Failing Fast, Failing Often

Alex Benson
Ideas by Crema
Published in
11 min readJun 24, 2016


Last week, I had the honor of giving the commencement address at my Alma Mater. Having just graduated the year prior, I decided to give the graduates a look at my path to where I am today, and the lessons that I learned along the way. The following is the transcript from that speech.

It is an honor to be here today. A year ago, I was sitting where you are now, hopeful, excited, ready for the future. I never could’ve imagined that a year later I would be up here addressing another group of graduates. I’ve never done one of these before, and so I asked around for some advice, I watched a lot of commencement speeches, and spent some time thinking up some witty jokes to break the ice. But then I thought back to when I was sitting where you are, what was going through my mind, how different of a person I was just a year ago. I thought about what I wished someone had told me that day.

I decided to come here today to tell you a story. This is not a story about how I graduated and woke up the next day with everything figured out. Or how someone walked up to me on the street and offered me my dream job. And this is not a three point plan to become successful. This is a story about failure. This is a story about falling down.

This is a story about failure.

People enjoying success have a tendency to tell their stories in a positive light, focusing on the good bits and the things that they are doing right. Not necessarily on purpose, but because people are always telling them what a good job they’re doing. But success isn’t always about the things that go right. Many times its about the struggle, and the failed attempts that eventually lead us to the opportunity we were looking for. Nothing worth having in life comes easy.

Anyone who knows me will tell you there’s one thing I for sure believe in. And that is this: Anyone can achieve anything at anytime with any means, as long as they try. The only thing standing in between you and your future, is you. Don’t have the money? Save for it. Don’t have the time? Make time. Don’t know where to start? How about right now? Every day you don’t move forward on your dreams is another day delayed. And if you don’t care enough to move on it, then its not worth having. If you’re not passionate about it, find something else. And if you don’t know what you want, then start looking. You’ll know it when you see it.

I almost didn’t graduate college. I almost didn’t graduate high school. I got into a lot of trouble growing up, getting kicked out of schools, skipping class, and getting arrested. My single mother didn’t know what to do with me. She tried her best to get me involved with activities and expose me to things to try and keep me out of trouble, but I was a handful.

I got involved with theater and photography and that kept me out of trouble for the most part in high school, but by the time my senior year came around, it seemed as though my slacking off would come back to haunt me. I wouldn’t have enough credits to graduate. I hadn’t thought much about going to college, or my future. If it wasn’t for my friends, and a teacher who took me under his wing, I might not be here today. I worked hard that last semester of high school and graduated with just enough credits to walk. I started at UCM that fall.

When my mom and I toured the campus, we made a deal. She would pay for a part of the first year of school, but I had to promise her something first. I had to promise her I would finish. My mom was in school 18 years earlier. She was working towards a degree so she could become a social worker but she had to drop out of school, and put her dreams on hold, to raise me.

I had to promise her I would finish.

She would try several times again to return to school, but demands on her as a single mom raising first me and then my sister meant that she had to work to provide for us. It wasn’t easy, and we didn’t always get everything we wanted, but she did well by us. I never remember missing a meal or being afraid of not having a place to call home. I told myself growing up that I wanted better than what we had, and she wanted the same for me. So I stood there in the quad and promised her I would finish.

I began my college career as a theater major, and then a history major, and then an education major, then a photography major, for about a day, and then finally back to a theater major. After a year of studying and partying, I realized I couldn’t afford to stay there on my own. So I returned home. And again, I promised her I would finish.

I decided to attend community college, to knock out some general studies classes and work while living at home to save money before I returned to school. I enrolled in a photography class, thinking it would be an easy A, however I found out I needed to take a prerequisite class first. The class covered Photoshop, Illustrator, and I’m about to date myself, Quark Xpress. I remember thinking I’d slide by with a passing grade, and get my easy A during the next quarter.

I never ended up taking that photography class. During the second week, I approached my teacher and told him I knew what I wanted to do with my life. I wanted to be a graphic designer.

I moved back to my hometown, Minneapolis, shortly after to attend the Art Institutes International — Minnesota. I stayed with family, worked full time and pushed myself to soak up everything I could while I was there. I stayed for a year before realizing that an art degree cost even more than a liberal arts degree, and again, I moved back home. And again, I promised my mom I would finish.

I took the next few years off from school. I took a job bartending, saved up enough to buy a laptop, and poured over designs online, in magazines, anywhere I could find it. When I wasn’t behind the bar, I was sitting at the bar, learning everything I could, dissecting designs I found appealing and wanted to emulate. I worked that job for 2 years before being able to go back to school.

Everything seemed like it was going well, until I took a different job that worked better with my school schedule. When that fell through I ended up blowing through my savings trying to pay rent and tuition. This was probably the darkest time of my life, I wasn’t sure if I would be able to pay my next month’s rent. I didn’t know if I was going to be able to afford ramen for dinner. I was at the end of my rope and it didn’t seem like there was any option. But I wasn’t going to quit school again. I wasn’t going to start over again. I started looking online for any opportunity to make money: mowing lawns, photography sessions, cleaning people’s houses. I was asking friends if they needed me to do any work for them, anything to get by.

I got a call from a friend of a friend, saying they heard I was looking for work and they were looking for a designer for their startup. I interviewed three times and got the job offer. They could only afford to take me on part time though. So I spent the next 5 months working and going to school from 7am-11pm, and any time I had after that I spent teaching myself how to code. I took every opportunity to meet people, learn new things, and position myself for more opportunities. I knew this was my big break and I wasn’t going to squander it. Looking back, I don’t know how I kept that up for that long, but I’m glad I did.

That company folded at the end of that 5 months and they had to let me go, but because of the connections I made I had a new job offer by the end of the day without even asking. A month later I went full time as a designer and haven’t looked back since. I was fortunate to work for companies that valued that I was receiving an education. They let me take the time off I needed to attend classes and get my schoolwork done, working with me to make sure I still met deadlines. I think I learned as much from these companies as I did at school during this time. And as I’ve mentioned, last year, I graduated with a degree in Graphic Design. I kept my promise.

…it might be easy to say that was the obvious choice, but it wasn’t an easy choice…

Looking back, quitting my job and joining a startup was one of the best decisions I ever made. It directly led to me being where I am today. And it might be easy to say that was the obvious choice. But it wasn’t an easy choice. As I’ve mentioned, I had changed jobs in the attempt to work and go to school. That job didn’t pan out, and I ended up broke. I had to go and ask for my job back. I was a hard worker, and thankfully they rehired me. And I worked for them the rest of the summer. So when another seemingly perfect opportunity arose that would require me to quit again, I was understandably hesitant. Startups are not known for their job security, nor their longevity. And while the pay they were offering was good, I could very well be unemployed again in a few months if things didn’t go according to plan.

Theres a saying in my industry: fail fast, fail often. That might seem counter-intuitive, wanting to fail. But the idea behind it is so much more. Success rarely comes before failure. Thomas Edison didn’t invent the light bulb without failing 100 times. Steve Jobs didn’t announce the iPhone without first being fired from Apple. Nothing in life worth having comes easy. True innovation takes more than talent, and more than hard work. Its a fine balance between the two, along with a little luck. The key isn’t to avoid the failures, but to learn from them.

Nothing in life worth having comes easy.

Opportunities don’t happen in the past, they are happening now, in the present. Sometimes, it will seem like a big risk, and the thought of failing seems too daunting. You might not feel like you are ready to take that leap. I took that leap, and although there were many times I fell, hard, I always got back up and jumped again. Give yourself permission to fail. Take that leap, because the truth is, no one ever got anywhere doing what was safe.

Around the time I took that leap, I had the great fortune to meet someone that would change my life, though I didn’t know it at the time. An owner of a local agency took some time out of his day to sit down with me and talk about my designs. I had just started full time, and had never had any training in designing web products. Designing for the web was a foreign concept for me, and I had sworn that I would never learn to code. I was a designer, that was beneath me, too hard, not real design work. But here I was, in a job that would change my view on design, talking to someone who would dramatically shape that view. I listened as he gave feedback on my designs, and took every word in like it was gospel. It wasn’t obvious to me then, but as time went on, and as he mentored me, I knew what my next step was: I was going to work for him one day. And this wasn’t one of those, I wish I could, or, maybe one day, type of things. I knew I would work there. I didn’t know how, or when, but I knew I would. One thing was clear. I had to get better. I worked hard, literally burning the midnight oil and watching the sun come up from my desk more times than I can remember. With each new client, side job, or personal project, I always tried to challenge myself to do better than the last time. I wasn’t satisfied with where I was, I wanted better. It took two years, but 6 months ago, I started my first day at Crema.

But it wasn’t a straight shot. It didn’t happen overnight. It took time, passion, and most importantly never giving up. And because of all I went through I am in the unique position to say that I, truly, have my dream job.

One theme you can probably see in my life is self-learning. I’m a big proponent of it, and I wouldn’t be where I am without it. Thats not to say that traditional education doesn’t have its merits. I learned a lot from this school, and with the foundations I received here, I was able to go on and learn and accomplish even more. Everyone graduating today is not the same person they were when they walked into school that first day. Learning doesn’t stop after the last test. It doesn’t stop after walk across this stage. The world is moving too fast, new skills and technologies seem to pop up every week, and those coming after us are going to be smarter than we were leaving here. So don’t stop learning. Always be improving. Find something that challenges you and work at it. Its the only weapon I know for fighting stagnation.

Find something that challenges you and work at it. Its the only weapon I know for fighting stagnation.

Jim Carrey gave a commencement address several years ago, and he said something I want to share with all of you. And if theres one thing you take away from today it is this: Like many of you I was concerned about going out into the world and doing something bigger than myself. You can spend your whole life worrying about what will happen in the future but all that will ever be is what happening here in this moment, and the decisions we make in this moment which are based in either love or fear, so many of us make our decisions based out of fear disguised as practicality. And what we really want seems impossibly out of reach and ridiculous to expect so we never dare to ask the universe for it. You can ask the universe for it. You can fail at what you don’t want, so you might as well take a chance on doing what you love.

Take a chance on doing what you love. Don’t settle for the mediocre. Don’t be afraid to fail, because it is only through the failures that we see the way forward. Samuel Beckett said, Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.

Congratulations Class of 2016



Alex Benson
Ideas by Crema

Prouct Designer at Facebook in Seattle. Originally from Minneapolis/Kansas City.