How to Find Success in Your Second Career

When she was laid off at the age of 50, Jacqueline Brown found inspiration in a new job field. Here, she shares her story—and experts offer five tips on finding your own second career.


When Jacqueline Brown was asked to come in for a meeting on a vacation day she knew something was amiss.

Layoffs had become a regular occurrence at the educational publisher where she’d been employed for five years, and most of the employees had become quite acquainted with the dismissal process. Brown’s meeting request had all the familiar characteristics: it was flagged as mandatory, had a strange title—and she was the only employee invited.

For Brown, the tip-off was enough to allow her to clear out her office in advance—which turned out to be a small victory. After the poorly disguised “meeting” was over, she avoided the humiliation of waiting on security guards to box up her possessions. Her preparedness, however, would end there. “It was heartbreaking losing my job,” she says. “It took awhile just to heal from that.”

Not only had the 50-year-old Brown enjoyed her time with the company, but work had become more than just a job for her: She’d made new friends, attended the wedding of a colleague and built her life around her career. Most disheartening though was how hard she’d worked and how little that had meant in the end. “Sometimes you’d be up until 2 a.m. working for them,” Brown recalls. “You give a lot to your job and yet there’s not really any loyalty.”

Her initial plan was to move away from her area of expertise entirely. But Lee Weisser, a career councillor at Careers By Design in Toronto, says changes on the job front don’t have to be so drastic. “The reality is that many people are able to use the skills and strengths they’ve developed over the years and tweak those into something different,” she says. When Brown’s severance package allowed for some time to think things through, she did exactly that. Combining her expertise in publishing with her love of writing, she interned at a literary agency and soon obtained a position coaching writers.

For Brown, making use of her existing skills was also about proving something to herself. Despite her best efforts, she’d lost some of her confidence after her termination. But Elaine Sigurdson, a career coach with Insight To Action in Toronto, says the advantage of experience shouldn’t be forgotten. “The important thing is to own the strength of what it is that you’ve done,” she says. For Jackie, that strength was something she had to take back—and once she had, the day she was laid off began to take on a new significance.

Her position at the literary agency allowed her to take on her own clients and had solidified her realization that she didn’t need an employer. “I deserved a respectful environment,” she says. “That’s why I decided to create one.”

In that vein, she created Susumai House, a non-profit facility that provides treatment for acute depression in a retreat setting. Although she was straying quite a distance from her area of expertise, she found her previous position of managing authors, editors and procreators valuable. Entering unfamiliar territory, she would call on those management skills to effectively communicate her idea to experts who would help develop and execute her treatment plan.

Weisser says that soft skills can be just as important as the hard skills that take front and centre on a resume. “Those aren’t things that people can learn instantly,” she says. “You learn them over time and that’s why older workers bring a lot of value.”

Weisser also says that a second career presents older individuals with an opportunity to be more intentional. “Examining what your values and interests are is important in determining if it’s going to make you happy and if it’s going to be a good fit.”

In Brown’s case, Susumai House—what she calls her “heart project”—was something she’d had a personal connection with from the start. In supporting her son, who suffers from severe depression and anxiety, she witnessed the inadequacies of the mental health system first-hand. She can still recall when her son once waited three weeks for an appointment and was told to keep a journal of when he felt anxious or depressed. “It’s just not enough,” she says. “People who are as depressed as my son, every day they feel like killing themselves.”

The idea for Susumai House came about after she searched out residential treatment for her son. Private treatment facilities were far too expensive and the hospital only offered residential care to those who had attempted suicide. “The solutions aren’t there because you’re not considered ill enough,” Brown says. With Susumai House, Brown hopes to provide that level of commitment from the onset of an individual’s illness. “We own your problem in a way,” she says.

Jacqueline Brown, holding up a copy of her Outfox magazine.

However, her heart project was difficult to fund. To supplement her income, Brown returned to the familiarity of publishing by coaching writers through her own service called Jackie Brown Books. Her new-found interest in mental health also started to bleed into her expertise in educational publishing. As a result, she and a friend created Outfox Magazine, a custom-made educational publication for children with autism spectrum disorders.

Once again, Brown had found meaning and purpose in her work. But also, she’d discovered something that had been stifled during her previous employment. “I became less willing to speak my mind because you had so many people who weighed in on things,” she says. “I like being able to create things and not have it weighed down by bureaucracy.”

Sigurdson says that creativity is important from the start. She likens the search for a new career to “standing at the drawing board of your life.” And while Brown may not have seen it that way at first, today she looks back on the day it all started with no regrets. But it’s not because it’s gotten any easier—her work schedule likely doesn’t differ much from the 50-hour workweek she previously endured. And it’s not about money, either. It’s that now her work produces a different feeling.

“You need that awareness of why you’re doing it,” she says. “If I’m going to work this hard, I’d rather feel some love.”

Here, five tips to keep in mind when finding your own second career: 

1. Take time to reflect: Deciding on a new career involves a two-pronged approach. While it’s largely about uncovering your strengths, values and passions, it also involves assessing the current job market. Elaine Sigurdson says you can’t make the decision in a vacuum. “You have to have conversations with people,” she explains. “In addition to looking within is a conscious exploration of options that are out there.”

2. Crunch the numbers: It’s important to understand exactly where you are financially during a career transition. If you find yourself unemployed, calculating how long you can spend without an income will give you an understanding of your options. Also, knowing what you’ll need to earn money to live comfortably may prevent you from making any rash decisions. If you’re not much of a number cruncher, visit a financial planner or your accountant.

3. Manage risk: Your second career is a chance to be more intentional—not unrealistic. Try not to stray too far from what you know. A second career should still reflect your core skills. If you’re starting your own business, consider your financial situation and don’t spend any more than you can afford.

4. Become web-savvy: Whether you’re starting your own business or re-entering the workforce you’ll need to make yourself searchable online. Start by building or updating your LinkedIn profile. Employers will often search LinkedIn for candidates and it’s a great place to connect with potential business partners. Following companies you’re interested in on Twitter can also help you stay connected to your field of interest.

5. Test the waters: “It’s always a good idea to give a new career a test ride because that’s going to lessen some of the anxiety of making a big change,” Lee Weisser says. This can involve shadowing a professional in the field, volunteering or taking a course. For those careers that aren’t conducive to a “test rid,” Sigurdson says that simply meeting someone in your desired position can be helpful.”What’s a day in the life?” she says. “That’s the most important question of all.”