data out of Salesforce and giving it back to the parents and the students, allowing them to check in on their own.

[It was good] seeing how that not only made their experience better but also helped the people in the office, all the admissions counselors, because they didn’t have to necessarily field all those calls from people checking in on things. They could focus on developing other relationships or just using their time a little bit better.

Columbia College Chicago is also really neat because since it is an art school, those kids are so wildly talented — and they’re also so wildly themselves. It was very freeing to be in that environment. I guess, the other part was, it is art school, so it’s a hard sell for parents a lot of the time. So, it was also really neat, again, to think about how people view their problems, thinking through what their potential hurdles or objections were to sending their kids off to a private art school: reaching multiple audiences at the same time. There were just all sorts of really fun problems to solve.

It was also a safe-place-to-fail environment. We didn’t have big failures, but there’s definitely value in having that safety net underneath you.

HappyFunCorp: Yeah, that’s something that we try to cultivate here, referring to the concept of psychological safety: being able to speak your mind, be accepted, take risks when it makes sense. I think that’s something we value a lot because it’s the difference between being able to grow rather than just kind of doing the same old thing.

Nate: Yeah. And that reminds me of where I was right before HFC.

It was a startup in the Chicago suburbs. We were very product-driven, and the CEO was not only product-focused but design-focused as well. He had this idea about being able to buy cars online and have it go through existing dealers instead of like, Carvana or something like that. We had so many different iterations of the product and I gave a presentation at one of our all-hands meetings that was just failure after failure after failure.

I mean, those were the headings on my presentation! It was like, “We tried this. It failed.”

But the goal was just like, I’m going to reiterate these seven failures we had that were pretty big failures, but we just learned from, continued on, and ended up with a really successful product. I was trying to communicate and sort of fail-by-example to everybody else in the company, because I think when I started I was maybe the 36th employee, somewhere around there. By the time I left we had over 700 employees. So there were a lot of new people who were coming into a completely different organization.

Being able to reassure them that they still need to try and they still need to fail, and that’s really what was pushing that organization along — that was a fun presentation to give.

HappyFunCorp: So, what made you look for HFC? How did you find out about us and become interested?

Nate: I was still with that same company and I had left the product management side. I was doing product design and leading the product design department.

It was really rewarding and fun to be able to mentor other designers, lead that team, and lead the direction, but I also wanted to get back into designing myself — and also wanted to kind of mix it up and have new experiences. I came to appreciate and realize in myself that I really wanted to have new things. I wanted to feel uncomfortable; wanted to have new things to learn, new relationships to make, and new challenges to crack and figure out.

It was a really fun conversation with Milos to get a better sense of what HFC was all about and how that could come in. It still is uncomfortable. Like, it was an uncomfortable move! But it’s good, in that discomfort brings growth and the ability to be confident enough to listen, propose bad solutions, and then propose good ones. It was fun. I’m glad that I took that jump.

HappyFunCorp: And what would you say the differences are between your perception now, when you’ve been in it for a bit?

Nate: I think it’s actually pretty true. I think it’s a little bit hard, because [Milos] is so experienced and so skilled with this world that he just sort of excels.

HappyFunCorp: The fish-doesn’t-know-that-he’s-wet kind of thing?

Nate: Yeah, exactly. Exactly.

It does ring pretty true to what we discussed and how the culture is depicted on the website. There hasn’t been any sort of disillusionment when it comes to what I expected versus what it is.

HappyFunCorp: I’m glad we didn’t get to disillusionment.

Nate: That’s stage seven.

HappyFunCorp: “Come work for us, you won’t be completely disillusioned!”

You talked a bit about some of your projects at HFC. Are there any other projects, highlights, or lessons learned that you think would be instructive, whether it’s here or just throughout your career?

Nate: I think I had a really interesting mix of a background to come into being a head of product design, and to, even now at HFC, be able to embed into existing design teams. Because I know when I was in product management, a lot of that was backlog management, working with the teams, doing sprint planning and all those Scrum ceremonies. There’s so much that engineers do that they’ve figured out how to be really ruthlessly efficient if they decide to be. I feel like they have a lot of process around double-checking and peer reviewing and pair programming — all of those things that a lot of design organizations do, but aren’t pervasive everywhere.

I think bringing that experience of what can allow engineers to flourish into design organizations has been a really, really powerful thing that I didn’t anticipate having: being able to apply processes to design organizations or designers that don’t slow them down, that aren’t necessarily burdensome, but can really make a lot of decisions easier and help designers get through a lot of the other steps that can cause them to stumble.

HappyFunCorp: I’m kind of curious what practices you’ve seen work, and maybe what some of the caveats are.

Nate: A lot of it came from firsthand experience in the startup where I was before.

A lot of times, the CEO would have a product concept and then we’d get a Slack and it would be — I’d be the product person, there’d be a marketing person and a designer, and the four of us would go into the CEO’s office and he would be like, “This is what I want to do.” We’d be like, “Well, that sounds really cool,” and then the designer would go away from his regular scheduled job that he already had a plateful of work to do for, and he would have to knock out designs for this sort of vague concept. That just really wasn’t sustainable. I mean, we did our best to work through any of the things that weren’t necessarily filled out in the concept and be very collaborative with the CEO. It worked, but it wasn’t very sustainable. I could see how exhausted the designer got.

So, I think applying pretty simple processes like making sure that we did low fidelity first, making sure that we had user stories built out, and even building flow charts to make sure we weren’t missing any of the steps of the user journey — or going through and building intentions out so that we could label the flow chart and correlate those to what the user was hoping to achieve at that step, really making all that a lot more explicit.

And then once we got through the functionality? Incorporating engineering reviews as well, so we could make sure that whatever problem the design team was trying to solve, the engineers could confirm it was feasible — but also, so they could look at it through their engineering eyes and see if there was a different solution they would propose. And then going back through into high fidelity, into prototyping, and engaging stakeholders as well as engineering at that point as well.

It’s not anything earth-shattering or wildly different, but it was really building up those steps and refining it with the team — and then incorporating those into Jira and all of the different places where our work or additional content was managed.

HappyFunCorp: Was there a particularly tough project that you worked on, whatever the outcome, where you feel like you learned a lot?

Nate: So, diving into the automotive world, there’s this weird thing where every month the manufacturers release what the specials are for the month. So then individual car dealers want to advertise that Honda Accord at $369 a month, because that’s what Honda said yesterday it was going to be. There are also certain manufacturers that change it more: several times a month. But in order for the car dealer to be able to advertise that Accord at $369 a month, you have to generate all the assets for it.

Since most of that gets frontloaded into the first week of the month, there was this weird imbalance of time when those designers would have to create all the ads. So I worked with a product owner to go through a pretty complex flow of how we could not only balance the design team’s time and how much they were working per week over the course of the month, but also encourage the car dealers to use our new process.

It was really enlightening to be able to see what the benefits would be to the design team: how they could not only balance their time and their inner peace throughout the whole month, but also not just rebuild the same templates week after week or month after month; to encourage them to have more creative impact in what they were generating. And then simultaneously to work with the car dealers to give them something they didn’t know they wanted or needed yet.

That was a really empowering process to work through with the product owner, because it was sort of an uphill battle from the beginning. It wasn’t something that anyone was asking for. We had a lot of internal selling and internal convincing. The more you would talk about it, the more it would sort of dawn on people: “Yeah, this is actually a really good idea. I don’t know why no one is doing this yet.”

It was a lesson in patience and perseverance, but also a really reaffirming lesson in listening to your gut if you yourself are really convinced that what you have is worthwhile.

HappyFunCorp: That’s a good one. And I suppose eventually you’d probably automate a lot of that stuff?

Nate: Yeah, that was definitely the longer-term goal. Once we had freed up the designers, instead of cranking out the same thing over the first week of the month, they could contribute to a design library. And then once that design library was large enough, we could move in the direction of having an automated service layer. And then if we had premier clients, then they could get custom ads and sort out how those two different revenue streams could grow.

It would be an uphill battle at the beginning to convince people that that was okay, but that’s essentially what they were getting anyway — and then we’d be able to split that audience a little bit.

HappyFunCorp: All right, switching gears. Do you have highlights in your workspace? You’ve been working remote with us this whole time. I see a lot of plants.

Nate: There are lots. I’m no longer allowed to buy any more plants. [laughs] I’ve been forbidden.

HappyFunCorp: Is that sort of like the secret sauce to your workspace or do you have other stuff?

Nate: I really like the plants. I also really like how it’s very white and almost bleak. I guess it’s very simple, behind me.

I noticed when I was interviewing with Milos that he had a really nice camera. So I figured if I’m going to be talking with people exclusively online, I should probably upgrade a little bit. Having that nicer camera and some lighting and things like that has really helped make me feel like a real person, because I’m interacting with all these people remotely.

HappyFunCorp: So, now that you’ve been with us for over six months, what would you say is keeping you here? I think most people who work with us could do a lot of other things. So, I’m kind of curious: What’s the attraction still, or what do you look forward to in the future with HFC?

Nate: I really love the variety. I love knowing that I can make an impact with one of our clients and then once that specific problem for them is solved, there’s somebody else who has a wildly different problem in a vastly different vertical. It’s just fun to learn something new and be scrambling to figure out not only what their specific problem is, but sort of the layout of their universe.

I think it’s very interesting; it keeps me engaged. It’s very motivating to have a new challenge like that all the time. I know I talked before about being uncomfortable and how it was sort of an uncomfortable jump but in a positive way, and I just feel like it’s just perpetually uncomfortable, which is — in a good way. I mean, come on, it’s good.

HappyFunCorp: So at HappyFunCorp, it should just be uncomfortable? [laughs]

Nate: [laughs] Uncomfortable, yes.

But on the other hand, I mean speaking of HappyFunCorp: it’s the people. It’s that Jen Slacks me and wants to talk about her tattoo or that Milos is — we spend part of our design meeting talking about his motorcycle. There really is a community here. We don’t necessarily get to all see each other face-to-face in real life all the time, but I feel connected with all of my co-workers.

It’s also reassuring that they all really know what they’re doing. I’ve never felt like I had to cover for anybody else or make up for somebody else’s lack of preparedness or experience. I feel like we’re all on the same page of, “Let’s figure this out together,” and we will support each other. None of us may have experience with a new client, but we’re all going to do it together and it’s going to be weird and awesome.

HappyFunCorp: You can’t be expert in everything, but you can approach things as an expert.

Nate: Right, yeah, absolutely. It’s vastly different from anything I’ve experienced before, where I don’t necessarily have anybody else on the team to bounce ideas off. Like, the designers get together three times a week for half an hour, and if there’s anything we’re stuck on or anything we want to brag about, that’s the time for it. But also, it’s kind of freeing, in a way, to know that I can figure it out and have the freedom to work in the best way for me and the client.

It’s an interesting mix of feeling supported when I need it, but also feeling like the rest of HFC believes in me to do what’s best. There’s a certain level of trust in sending a person to represent the company and then you’re the only one, especially when it’s like a team build like my two projects right now. You’re not having meetings all the time with the main contact there. A lot of it is just me on my own and their team — and that’s a lot of trust to put in somebody.

It’s also been fun jumping into BugReplay a little bit as well. It honestly kind of blows my mind, both with GlobeScan and BugReplay, working with our engineering team. It’s crazy. I mean, they’re so skilled and it’s been a really collaborative experience with them. There’s so much confidence that I can have that they’re going to build exactly what is needed to be built. There’s just so much skill there. That’s been a really fun thing that I haven’t — as you mentioned, most of my experiences are just the team build, put-me-on-an-island. But it’s been really awesome to dig in with other HFCers and tackle problems together.

HappyFunCorp: Yeah. Hopefully we’ll get you back into the fold in building more stuff with our engineers.

So, do you have things that you’re excited about in the tech world or in terms of design and how it’s practiced?

Nate: I guess I get really nerdily excited about Figma and all of the improvements they’re making; that they just are consistently keeping me excited about what’s possible. I mean, they just released forking a while ago, which is really fun to be able to — again, looping back to engineering practices that work really well that designers have struggled to replicate. It’s just built in now. That’s been a really fun new feature to that tool.

I’m reading more and more about Web3 and trying to contemplate how design fits into that. Obviously design will play a huge role, but like what type of design and, selfishly, how do I fit into that? Just really mostly reading about that right now.

HappyFunCorp: So, I always close with this, and I think you’ve already given some on the way, but: What advice would you give to somebody who’s starting at HFC today?

Nate: For somebody who’s starting at HFC today? To believe in your abilities. Believe in what your hiring managers saw in you to hire you. There’s a reason that you’re with HFC, that you’re starting with HFC, and sort of — doubt your inner voice if your inner voice is doubting you. Listen to everybody else who has interviewed you and talked to you and believes in what you have to offer.

HappyFunCorp: I think that’s good advice in general: Turn off the doubting voice.

Nate: Yeah. I mean it’s hard if you — I forget how it’s totally worded, but I read something that was essentially like, “If your inner voice is doubting you, why aren’t you doubting your inner voice?” Why aren’t you believing what everybody else sees if your inner voice is saying that whatever you do isn’t worthwhile? Why is that suddenly worthwhile? Like, you should put more stock in what other people are seeing if your inner voice is what’s doubting you.

HappyFunCorp: That’s probably a Brené Brown quote or something.

Nate: [laughs] Probably. We’re veering into podcast territory.

HappyFunCorp: I mean, I’m always right on the cusp anyway.