Disruption and Reinvention: Starting a Second Career in your Forties

This week Jackie is joined by Caroline who is a Co-Founder and Co-CEO of the Canadian Leadership Congress, an organization dedicated to events and education for Canadian asset owners. She has 20 years of experience working with pension funds both in Canada and globally and she spent 18 years editing a research publication for Canadian plan sponsors. Let’s dive into the conversation.


Tell us about your journey of disruption and reinvention in your career

Caroline has had 3 different pivots in her life where she ended up in a different career. One of the disruptions happened after her PHD in Europe where she was really looking for an academic job but to no avail. She tried to keep the momentum by publishing papers which kept her busy but still wasn’t the dream job. To pay the bills she also took on a job wrapping gifts with little to no experience which was a struggle as she simply was not blessed with this skill set. Over time, she landed an opportunity to become a teaching assistant at the Toronto stock exchange-a job she fell in love with! Eventually she came to realize that her background in academia boxed her in and most of the people with her background rarely had any work or life experience in the real world.


What challenges did you face with switching industries?

Caroline was never forward about letting people know she had a PhD, especially since she wasn’t really working in her field. At parties, when asked she just says she’s a caterer and most people find another person to talk to who had a more interesting career. The thing with judging people based on what they do is that you are instantly making an assessment of who a person is based on their work and not who they truly are which is not great. Instead ask questions like, what do you do for fun? What is your favorite Madonna song? What are you excited about? These are great questions because it is a way to really tap into who the person really is. Caroline eventually went to become an editor for a pension fund company which eventually fuelled her consulting business that she has been successful at for the last 20 years.


What were some of the key lessons you learned on your journey to becoming a business owner?

You really must be open, as much as it can be hard to make that move, there are opportunities available to you as long as you are willing to be a keen observer of what is happening around you at the time. What is happening in your industry and the industry you may want to go into? What can you offer that makes you unique? Are you prepared to check your ego in case you don’t get the response you were hoping for from the market? Are you willing to fail and try something you haven’t before? You also need to be a great listener when getting feedback from others. Try to strike a balance with what is available in the marketplace and what you are passionate about. You must be prepared to fail and be open to take an opportunity that isn’t as popular because it could be the niche opportunity you need to build a strong career. Be open and be humble throughout your journey and look out for mentors that are in line with what you are doing. Caroline was able to do this in the pension space and has carved out niche events for this community by taking feedback from what stakeholders told her they were looking for when sponsoring events.


How did you find your mentor?

Caroline just put herself out there and got to know different people. It’s important to not be stuck on what you think a mentor should look like. Best approach is to have honest conversations with people you connect with that lets you get a sense of who they really are. Also be willing to be vulnerable and ask for help. Making connections with people of different skill sets helps you to find the right attributes of people that can guide you to where you need to be.


Any advice for people going into a transition?

One big thing to have a plan! Don’t just jump off a cliff and follow your passion. Know your numbers. How much will you need to set aside per month to pay the bills until you land your next career or your new business idea brings in cash! What does it cost to live each month? What is your net worth? And how will you fund your life in the meantime? How long will the cash you have saved last? How will this affect your retirement plans? Before you move forward with the transition, Reach out to us! Follow your passion and be realistic with what your finances would look like and what you will do next when you maybe start to run out of funds. A financial plan can help you to sleep better and make the best money decisions along the journey of reinvention!

We are happy to have a 30-minute conversation where we delve into a customized financial plan for you. Please reach out to jody.euloth@askjackie.ca. Also, feel free to share your questions with us here or on our social platforms

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