Explore Stephen's work: stephenpickens.co | IG: stevepickens
Some creative careers begin with years of uncertainty. Others start with a kid opening Photoshop on a family computer and realizing they've found something they love.
In this conversation, we sat down with a creative director and designer whose journey began with sports collages, self taught design skills, and a curiosity that eventually grew into a thriving career. We talked about the realities of creative direction, balancing art and commerce, developing taste, building a portfolio, working with clients, and what it really takes to make a living doing creative work.
Their insights offer valuable lessons not only for designers, but for anyone pursuing a creative path.
Q: When did your creative journey begin?
I feel like I was always a creative kid. I was always drawn to visual creativity, doodling, drawing, all of that.
What really kicked off my pursuit of design and graphic media was finding Photoshop on my dad's computer when I was around ten or eleven. I started playing around with making collages of my favorite sports players.
It just grew from there. I taught myself Photoshop, then taught myself Illustrator. By the end of high school, I kind of knew I wanted to do design as a career.
It was a pretty smooth path from there, and I was very fortunate to know what I wanted to do from an early age.
Q: Is your dad a creative as well?
No, he's a software engineer. He just had Photoshop. He's a very techy guy and has a lot of different software.
Q: Did you go to school for graphic design?
No, I went to school for marketing.
I felt like I already had the design skills, and by the end of high school I knew a design degree probably wouldn't get me much further than my portfolio at the time. So I decided to focus on marketing and expand my skill set a little bit.
Q: You're a creative director now. What does that role actually involve?
I feel like it depends a little on what industry you're working in.
Working as a creative director for a B2B tech company is going to look very different than working in consumer goods or agency life.
In general, what I do day to day is lead the big picture creative strategy. I mostly work with food and beverage brands. If we have a new product launching, I'm thinking through everything from packaging to social media, websites, ads, and all the touchpoints. What does that look and feel like to the consumer?
A lot of it is creative strategy. If we want to target thirty five year old women, how do we strategically create something that appeals to that demographic?
It's a lot of big picture thinking.
Thankfully, I still get to do actual design work too. I've talked to creative directors at large agencies who say, "This is great. I'm getting paid well and have a lot of responsibility, but I don't get to do the thing that made me fall in love with the work in the first place."
I'm fortunate that I'm still able to do both.
Q: When you're building campaigns, are you the idea person or the executor?
It depends on the project and the client.
Sometimes clients already have established brand standards and they want something that stays very close to that world. Other times they're starting from scratch. They barely have a name, let alone packaging.
Most of the time it's collaborative.
That's what I love about this work. I get to collaborate and bounce ideas off smart people. I think that's where the best ideas come from.
Q: How do you balance the strategic side of design with the artistic side?
That's a foundational question that I think about a lot.
I bump up against it constantly because there's always the question of, "I really like the way this looks aesthetically. It's prettier this way." But maybe that's not the way it sells best.
In commercial work, you're always going to go with what sells.
It's a collaboration with sales teams, marketing teams, and everyone else involved. You're trying to marry the two.
My favorite work in the world is the work that does both. It's beautiful, it feels like art, and it also performs.
That's the kind of work I try to create.
It feels like a dance or a balance in a lot of ways.
Q: How much of your work revolves around storytelling?
I think every piece of art is some form of storytelling.
That's one of the common threads across every artistic medium. Every artist is telling a story.
For brands, that's really what branding is. Companies are telling a story whether they know it or not.
My job as a creative director and designer is to visualize that story and tell it creatively in a way that's truthful to the brand and appealing to the consumer.
Q: For someone who wants to pursue design, creative direction, or art direction, where should they start?
Create things and have fun doing it.
If you're early on, whether you're in high school or college, just make things that you think are cool, fun, beautiful, or exciting.
And then hone your taste.
Those are the two biggest things.
I could talk about career strategy all day, but so much of that changes year to year. The bigger picture is creating things and refining your taste.
You're never going to create things that are better than your taste. Your taste always needs to be a step ahead of your abilities. Otherwise you're not going to keep improving.
Q: How do you refine your taste?
That's an interesting question.
I think it starts with consuming art and noticing art. Notice beauty. Notice why something works and why something doesn't.
Expose yourself to a wide range of styles and mediums.
Don't get too comfortable thinking, "This is the exact style I like."
Even when you come across something you don't personally enjoy, ask yourself why other people connect with it.
Why do they appreciate it?
When you start looking for those answers, your taste expands.
Q: What stands out when you see truly exceptional creative work?
When I've worked on projects with really talented people, it often feels like we're creating something simply because we want to see it exist in the world.
It's almost indulgent.
I feel like a lot of great art comes from allowing yourself to indulge in an idea a little bit.
That might sound like it contradicts what I said earlier about commercial work, but there are moments where you can indulge creatively, and when you do, something special can happen.
Q: When reviewing portfolios, what makes someone stand out?
Their taste. A million percent.
If I look at a portfolio and see three incredible projects and one bad project, I stop trusting their taste.
We've all made bad work. I've made bad work. The difference is I don't put that work in my portfolio.
If you're including weaker work, it tells me your taste isn't developed enough to differentiate between good and bad creative work.
I can teach skills all day long. I can't teach taste.
If you can't look at two designs and tell me which one is stronger, and ideally why, then that's difficult to teach.
Q: So quality over quantity?
Absolutely.
I'd rather see two projects that someone absolutely crushed than a portfolio packed with mediocre work.
If they included those projects, it tells me they know what excellence looks like. It tells me what they're aiming for.
I want someone who knows good design when they see it.
You're only as good, in my opinion, as your worst portfolio piece from a recruiter or employer's perspective.
Q: How do you handle creative differences with clients?
I try to get as objective as possible.
At the end of the day, the client has the final say. They're hiring me. I'll do my best to persuade them toward what I believe is the strongest solution, but they're the decision maker.
Early in my career, I would put work in front of clients and assume they'd automatically know which option was strongest.
I learned that's not how it works.
There's a running joke in the freelance design world that if you present three logo options, clients always choose the weakest one.
I've definitely experienced that.
What I learned is that you have to sell your work. You need to explain why you believe something is the best option creatively.
When you do that, it also forces the client to explain why they disagree.
That's where productive collaboration happens.
Q: What's an underrated skill for creatives working with clients?
Learning how to make your second favorite option as good as your first favorite option.
There have been plenty of times where my preferred idea wasn't chosen.
I could get frustrated and think, "Fine, this project isn't going to be good."
Or I can see it as a challenge.
If the client chooses what I think is the weaker option, how do I build a brand around it that makes it as strong as possible?
That's a much healthier mindset.
Earlier in my career, I probably wouldn't have approached it that way. Now I do.
Q: What advice would you give someone pursuing freelance work?
People value your process just as much as your final work.
You can have incredible work, but if you're difficult to work with, don't communicate well, or create a frustrating experience, people won't hire you again.
Make the process as beautiful as the final work.
That's what's going to lead to good things.
A lot of clients have no idea how creative work happens. They're not hiring you just for the final deliverable. They're hiring you because you understand the creative world.
It took me years to realize that.
People are paying for guidance as much as they're paying for the final output.
Guide them through the process. Communicate clearly. Help them understand what's happening and what comes next.
Q: Are there any artists or creatives inspiring you right now?
Nicholas Scarponado is a visual artist whose work I love. He creates editorial and commercial photography that is just stunning.
He's one of those people where you can tell he genuinely loves the work. Every project feels playful and full of curiosity.
I'm also inspired by Mark Maggiori. He creates western style fine art paintings that are incredibly inspiring.
And then there's Pablo Rochat. He's very well known on Instagram.
I don't even know how to categorize his work. He's one of the most creative minds I've seen in a very long time.
Q: When did you realize this could become your career?
It was gradual.
I taught myself design, and in high school family friends started paying me for work I was already doing because I loved it.
Someone would ask me to design a T shirt or a flyer, and suddenly I was getting paid a couple hundred dollars to do something I would have happily done for free.
I still have moments where I pinch myself.
Sometimes I'm designing something really cool and I think, "I would be doing this on a Saturday morning anyway." The fact that I get paid to do it is crazy.
I feel very fortunate.
Q: What would you say to artists who want to make a living from their work?
First, it doesn't have to be all or nothing.
People often think they're either fully committed or not committed at all.
Just create consistently.
Then see if there's a market for what you're making, whether that's fine art, photography, design, or something else.
This might be a hot take, but if you're good enough, there's a market.
So get really good.
The early stage of your career is about improving your craft and becoming the best artist you can be.
Because when the work is truly excellent, people will find value in it.
Key Takeaways
1. Create First. Strategize Later.
Many creatives spend years looking for the perfect roadmap before they begin. The reality is that careers are often built through action. Creating consistently, experimenting, and following curiosity creates momentum that no amount of planning can replace.
2. Taste Is One of Your Greatest Assets
Technical skills can be learned. Software changes. Trends evolve. But developing the ability to recognize quality, originality, and strong creative work is what separates good creatives from great ones.
Refining your taste requires exposure, curiosity, and a willingness to study work outside your comfort zone.
3. Great Creative Work Lives Between Art and Function
Whether you're a designer, photographer, filmmaker, or artist, the challenge is often the same: creating work that is both meaningful and effective.
The strongest creative work doesn't force a choice between beauty and purpose. It achieves both.
4. Your Portfolio Is a Reflection of Your Judgment
A portfolio is not a collection of everything you've ever made.
It's a statement about what you believe your best work is.
Curating carefully demonstrates maturity, confidence, and creative discernment.
5. Communication Is a Creative Skill
Freelancers and creative professionals are not only hired for their craft. They're hired for their ability to guide clients, communicate clearly, solve problems, and build trust.
The experience of working with you matters just as much as the final deliverable.
6. You Don't Have to Choose Between Passion and Sustainability
One of the most powerful ideas from this conversation is that loving your work should not diminish its value.
Creative careers are not hobbies simply because they are enjoyable.
Art, design, storytelling, and creativity shape culture, businesses, and communities. They deserve respect, investment, and fair compensation.
7. The Best Time to Start Is Now
You don't need permission to begin.
Make the work. Improve your craft. Develop your taste. Stay curious.
Creative careers are rarely built overnight, but they are built one project, one experiment, and one opportunity at a time.
📢 Check Out the Full Interview
Watch the full interview with Stephen Pickens below or youtube @ainahcommunity
Explore Stephen's work: stephenpickens.co | IG: stevepickens
