Career Stories

How I Launched My Career in Design with a 365-Day Challenge

Tatiana Bischak
December 2019

I learned from the internet, and I have no traditional education.

I was raised by an architect and an artist—two very creative people. I was an only child, and we didn’t have a TV, so I would draw toys and play with them. I’d literally draw little characters then cut them out and play with them.

Most kids wouldn’t get excited by a scrap piece of paper with a dragon on it, but I would because I drew it, and I knew it’s backstory. I could literally create any toy I wanted.

A preview of some of my childhood drawings.

Around the time I was about to start college, the recession had just begun. Obviously nobody’s buying oil paintings or building houses during the recession, so it really hit my family hard.

I was discouraged from pursuing any sort of creative career and encouraged to focus on a career I could survive in. Since I was an avid skier, my choice was clear: go to the only engineering school in Michigan that owned a ski hill and get a degree in mechanical engineering for designing skis and snowboards. 

There I slipped into the drinking culture, and my grades slipped as a result. My parents filed for divorce, and rather than face the reality of the situation, I booked it to Ireland with the cash I had to live with my Irish boyfriend for three months.

Mechanical engineering was no longer a viable option for me—the rigidness of the profession was breaking me mentally, and if I had to work in that field for the rest of my life, I was sure that I wouldn’t feel fulfilled or sane.

My boyfriend was encouraging me to create more art, but for my entire life, I’d been told this wasn’t the way to make money and that if I did become an artist, I would be poor and unable to pay bills. Even complete strangers will laugh if you say you want to be an artist as a child. But I started to do it on the side, and it did start to pay the bills.

I started with a crowdsourcing website called DesignCrowd, and I actually started to win a few logos on there which made some money. It definitely helped me get my footing, and I’m still in contact with some of the clients I met through DesignCrowd.

After doing that for a while, one of my friends started a business and offered me regular contract work. As a designer just starting out, this was a huge opportunity and break—it meant I could pay my rent and maybe change my windshield wipers if I needed to. When you’re working poor, it’s scary to buy even the smallest of necessities sometimes, and I was thrilled I could meet my basic needs.

At that point in my career, I was basically just doing graphic design and trying to hack it at logo and branding. My education had been simply observing other designers on the DesignCrowd and browsing illustrations on Pinterest.

But I felt completely alone; I didn’t know anyone in the design community. I was working on the field, but I had never had a discussion with anyone about it.

In 2015, I was assaulted. I fell into a depression, and I felt like I couldn’t leave my house. I didn’t want to see people. I lost my friends, and it was a very solitary time in my life.

I tried to find things at home to keep me occupied because I was housebound and felt useless. That’s when I saw an ad for Skillshare on Facebook. It was 99 cents for three months—and even a working poor person could afford that. So I got it.

I started taking classes on design because I wanted to get better. And I just wanted an excuse to sit inside and not see anyone.

Through Skillshare, I met Hayden Aube—who is one of the best humans I’ve ever met in my entire life. I didn’t know how much of an impact he would have on my life. He’s one of the top teachers at Skillshare, and he’s one of my good friends. 

We met through a contest he held in one of his projects. He was going to do a 30-minute call with three of the students who won, and I was one of the students whose work got selected. I think our 30-minute call turned into an hour and a half. We ended up talking about my situation—about how alone I felt, about how I hadn’t gotten a traditional education, and how I was searching for that online. 

I wanted to be part of a group again, but going about that was intimidating to me. Hayden encouraged me to reach out to other illustrators, and he actually started a design Slack group to connect solo creatives who needed to connect. He took time out of his life to run and curate a Slack group out of his students, and he invited me to it so I could connect with people there.

That’s how I met Matt Legrice. I remember the first thing he ever posted was a picture of a tattoo he had designed for the back of his calf. Matt is such a fantastic guy. He taught me how to do the business side of design, like how to hold a client’s hand through the process and be patient and understanding. It may seem like an obvious concept, but there are so many things that are lost over email and miscommunication, and 80% of this business is being an enjoyable person to work with. I’d never met anyone like that before who is so dedicated and caring to a customer. That really had a big influence on how I work with my clients.

I met Razvan Vezeteu—who is another fantastic person and designer. Raz is a Romanian illustrator and really well-known in the design community for doing 365 days of design challenges. He really encouraged me to take on a 365-day challenge and told me how great it could be for my career. I told him I would never have time to do that, and it sounded nearly impossible. But Raz continued to encourage me.

Then one night I got drunk with a friend over video chat—Andrea Lazzarini, another designer from Argentina I’d met through Slack—and we decided we were going to do it together. We were going to do this impossible 365 days of design challenge.

So we did it. And I made it through 275 consecutive days.

It wasn’t easy. It felt like I was rewiring my brain. You know how they say it takes so long to develop a habit. Well, if you’re designing something every single day, and you do it for 275 days straight, you reach a point where, when you wake up in the morning, it’s like you have no other choice because there’s nothing else you’d rather do. You’d rather draw than eat. 

That can really break you. But it can do wonders for your career, too.

At around day 100 days, my first big client contacted me out of the blue on Dribbble. It was the marketing company for Dr. Pepper—they wanted a SnapChat filter. I honestly thought it was spam. But as I started reading it, I realized that it was an actual client inquiry. I was telling myself, “I can do this, I can do this. It’s a big name.”

The Snapchat Geofilter I created for Dr. Pepper.

That was the first client other than family or friends that ever contacted me for work. I remember wondering to myself, “How did I get this client right off the bat?” I was so nervous.

Right around the same time, my stepdad was dying of cancer. He was so proud of me. I’d been sending him my 365 designs every single day hoping to cheer him up. That was a big part of why I continued. I felt like if I stopped I’d let him down, and seeing him smile from my work was such great encouragement to keep going.

My first big client was really kind and was a big lesson for me. My stepdad ended up passing away in the middle of the project, and I nervously asked if I could take just one day off to recover. They were incredibly understanding and told me to take all the time I needed. 

This is an illustration I did after I lost my step dad.

That was my first time working with an art director on a project as well. It was a really important and eye-opening experience—he would communicate and break down exactly what the client wanted or didn’t want and translate that into design improvements. It was such a new experience having someone in your corner helping you translate the needs of the client and creating art to reflect that.

I remember thinking, “This is amazing. Why have I never had an art director before?”

I did that project and ended up getting a few other small clients on the side. I was working part-time at an iPhone repair shop so I could still pay the bills, and my employers there were thrilled that I was educating myself. They allowed me to work on my illustrations in my downtime, which allowed me to continue building my portfolio through the 365-day challenge. 

By the end of 2017, I’d made it into Dribbble’s Top 50 Most Liked Designers of 2017.

Thinking back, it’s almost like I forced my way into the list with how much I’d created. I mean, when you put something out every single day, eventually you’ve got so much content in the feed that people would have slipped and given me a like.

Still, I felt like an imposter, and that’s when Leon Ingram (another illustrator I had met) taught me about imposter syndrome. My community was supporting me, and before, I would have allowed that negative thinking to overcome me, but now I had people supporting me and keeping me up.

I had gone from a deep depression to feeling like I had hope and purpose—all through design and the community of incredible people I’d met. My new friends and fellow artists genuinely cared about my wellbeing and encouraged me to keep creating and to keep growing, as an artist and a human.

Over the past couple of years, I’ve worked with some incredible companies and people—full-time and freelance—all through introductions from people I’d met because of design and my substantial portfolio which I built with my 365-day challenge. And in July of 2018, I left my day job to be a freelance illustrator.

I’m currently working with some of the best clients I’ve ever had—their respect for me, my well-being, my creative freedom, and my rates is the best I could hope for. I’ve never experienced anything like it.

I know my story is not the most standard way of becoming an illustrator, and I never meant to become one. I didn’t think I was talented enough, and in truth, I accidentally became an illustrator because I did a 365-day illustration challenge instead of focusing on logos and branding. As a result, I built my portfolio and skillset in illustration, but I couldn’t be happier now. I still support people’s brands, but it’s with artwork now instead of design.

And that’s what I love doing today—being able to sit down with a company and taking them through the creative process, trying to figure out what they want to change in the world, and helping them support that through art.

So if you’re struggling with your start, keep going. Support other people in your field, learn from them, find what really ignites your passion, and work tirelessly to improve your craft. Work at it every day—you’ll have to make sacrifices, but it’s worth it. We all have bumpy, roller-coaster-rides through life, but we have to remember to keep going. Take care of yourself, never stop learning, and be kind to yourself—no one enters any industry a master. You’re going to do just fine. 


Tatiana Bischak is a freelancer specializing in illustration, graphic design, and logo- and brand-development. Helping other artists and creatives find their voice and footing in the industry is what she does for fun when she’s not creating.

To learn more or check out Tatiana’s work, visit her portfolios:

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