Chicagoans in search of career satisfaction trade cushy corporate jobs for more meaningful second careers

by Lisa Davis



photo by Daniel Peter

Think you can’t have a second career in a down economy? Think again. Not only can you make it happen, you can do it in a variety of ways, with major leaps and even small steps. “Despite this down economy, I am working with clients who are leaving their traditional careers for more fulfilling and non-traditional work on a self-employment level,” says Lauren Milligan, a career advancement specialist with Chicago’s ResuMAYDAY (resumayday.com). “I have a woman who is a senior-level IT manager who wants to start her own Reiki studio. I also have a man who is a sales rep but wants to go into non-secular ministry.”

Milligan says one of the biggest challenges her clients face is giving up their comfy corporate perks for what at first can seem like the unknown. Her advice? Take baby steps by starting a dream job part time while still bringing in money from a main job. Alexandra Levit, Chicago-based author of How’d You Score That Gig?, also recommends volunteering or taking an adult education workshop to see if the second career is the right fit.

Chris McAuliffe, a senior account executive for a Chicago-based wholesale mortgage-lending company, had no reservations about what he wanted his second career to be: real estate development. Working full-time, he started a real estate development LLC on the side as a way to create a financial cushion in this down economy and as a way to launch something he ultimately wants to do full-time. McAuliffe’s secret for success with juggling two jobs? Staying organized and being committed, as he often works weekends rehabbing his properties. “It also helps to partner with someone you trust and develop a thorough business plan,” McAuliffe says. “And do your homework. I researched banks for funding and found one (Shore Bank) that is geared toward small developers.”

Starting a second career can come with a price tag. McAuliffe’s initial investment to start his real estate development LLC was around $500. For others, such as Lauren Johnson, a manager for a marketing company in Chicago, the bill can be much higher. The tab to kick-start a career as a Pilates instructor? Closer to $5,000.

Because of the hefty start-up cost, Johnson is keeping her 9-to-5 gig to help fund her training, which she does at night and on the weekends. But the financial pay-off is worth it: Liv Berger, owner of Body Endeavors in Lincoln Park, where Johnson is doing her Pilates apprenticeship, estimates that income for instructors teaching full time can be as much as $60,000 a year. For Johnson, it’s more than the money. “Teaching Pilates is about creating a lifestyle and doing something I am passionate about instead of just going to work everyday,” she says.

You can also take a major leap and buy the business you want as a second career. Marcia Hemphill, a former sales associate for Chicago investment firm Oppenheimer & Co. Inc., bought her dream company in early 2008: An Urban Affair (anurbanaffair.net), an event and wedding planning company. “With the economy tightening and my job not lending itself to growth, it was the right time to move into wedding planning, which has long-term potential for growth and happiness,” says Hemphill, who worked at An Urban Affair to learn the ins and outs of her new industry before buying the company.

For Hemphill, the major pro to starting a second career was a fresh start. The defining con was having to prove herself to new clients—even with her business credentials from corporate America. She is currently making less money than when she worked for Oppenheimer, but she is seeing the fruits of her labor, which she never saw working for someone else. “I am on track to well exceed my previous income,” she says. “I just have to look a little into the horizon.”