In the sleek corridors of the creative industry, where innovation meets inclusion, Dionna Marie Dorsey has mastered the art of transformation. As the magnetic force behind The Creative Ladder—a nonprofit she orchestrated alongside Hollywood heavyweight Ryan Reynolds—Dorsey isn’t just opening doors; she’s architecturing entirely new buildings.
Her evolution from a fashion designer navigating the 2008 financial crash to a powerhouse entrepreneur redefining diversity in creative spaces reads like a masterclass in resilience.
With District of Clothing, her zeitgeist-capturing lifestyle brand, she turned apparel into armor for social change, creating pieces that spoke truth to power long before it became fashionable. But it’s through Creative Ladder that Dorsey’s vision truly soars—a vision where young creatives from underrepresented backgrounds don’t just get a seat at the table, they help design the entire dining room.
In this candid conversation, she unfolds the layers of her journey, revealing how she’s transforming the creative industry’s landscape, one rising leader at a time, while proving that sometimes the most powerful acts of revolution start with a simple coloring book and end up reshaping entire industries.
Tell us about your journey from being a business owner and designer to co-founder of Creative Ladder
In 2008, I was living and working in New York City as a fashion designer. The economy collapsed. The fashion industry was the first to go. I was blessed to have a home to come home to in Washington, DC, which happened to be the only place in the country that wasn’t suffering economically.
I assumed I’d be able to get a great job in DC. Wasn’t necessarily the case. After a couple of months of searching, couldn’t get hired, hired myself, I started Deanna Dorsey Design, picked up a couple of clients. My prime client went on a spending freeze, at which point I realized that I needed multiple streams of income.
That led me toward creating District of Clothing in 2014. District of Clothing was the little engine that could and did. 2020 was such a challenging horrific hard year for humanity, but it was actually my best year as an entrepreneur because the messaging that I was using and the tool that I was creating through District Clothing met the moment.
We had been telling the truth that we knew to be true long before then: Stand with black women, Trust black women, 51 for DC for statehood, Do not touch the artwork. All of the messaging that we were sharing on our apparel were truths that we had known to be true for forever and it was positioned well to meet the challenges that came in 2020.
How did Creative Ladder come to be?
My co-founder, Ryan Reynolds, was the keynote speaker for Ad Weeks Brand Week. He was being interviewed by my second co-founder, David Greiner, and the conversation was, how can we take some of the work that Ryan had been doing with inclusion and belonging in entertainment with his social impact organization which is called Group Effort Initiative, GEI.
How can we take that and implement that in advertising and marketing? It was sort of like, oh, this is an idea! Because of the work from District of Clothing and Deanna Dorsey Design, they contacted me within a couple of weeks of that in 2020, and before I knew it, we started. We had our very first meeting the first week of December 2020.
Never would have imagined that the pandemic would have lasted as long as it would have never could have imagined that the IRS would be so backed up. It wasn’t until June of 2022 that we actually launched and that was in Cannes France at the Cannes Lions Creative Festival.
What do you consider your superpower, and how does it manifest in your work?
I think one of my superpowers is understanding my purpose, and also understanding that that might change or that it might evolve. Another superpower of mine is relating to people and understanding how to relate to people. Because of those two things connecting them with my creativity helps me to create timeless, memorable, easy to relate to things.
My goal is always to tell the truth as I know it to be, and to share that with the world, and to hope that that progresses us to move forward. Another superpower of mine is community building. I do a pretty good job of bringing people together.
What inspired you to launch Creative Ladder, and how is it making an impact?
I’m 44, and I really have never had a mentor. I’ve always had business adjacent mentors. I’ve had people said, Oh, I can help you with this, but I don’t know anything about that. When the idea was first brought to me, it was just sort of like duh. As creatives, oftentimes we’re creating our own pathway forward, and it doesn’t look like what’s already been there, because it’s in our head, and it’s coming from our spirits.
It felt like it was the ability to bring all of the work that I had been doing over the past 20 years together, and putting that into pouring into this next generation.
Can you tell us about the impact Creative Ladder is having on young creatives?
I was speaking with one of our rising leaders today. That’s what we call the young people in our community. And they’re generally creatives from underrepresented backgrounds, black, brown, immigrant, neurodivergent, queer folks, with visible and invisible disabilities, as well as those who have been affected by incarceration or addiction in their childhoods.
She said, “I wouldn’t even have this job if it weren’t for the Creative Ladder.” It hits you. Understanding that she has people, peers in her age group to connect with, to discuss the challenges that she’s exploring, and then that she still can rely on the Creative Ladder as an organization to support her right now. It is not me, by any means.
I have an amazing team, a teeny, tiny, mighty team, and the power of my team is really, truly just a reflection of the amazing incredibly talented folks that we are supporting. They have the ability. They will be the next leaders of this of the creative industries and advertising and marketing.
They just don’t often have anyone that looks like them or understands their backgrounds or their experiences on their zoom calls or in their offices. Many of them have never been in offices full time before. Many of our folks maybe started working just before the pandemic, or they got their first job just toward the end of 2019, beginning of 2020.
The return to the office is very, very challenging for some of our folks. And they’re also returning to an office during a very challenging time.
What programs does Creative Ladder offer?
We’ve affected and touched over 7,500 people in the country, and sometimes even beyond. Our most notable programs would probably be our leadership boot camps. What’s special and unique to them is, once you walk into the room everyone looks like you or understand your background, or where you’re coming from.
You don’t feel like you’re the only one. It’s the first time many of our cohort members are coming into a conference of 100 to 150, and they’re not in the minority. They immediately feel supported, seen, heard, valued, and we do everything that we can to create that to be both a brave and a safe space for them.
Those have occurred thus far in New York City, Los Angeles, Chicago, Washington, DC, and Atlanta. We also have summits, which are just sort of a similar version to the boot camp. The boot camp has various different workshops throughout the day for people to attend, based on their skill set, and where they are in their career.
Our summits have more panel conversations to help open up the conversation, so that we’re hearing feedback on the floor immediately, and people are able to get more of their questions answered.
What other programs does Creative Ladder offer?
We have RLA, which is our Rising Leader Academy program. That’s a 6 month virtual, incredibly intensive program to help folks in that 5 to 6 year range, where they’re getting ready to become managers, where they’re learning how to lead themselves, understand more about their leadership skills, the things that they need to hone in and to help them sort of continue to climb the creative ladder.
We also have conference cohorts where we take cohorts to the biggest and most impactful conferences in the country, so that might be Adobe Max or the possible, even in Miami can create a festival, Can lines excuse me, create a festival, and can France.
We take them to these conferences, free of charge and pay for their travel and lodging, and then we connect them with the keynote speakers who were coming off the stage so they can meet with them. Perhaps they’ll have lunch with them, but it’s just It feels a lot more tangible. You see that oh, sure, they were just on that keynote main stage, but they’re standing right here in front of me, and they’re human, too.
There’s not much difference between them and me. It’s just some years and we try to provide them with very unique experiences and having them sit in some meetings and conversations that they wouldn’t usually have access to otherwise and connect with folks just to help them.
It’s really just access and opportunity. Once they feel seen, heard, and valued, it sort of changes. You can see the difference from the first night of the conference to the last night of the conference.
How do you find inspiration in chaotic and uncertain times?
For me, my inspiration and my grounding comes from my faith and my family. I really lean into the quote by Jimmy Baldwin, James Baldwin, that as an artist my role is the same as the lover, and it is to help.
The truth is, I know it to be true to share that with you. I came across that quote some time ago, and it just struck me in the deepest way, and it has been very much a guiding principle for me in terms of my creativity. Anything that I’ve done with District of Clothing, anything that I did with Deanna Dorsey Design, what we’re doing here now with Creative Ladder.
It’s really helping others to see what we know to be true, what we hold and value dearly. I do very strongly believe that creatives are the key to unlocking many of the world’s issues because we are innovative and we’re thinking out of the box. And we’re not necessarily rule followers. We have the ability to color outside the lines and create new lines which help us continue to move forward.
What’s your advice for creatives navigating today’s challenges?
Just be encouraged. I know it was really dark and really challenging right now. I think it’s really important that we sort of do whatever we can to remove the distractions.
There’s lots of distractions that are happening, take the time that you can to remove the distractions so that you can focus in and hone in on who you are and what you need right now and then bring those distractions back in and move forward through them. So just be encouraged. I know it’s really hard right now, but we’re gonna be alright.
Where can people find you and learn more about Creative Ladder?
On most socials you can find me at Deanna Dorsey. Definitely connect with me on LinkedIn. Creative Ladder is at creativeladder.org, and we are @creativeladder.org on Instagram and my website is dionnadorsey.com.
