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Published: Feb 15, 2018 6 min read
Darryl Armistead preforming stand-up comedy at Finley Dunne’s Tavern, Chicago, IL.
Darryl Armistead preforming stand-up comedy at Finley Dunne’s Tavern, Chicago, IL.
Photograph by Saverio Truglia

Many musicians take side jobs for additional, steady income. Darryl Armistead did the opposite.

A life-long piano player, Armistead took a job at an insurance firm right out of college. His parents had nurtured his love of music but discouraged him from making a career of it, since you couldn’t count on making enough to cover rent. So over the next several decades, he supplemented his steady day job with music gigs on the side.

These performances nurtured his passion and boosted his income, all while laying the groundwork for a retirement where he could focus on music full-time. Now 68 and retired for 11 years, Armistead, of Hawthorn Woods, Ill., performs up to four nights a week, playing piano and singing, at venues around Chicago.

“Plan your working career to make your retirement viable,” he says. “As a teenager, I formulated a plan to find a good job after graduating college, save as much money as I could and retire early to only do music.”

Here’s how he did it.

Don't Sweat the Dips

When Armistead was 57, his employer, Allstate, offered a voluntary retirement option to certain workers with more than 30 years of service.

He jumped at the offer, calculating the retirement bonus would cover his living expenses for the next two and a half years, until he could tap his Individual Retirement Account (IRA) without an early-withdrawal penalty. In addition to the retirement bonus, Armistead opted to receive his pension as a lump sump, which he rolled over into his 401(k).

That was in 2006. When his portfolio plunged two years later during the Great Recession, Armistead didn’t sweat it. Living off his cash bonus, he could afford to leave his retirement portfolio where it was and give it time to recover.

Allstate also provided group retiree medical coverage, which helped control his medical costs until he went on Medicare at age 65.

While Allstate gave him a generous send-off, Armistead had done plenty of his own work to prepare financially for early retirement. Married with no children, he had begun maxing out his 401(k) early in his career. Between his own savings and the lump-sum pension, his retirement nest egg was in the low seven figures when he stopped work. These days, he supplements his savings with roughly $50,000 a year in gross income from his performing career — an impressive figure any working musician would be happy with.

Darryl Armistead at Finley Dunne’s Tavern, Chicago, IL.
Photograph by Saverio Truglia

Network, network, network

Armistead’s musical sideline largely stopped about 10 years before retirement, when he moved from his native Indiana to Illinois to take a position with the home office that required a lot of travel.

That meant when it came time to retire and focus on music full-time, he needed to rebuild his musical Rolodex. He did that by going out to see shows and chatting up the musicians during the break times. He also connected with prospective band mates on Bandmix.com, a web site he still uses to find collaborators.

Armistead plays regular gigs, both solo and with different bands, at restaurants and nightclubs, and also does one-off gigs at weddings, corporate events and festivals. He has a wide repertoire, but his favorite song is "When I Fall in Love" by Victor Young, as performed by Nat King Cole. "At heart, I am very much a sentimentalist," he says.

Armistead passes himself off as 58 in his online posts and auditions. “I look younger,” he says. He dyes his hair and maintains a trim physique. Once other musicians have heard him and like his work, he lets them know his true age. “I just can’t make that initial connection at 68,” he says.

He and his wife, Mel, plan to put their home on the market this summer. They might relocate out of the area. Armistead isn’t daunted by the prospect of networking from scratch. “I can probably regain my current activity within six months anywhere in the world.”

Continuing Challenging Yourself

Last year, one of Armistead’s friends reminded him of a promise he had long forgotten: to try comedy in retirement. “I felt like I had to make good on that,” he says. So he enrolled in a standup comedy course at Chicago’s The Second City, a breeding ground to talent such as Tina Fey, Stephen Colbert, and Amy Poehler. His homework? Doing stand-up around town.

Armistead wasn’t scared. “I’ve been in front of people my whole life,” he says. The son of a Baptist preacher, Armistead says he gave his first sermon before the congregation at age three. He now picks up the occasional paid gig as a comic.

What’s more, he’s used to trying new things. At age 50, he took up the guitar and says he stopped watching television to make the time. To this day he hasn’t turned it back on.

As successful as his second act has been, Armistead still has some stretch goals. He’d like to let the late-night Jimmys—Kimmel and Fallon—know that they can book him any time.

“What I’d hope to be lucky to do is have one of these things hit,” he says, “and I’d find some fame or notoriety.”