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Russ Perry of Design Pickle: “Ensure you’re training in all areas of your life”

The first is to do things you don’t want to do. If there is a cold pool, go jump in it. If there is a hard conversation you don’t want to have, have the hard conversation. When we do things we don’t want to do, we actually build the decision-making process to pursue and persevere […]

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The first is to do things you don’t want to do. If there is a cold pool, go jump in it. If there is a hard conversation you don’t want to have, have the hard conversation. When we do things we don’t want to do, we actually build the decision-making process to pursue and persevere through the hard moments that end up allowing us to become more resilient. When we allow the “no’s” to creep in, we enforce the opposite of resiliency, like complacency or idleness.


In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Russ Perry.

Russ Perry is the Founder & CEO of Design Pickle, an unlimited, flat-rate creative services platform. Under Perry’s leadership, the company has grown its global network of designers from 2 to over 500, completing over 835,000 creative requests since its 2015 inception. Perry resides in Scottsdale, Arizona with his wife, Mika, and their 3 daughters.


Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

After graduating from Arizona State with a degree in industrial design, I was all set to go to work for a creative agency. At the same time I was getting ready to move across the world, though, I found out I was going to be a father. My perspective on my career path shifted completely — I knew I needed something stable. Something that would provide for my daughter. Apple was a company I had long admired, especially after working for them as a sales rep throughout college. I decided to pursue a career with them at the retail store here in Arizona, but quickly realized that retail was not my passion.

Around the same time, I was taking on more freelance creative work. What started as a side hustle ended up as a fully-fledged creative agency. Even though I loved the work we were doing, it’s safe to say there were a ton of ups and downs over the eight and a half years we were in business. We were all over the map with clients, and there was definitely a period where we took accounts just to have a source of income. It was not what I would call a success — we closed our doors in 2013 rather unceremoniously.

I didn’t know what to do next, but I did know I wanted to work with creatives and help clients of all shapes and sizes. In 2014, the idea of a subscription service for graphic design kept coming to mind. I experimented with this concept for my freelance consulting clients, and soon realized it was a legitimate, viable business model. In January of 2015, Design Pickle was born.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

With my first creative agency, I tackled challenges and feelings of uncertainty, stress, and worries by relying on alcohol. I was drinking heavily and self-medicating in an attempt to push issues with cash flow, clients, and employees out of mind. I struggled to keep the business afloat. There were holidays with credit card bills galore and the ever-present question of “Where are we going to get the next check from?” Unsurprisingly, the stress, the alcohol, and the vicious cycle I was stuck in led to some terrible decisions, which ultimately led to the business closing itself. You can only go through the cycle so many times before the wheels start to fall off the wagon.

From my addiction, and then my sobriety (going on seven years now), I learned you can’t do it alone. Entrepreneurs tend to isolate themselves right from the start. If you think about it, most entrepreneurs are not surrounded by others in the same boat — friends, families, and colleagues often have a hard time relating. But you must have a network and have people in your life you can trust and to whom you can pour it all out. Doing it alone puts you in a state of isolation, which can lead to those destructive habits of self-medication.

I found that surrounding myself with other entrepreneurs with the same values and goals made a huge difference. It allowed me to grow in an accelerated, healthy way. If I ever felt at risk of those destructive habits returning, there were people around me who had been there. That’s one reason I share my story about it — there could be people reading this who are finding themselves in a similar situation.

What do you think makes your company stand out? Can you share a story?

We have a pickle in our name and logo, so it’s no secret that we’re a fun and quirky brand. And I’m really proud of how this is reflected in our company culture, both internally and externally.

Beyond our creative services, we aim to go above and beyond to make sure any touchpoint is a positive one. Every new hire gets a pickle suit. We hand out monster-sized pickles at events we sponsor. Every customer gets a weekly dose of pickle puns in our newsletter. It may sound trivial and small, but all of these items add up to our company culture and play into our vision of changing lives through creativity.

One story that comes to mind is from an event we sponsored in 2019. As anyone who frequents conferences knows, they can get a little redundant and stale. So to spice things up, we hosted a jazzercise class…while wearing our pickle suits. Did it sell unlimited graphic design? No. Did it make people laugh? Absolutely. At the end of the day, those types of friendly, quirky interactions — whether virtually or in person — are what set us apart.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

One of the most influential people in my business career is a coach and mentor named Garrett J White. He runs a personal development program called Wake Up Warrior, which is pretty polarizing. Regardless, he’s helped me unlock my own ability to find and seek clarity, to not be afraid of interpersonal conflict and challenges, and to live a lifestyle of growth and expansion.

I first met him at a five-day boot camp intensive with eleven other guys. I had no idea what I was signing up for. To put it in perspective: three minutes into the event, all twelve of us were doing planks on Pacific Coast Highway in the summer sun. There was a lot of yelling throughout the entire event, but it was for a purpose. It challenged me and made me realize what is possible for myself, which helped set Design Pickle on a much higher trajectory.

Garrett is very persistent about the idea that your life can only rise to the lowest level of where you are in a given moment. If you’re struggling in business, it’s usually not that you have a business problem — it’s that you have a problem in another area of your life that’s holding the business part back. Being able to diagnose and evaluate all areas of life isn’t revolutionary, but for me, it was something I found to be packaged in a clear way inside that program.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

I think resilience and tenacity go hand in hand, but resilience is having the internal conviction to do the work that’s required. What are you doing to push yourself to the path you want? How are you doing it?

Conviction, certainty, grit, hard work — that’s what resilient people are made of. There is no resiliency to be found in the easy path. The strongest people I know are in pursuit of something challenging or hard — and take pride in enjoying the struggle.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

When I think of resilience, I think of our creative designers at Design Pickle. They show up every single day with a mountain of creative work to do from clients who are all over the map — from rude to indifferent, to over communicators, to those who don’t provide any direction.

They persevere through all of that because they have a greater vision for themselves and where they want to go professionally. While I love our clients dearly, not all of them are gracious. Sometimes they’re very challenging to work with, and yet our team shows up day in and day out with friendly, hardworking attitudes. It’s inspiring.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

Although I recognize the privilege and advantages I’ve had in life, there were still sociological challenges my family faced during my childhood. I had a single mom with a low income. My parents divorced when I was two. Addiction runs on my dad’s side, hence the alcohol I mentioned earlier. For me to get a full ride scholarship, have a daughter at the age of 22 (I now have three daughters) in college, get married, start two businesses, and close both — that was already a lot more than anyone expected.

Then finally getting to this point in my life. Was it impossible? No, but I think there definitely were times where through luck or God’s grace or something in between, I was able to get through the tougher moments.

I’ve always had a vision for where I wanted to go, whether it was the school I wanted to attend, the dorm I wanted to live in, the degree I wanted to get, or the kind of dad I wanted to be. Having that vision has helped me navigate through life regardless of the challenges. It’s something I refer back to every day.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

At just 22 years old, I found out that I was going to be a father. I wasn’t married; it was unplanned. I found out two months before the baby was due to arrive. I had plans to move to Australia that had to be unwound. My path completely shifted overnight, having to absorb the idea of being a father and what I was going to do about it. I wouldn’t call it a setback, but it was a curveball.

I had to change my life completely, from where I was going to live, to custody arrangements, to parenting classes. I went all-in on everything that came along with the responsibility, though, and found myself loving it. I still do to this day. She’s 15 and a sophomore in high school; she’ll be going to college soon. It’s crazy to think about. By having someone else in my life that I became responsible for, I found I had no choice but to grow. It allowed me to expand in ways I never thought possible, and still does to this day. Children challenge you in next-level ways, but these ways have allowed me to become a better, bigger, more capable person in all other areas of my life.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

I think resiliency has a lot to do with determination, in that those who are resilient inherently have a ton of determination to push forward and find a path no matter the challenges. As I alluded to earlier, I had plenty of challenges with alcohol growing up — it had been a taboo presence in my life for as long as I could remember. Alcoholism was rampant in my father’s side of the family. His drinking eventually led to my parents’ divorce when I was two years old. Because alcohol was such a source of pain in her life, my mother made one thing clear: alcohol was bad. That’s it, case closed. And because it was vilified in this way, I ended up minimizing the risks I saw in my dad’s behavior. As I got older, alcohol started to seem pretty cool.

Once I entered high school, my alcohol-fueled rebellion really began. By the time I graduated, I already had one run-in with the police. And like many other young college students, I fully embraced the lifestyle at Arizona State University.

This continued well into my adult life. Some nights were a whirlwind of fun — including the first date my wife Mika and I went on. But some of the worst nights of my life also involved drinking. I reached a new low the night I woke up in a jail cell in Clark County, Nevada, with no idea how I got there. Turns out I’d been resisting arrest for drunk and disorderly behavior.

At my lowest point, it became pretty evident that the only way I was going to live the life I actually wanted was to quit alcohol. I was the only one that was going to make it happen, and was determined to do so. Battling this taboo and trying to figure out my path without a doubt contributed to my resilience today.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

The first is to do things you don’t want to do. If there is a cold pool, go jump in it. If there is a hard conversation you don’t want to have, have the hard conversation. When we do things we don’t want to do, we actually build the decision-making process to pursue and persevere through the hard moments that end up allowing us to become more resilient. When we allow the “no’s” to creep in, we enforce the opposite of resiliency, like complacency or idleness.

Number two is to ensure you’re training in all areas of your life. You can’t become more resilient if you’re fatigued all the time; you can’t become more resilient if you’re not mentally clear. Determine what you can do to improve in certain areas, and commit to it.

Number three is to challenge your mind through reading, and to consume media that is the opposite of what you would normally read. Consider perspectives and points of view that are factual and well-researched. When you read credible and international news sources that have different points of view, you proactively combat the negative feelings you may have when being presented with an opposing opinion. By actively seeking those out, you’re training your mind to become more resilient.

I also think you should voluntarily put yourself in challenging situations, whether physically challenging, mentally challenging, or somewhere in between. Physicality can build resilience that translates mentally. It can be anything from a long-distance run or a two-day talking meditation retreat — equally challenging, just in different ways.

Lastly, enjoy it. Building resilience is about the process. When you’re in the middle of that long run, or you’re having that hard conversation, just know on the other end is someone who has improved. Enjoy the process.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Educating and training other countries on the importance of creative services and careers would be at the top of my list. In so many countries, the creative industry is scoffed at. It’s considered a non-viable career path. In reality though, all you need is a computer and an internet connection, and you can have a lucrative, fulfilling career.

In either this chapter of my life or the next, I would love to promote and support creative education, provide it to those in need, and help build programs like tech bootcamps. To be able to build avenues for people to find amazing careers and have new paths to change their families, to inspire others to do the same — that would be a movement I could get behind.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

I would love to share a meal with either Ray Dalio or Reed Hastings. Those two gentlemen — wow. I can’t say enough good things about them. I love their content, their writing, their visions, who they are, and what they’ve built.

How can our readers follow you on social media?

I’m not on social media, but I am on my website, russperry.co. You can send me a message there, or of course, through the Design Pickle channels — we’re @designpickle across platforms.

This was very inspiring. Thank you so much for joining us!

Thanks so much!

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