10 Tips from Creatives Offscript Guests on the Path to Success


By Assemble

November 15, 2022

No one knows how hard it is to break into a creative industry more than the people who started as interns, freelancers, or receptionists. Whether it’s saying yes to every opportunity or simply being lucky by being at the right place at the right time, there’s no clear answer for breaking out as a creative. 

In some cases, it can come down to who you know, and whether you’re able to adapt quickly to a situation. Whatever the case, the guests on Assemble’s Creatives Offscript podcast know all too well what it takes to land a role as a top creative. 

With stories told by the people who have started from the bottom and worked their way to the top, we’ll guide you through the career paths of the some of the most talented creatives in their respective industries. Whether you’re an aspiring director or a creative mind looking for a different perspective, this article is a treasure trove of insight pulled from our very own podcast. 

Whatever It Takes

Dreams, no matter how real they feel, are not a guarantee. Even if you work hard and do everything right, it doesn’t mean you’ll land that dream job or work with the ideal clients. But it’s the “whatever-it-takes” attitude of these creators that got them started. A lack of industry connections, prior experience, or money didn’t stop them. Neither did the thought of failing. 

Whether it’s the ability to outwork everyone, including your boss, or living in your car, what matters is getting your foot in the door. And if no one will open the door for you, then you make your own door, as Ryan Connoly did. 

Ryan Connolly, Film Riot, on Following Through 

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From his very first time using a VHS at age eight, Ryan knew filmmaking was his calling. Watching Jurassic Park a few years after only confirmed it. So he went to film school like aspiring filmmakers do, and then he created the Film Riot channel, posting on a weekly basis while having a full-time job. That went on for a year until he decided to quit his job to work on Film Riot full-time. But with no money coming in through the channel, he was ready to live in his car to follow his dreams. Fortunately, a friend offered a place to stay, which fired up Ryan even more, pushing him harder to pay back his friend. 

Ryan has picked up a lot since then, directing 18 short films to hone his craft. Though, it was starting Film Riot that taught him how to be more efficient as a creator. It forced him to be less precious about projects so that he could follow through. 

“Doing Film Riot forced me to make something every single week without fail but at a certain level. It had to be finished. 

So that really taught me a ton and taught me speed. What was interesting is it didn’t let me be precious about anything, and it forced me to be creative quickly. It worked out those muscles to where I got out of my way after a while of getting used to doing that, of being overly precious and not trusting first or second ideas instincts of, ‘Hey, this is funny. Run with it,’ especially when it comes to comedy.”

Matt Alonzo, Director, on Growing as a Creative 


Matt has worked with some of the biggest names in hip hop, making music videos for artists like The Game, Tyler the Creator, Justin Bieber and Lil Wayne. The now-famous director got his start working for a record mogul in LA, getting hired on full-time as soon as he got his film school degree. The money was great, but Matt felt stuck as a creator. Because he worked alone, he had no one to learn from. What he yearned for was growth, mentorship, and the opportunity to do more. So he did the only thing he could do: he left. 

“I just grabbed my backpack and I just walked out. I didn't say anything to anybody. Then my car got repossessed, apartment was gone; Top Ramen. But, I couldn't do it anymore... Just creatively, there was no growth. I was already at the peak. I was already at the highest level I could possibly be at this company. And there was no point for me to stay. So I had to move on.”  

“My biggest, biggest, biggest words of wisdom, advice would be to find somebody, whether it's an internship or mentor, somebody that you can prove yourself to, so that they can open the doors to whatever access they have.”

Ali Brown, Prettybird, on Making Yourself Indispensable 


Though she’s now the president of Prettybird, Ali’s journey to the top was unorthodox. She moved to LA wanting to make documentaries but lacked a film school degree or connections in the industry. That didn’t stop her. Ali sent hundreds of resumes to production companies around the city until she finally got an opportunity to work at Atlas Pictures as a receptionist. While not her dream job, she grabbed the opportunity with both hands, making herself indispensable. 

“I’ve always kind of had the mindset of ‘it’s survivor.’ You have to outwit, outlast, outplay... I felt like I was never the person that could be the best at everything, but I did feel like I could work the hardest.

I just kind of made it my mantra. Every single person that I would pass in an office, I would say, ‘Do you need help? Was there anything I could do?’ If I saw anyone staying late, I would stay late too, whether I needed to or not. I was like, ‘No boss is going to go home before me.’

You have to have a company that’s greater than any single person. But if you can make yourself as indispensable as possible within that ecosystem and have as many skillsets as you possibly can, your chance to have more opportunities just raised.” 

Believing in Yourself

Belief and confidence in yourself and your abilities can be a powerful tool. Because as a lone creator that’s yet to “arrive,” there won’t be people in your corner to hype you up. 

Often, believing in yourself means betting the farm, risking everything you have to make your dream a reality. Daniel McCarthy is the perfect example of this. Where others see risk, Daniel sees success because failure is simply not an option. 

Daniel McCarthy, Musicbed, on Taking Risks

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Is it worse to lose money or miss out on an idea? For Daniel, it was the latter. So with an idea in mind that would revolutionize the music industry, he sold his house and used the profits to start Musicbed. Now, Musicbed is the go-to service for creators, making the act of licensing music a hassle-free experience. But without taking that risk of selling his home — while expecting a second child, mind you — Musicbed might have been someone else’s idea. 

“When you’re an entrepreneur or when you have this gigantic vision, risky feels … it feels more risky to not do it.

I saw what Musicbed could be, I saw the need in the industry, and we probably needed $100,000, but all I could squeeze out was $25,000.

I just knew it was going to work. That sounds weird and cocky, but every entrepreneur, or any of those creatives that have had a job and have jumped into freelance or whatever, it’s like they all know that feeling which is just, ‘dude, I just got to do it. I mean, there’s no plan B.’”

Patrick Holly, Upwork, on Going for it Even When you Lack Experience


Now the Executive Creative Director of Upwork, a global freelancer platform, Patrick Holly has worn many hats as a creative. His first job in PR led to a job as a copywriter, which led to a job at an agency, eventually landing at Apple. When he left Apple, he felt the agency world calling out to him, joining AKQA to work on the Jordan Brand account. All those opportunities opened the door to work with NBA stars like Steph Curry and Giannis Antetokounmpo, where he taught himself photography out of necessity, which led to even more opportunities. But he remains modest.

“We [Giannis Antetokounmpo and I] ended up spending about two weeks or so together in China. And then after that, his agent Alex ended up asking me, ‘Hey, we need to do this campaign for a deodorant company.’ He’s like, ‘Do you wanna shoot it?’ And I was like, ‘I mean, I guess.’ So I ended up basically learning [photography], calling all of my photography friends, being like, ‘can you please teach me how to do, proper lighting and how to do, you know, everything, literally everything?’ And I ended up shooting that campaign for Giannis.

I wouldn’t say I have a background in photography. I’d say that I’ve dipped my toe in, and they’re obviously much more talented folks out there in the world than me, but I just kind of grabbed a paddle and rowed, as they say.”

Carolyn Tisch Blodgett, Peloton, on Being your own Cheerleader 


Before she left Peloton, Carolyn was the Global Head of Marketing. Carolyn took the brand to astronomic heights while at Peloton, increasing brand awareness to over 65% and being a key figure in the company’s eventual IPO. But Carolyn wasn’t sure if she could take on such a large leadership role. It was scary for her at first, though she believed in herself, which she says is one of the biggest lessons she’s learned the hard way. On advocating for yourself, Carolyn says:

“I think there were many times where I just kind of sat back and assumed that someone else was going [advocate] for me, and they often didn’t. 

I often talk to my team about [how] I will never get annoyed with you asking when you’re getting promoted, or I will never get annoyed with you asking why you weren’t included in something.

Whatever your gender is, whatever your background is, you have to advocate for yourself because no one else is going to. That’s something that I’ve learned along the way.”

Davey Spens, EP of Branded Entertainment at Stept Studios, on Knowing your Strengths


Davey Spens has done it all. He’s the type of creative who follows his curiosity and works on whatever project is the most interesting. Davey has worked in radio, television, print, music, and advertising. He’s a multi-hyphenate creator that can’t be put in a box. 

Davey, like the other creators in this list, believes in himself. Still, he has his limits; he’s keenly aware of his strengths and weaknesses. It’s not that he’s not confident, he just knows where he’s the most effective. Because although absolute belief in one’s abilities can be a plus, the downside is that it can lead to hubris; the proverbial flying too close to the sun. 

“I kind of describe myself as an originator. I'm not especially good at detail. I'm more kind of a big picture person. I've always found, people said to me, ‘why weren't you a director?’ And I was like, ‘Well, there's always people who can execute things better than I can.’ 

I always feel like my strength is coming up with ideas, originating new thoughts and doing a million things at once. I love the ability to work over a portfolio of projects at one time and find space between things and come up with new stuff. I’ve always struggled with a job title... Is it Showrunner or Executive Producer? I think it's all of these things. I just love to bring this kind of instinctive energy to projects.”

Managing Success

Reaching the top of your industry, whether that’s a Creative Director or Chief Creative Officer, is a major accomplishment. Once you get there, however, you have to learn how to stay there. For creatives like MediaMonk’s Olivier Koelmij, who founded the company’s West office in LA, that means finding the best people. 

The throughline here is that the top shouldn’t be lonely. A good manager continues to succeed by building up their team. In other words, a high tide raises all boats. 

Olivier Koelemij, MediaMonks on Running a Successful Production Company


With 21 offices around the world, MediaMonks is one of the largest creative production companies. Olivier is the founder and managing director of the West office in Los Angeles. Originally from the Netherlands, he grew the LA office to over 100 employees in five years. He knows what it takes to run a successful production company, which he attributes to: 

“Grit, positivity, energy, and finding the best people that you can find and surrounding yourself with them. I think, in a nutshell, those are the key things.

Passion has always been a driving factor for success. The other thing is looking at who we are, and what we’ve been doing for over two decades. At MediaMonks, we’re makers. We are production-oriented folks, and having that mentality is vital. [So is] being action-oriented, as well as being a team player.”

Margaret Johnson, Goodby Silverstein & Partners, on Finding Talented People

margaret johnson goodby silverstein

Margaret works closely with creative directors to deliver what clients are looking for. She relies on her team to execute the client’s vision, which is why talent is so important. For her, cultivating talented people means encouraging others to acquire different perspectives.

 As a top advertising executive, she wants people who have other interests besides advertisements. On finding and nurturing creative talent, Margaret says: 

“Another thing that I always do is really encourage people to do things outside of advertising because you want to be inspired by art, and shows, and music, and books. That is going to lead you to fresh or more interesting ideas that come from a different perspective.”

Ian Pons Jewell, Director, on Blocking out the Noise


Ian Pons Jewell has a made a name for himself directing commercials, working with some of the biggest brands in the world and being ranked as the number one commercial director two years in a row. The road that led him to this point had detours, but one thing he never stopped doing was creating. 

Ian took on any work early in his career to pay the bills. That meant working weddings and corporate events, which didn’t help get him exposure. So with a need to create something that would put his work in front of as many eyeballs as possible, he began directing music videos. And it worked, eventually landing him a job directing commercials. 

His need to work and create something propelled him forward. His advice to aspiring directors: 

“Don't listen to the noise... It's great when nice things are being said about you, or you're getting recognition in this and that, but you also have to block that out somewhat because, ultimately, that's not going to help you make something.

If you've got this need to make work, then you do that and don't listen to the noise. Block it out, but always be trying to [work on a] project. Have something going, even if it's shooting it.”

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