Matt: I met Nathan back when his design company Heist was just getting started. I admired that he and his partners were shaking up the digital services space with a new innovative approach to building digital products. Unfortunately what they were trying to do may have been a little too soon to market as the company closed it's doors this past spring after 3 years in operation. I sat down with Nathan to discuss his career so far and chat about what he does to stay on top of an ever-shifting space.

Tell us a bit about who you are and what you do?

Well, I’m a bit of a Product Designer and Design Manager hybrid. I’m in a weird position at this stage in my career where I’m still doing hands-on design work but recently I was also managing and leading a design team at Heist.

It’s a really interesting spot to be in. I’ve got the opportunity to contribute through designing and shaping experiences myself, but I’m also able to help other designers do really great work.

What was the path to becoming a designer like for you?

In high school I tinkered around with motion graphics and computers, and I knew that was something I was really interested in. I stumbled upon the New Media program at Ryerson University, which is like this mashup of fine art, interaction design and physical computing with Arduinos, soldering and stuff. It was a great program to shape my thinking as a designer about how we - not just interact with screen based experiences - but also physical experiences. So I was really fortunate that I stumbled on that.

After that I ended up getting an internship at an ad agency, my internship turned into a full-time job, and then I think it was on the fourth month I got fired [laughs]. I was a horrible designer, I was not properly equipped to have a job as a designer. In school we had the tools to design experiences, and think about people and technology in really impactful ways but there wasn’t the “this is what a comp is”, or “here’s how to use type on a grid”. So, I got fired.

One of my friends from school was a developer at this other ad agency, and I asked him if they needed designers and he said, “oh yeah we need designers!” So I showed up there doing contract work - I think I did web banners for 5 or 6 months - just web banners. I hung around there and it was eventually acquired by a company with a strong user-experience design team and they brought in some smart people that I was able to learn from on the job. Understanding how to structure experiences, what a customer journey map was, and how to add visual range in your design abilities etc.

I did a little stop at Teehan + Lax which had been my goal all along, so that was a really amazing experience to be able to work there and work really closely with Jon Lax.

Some of the guys that I’d worked with at other design agencies, we all got together to start Heist after I did Teehan + Lax, which was weird to give up. I’d always wanted to work at Teehan + Lax, it was my dream in highschool but there was a really amazing opportunity to try and go build something myself.

So why did you go and start your own company? Like you said you had kind of made it to your goal, why quit and start your own company?

Well, like I said going to Teehan + Lax, it was where’d I’d always wanted to go. Chris, one of the other partners at Heist, had kind of been bugging me to start something before I came to Teehan + Lax. I’d gotten the taste of where I wanted to be and I wanted to try and go build something on my own. I realized that it was really great to be able to work around the people at Teehan + Lax and I could either be on the ground floor of something myself, or try and work my way up at Teehan + Lax. I thought I’d learn more by cutting it on my own, so it was a good opportunity to go chase.

Looking at the course of your career so far, are there any points that were game changers - where you really thought you became a better designer?

Starting Heist definitely was a game changer in terms of becoming a better designer. It’s funny when you’re doing more design management you have this fear that you’re going to get rusty or that you’re falling behind or your skills aren’t where they should be. It’s something that I’ve found by doing more design management, it forces you to deconstruct and communicate what works, and what doesn’t. So when you go back to designing yourself it really helps you make more deliberate decisions quicker. Rather than spending some time chasing down a path that might not be fruitful you’re able to deconstruct your own work and make more deliberate decisions in your designs. So that was something that at Heist I was really able to practice and learn and overcome that fear of becoming rusty or falling behind. I think a lot of design managers struggle with that.

Another point was definitely getting fired from that first job [laughs]. Realizing that you have to have a solid grasp of the foundations of design and be able to actually be a designer is much more than just the skills of design. It’s a much more complete skillset that you need to have, beyond just being able to use Photoshop. You can’t just be a technician you have to actually be able to work as a designer and work with others to really provide any value.

You allude to some of the challenges faced by design managers now - so what are some of the challenges that you’re currently facing as a designer?

I’m still very new at the design management side of things. I’ve really only been doing it since we started Heist about 2 and a half years ago, so it’s still something that I’m studying and learning about. I’ve been doing a lot of interviewing for both design management and product design roles and it’s been interesting to see where design managers fit, and in what types of companies and how that role is defined across different organizations. It’s interesting to see the challenges that some design managers are having in terms of scaling a design team or working with a remote team. Those kinds of challenges and themes have definitely popped up as I was interviewing with a lot of different companies.

I’m very much in between both worlds where it’s a lot of context switching day-to-day, when you’re being a designer and a design manager, you’re working right down to the pixel level but then also up to the 1000-foot level. I think that’s something that as a designer you have to do in terms of stepping back and looking at a customer journey for example. When you’re working as a design manager you kind of have to level up beyond the work and think about how the team is being designed, and how the company is being structured. Thinking about what kinds of processes do we have, how are people communicating, are they communicating, what amount of structure is too much for a design team, what amount isn’t enough? Understanding, not just what a designer’s skills and strengths are, but also understanding what kind of environment and structure is best suited for that skill set. That’s one thing I’ve been thinking about a lot lately.

What do you do to stay on top of trends in the industry?

It’s probably the normal Twitter and reading. When I was teaching at Bitmaker Labs I’d always encourage the students to create a Twitter list of people to stay on top of in the industry. Overall, I’d say the usual Twitter, a lot of reading, popping into SiteInspire, curating the newsletter mix is important. There’s some really good design and tech newsletters out there to provide some pretty good perspectives.

What are some of the tools you use on a regular basis?

Slack - I use Slack for teams that I’m working with but also for design communities. I’m in a tech management one, I’m in one for the design details podcast. I’ve got a lot of Slack teams that I hang out in, that’s becoming a really great source of productivity inspiration.

Asana - I’m still on Asana as a hold over from to-dolists from Heist. I hate Asana though. It’s probably the tool I use the most that I absolutely hate.

Google Calendar - They’ve done a great job of rethinking the structure of a Calendar.

Best way to stay on top of email?

Oh, I don’t try - that’s the real trick. You have to stop trying. There is no way to win email. I’m not an Inbox Zero person, I just ride the stream. I don’t try to conquer email or action everything or properly label things. I just ride the wave and try to move as much as I can to Slack.

If it’s not important I try to delete it or unsubscribe if it’s possible. If it is important I’ll leave it as unread and come back to it. I don’t try to master email, I don’t think it’s something that can be done.

What's the best career advice you've ever been given?

I don’t know if someone gave it to me, but it’s definitely something I’ve been doing as a piece of career advice… Since I graduated, I’ve always tried to focus on running towards things that I’m afraid of.

I did a guest lecture at Bitmaker Labs for example and I was terrified out of my mind giving this guest lecture. I had the opportunity to do it part-time and I jumped on it.

When I was interviewing for jobs too, there were places that I interviewed that I was intimidated by and some that I wasn't, and that’s normally a good indicator of your gut telling you that it’s something you should go after.

So running towards the thing that you’re afraid of is something that I would go by, as a gut check for whether you should take on a side-project or a new role.

Why do you do what you do? What makes it all worth it?

I guess it’s a little cliché but it’s definitely the joy of having something you make be useful for a lot of people. Being able to create something and make something that a lot of people find helpful or useful or makes them smile at the kind of scale that designers are able to do, is pretty magical and a pretty amazing opportunity.

Designers for a long time were relegated to billboards or designing books which obviously quite some time ago had an immense scale, but given the way that designers are now able to design technology is pretty insane historically. The size of the opportunity is something that I find fascinating. If you look at the history of technology in the world there hasn’t been a period in time where you could go design something and it be used by millions or hundreds of millions of people. To have a lot of opportunities for different designers to work at that scale is fairly new. It’s not like there’s 5 designers or 5 places where you could go to do that. There’s a lot of places for designers to go do that at this point in time and I think it’s a really great opportunity. I guess I could’ve pulled the shoot at some point and gone and done industrial design or some kind of mechanical engineering, but the scale of usefulness that you can create is pretty powerful right now as a designer. I think that’s a great opportunity to have.

Who would you want to see on Ways We Work?

I’d love to see - I can’t say Slackbot can I? No, I’d love to see John Thai over at Google, he’s working on some really crazy stuff.