In this powerful interview, we speak with Desmond Devenish, a multi-disciplinary creative professional whose career spans film, theatre, performance, and personal development.
Known for his work on Eddie & Sunny and his upcoming solo show The Forum, Desmond shares raw and honest insights into the realities of building a career in the creative industry. From failure and fortitude to focus and self-discipline, his story offers invaluable lessons for creatives navigating their own paths in the arts.
The Reality of a Creative Career: Growth, Sacrifice, and Self-Belief
My career path has been the single hardest challenge of my life. Nothing has come easy—I wish I could say otherwise. I’ve had fleeting strokes of luck, but nothing lasting has come without grit, pain, suffering, triumph, failure, darkness, power, inspiration, support, love, help, the talent of others, the influence of my predecessors, and a boatload of educated risk.
I explore much of this in my book Freedom From Failure. My courses and audio sessions on Insight Timer also dive into these experiences in depth. Find a system that works. A good, reliable system. Be organized. Be structured. So much of this game is in the doing. If you’re not doing it, then you’re just thinking about it.
“My career path has been the single hardest challenge of my life. Nothing has come easy—I wish I could say otherwise… grit, pain, suffering, triumph, failure, darkness, power, inspiration, support, love, help, the talent of others, the influence of my predecessors, and a boatload of educated risks.”
Be active. Take incremental steps. Don’t worry about others—they’re likely doing the same as you, or less, or more. But it’s immaterial. Have a roadmap. An outline. A game plan. A task manager. All of it. You have to treat it like a business—because it is.
You need to be the CEO of that business, knowing everything there is to know about how to get the best performance out of your employees. If you’re the only employee, then by all means, you’d better be giving yourself the best working environment possible.
Why the Creative Industry Chose Me
This career chose me. I’ve always wanted to be involved in the creative arts because it makes me feel more alive, more aware, more hungry, and ultimately, happier.
Lessons from Failure, Surrender, and Patience
Failure
Failure has taught me everything I know—far more than success ever could. I’ve
experienced significantly more failures than wins, and I don’t get caught up in the semantics of those words anymore. To me, they’ve become interchangeable. Failure is success. They feed each other. They’re symbiotic. If you’re not failing constantly, then you’re probably not doing half as much as you should be. That’s just my two cents. Every meaningful leap I’ve taken has been on the back of something that didn’t work out—until it did.
Surrender
Surrender is how you learn to play ball with the universe. It’s not weakness—it’s
intelligence. It’s humility. It’s the path of the warrior. Learning to surrender helped me melt away inner resistance and clean my mind out like a temple. That clarity made my thinking faster, my actions sharper. The more I surrendered to what is, the more power I found in what could be.
Patience
This one hit me hard. I lost it all once because I was recklessly ambitious—burning out, overreaching, rushing the process. That lesson humbled me. It made me appreciate the sniper, the cheetah, the chameleon—all the beings in nature that are willing to wait like a rock… even while having a Lamborghini engine under the hood. That’s the kind of patience I had to learn—the kind that’s calm, coiled, and devastatingly precise when the time is right.
Investing in Yourself: The Cost of Creative Commitment
Yes. Looking back, instead of buying a home, I would have used that money to make films. I did end up selling the home to finance my first film, but had I done this from the start, I could’ve easily made two more films.
Anyone who tells you not to use your own money for your career has likely never
rolled the dice on themselves. You can wait for permission, or you can take the reins and do it yourself. You only get so many shots at this, and life moves faster than you think. I will never regret spending money on my career—never. No matter how much I’ve lost or how much I’ve gained. If I expect anyone to believe in me and take a chance on me, I have to be the first person to exercise that belief.
And I’m all in. I’ve put everything on the line. Whether you take out a loan, borrow
money, inherit funds, earn and pay back, use credit, or co-finance, you’ll have to
leverage some form of currency—whether it’s money, reputation, or something else —as collateral for the risk you’re taking.
“Looking back, instead of buying a home, I would have used that money to make films… I’ve made money, bankrupted myself, made money again—I’ve done whatever it takes to make my art.”
If I have it to spend, I won’t hesitate. I’ve made money, bankrupted myself, made money again—I’ve done whatever it takes to make my art. That’s my responsibility. If you’re not doing everything imaginable to realize your dreams and live the life you preach, then you have no place to complain.
Complaining is useless anyway—it drains your energy. But more importantly, like any journey, there will be sacrifices you’ll need to make to reach your goals. It might be a relationship, money, a house, or something you need in the moment. To move forward, you’ll have to let go of something important. This isn’t a fairytale, it’s the reality of growth and ambition.
In those moments, it will be up to you to reconcile how much that means to you. And honestly, at that point, it won’t even be about the art. It will be something much deeper, something that resonates with your soul. Your spirit will try to dig into depths you never knew were there. That’s how up-leveling works. It’s ugly, messy, confusing, tiring, lonely, and at times, unbearable. But those are the hard lessons that show you, without a doubt, who you are and what you’re made of.
So yeah, if I could go back, I would have spent barely any of the money I had on
comfort or security, and instead invested every penny in my career. That’s not for everyone, but for me, that’s my story. My hindsight is crystal clear.
Creative Discipline: A Day in the Life of a Multi-Hyphenate Artist
A typical working day varies, but first, I need to feel limber and mentally clear. That starts with a healthy breakfast, a juice, a swim, run, stretching, meditation, and outlining the day ahead.
Next, I task-manage—refer to the calendar, and keep calls to a minimum or schedule them for later in the afternoon, as my sweet spot for work is in the early morning. After exercise or a nap, I can hit another flow. If I’m on a roll, I can churn out four great work sessions of about two hours each. Anything after that feels like a stretch.
“A typical working day varies, but first, I need to feel limber and mentally clear… I can churn out four great work sessions of about two hours each.”
I can work seated for ten to fourteen hours, but I’ll usually pay for it the next day. If I can knock off anywhere from two to four major tasks off the checklist, that’s a
successful day for me. Prioritizing and managing time is critical so I don’t get bogged down by too much admin, research, or smaller minutiae. It’s easy to justify getting stuck in these, but they can quickly turn into unnecessary distractions.
I also listen to good music—Brain.FM or some playlists by Spotify. Even during
breaks and lunch, I strive to keep my focus sharp so I can jump back into work with a clearer mind. It’s not just about the time you spend working; if you really want to maintain fanatical focus, you need to be disciplined during your breaks as well. I actually have a course called Fanatical Focus on Insight Timer if you want to dive deeper into this approach.
Overcoming Challenges in the Creative Industry
The most challenging aspect of my role is that you have to be your own
disciplinarian. You can’t rest on your laurels, and you need to be an extremely
focused manager of time. This is at the heart of productivity and results. The ability to switch off devices and digital distractions, and get serious, is key.
It’s also about embracing the things that almost no one cares about when you tell them that’s what you’ve been doing. You have to learn how to be somewhat of a lone wolf, even if you have a decent support system. You can be your best ally or your worst enemy. It all comes down to how you direct yourself and hone your craft.
“You can be your best ally or your worst enemy. It all comes down to how you direct yourself and hone your craft.”
One thing I can absolutely testify to is that if you put in a sufficient amount of time, you will start to see improvements. The tricky part is, you just don’t know when that will happen. You have to work for the love of the craft, not for what the craft will do for you. This has been my mistake for years until I made a major shift and became a true devotee of the art itself. When you can approach it charitably and systematically, that’s when you start finding your edge and developing that almost machine-like, relentless warrior spirit.
Creative Projects That Define a Career
All of my projects have been favorites for different reasons. My last film, Eddie &
Sunny, was particularly rewarding because I had the opportunity to work with
exceptionally talented people and fulfill my promise to those who believed in the
project to get it made.
“My last film, Eddie & Sunny, was particularly rewarding… My latest project, a solo show called The Forum, marks my return to the stage.”
My latest project, a solo show called The Forum, marks my return to the stage. I’m excited about this one, especially the chance to play multiple characters in a piece that’s deeply personal to me.
Setting Trends, Not Following Them
Instead of chasing trends or following other people’s success paths, I believe in
being the change and setting new trends. Express what calls to you and ignites your passion. When it speaks to your soul, it will naturally be raw, new, and innovative.
Words of Wisdom for Aspiring Creatives
Everything you do should be the best thing you’ve ever done.
Understand that this is a life contract. Be prepared for both the highs and the lows that come with it if you truly want to engage in this field.
Describe your career in 5 words!
An indefatigable, relentless mountain climb.
Biography
Desmond Devenish is a multi-disciplined Director and Writer | Film and Theatre
Producer | Performer | Speaker | Teacher | Fortitude Facilitator. Known for
Eddie and Sunny and Misfortune, he began performing on Broadway and will be
debuting his solo show The Forum at the 2025 Edinburgh Festival Fringe.
