A Hollywood Director on What It's Like to Ditch a Steady Career to Pursue a Dream

"With personal finances, the only person that's going to be disappointed [if I don't follow through] is my future self."

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On the eve of September 11, 2001, Jeff Grace, then a successful advertising executive in his late 20s, was stuck on the tarmac at Newark airport as thunderstorms rolled in. Initially, the pilot announced they’d have to return to the gate. But then the sky briefly cleared up, and they were able to fly out.

He arrived at work the next morning to find 17 messages from his mom. On a TV at his office, Grace watched, shell-shocked, as the second plane hit the World Trade Center.

He remembers feeling overcome in the days that followed with a deep sense of discontent. “If I died on one of those planes for some new business pitch, I wouldn’t feel like I was living a fulfilled life,” he says. “I asked myself whether I was pursuing what I was really meant to do.”

He started taking classes at the famed Second City comedy club and found he had a knack for stand-up. “I’d thought comedy was a crazy lark,” Grace says. “But a guy at Second City told me I could make a career of it.”

When he was offered a big work promotion a couple years later, the uneasiness he’d felt since 9/11 bubbled up. He quit to pursue stand-up comedy, then acting and directing. His first feature film, The Folk Hero & The Funny Guy”—which he wrote and directed, and stars Alex Karpovsky from “Girls” and Melanie Lynskey of “Two and a Half Men”—was just released.

We talked to Grace about navigating the tumultuous entertainment industry, managing unsteady paychecks—and why the Hollywood pressure to overspend doesn’t phase him.

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How did you support yourself after quitting your job?

I’d built up a nice nest egg—enough that I wouldn’t have to work for a year or two if necessary. I maxed out my IRA from day one, even when I was making $26,000. I had also been putting 20 percent into a brokerage account.

Still, I got a job waiting tables. A lot of ‘real’ actors and comedians were waiters and bartenders, so it felt like a legit part of being an artist. The only place that would hire me was the restaurant I used to take clients to on the first floor of my former company’s building. People would run into me and say, ‘Hey Jeff, what account are you on right now?’ And I’d say, `I quit my job a month ago. Would you like me to show you to your table?’

When did your career finally start to take off?

Chicago is an SNL-or-bust town. My only career path was performing at Second City and hoping Lorne Michaels would come to a show and cast me. It’s a low-odds game, so in 2006, I moved to L.A. and booked an episode of ‘Mad Men.’

I was in my early 30s and [felt] way behind the curve. I felt that in order to make it, I had to make my own stuff, so I started an improv group. In 2008, we wrote a viral video called ‘Google Maps that got [millions of] views. Google flew us in and wanted us to make more videos for them.

Our comedy group then moved into feature films. I worked with director Tom Berger to produce two comedies, ‘The Scenesters’ and ‘It’s a Disaster.’ I make enough money commercially to pay the bills, but I still don’t feel like I made it.

How did you pivot your career into directing?

Directing is a jack-of-all-trades job. You have to be good at technical stuff, working with actors, visual aesthetics, sound and music. It’s perfect for me because I love all those things.

I knew that in order to direct, I had to write something. In 2012, two days before the deadline for Sundance, I decided to submit a script [for “The Folk Hero & The Funny Guy”]. It didn’t get into the competition, but a lot of people liked it.

You ultimately raised money to make the movie. How has it been received?

Film festivals really responded to the film. We got into 20, including Tribeca. I got to go to Maui, Napa, Key West and Trevor City, Michigan, where I hung out with Michael Moore. As a first-time filmmaker, I couldn’t have asked for a better experience. Now it will either spark into the zeitgeist, or it will disappear.

Without a predictable income, what’s your strategy for long-term financial planning and sticking to a budget?

I’m trying to figure that out. I can’t take too much out of my checking account because I don’t know how far away I am from zero. I’ve had years of making $100,000 and years where I’ve made $30,000.

I used to be able to make $40,000 to $100,000 for a national TV commercial. Now most commercials run only on cable or the Internet and the pay [can be] as low as $1,250… I recently got a permalance job as a writer and director for Vox Studios, which gives me a steady paycheck that pays the bills. I have $500 a month automatically taken out of my paycheck and deposited into a savings account. Another $200 goes directly into an IRA.

What money lessons did you learn growing up?

I was obsessed with having a savings account as a kid, and was a political economics major in college. I understand economic concepts, but implementing them into my daily life has not proven as easy.

I get engrossed in projects and tend to let bills stack up and ignore where my money goes. With everything else in my life, I have someone to hold me accountable, but with personal finances, the only person that’s going to be disappointed [if I don’t follow through] is my future self.

Do you feel the Hollywood pressure to overspend in order to project a more glamorous lifestyle?

I don’t get impressed by fancy, slick things. I am more attracted to the idea of financial freedom than I am to having a Porsche or mansion.

The career I’m in is about delayed gratification. You have to struggle for years before you see a shred of evidence that you’re on the right path. [Similarly], if you are willing to look at your friends having sushi dinners without too much envy, down the road you might be able to have a career you love and be financially secure.

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