Lisa Taylor: Challenge Factory

By Sheryl Smolkin

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Today I’m interviewing Lisa Taylor, the president of Challenge Factory for savewithspp.com. The Challenge Factory offers a broad range of services to both employers dealing with an aging workforce, and individuals looking for a career change or transition. We are going to talk about how career timelines have changed, and how you can define and embrace encore or second act careers. Welcome, Lisa. 

Thank you. It’s a pleasure to be here.

Q: Lisa, tell me a little bit about your own background, and when and why the Challenge Factory was born.
A: In 2003 and 2004, the question that intrigued me the most, was why was it, even in fantastic companies, so many people were successful in their jobs but not satisfied. They were seeking something else, but also not willing to take the risk to make a move. As a result I did some research. That led me down the path of really understanding demographics and the workplace.

Q: When did you actually start the Challenge Factory?
A: The Challenge Factory started in 2009. It really grew from my initial experience meeting people who wanted to figure out how to make meaningful change later in their careers. 

Q: What other professionals do you have on your team?
A: Challenge Factory is made up of a wide variety of professionals. We have career coaches, HR and management strategy professionals and analytic specialists that work with our corporate clients to help model out what the cost would be of shifting the workforce around in different ways. 

With our individual clients, we have a really unique body of over 160 experts who are top in their own jobs, and they agree to take on Challenge Factory clients for one day test-drives.

If you’re in one occupation, and thinking that you might want to do something totally different, the best way for an adult to make decisions is to do a dry run. This gives our clients an opportunity to spend a day with an expert in that particular field to find out if their assumptions are really true and whether the job is really as great as they thought it would be. Between our coaches, our consultants, and our test-drive experts, we have a really diverse group of people who are all there to support the clients that work with us. 

Q: Do you draw on these experts on an as-needed basis?
A: Yes, based on what’s relevant to each individual client or group that’s going through the program. 

Q: We hear more and more in the media about encore, or second act, or legacy careers, tell me what those terms mean for you.
A: Whether it’s an encore career, a second act or a legacy career, I think what the terms are demarking is that this isn’t just an extension of mid-career or mid-life. It’s not just doing the same thing you’ve been doing but doing it longer.

A lot of times when people hear about working longer, they sigh and say, “Oh my goodness, I’m ready to be out of here.” But they’re not actually ready to stop making a meaningful contribution. I think that those terms help us to draw the line in the sand, to say it’s okay to think about these next 20 or 25 years differently than you’ve thought about the last 20 or 25 years. 

Q: Is the encore idea only focused on paid work?
A: Not at Challenge Factory, and not from my perspective. The purpose isn’t necessarily to define paid work that people can move into. For some people, that’s a very core part of their plan for their 50s, 60s, even into their 70s and beyond. For other people, it’s really about coming up with the right portfolio of activities. We call that the career portfolio plan. 

The encore concept really says, “What’s the balance between stable work, hobbies and interests, and risky or entrepreneurial ventures — things that may or may not pay off in the future, but you know what, you’d love to give them a try and see what happens.” 

Q: How do new careers in later life typically differ from the kind of careers people embark on right out of school, or the careers they left behind?
A: I think the biggest difference, when you’re making a transition and it’s later in life, compared to when you’re right out of school, is how significant what you do, or what you have been doing, is tied into your sense of identity. 

We introduce ourselves by using what we do as the social placeholder so that we can figure out quickly who everyone is at the cocktail party or at the meeting. Even at the family barbecue when there’s someone new, we often will ask as a very first question, “It’s nice to meet you. What do you do?” 

After decades of explaining what you do, starting to identify what else you could really do and what you want to do separate from that particular way of describing yourself is very difficult. 

Q: Is an encore career a luxury for people who’ve saved enough money so they have choices, or is the concept relevant for a broader group of people?
A: The relevance of an encore career for everyone is to recognize that it’s not about an aging workforce. It’s about the benefits and the impact longevity brings. The longer we live, the more time we have to contribute in different ways. There is a way for anyone to think about how they want to spend the next 20-25 years of their life.

Q: Do you think the desire to work at something different later in life is more a factor of knowledge workers, or does it also include trades people, independent business owners, blue collar people etc.?
A: It’s assumed that it’s really just for the professional sector. But it’s not true. The Challenge Factory works with individuals looking for their legacy career, for their next step, and they come from all different sectors. We also work on the other side of this equation — inside organizations to see how career paths can change so that their workforce can continue to contribute and deliver value for longer periods of time. 

Q: You provide career exploration services on both a group and a one-on-one basis. Your offices are in Toronto. How do you accommodate people outside your geographic area?
A: Challenge Factory is headquartered in Toronto, but we offer services in cities across the country, North America and Europe using technology.

Q: Participants complete 19 assignments using an online collaboration tool. Can you briefly tell me a little bit about these assignments?
A: Sure. Different programs have different numbers of assignments. Our whole career transition program has 19. These assignments are short, but very pointed questions that require our clients to go out and experience something new, talk with friends and family and then reflect on the responses, or do some reflective writing on their own. 

We have an online collaboration site where our clients complete their assignments, and their coach and anyone else that they’d like to can see their responses as they work their way through the program. This is in between the coaching sessions. 

If they are not meeting with their coach, or their group isn’t meeting again for another two weeks, but they’ve just had a real significant breakthrough, and have written something that’s very meaningful, their coach will see that and be able to respond back to them online within a short period of time.

Q: Can you give me an anecdotal example of a client who went through your program, and his before and after careers?
A: Sure. Frank was the COO of a family-run print business. He had been with the organization for a very, very long time, had really loved his career, but had started to find that he was ready for something new. He was pretty sure he wanted to make a radical change. 

In talking with us, one of the things that he found was that there were a couple of aspects of his career that had always made him really excited. One of them was in a particular sector that provided services to his company. 

On further exploration, he actually found that there was an organization that was looking for senior-level expertise to help them improve their relationships with their customer base. He was able to step out of his COO role and move over into an organization he had always held in high esteem, in a totally different sector, by leveraging the experience he had by being a client for so many decades.

Q: How long do encore careers typically last? After all, retirement has been described as three stages: go-go, slow-go, and then no-go, although the age span will be different for everyone.
A: This new segment, this language, of encore, or legacy or second act careers, helps to differentiate that you’re not in retirement for decades. That period of time at the end of your life where you actually withdraw from, whether it’s paid or voluntary contribution to society, is a specific moment in time because it’s time for you to start to take care of yourself and to really focus on what’s important as you get to the end of your days. This instead of putting a line in the sand that says, “You know what, by the time everyone is 71, that’s got to be finished.”

Q: Thank you very much for your insights, Lisa. It’s been a pleasure to talk to you.
A: And with you.

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