In the future when we all look back at our careers, we probably won’t regret taking too many risks.
On the contrary, most of us are experts at playing it safe.
Why are we so chronically cautious? For those of us with creative businesses, getting in a rut can be a fast-track to failure.
Calculated risk-taking, however, can help us gain new skills, land new clients, and grow personally and professionally.
I’m not talking about impulsive or self-sabotaging risk-taking, where you bet it all on one roll of the dice. I’m talking about the calculated kind—using intellect, effort, and resourcefulness—to take your creative business to the next level. It’s not easy, but it’s worth it!
In my experience running my own small creative business (we make videos for international development organizations), here are 7 of my best calculated risks and what I learned along the way.
1. Go for it!
The year was 2000, and barely a year out of my Master’s program, I was a writer for the World Bank Group’s external website and internal online daily, “Today.” It was a good job in the field of economic development, exactly where I thought I wanted to be. I liked interviewing the diverse staff and writing about something different every day. But there was a glass ceiling: after a while, I wasn’t doing anything new. And I had a nagging feeling that what I really needed to be doing was making documentary films. Yet I had no relevant education, experience, or mentors.
Against all good judgment, I struck out on my own. Thanks to the reputation I’d built as a quality writer, I landed several contracts right away. The lesson here is to listen to yourself. When your inner voice starts telling you that you’re settling, don’t settle. If that means you need to become your own boss, then make it happen. It’ll be easier if you’re at a point in your life, like I was, without children or a mortgage. If you fail, find a way to fail forward.
2. You have to give to get
During the summer of 2001, still hungry to learn more about documentary, I attended the DoubleTake Documentary Institute held at Hampshire College. Ken Burns, Fred Wiseman, Ira Glass, and others held master classes on documentary and storytelling across disciplines. It was inspiring, and made me want to make videos more than ever! Meanwhile, as a freelancer, I was making progress, doing writing, web, and multimedia jobs—but not any video yet. Something had to give.
At the time, my friend Darin ran a nonprofit benefitting D.C. schoolchildren. What if I made him a free video? Sure, he said (surprise!). Suddenly I had to figure it out. Yikes! I had no idea how to shoot, direct, or edit. So I hired a talented shooter and editor, and I did the rest. Somehow it worked! The Heads Up video turned out great, Darin was happy, and I had the beginnings of a portfolio. During the next year, I repeated the “Free Strategy” several times. It was a pretty bad business strategy: I was robbing Peter (my freelance business) to pay Paul (the free videos). But this was the start of an education in video production I never had. Within a year, I had a solid portfolio.
The lesson: I knew a couple things about myself. First, I didn’t want to go back to school to learn video. Second, I didn’t want to work as an intern at a video production company to gain skills and knowledge. My “Free Strategy” gave me a real-world situation where I had the incentive to make quality videos for real clients on a real schedule. I gave my time and some free videos. But I got much more. I learned a lot, and fast.
3. Fake it ‘til you make it – just surround yourself with creative talent
By the end of 2003, I was getting pretty good making short videos for nonprofits, but I’d never done anything too complex. When I bid for a campaign of videos in Tokyo, I didn’t think I had a chance. I simply didn’t have the experience or portfolio.
I won the contract—undoubtedly because I underbid significantly. Initially, I was in over my head. Pre-production was exceedingly tough. Fortunately, I hired my former schoolmate Kayo to serve as Tokyo-based Unit Producer: she also co-wrote the script, translated, and was a total rock star. We engaged a local crew and used 10 actors, and ultimately spent an exhilarating week at some of Tokyo’s most beautiful locations. Less than four years after starting my company, I pulled off a complex international bilingual production. The video even won an award.
The lesson: Most importantly, I continued my education. The talented Cinematographer Stefan Weisen came to Tokyo with me and essentially co-directed. And eons before he launched his uber-successful creative agency, Gigawatt Group, Mark Devito edited. Two super creative, talented partners. This project was really a watershed point for me. Before, I was doing small stuff around D.C. After, I believed I could pull off any video production anywhere in the world. The lesson: you really can “fake it ‘til you make it” if you’re prepared to surround yourself with talented people and work your tail off.
4. To be uniquely creative, use your special networks (and a credit card)
The year was 2006. I was getting adept at writing, directing, and producing all kinds of corporate videos, but I still hadn’t made a long-form documentary. Looking around for a subject, I kept thinking of my experience living in Africa. My idea: make a film about the most extreme running race in the world—the marathon-distance trail run up a live volcano in Buea, Cameroon. The problem was I just didn’t have the budget. What to do?
I remember sitting down to lunch in January 2006 with an old friend, Paul McKellips, who’s made his share of indie features. He saw me waffling, and gave me a good motivational drubbing. His message: you have a great story. Now go to Africa and tell it! The next month, I put everything on my Visa card and flew with Dan Evans and Ryan Hill to Cameroon. I relied on Ryan’s experience with Nat Geo, Dan’s resourcefulness, and my network—which was key. My best Cameroonian friend, Jean Paul Fosso, was working with the Cameroonian Sports Ministry, so I had full access, and even ended up shooting from a helicopter during the race (crazy scary!). Another close friend, Louise Mbango, connected me to Moki Charles, a producer for Cameroonian Radio and Television. He took a week off from his day job to be our Unit Producer and hired seven additional shooters to film on race day. I directed the 10-day shoot. Then Dan and I scripted and edited for a year, working in between paying gigs. Awesome!
Ultimately, Volcanic Sprint won the non-fiction category at the Big Bear Lake Film Festival and was an official selection of the Jackson Hole Film Festival, Hot Springs Documentary Film Festival, and Boulder Adventure Film Festival. It was distributed globally by American Public TV Worldwide. You can even watch it on Amazon and iTunes today (and it has an 8.8 rating on IMDB). I earned back my investment and then some.
To tell this unique story, I needed my friends to give me rare access. My hook-up with the Mt. Cameroon Race of Hope was one-in-a-million. The lesson: look again at your own networks. They may inspire more creativity than you give them credit for!
5. Target your weaknesses
The year was 2008. My business was taking off. I had hired Dan full-time and we were scrambling to finish a lot of corporate videos. We started our second documentary, Shattered Sky, which contrasted America’s leadership preserving the ozone layer with inertia in the face of climate change. The problem was, from my standpoint, Dan was having all the fun, shooting and editing. I was the one wearing the monkey suit, writing proposals, going to meetings, producing, bent over my computer. I had the itch to be more creative. I wanted to shoot.
Sure, I’d been shooting for years, first with the Panasonic DVX100 before HD was a thing. But I wasn’t proficient yet. So I started taking the Sony EX1 home to practice at night and on weekends. It didn’t come naturally for me. But I kept at it, and gradually improved. So when Dan moved to Portland to start his own production company, I had the confidence and ability to do all the shooting myself. Since then, I’ve spent thousands of hours behind the lens, first with the Canon 5D, then the Canon C100, the C300, and now on my Sony FS7, which for my money is the best documentary camera value out there.
The lesson: shooting didn’t come nearly as easy to me as writing and producing. But I worked really hard. I targeted my weakness.
6. Forge unorthodox partnerships
The year was 2013. The previous three years had been the most fulfilling in my professional life. I wrapped Shattered Sky, and then shot, wrote, and edited 10 episodes of a documentary TV series called Bench to Bedside. Less than three years after learning Final Cut Pro, I was nominated for an Emmy award for editing. I was doing every aspect of filmmaking and loving it!
Meanwhile, I was directing a commercial shoot one day working with DP Doug Gritzmacher. It was intense: 20 actors, 9 scenes, a big crew. It was approaching midnight and we were about to get kicked out of our location (Frederick Memorial Hospital). I was tired and couldn’t visualize the last scene the way I’d scripted it. There was no way we were going to finish in time and I was stressed out! Fortunately, Doug changed it up on the fly, basically directed the scene for me, and saved the production! The next month, he hired me to direct some interviews for a DirecTV documentary, MLK: More than a Dream—and I got to interview Colin Powell, James Brown, and the incomparable John Lewis. Month after month, I hired him or he hired me for various projects. But along the way, he started packing—to move to Denver!
Doug’s choice was an odd one. He’d spent 15 years building a clientele in D.C. and he was leaving now? (He wanted to settle in a place where he could ski, hike, and mountain bike in his backyard, which I couldn’t blame him for!) So in part to cement an emerging partnership, we launched Z-Channel Films, a full-service video production company. We really had no idea what our business plan was, but it felt like the right thing to do. It was certainly unorthodox timing. I helped Doug pack the U-Haul the same day our website went live.
Ultimately, Doug and I were rewarded for our efforts. Z-Channel won a Telly Award for one of our first collaborations, Saving Sally (the one where he saved the shoot). Then when AARP hired me to direct a couple projects in California, I had them fly Doug out from Denver. Those two short films – Skateboard Mom and then Super Humans Unmasked—surpassed 5 million views on Facebook! And then the incredible happened. Z-Channel Films was the first production company DirecTV chose to work with to make a documentary out-of-house. On Veteran’s Day 2015, Jobs for G.I.s premiered nationally on DirecTV’s Audience Channel.
The lesson I learned: be open to new partnerships, even when it doesn’t seem that logical at first.
7. A.B.L.: Always be learning
The year was 2013 and drones were in the news. When DJI released their first Phantom copter, I was fascinated. Although I had zero experience flying, I immediately bought the first-generation model and started practicing. But the first six times I tried to fly it, I crashed. But I kept at it, and my (empty) neighborhood soccer field became my practice grounds. Gradually I got proficient. The problem was, the Phantom didn’t have a gimbal. So when I MacGyvered a GoPro on it, the footage was shaky. Try as I might, I couldn’t use the footage.
Fast forward a year. A local production company hired me to field direct and run second camera for a new Red Bull Channel series. The night before my first gig they called: “Can you fly a copter?” Sure, I bluffed, even though it’d been a year. I arrived in Key West to find the audio grip holding a brand-new Phantom 2+ still in the box. I put it all together—on the boat!—as we motored to our location. I knew the Phantom 2+ had a gimbal and a pretty good camera. But my stomach was churning: would this thing even fly? If so, would I crash it in the Atlantic? Fortunately, on that first harrowing mission, I barely avoided baptizing the copter: Here’s a YouTube clip. Red Bull liked the footage so much that in subsequent months, I flew the Phantom in Portland and Jamestown. Here’s my blog about the experience. These days, I fly the Phantom 4 all the time. It’s a great tool for cinematic aerials: check out what I did last month in in Dakar, Senegal.
The lesson: Always be learning. We may not be able to use our knowledge right away. But in this business, learning is the best calculated risk you can take!
Also published on Medium.