Why I Made a Midlife Career Switch

For most of my career, I worked in wealth management at major insurance companies. I’d studied math and graduated right during the 1994 recession, so I was grateful to land a job but not exactly thrilled by it. I loved the customer service aspect of my work the most, and connecting with people was my strongest skill. But the pressure of being on the clock meant every interaction was rushed, leaving little room for real engagement. From 2003 to 2012, I also commuted every day from Keswick, Ontario, to the head office in downtown Toronto. At first, the trip took about an hour each way, but over the years it grew to more than two hours. Losing four hours a day to traffic felt like such a waste.

My daughters were born in 2005 and 2007. By the time they were ready for daycare, commuting had become a serious issue. One daycare warned me that if I was more than a half-hour late picking my kids up, they’d call the police. I was constantly caught in a tug-of-war between my 10-to-six workday and my family’s needs. Most days, I only saw my daughters for an hour at bedtime. Once, in a desperate rush to get home to them, I even blew the motor in my car. 

I’ve been married to a contractor for 26 years and, when he was laid off in 2007, we decided he should start his own firm for more flexibility—someone had to be available for the kids, who were constantly getting sick or needing rides. The following year, my husband launched his business, and three years after that, I was transferred to a new role and began pushing for remote work. They let me work from home one day a week at first. But six weeks later, I broke my foot and couldn’t drive. Faced with a choice between medical leave or remote work, my department made me their first fully remote employee.

Things went smoothly until 2013, when they mandated me back to the office. It was tough to give up that flexibility, but my family and I wanted security, so I reluctantly returned. The next few years were brutal: my mom was diagnosed with dementia in 2016 and died a year later, and then I was in a serious car accident in 2018. It felt like the universe was urging me to re-evaluate my life. I wish I’d quit then, but I didn’t. Instead, I joined a new company just before the pandemic, only to be laid off in 2020. They basically handed me the keys and told me to walk away. I hired a lawyer, got a severance and then—the absolute worst part at the time—wasn’t able to work for 17 months. 

That time off was rough. I realized how much of my identity had been tied to my job. When people asked me what I did, I liked to say the company’s name for the brand recognition—it made me feel accomplished. But now, I had nothing to show for it. At first, I was furious, but then came the grief. I started meditating to help shift my mindset.

I started to think about what I’d done over the years that felt meaningful and had an impact, and my thoughts kept returning to my remote work. I had advocated hard for it, practised it and, because of the pandemic, now everyone was doing it. I realized I had a lot of valuable advice to give. And it became clear I could start a business consulting organizations on hybrid and remote strategies, helping them design a work culture that prioritizes flexibility and employee autonomy.

I’d learned a lot about running a business simply by watching my husband do it first. I knew how to apply for grants, file taxes and tap into available resources. There were no training requirements for what I wanted to do next, but there were areas where I needed depth, so I enrolled in government-funded leadership training programs and business courses to sharpen my skills. 

Starting a business in a new industry was terrifying, but not for the reasons people might expect. I could figure out the funding and, while it’s easier to launch a business at 25 years old than 50, my age didn’t concern me either. The hardest part of my career switch was its impact on my identity. For many years, whenever I went to the bank for a loan, I’d be the first to be approved because I had a corporate job and looked so stable. Now that both my husband and I are self-employed, I know enough about finance to know it doesn’t look great on paper. In the end, knowledge-based businesses like mine rarely get the same funding as those offering tangible products, so I self-funded my company without a loan. The business is still in its early days, and it’s been a challenge to make it financially viable, but I believe in what I’m building—and in myself. That’s a confidence I never felt while working in wealth management.

I realized that nearly everyone I knew was connected to the company where I’d spent 17 years, so I expanded my network aggressively. I became much more active on LinkedIn, and now many of my clients come through networking and referrals. I call myself a hybrid and remote-work futurist. I help large corporations restructure to accommodate remote work. Studies show that hybrid work has become Canadians’ top priority after salary, and 84 per cent of Canadian companies currently offer flexible work locations. So, designing and implementing effective hybrid or remote work policies is key to attracting and retaining staff, which is where I come in. 

I start with an assessment at the C-suite level to gauge the company’s mindset, then collaborate with HR or its equivalent to ease the workplace cultural shift. Everyone has to be on board, and the change typically takes 12 to 18 months, so I guide the process every step of the way. Anyone can teach Zoom or time management, but few are helping organizations to rethink their core identity and embrace what the future of work could be.

These days, I have complete autonomy over my time. I start my mornings with meditation and a walk with the dog. I usually begin work around 10, spending a few hours in meetings and interviews. Most of my job now involves talking, so I wrap up by two or three. I’m far more productive in those five hours than I ever was in a full day at the office; I work faster and more efficiently because I enjoy what I do and the earlier I finish, the more time I spend with my kids. I block off Mondays for marketing and Fridays for follow-ups and admin work. All this is very flexible, however—I can do whatever I want and whatever needs to be done. 

—As told to Rosemary Counter