Jeff Shin is a lead designer on the community team at 500px in Toronto. After his first year of University he made the decision to drop out of school and pursue a career in design. After three years being out and working in the “real world”, Jeff shares what he learned from taking that path, the main challenges he faces in his work today and his role at 500px. Talking to Jeff he has this confidence about him that is rare, especially amongst young professionals. He has great points to share about sticking with your decisions and learning how to handle discomfort.

Tell me about what your current role is and the work you’re doing?

Sure. I'm the lead designer of community at 500px. The community team at 500px builds consumer products that millions of people use. The photographers, the photo lovers, the curators, and the people that just like looking at photos.

We oversee the main website, the iOS and Android apps. We also get to work on some smaller projects like an app for Roku or for Android Wear. I'm the lead designer on this team, which is made up of three people.

What does your role look like within that specifically?

I try to do a lot of designing, but it's definitely a lot less than it used to be. It's now a lot more of helping the other two designers and making sure that they are given the right priorities and product direction from the product managers and the executive staff.

Though I do still design quite often. In startups, given the resource constraints, you have to be a generalist. So I wear a lot of hats within product design, like defining a product, wireframing, mocking it up, prototyping, to even writing a lot of production code. All of our designers are great at being generalists, so we all help out where needed.

Being a self-taught designer, what were some of the resources for you getting started? Did you learn from anyone? Or was it mostly online self-teaching?

I got started in graphic design. It started with a lot of reading tutorials online on how to achieve a certain look in Photoshop. I was just drawing inspiration from things I liked such as films, posters, fashion and architecture. I grew an eye for visual design through being inspired from the outside world.

As for the technicalities of design it was two things:
One was looking at the websites or the apps that I admired and trying to break them down myself and figure out what the steps were for that person to design something like that.

The second thing was pure trial and error. I remember the first time I tried interface design when I was really young… just remembered this now. It was the worst thing to design if it's your first try at interface design - I tried to redesign Mac OS X. I was a kid who knew absolutely nothing about interface design, and I was naively thinking “oh, interface design is probably just like graphic design”. I quickly realized how wrong I was.

Fortunately this was a time where people were writing a lot of stuff online about interface design and interaction design, so from there I just started reading a lot, and my designs slowly got better and better.

You dropped out of University after your first year and wrote a great post about it on your site. That was three years ago now. In retrospect, what was the greatest benefit of doing that, and the greatest challenge?

I think the biggest benefit was that it put me in an uncomfortable situation where I had to carve out my career path. When you're in university, there's at least a couple of steps you can see ahead of you that you know you need to take in order to achieve success, whatever that means to you. Dropping out of school left me in this place where I didn't know what my next step was.

I didn't even know what success meant to me. It pushed me to think creatively about what it meant to me, and how I could get there. The removal of the safety net of school put this fear in me that propelled me into a year or so of some of the most packed learning I've ever done in my life. I don't think I ever learned so much as I did in the year after dropping out. To me, that could only have happened if there was no safety net.

It's interesting because I thought the toughest thing about dropping out of school would be professional or career related. I thought it would either have to do with me not being able to find a job, or work in the states because I didn't have a degree. Things like that.

But the biggest thing for me was more emotional and mental. I think when you're young, you can't wait to grow up. When I was in high school I couldn't wait to be in university, and when I was in university I couldn't wait to be out in the 'real world', making money. I was just fantasizing about and glorifying adulthood.

I realized after that you only have a couple of years where you can be young and explore different career paths. You can take the time to figure out who you are and what you want in life. For me I felt like I didn't really have the time to do that, and I was a bit rushed into it all.

Back to the present day what would you say are some of the main challenges that you face in your work right now?

I think growing pains are a challenge for us right now. Things are moving fast - the company is scaling, the products are scaling, and we even recently did a rebrand. As we scale, the processes have to scale as well, so for us, it's important to really nail down the process before we get even bigger, like 100 or 200 people. So we've been thinking a lot about our processes, and carefully evaluating them. Like how we come up with product ideas. We've tried a couple different methods that didn't go so well, so we keep trying to improve. The same goes for our design process.

We recently brought on a dedicated UX researcher, so we had to think about how to integrate that into our overall process. How do we user test? What do we do with the findings? How do we communicate the results?

So it's a lot of figuring out what the best process is - but also remembering that too much process is the worst kind of process. So a lot of it is trying to find out what the right amount of it is.

What does a typical day look like for you, the main components of your day?

A big chunk of my day is spent with my fellow team leads - the product lead and the engineering lead. The three of us oversee the vision and growth of the community, so we spend a lot of time talking about planning the roadmap and future products, making sure that the products in the pipeline have solid release plans, coordinating with other teams on projects, etc.

A lot of my time is spent on design work as well. Working with other designers and coming up with wireframes, mockups, getting them tested, going over test results and designing iterations. Oftentimes I'm coding, polishing animations and styles, or fixing UI and usability bugs on the site. The design team works really closely with one another - doing critiques of each other's work, doing design reviews, and having project kickoffs.

I'm spread a little bit thin, so there's a fair amount of context switching throughout the day that I'm trying to minimize.

What are the top 5 tools you’re using on a regular basis?

A Pen - a Bic pen specifically. It comes in handy when you're sketching out an idea or making a quick note to yourself on paper. But you will always see me with the pen in my hand, spinning it, even if I haven't written anything the entire day. I always have a pen spinning in my hand, it's like a generator for my brain. That's probably really weird [laughs].

Slack - I think everyone's going to say this but Slack - it's amazing. We use it a lot.

Asana - Especially given that I'm switching contexts between designing, coding, and planning, Asana helps me out. I often use it as my playground to organize thoughts and ideas and things like that, which end up turning into tasks.

500px website - I use the site a lot actually. Often it's just to slack off and look at cool photos, but it keeps me reminded of the awesome products that we're building. It inspires me visually and creatively by looking at these amazing photographs taken by really creative people, but it also makes me think 'this is awesome, this is what we built'. It's an energy boost to keep me reminded of why we do what we do.

Photoshop - We have some designers that use Sketch, but I'm mostly still in Photoshop, which sounds like the old school thing to say nowadays.

How do you find managing and staying on top of an email and communications? I find it’s something a lot of people struggle with. Do you have a process?

For emails I just generally try to keep my inbox as thin as possible, and I'll only leave items that I need to address in my inbox. I have this thing where I'll be really annoyed if there's leftover items. I'm sure this is the same with most people. So if there's emails that I need to respond to or take action on, I'll just keep them there, and generally my need and desire to clear that thing will soon force me to deal with them.

As for Slack... I'm in a lot of channels that I don't really need to always pay attention to. But it's always tempting to check it if there's a new message in that channel. So I just mute as many channels as I can, and only get notified when important messages are posted.

You talked about context switching earlier, and over planning certain things. Do you find it difficult limiting the time you spend organizing tasks versus doing the actual work?

I don't like to do that because it's feels like work that doesn't really produce anything. I can sit and code for an hour, and I'll have an hours worth of code. Or I can sit and design for an hour, and I'll have an hours worth of design. But if do an hour of moving tasks around, I come out of it and I'm like, “what did I just do for the last hour?” Obviously the reason to do it is because it actually does help, but to me it doesn't feel like I've been very productive, so I try to keep it as thin as possible.

I do that by talking to team members in person whenever possible. I can either create an Asana task and write this long description, make it super bulletproof, then ping someone on it and say "hey can you read this?" Or, I can just walk over to them and speak much faster than I can type. I can get their questions right away and answer them. I try to do that a lot because I feel like it cuts down the amount of time that you spend planning.

You have an interesting perspective having left school and started working much earlier than most people. What would your best advice be for someone maybe trying to break into design or a similar industry?

The advice that I would give is that choosing this path where the steps to achieve success is unclear is an explicit decision. You have to know what it involves, own it, and live with it. I'm surprised that I didn't see it coming back them. I would have told myself, "look, if you're going to drop out of school and you think you're going to find a career in design, great. Just understand what that involves. Understand that it's a risk, understand that things are going to be unclear and understand that you're never going to have a clear step two."

This is a path that requires you to be someone of a specific calibre. It's not to say that it's super difficult - a lot of people can do it - but you have to be someone who's incredibly driven, who's a risk taker, who is willing to try a bunch of shit that does not work. You need to be okay with being uncomfortable. So I would say just know what you're getting yourself into, then brace yourself for the discomfort that may come. It's all worth it in the end, however.

Why do you do what you do? What makes it worth ... Why did you drop out of university to do it? What do you love about it?

I love making things. I like that I could go from there being nothing to there being something. That act of creation - especially without physical materials like wood - I feel like it's almost magical. You can make something that people from all across the world can appreciate, use, or see, just by typing into a little box on your desk.

Also, as someone who had to carve their own career path by learning a lot on their own, I relied a lot on the tools that helped me get there. Tools like Dribbble, Photoshop, and Tumblr - I owe it to these tools, services, and companies for helping me find success in the creative world. Now, I get to build one of these tools. I get to help people who are getting into photography, whether they're just starting to shoot on their iPhone or their dad's DSLR.

I see a lot of the work that I do at 500px as me giving back to the creative community, because without the tools that the community gave me, I wouldn't be able to do what I do now.

Who would you want to see on Ways We Work?

I want to see my friend Tom Cardoso. He's a designer at The Globe and Mail who does a lot of the infographics and the data visualizations. I think that's super interesting and I'd love to hear about some of his challenges and what tools he’s using.