Top Questions to Ask Yourself Before You Retire
In this episode of the Women’s Wealth Canada Podcast, host Glory Gray welcomes certified retirement coach Anna Harvey for an insightful discussion on the often-overlooked emotional and social aspects of retirement. While financial planning is critical, many women are unprepared for the mental and emotional transitions that come with leaving their careers.
Anna shares the top five hidden benefits that careers provide—structure, status, socialization, purpose, and financial confidence—and how retirees must find ways to replace these elements in their new chapter of life. She also highlights the importance of being mentally and emotionally ready for this next stage and offers practical advice for transitioning smoothly.
Whether you’re considering retirement, actively planning for it, or already retired, this episode is packed with valuable insights to help you retire with confidence, clarity, and purpose.
Learn more about this episode's guest, Anna Harvey at https://www.boostpotential.ca
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Top Questions to Ask Yourself Before You Retire with Anna Harvey
The Women’s Wealth Canada Podcast
Introduction
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Hi, everyone, I’m Glory Gray, and welcome to the Women’s Wealth Canada Podcast.
My guest today is Anna Harvey. Anna is a certified retirement coach. She helps women in any stage of retirement design their next life chapter with confidence and clarity by rediscovering who they are and who they want to become.
Today, Anna and I talk about the emotional and social side of retiring that we often don’t talk about. Join us as we discuss the Top Questions to Ask Yourself Before You Retire.
Glory Gray:
So, Anna, financial planners like me often talk about the financial side of planning for retirement. So even if someone wants to continue working past the traditional age of 65, they still want to make a plan for what happens if they are no longer receiving an income from working.
The Emotional Side of Retirement
Glory Gray:
But I've heard you talk about how we need to be mentally and emotionally ready for retirement. So what can you tell us about that?
Anna Harvey:
It's such a good point, Glory. It's really, it's one coin and there's two sides, and there's no diminishing the importance of the whole financial piece. Absolutely, that's the piece we all know. But what gets left behind and ignored is the other part of the coin, which is the fact that every other life transition that we've gone through that we know came with a social script.
And then we get into retirement, and we don't have a current social script for today's retirement. What we have are lingering memories of how our grandparents might have done it, or how our parents did it, which was much more the "I'm going to work, and then I'm going to stop." And so we equate it with a stoppage.
And that's just not what it is these days. So now this is all about transitions through several stages that we're going to do in this new retirement. And we need to know about that and know about the impact it's going to make on us mentally and emotionally.
Hidden Benefits of a Career
Anna Harvey:
We need to know that we're leaving behind a career that for many of us gave us many hidden benefits like status and purpose. And all of a sudden, we get into this new stage with no script. We don't know what it is we're supposed to be doing really, and we don't know how to replace those hidden benefits. And I'm happy to go a little bit more into that because there are really five of those hidden benefits that we absolutely need to replace if we're leaving a career and we want some sense of fulfillment and that we know what we're doing. So shall I elaborate a little bit on these?
Glory Gray:
Yeah, because I’m just thinking many of us were proud of the things we accomplished when we were working. And after we retire, we feel like we were the persona of that vocation that we had. So yeah.
Anna Harvey:
Yeah, so to that word accomplishment, I hear that all the time in my clients, right? Because we've been very bright, we've been educated, we've been engaged in our career and in our world, and we've got this sense of achievement and of accomplishment. And then all of a sudden, if we're not getting that, that for us becomes a big void, just that one point alone.
But the traditional five, I think of them as must-haves. These essential pieces that we must look at after we've left our careers. First and foremost, it's the financial. So, we've talked about that. That's your realm. We know that's in good hands.
The Importance of Structure and Status
Anna Harvey:
But on the other side, one of the hidden benefits is this whole structure piece that work gave us that we need. We need to know when a weekend happens. We need to know when summer is. And the thing that I hear from clients is, "Oh man, retirement, I thought it was going to be so great. It's like Saturday all the time." And yet what we know is after a period of time, Saturday all the time—that's not cutting it. We need some structure. That gives us comfort to have some structure. So one of these things is that the time management structure piece is essential to replace that after we've left our careers.
Then another one is the whole piece about status. Most of us had business cards. It told us who we were, right? And a lot of us have a big identity around status. I think the ones that I've noticed over the years that I've been doing this are the professionals—so lawyers, doctors, any of those, professors, any of those that are in those true professions—they struggle because they are so strongly identified with that title that they, man, put a lot of hours, money, time, investment into becoming that. But after 40 years, 30 years of that, they leave that career, and then they ask, "Who am I if I am not a professor, if I am not a lawyer?" So, they particularly struggle.
Another group, which I'm sure you can relate to because you're entrepreneurial as I am, any of us who have our own businesses, we've gone into it through some passion, usually some care point that we've got, and our businesses are our babies. Oh, my stars. It's hard to get entrepreneurs to retire. They're in the group that says, "I'll never retire." That group right there just—they just want to hang on to it. Can you relate to that?
Glory Gray:
Oh yeah, absolutely. And I still am on—I have to make plans for succession for my business, but retirement, I don’t know.
Anna Harvey:
Yeah, it's the same for me. I love the work that I do. It's of my creation, and the thought of stepping away from it in retirement—it's, ooh, yeah, it's a real tough one. So that status piece is really important. Interestingly, I hear this often expressed in a different way where people get into retirement and they say, "I just, I don't feel relevant anymore." And that's a little bit of that status piece—that hidden benefit that we got from our careers, like we knew we were relevant, we knew we had this status. We had so much of it, employers were willing to pay us for that, so that really gave us something to hang on to.
And then all of a sudden, we're not as relevant as we used to be. And that can be heartbreaking for some people. That's a real emotional hit for them. So that's a really big piece, yeah.
Socialization and Purpose in Retirement
Anna Harvey:
I'd say another place where we really feel the loss in retirement, again, speaking of that mental and emotional side of us, is the whole socialization thing. For many of us that have worked in any size of office or team environment, those people over time start to grow into even more than teammates often. And some of them even become a best friend to us just because we're hanging out a lot together, right? And then, to be unaware that’s going to largely disappear when you retire—that's a huge hit. It's a loss. It's a grieving—that I've left behind these people that were so important to me. So that whole piece about socialization too is another piece we've really got to be aware of if we want to be emotionally and mentally and psychologically prepared for that.
And then, of course, the big thing that work gives us is the whole purpose piece—that whole sense of purpose. I've got a reason for getting out of bed. Whether we grumble about it a lot, like many of us did during our work careers—“another day at the office”—but regardless of that, it gave us purpose. We knew why we were getting up. We knew we had a focus point. We knew we were contributing in some way. And that's really important. And, man, when that disappears, purpose is often one of the big things that people say, "I'm lost. I need new purpose." So yeah, all of those, we take a mental, emotional, and psychological hit on when we step into retirement that generally speaking, our employers don't prepare us for.
Glory Gray:
It's funny. You were talking about the business card thing, and I do remember a gentleman who was recently retired. And you know what he did? He went out and had some business cards made that said something like "Old Retired Guy," and his phone number and his email, and he would hand those out until he got comfortable with the idea of being retired. But at least it helped him make that transition and feel like he wasn't left out in those networking situations.
Anna Harvey:
Yeah, absolutely. It's a bridge, right? And that's often what we need in any kind of a transition—to get from point A to point B, and anything that can help that journey, that crossing. So, anything that acts like a bridge would be good.
Ageism and Cultural Perspectives
Anna Harvey:
Here's my comment on that, if I can make a comment on that part, that one, is the whole ageism thing, which is coming so much more to light for us right now as this whole boomer cohort heads into retirement, right? We are people of a certain age. And research shows we're all feeling about 18 years younger than we really are, which is interesting. Anytime I talk to friends. Yet there is ageism. We revere the young typically right in life. And we're not a culture here in North America that esteem our elders our seniors, right? So, we have to be, in my opinion, we have to be careful that we ourselves aren't our own worst perpetrators of the ageism thing, right? That we aren't making those kinds of comments or business cards about ourselves, right?
Glory Gray:
Yeah, that's interesting. Yeah. For example, I think I can't honestly remember what his business card said, but I'm sure it was something like “old, retired guy.” And this was at least 30 years ago.
Anna Harvey:
Oh, yeah. Yeah.
Glory Gray:
So, it was a different time but you're right. I think he had, if he was retiring today, he would probably say, you know, wise guy or something like that, something. Yeah. Have some fun with it but also pay homage to the fact that he has wisdom and can share. I'm hearing more and more actually about businesses that will have, particularly those that are indigenous run, they will have five generations, purposely have five generations in the staff.
Anna Harvey:
I love that.
Glory Gray:
So yeah, so that they could share those ideas.
Anna Harvey:
Yeah. And that comes back to the cultural thing, right? Because my understanding of the Indigenous way of life is to think in terms of seven generations, right? And so, it doesn't surprise me to hear you say that. And how, ah, it's just, it's such a wonderful model, because I think the, what a combo, the energy of youth with the wisdom of the sage together? That can move mountains, I think. This is a benefit, eh?
Glory Gray:
It's worked for the monarchy. How many prime ministers did Queen Elizabeth go through?
Anna Harvey:
It's so true.
Glory Gray:
And she was the thread of consistency and wisdom.
Anna Harvey:
Yeah. And the rock, like it's just, I think we need that in our families. I think families are stronger families when they’ve got the young ones coming up and they've got the seniors and the elders. And then companies too. I just think that's the model. We'll get there, I'm hoping, in time.
Glory Gray:
Yeah. So, these benefits, can you name them for me again? Have you got them listed? Is that possible?
Anna Harvey:
Yep, yep, so financial would be the first one. I call it financial confidence, Glory, so that if we don't have financial confidence, we worry. So that's key, right? So financial confidence, structure, status, socialization. And a sense of purpose.
Glory Gray:
And do you think we could maybe go a little deeper into one of those and talk about how you might work with someone on one of these particular important points as they transition.
Anna Harvey:
Yeah. It's an interesting question. And I think what I'll contribute to that is that working with one in isolation doesn't do the trick. And that's why when I work with a client, what we're doing is we're looking at all of that and what becomes interesting for them. One of the things that I get them to explore, and this is one of the regular things that I do is I make them aware of these five must haves and I ask them to rank what order they would be in right now, assuming that they're still in their career. And then to project themselves forward a bit, and the forward a bit starts to be a much shorter time frame because we're finding that life is so dynamic, right? Life changes in a heartbeat these days. So, 10 years out is too far. But if they think three and five years out, what might the order of these things be? And that almost always will change for people, right? The drive for finances might be top right now while they're at work, and that would be like normal given where they are, but then they can see how it changes, and then purpose often starts to become more important to them because they understand that's where the meaning part of life is going to come from for them. And that's particularly true, Glory, if they haven't found meaning in their careers. And that's true, right? A lot of people do their careers because it provides them perhaps with the financial piece that they're looking for. But there's a piece that is part of who they're longing to be, what they want to contribute to their world, which would be the meaning piece for them and retirement gives them the opportunity to do that. So, the purpose piece can float more to the top. So, by unpacking these, we start to learn that about the client that I'm working with.
Glory Gray:
Do you find that is, is because of that purpose piece that many people decide to start a business in the final third of life?
Anna Harvey:
Yeah. yeah, yeah. This again is Boomer cohort. We're strong starters of new businesses. We really are; and that's because, again, we've got the we've got the jam and the recipe for what it is that we own in order to start that new business, right? We've got skills, we've got talents, we've got training, we've got expertise, we've got a desire. All of those combine to be the foundation for, hey, what kind of business could I be doing here? How can I take that? How could I be working in that? And the lovely piece of that for people who are retired, and I'm using that word only because it's a shorthand for what I really consider to be the next life chapter, so I'm using the word retirement in that way, but this next life chapter, they want to be able to do something like that, and they've got everything they need in order to do that, and it gives them that sense to, be who they've always longed to be. It gives them a chance to do work that they know will be meaningful for them and it gives them flexibility. Oftentimes people say when they're out of their career, I am so glad to leave behind that nine to five that I must have, but they still need to be, have some structure. Which a new business does give them, but they can flex it to how they want to show up and do it. Pace is a big word I hear. Pace. I want to do; I want to do life at a pace of my choosing. I say it's this, it's a shift from the race, which is we think of the rat race of work, the race, and deadlines being put upon us. And it moves from race to pace. And it's my pace of how many days I want to work, how many hours in that day, I want to work how many months of a year, even I want to work, right? So again, with some affluence, travel becomes a huge piece of people's retirement life. So, they want to be away. Yeah.
Glory Gray:
IT would be so interesting in another 40 years when the current generation that is just starting out work right now and they have a very holistic view of work and life balance. It's going to be interesting to see where we are in another 40 years and will retirement even be a thing? Or is it just simply part of our entire working lives? I don't know. What do you think?
Anna Harvey:
I think it's going to be hugely shifted by this next generation because of that holistic thing, right? Because even at 25, they are looking for work life balance, right? So, I think they've got that part right. I think there's still some kinks to be ironed out, but they've got that part right. And it, it very much speaks to next life chapters. I think those are going to start much earlier and they're going to continue longer. Centenarians right now, I think that's one of the, one of the demographics that's really on the grow in Canada. Even now, in a quick read of the obituaries will tell you, people are dying at 104, 102, made it to her 100th birthday, all of that. Um, I wonder about this next upcoming generation, like how much longer will they be living? So of course, they're going to be doing life, I think, in these chapters. That would be my prediction. And they'll change.
Glory Gray:
And even for us, there's a lot of living left.
Anna Harvey:
I know! I know! You can probably think of your own life, right? You think, okay, this is fabulous right now, and after this contribution of mine comes to some kind of a natural close, right? What do I want to do next? And you're a talented woman, so I'm sure there's many things that could be on your horizon.
Glory Gray:
Let's compare and contrast. How is that different today? I'm saying not so much looking at the future at young folks coming up, but right now today, how do you think our current retirement has changed from our parents and grandparents?
Anna Harvey:
I think that's in a nutshell, that's what we've been talking about. The old model of retirement, which we do have memories of, I think, if for no other reason that we grew up watching the Beverly Hillbillies, and we saw Granny in her rocker, right? And that was our definition of not only senior, but synonymous with that was old. Like everything was given up, we go into our rocker and we lived, of course, much shorter lives, so from the period of ending our work until death was a much shorter time. So yeah, it was a time of stillness, a stoppage. Then we grew into thinking, okay, maybe it's not stoppage. What it's really about is leisure. So, the next sort of iteration of this, a little bit of this, I think, is the Freedom 55, which didn't exactly turn out to be true for many of us, but from a marketing point of view, it was two Adirondacks on the beach, man and woman, martinis in hand, looking out into the horizon, right? So, it was very much portrayed as, wow, this is your time of leisure. As. We've grown and learned in the past that it's not about a life of leisure anymore. It's about a leisurely lifestyle. So, it's a lifestyle that includes leisure, but we know solid leisure doesn't work. We come up empty again. It's that purpose, meaning piece as you, I think started with talking about achievement, that's in us. So, after we've done a little bit of stillness, we're keen to start contributing again to learn, to grow. All of that is still in us. That's a big change too. And then now, of course, what we're seeing is people doing other and new work. Sometimes it's even a new career, they do a total career shift and think about doing something singularly for another, 10 years or something on the horizon. So, it's really changed. But the young ones coming up won't have the memories of the rocking chair, right? They're going to be looking at us and how are we doing it?
Glory Gray:
Yeah.
Anna Harvey:
They'll have their own ideas.
Glory Gray:
They have had a point of view that we, that many of us worked too much in the eighties, nineties.
Anna Harvey:
Totally. Absolutely.
Glory Gray:
Yeah. Did you say something, did you just say live style versus lifestyle?
Anna Harvey:
No, living is we thought it used to be having, living a life of leisure, but now it's a leisurely lifestyle.
Glory Gray:
You know what, I just, I think I just came up with a soundbite. “Live style versus lifestyle.”
Anna Harvey:
Ah, okay.
Glory Gray:
Lifestyle of, you're saying leisure, but there's live style, meaning having more purpose, something to do.
Anna Harvey:
Love it, Glory. Well done.
Glory Gray:
This is what happens when you mishear people.
Anna Harvey:
Good things are born.
Glory Gray:
Good things are born, great ideas. What else? What else are you thinking about? About this just this topic. What do you think people should know?
Anna Harvey:
All what we've been talking about here, I think the thing that I see trending is this interesting part about getting back into work and, originally when I first was doing coaching, I was doing a work life clarity coaching program that was something I designed because people were making career transitions. And the only thing they knew is they didn't want to do what they're currently doing, but they didn't yet know what they wanted to do. So, my program helped them discover that about themselves. So I think it's so interesting that even though I became certified as a retirement coach, thinking it was going to look differently, more and more, I see that the work that I did to help people get that career clarity is, also coming forward now into this retirement work that I do because so many of us want to work, which is just really great. And you know how wonderful for an employer we taught you talked about the work ethic, right? We contribute that when we go back to any kind of work. We bring that work ethic with us and that expertise, right? So, I think we're, should be a snap up by any employer. because of what we bring. If we can get over that ageism hump, that's the one thing I'm still hearing is it can be challenging. But I'm hopeful, I'm really hopeful.
Glory Gray:
That's a really good point. And I'm just thinking as you're speaking from a point of view of business owners and corporate owners. I'm sure that they were hesitant in the past because, let's face it, you put money into training an employee and you know that someone who is in their later years is probably not going to be there as long as someone who is 20. Now, of course, there's the caveat of nobody is there that long anymore. We don't have the 20-year corporate, same company jobs anymore. So, there's that.
The Role of AI and Coaching in Retirement
Glory Gray:
But also, in the training piece the cost of training that is going to go down with the onset of AI.
Anna Harvey:
Oh, interesting point.
Glory Gray:
I have no idea how that's going to come about, but certainly, I'm just thinking of, there's a tool that I use when I'm bringing on, I use a lot of subcontractors in my business. If I'm bringing on someone explaining, here's the process of how we're doing this, there is AI that I can use, software that I can use that will make a procedures manual as I speak. with screenshots. Here's what how you do this, and I don't have to write that manual through AI. And so, the cost of training someone, if that's going down, then we might be more willing to bring in someone who has something that we cannot buy from AI, which is all these years of real-life experience and personality and wisdom.
that might be an interesting thing.
Anna Harvey:
That might be an interesting thing. It's going to be a game, going to be a game changer as it is in everything, right? And it makes me think as you're saying that this is a good new thinking opportunity here because I can see also, what AI does well and it makes me think of the people component, which, that's the culture piece that I think someone who is more senior can contribute to a young leader being groomed. That's a piece of AI. I don't think it's ever going to be able to put its tech finger on because it's, I don't know how would you describe culture, right? It's essential, right? It would be essential for a new, an upcoming young person being groomed for leadership to be aware of that piece of the business, which AI can't touch. So, it's going to be really interesting, Glory. Totally.
Glory Gray:
Yeah, it's coaching. Yeah, it is coaching, mentoring that you can't it's just too personalized and too bespoke to have AI. And it's something that we definitely as elder employees and consultants could do.
Anna Harvey:
Yeah. It leads me to share this thought with you when you think of AI because I was both fascinated and shocked when a little while ago when AI was becoming more and more prominent, how it was so easy, seemingly easy to ask AI for coaching. And I looked at that with interest and I thought, wow, okay. And then I thought about it and what I absolutely know to be true is the value of a coach because left to our own devices we are for ourselves, our harshest critic and also the first ones to let ourselves off the hook, right? And that's the value of having the coaching experience when you're trying to move forward, when you're trying to grow, when you're trying to become more self aware, because a coach can take that role that, he or she is really listening and interpreting and can ask the good questions and not just allow you to automatically buy into what we've come to know as your BS, meaning your belief system about yourself.
Glory Gray:
I love it.
Anna Harvey:
And we embrace that and we think, okay, that's a really good point. I really should do that. And I'll get to that, at some point, but a coach can play the role of more holding your feet to the fire and say, you say you want this. And yet I noticed that this seems to be some kind of a barrier for you here. Can we look at that? What's that all about? So, I don't think coaches are going away yet. I don't think AI's replaced us yet, but yet is the qualifier.
Glory Gray:
But yeah, you're absolutely right. And it's a lot of what I, it's a lot of what I do is this, the coaching counseling piece and it's, it makes it so wonderful to be interacting with a human being.
Anna Harvey:
Yeah. And the huge benefit that they received, because of course I could type into AI, what should a financial plan look like for a woman who is X, Y, and Z, give the criteria, and it will output, but to blindly follow that, man, I am nowhere near that. I need someone to look me in the eye and say really, that doesn't match with what you told me last time we met, I would need that to make sure what I'm getting is customized and unique to me, right?
Glory Gray:
Yeah. How many people joined gyms and in January, and I love going to the gym in February because everyone's gone.
Anna Harvey:
Yeah.
Glory Gray:
By then we need that accountability partner.
Anna Harvey:
Absolutely.
Glory Gray:
We're human.
Anna Harvey:
Yeah, because we're human. And people often will say I can I'll get a book on retirement. And I think have at it, there's a gazillion, probably that's a low number of self-help books, right? Many of which have grown on the retirement shelf, because again, Boomer cohorts so large. So, we sometimes think we can get a book, and man I have done this myself, so I know this to be true. I get a book and it's even done in such a great way that it's giving me context and learning and worksheets, at the back of the book and I'm so enthused, but the reality is, I read it, and I think I'll get to that worksheet, and I never do. Never do.
Glory Gray:
Yeah.
Anna Harvey:
Right? And we can waste so many years in what I think is a really precious time of life wandering just lost and wandering, or reading books, hoping that I'll find the one answer to how I want to build my retirement, what I want my retirement to look like. And you know what? You can waste four years when you're 20. And it's nothing. I question whether many of us at this age, 65, 70, beyond 70, do we want to waste four years floundering and wandering and thinking that we're doing the right thing when we end up making so many false starts. I think we need to get on with it, try to be wise and informed about how to move forward in this next life chapter that we want to create.
Glory Gray:
Yeah.
Anna Harvey:
Same in, you'll be your world too.
Glory Gray:
Yeah, absolutely.
Conclusion and Final Thoughts
Glory Gray:
And I think that's a great place to end our conversation today. This has been wonderful having you with us on the Women's Wealth Canada podcast.
Anna Harvey:
That's been a true pleasure, Glory. I could speak with you forever.
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