There are non-financial areas of our lives that need to be thought about and planned for prior to making the transition into retirement. If we avoid or put these off, these areas become like “potholes” we encounter while driving in the spring- they pop up when we don’t expect them and cause problems on the journey to our destination.

My guest for this episode is fellow retirement coach and author, Mary Blissard. In this episode, Mary shares some of the major potholes people experience in their transition to retirement and how to avoid them. To read Mary’s entire chapter on this topic, pick up your copy of The Retirement Challenge- A Non-Financial Guide From Top Retirement Experts.

You can learn more about Mary and her retirement coaching at


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RWS: The topic for today’s episode is Potholes On the Road To Retirement. My guest is fellow retirement coach and author Mary Blissard. Along with her work as a retirement coach, Mary is also an airline pilot. She lives in the Washington DC area; you can learn more about Mary and her retirement coaching on her website, which is Flying Forward In Retirement.

Mary and I both wrote chapters in this book, The Retirement Challenge- A Non-Financial Guide From Top Retirement Experts. Mary’s chapter was titled Potholes On the Road To Retirement. I’m happy to have Mary here to talk about her chapter and share what some of these “potholes” are on the road to retirement, and more importantly, how we can avoid some of the potholes. So welcome Mary! Thank you for being with me today.

MB: Happy to be here!

RWS:  Good, good. So let’s jump in Mary. I wanted to start with at the beginning of your chapter, and I’m going to read it, because I think it really sets a good tone for your chapter. You point out that “a successful transition to a happy and fulfilling retirement begins and ends with your relationships both inside and outside of the home.”

So tell us why relationships both inside and outside of the home are so important in our transition into retirement.

MB: Well, the people, when you’re getting ready or looking forward to retirement, think about what you are anticipating, all the joyful use of your time. Also the rewards of having worked a full career and then now having the fruits of your labor being mostly the time you have left to spend with your friends and family. One of the things about relationships is that they are required. They’re like a garden. You have to keep nurturing them and fostering growth in them along the way, even though you might not have the time to do it.

And what I’ve found, a lot of people that I’ve coached in retirement, up until the time they retire, they haven’t even thought about their friends and families, and how they’re going to reintegrate back into that social structure. I think especially for people in long-term relationships, there has, has become a pattern of behavior that is just sort of taken for granted of how things are going to be.

MB: But as in many transitions like retirement, there’s usually some changes that occur both in both individuals and also and the people around them. So, what we found in our research was that the key to a happier retirement is having solid social connections. I think that’s been brought up in the news quite a bit lately about the importance of having a social, um, feeling of belonging or not being isolated.

And here’s the essence of it though. If you haven’t started working on it before you retire, it’s somewhat more difficult to make that transition after you retire. So I encourage everybody to start working on it sooner than later. Even introverts, I’m an introvert myself, and can benefit from penmanship, compassion and you know, the feeling that someone gets me. And it doesn’t have to be just couples, it’s also individuals as well. The conventional wisdom has been that retirement is a breeze if you have the money. But I really think the first thing you need in retirement are solid relationships.

RWS: Yup, I agree Mary. And I think that’s a good analogy. It is like a garden nurturing, especially for people like us who are aren’t a social butterflies and make friends maybe as easy or were considered introverts. So, yeah, that’s excellent. Let’s jump into the remainder of your chapter, where you really dive into and talk about the potholes. We don’t have time to cover all of the potholes for our listeners, but I did want to cover a few of those today.

And one of the things that you talk about- I think the first pothole is the importance of communication. And that communication is important in both our personal and our work lives. But, I think the important point that you bring home is that you find that communication is even more important as we transition into retirement. So explain why communication is even more important during our retirement transition?

MB: Well, we know that good communication is the key or the secret to a happier existence. And, as you said, in all environments both at work and at home. But especially there are some unspoken expectations or assumptions that may occur. I call it the mind melding phenomenon from Star Trek, where especially in long-term relationships, people feel like they don’t have to communicate what they need. The other person should know and it’s based on assumptions.

One of the problems with retirement transition, or a pothole that could occur, is if the couple or the individual has not talked about where they want to live. Or they might’ve mentioned 20 years ago that when I retire, I want to live on the golf course, or live on a resort, or getting a Winnebago and travel around the country, and the other partner assumes that is still a valid input or a valid premise that they’re going on.

MB: When, in reality a lot of people change over time and their actual communication about it has dissipated. So, all I ask my clients is to start an open and honest conversation as early as possible leading up to retirement. Because then they can start bringing out the visions, the hopes, and the dreams that they may have cultivated over those years leading up to retirement. And, the 25 year old Winnebago dream is not current. Once people start talking about this premise of what does the future look like, it’s really enlightening because you get to know more about how life has changed for both people.

And also what the expectations are for both people in their retirement journey ahead. I always say something as simple as having a coffee date, spending intentional time on this specific topic, well in advance of retirement, can do a world of good. It also fosters some bonding of we’re a team and we’re going forward and I want to support my partner or whoever is around me in their goals to get what their dreams, hopes and visions are for the future. And you also find the intersecting paths because sometimes they aren’t always the same.

RWS: You brought up two interesting points that people need to keep in mind. One is people’s retirement dreams change, right? What you think retirement will look like when you’re 40 and what you want it to look like when you’re knocking at retirement’s door are much different. And even sometimes as people transition into retirement there their needs, their wants, their dreams change. And so I think that’s one thing that’s really important that you pointed that out.

The second thing, too, is that couples need to talk about this together, because a lot of times couples are on different pages on what their retirement to look like, right? So, one spouse wants one thing and the other spouse wants a completely different thing. And, a lot of times they don’t communicate until they get to the point where they’ve already made or have decided to make that transition into retirement. So, communication really is an important piece of this (transition).

MB: And I think it could be, if it is a stumbling block for some people, to start that conversation. This is where a retirement coach really comes in handy. Because a retirement coach is the person who asking the relevant questions and listening objectively to the answers that the individual or the couple gives. And then asking, follow up questions to say… Well how do you see this fulfilling your dreams in the future? Where would you like to go with that? And this is (creates) sort of a safe space to be when you have this communication initially with somebody else.

But I also have heard from a couple of clients, their best conversations, and this is true I think for parents with children and teenagers, the best conversations often come in the car because you’re in a closed space, you can’t escape. But also, you don’t want to be, there is no hostility or there’s no barrier to the communication. So, friends of mine were driving across the country this week and they have brought the book and they’re discussing it chapter by chapter. And again, they have 10 years to go before they retire, but they want to keep those lines of communication open and start talking about it. I think once you break down that initial barrier to talking, then it kind of naturally occurs.

RWS: Yep, I think you are exactly right. I think the starting (the conversation) is sometimes the hard (most difficult) part. And that’s where having somebody like a retirement coach that can provide a little guidance to get people started helps quite a bit.

MB: Yeah. And also back to the expectations and assumptions. If there is a problem or they come across something that doesn’t jive together, especially for married couples, I recommend that they proactively seek a licensed marriage therapist whose specialty is in this kind of communication. It doesn’t always have to be a negative reason. You can be going for a positive reason. One of my clients did that because of the way there diverse (views). She and her husband had different ways of looking at how the days were going to be spent in retirement. And, they decided this because they had no idea what the other was thinking. They’ve talked with a counselor jointly and found a really good, happy medium, and it was positive for both of them.

RWS: Excellent, let’s jump into another pothole that you mentioned in your book chapter, Mary, and that is the loss of structure in our day. So let me ask you: why is having structure in our day so important in retirement? Because a lot of times we lose our structure, right? Our structure goes away. We’re so used to having this structure for our entire work lives, then all of a sudden we’re (now) in charge of our entire day. So why is it important, first of all, to have that structure?

MB: Yeah, as you mentioned, I think the biggest thing I’ve heard (feedback I’ve heard) is that it is completely discombobulating for individuals, especially high functioning people who have lived and died by a calendar and a schedule their whole careers, to come home and now have an unending stretch of days in front of them with nothing really planned or required to do. And, that discombobulation leads to, it’s sort of a time warp. Where did the day go (at the end of the day) at five o’clock somebody will be like, what? What happened? Where did that day go? And as you get older, you don’t want to waste your days or spend your days not knowing what you’re doing. So I highly recommend that, and this is one of those things that you’ve got to be ready for it.

It’s a universal experience that happens to almost everybody who’s ever had this calendar or schedule at their workplace. The one thing that is really critical, is that they find out some purpose or reason, or something with meaning, to put into every single day. And you know, and I’m not saying it has to be life changing and world shattering. It can be as much as or as little as going to the gym for a fitness class and being up and out the door by 10 o’clock in the morning and dressed. That’s one thing a lot of people end up finding is that social commitments, are very rewarding or (as is) volunteerism. Having some reason to get up in the morning and get out of bed is critical.

I’ll just throw out the example of my 84 year old mother, who when she retired, she finally got to volunteer at some place that she really values and treasures, And it is the thing that keeps her jumping out of bed every single morning. She literally jumps up (for the day ahead). And she also keeps her health in good shape because she wants to keep contributing in this volunteer organization. So if people can have a little bit of purpose and meaning, that helps bring back some structure to your day.

RWS: Yup. You pointed out some good examples, and I was going to ask a follow-up question, Mary. Maybe you and I can come up with some other ideas for the audience (too). What are some ways that we can create more structure in our retirement?

MB: Well, I would say besides having a regular event(s) that you look forward to, or contributing to and doing, within your own house, what are your goals or your vision for how each day, each month and each year are going to be lived in retirement? Some people have never thought about that. This is where retirement coach can really help guide you down the path of what is interesting to you and what do you want to do with your time? Because your time is your most valuable resource. And I think once you figure out what your meaning or purpose is, then your daily structure falls into place.

And you know, and of course it’s incorporating all the different facets of life, the family, the social, and the volunteer or contributing part of your life as well as, you know, regularly taking care of your health and sleep and all of that. But, it does help to write it down and articulate it because your time can be impinged upon as well if you don’t take care of those issues.

RWS: That’s one thing I was going to bring up too Mary, and I don’t know if you’ve had any clients that have done this, but simply taking a calendar and writing down what you’re going to do every day and every week so that you can see what your weeks and your months are going to look like. Because it’s very, when you have, when you’re used to having so much structure in your work life and in your daily life, if we have kids who are very active too, you’re used to your whole day being filled up.

And when you retire, now that calendar is really a blank canvas, right? And (we need to) figure out ways to fill that blank canvas. So, sometimes I think clients should just start with a calendar and start writing down, filling in times of the day that they can do different activities (have activities planned).

MB: And also it’s a useful tool to come back to for them to assess, am I spending my time the way I want to? Or you might find when you look at that calendar in hindsight, oh, I was way too invested in this particular activity where I didn’t get to do what my passion is as much as I wanted to. It’s a good feedback loop of how you spend your time.

RWS: Yeah, that’s a good point too. Let’s jump into another pothole that you mentioned and that is losing our social network when we retire and how important it is to have a strong social network. So why is it important to continue to have a social network when we retire?

MB: Well, back to the importance of relationships and how they boost our sense of happiness. One thing about leaving the workplace, especially if you worked there a long time and you had some camaraderie or a basic affection for the people you work with, that it was easy. It’s easy being with the people that we’re spending eight hours a day with because they understood you, they spoke your language, particularly about the work issues. And also, um, I think there’s that team orientation that does occur a lot of times in workplaces. And unless you’ve proactively tried to maintain that bond once you leave, some people believe absence makes the heart grow fonder. But actually really what has happened, and I’ve heard about this (from clients) is, out of sight and out of mind. And it can be very damaging, hurtful to the person who’s leaving the workplace to not have that social connection. So I asked my clients proactively to consider this, especially if they have people they really enjoy being around or staying in touch with.

MB: Of course, social media, if people like to use that, and you’re comfortable with that, can be sufficient using Facebook and LinkedIn are some ways to stay in touch. But for physical connection of being in the room with the person at the same time I ask my clients that before you retire, start establishing regular interactions, like maybe a monthly luncheon or a quarterly happy hour or even just a regular coffee meeting, so that you get that habit of connecting in person. Because there is a true benefit to one-on-one, or you know, you with the group of people who get you. Um, that really helps.

And then once you retire, that relationship, although it won’t be every day, every way it’s going to be established so you can go back to it and hopefully stay in touch. The other thing is…oh, I was going to say one more thing about, proactive, social interaction. You also have to start establishing who you’re going to interact with when you leave work, outside of work, if you haven’t already set up some kind of social engagements.

RWS: Those are good points. And I think one of the things that happens too, Mary, is when people leave the workforce, they think that they’re automatically going to be able to continue to be friends with these people. But as any of us know who have changed jobs over our careers, that oftentimes doesn’t happen. Everybody kind of goes their own direction, and when we retire we then lose a lot of those connections right off the bat.

And we almost need to start anew as far as developing connections and that’s where I think you brought up a good point, is starting to think about that well in advance. And I think that really ties into the whole structure to, of how we are going to plan our days, and our connections are really somewhat part of that structure because we can find new friends when we go to the gym or when we take classes or whatever we are involved in, (or) whatever activities that kind of help us set that structure for our lives. I think the connections and the communication within social network all become part of that.

MB: Yeah, and although it might take some effort to stay in touch, especially with your workmates, I would like to throw this out there, it’s worth it because (for instance) when somebody passes away that you were very close to and you had not been able to maintain that connection on any level, be it just Christmas cards once a year or seeing them every three months. You don’t want to be that person who goes to the funeral and says, I wish I could have seen them one last time. You know, that’s…It really helps set the retirees up to take an active role in trying to sustain this relationship and not wait passively for the work mates to reach out.

RWS:  So the final section of your chapter, and I wanted to talk about this one, because I really liked the way you titled the final section of your chapter and you called it My Time, My Way, My Retirement, Keeping Sacred Boundaries. So tell us about why you titled this section this way and why boundaries are so important in retirement?

MB: Well, Reid, I’ve heard from, and as a pilot, we have mandatory retirement at age 65. And I was working with some pilots who are retiring and they would call me and say, just tell me how so and so did it before me. How, how did he make that transition? How did she make that transition? And because people want to know, what’s the right way to do retirement? Not just financially but also life. And, um, I, I’ve heard some people say, well, I’m just going to do what my parents did or my father did. And I said, that’s not exactly right for you because you’re a different person.

Everybody has their own retirement journey. Even two people inside a couple, it’s your own independent way how you want to view the next chapter of your life. And so, I think sometimes we’re susceptible, baby boomers in particular are susceptible to other people’s inputs. And, and somebody might say, you know, you should go join the golf club, join our group and play three times a week. Well that might not be the right fit.

And so I encourage, as a retirement coach specifically, that everybody design your own retirement and do it your own way. That’s the only way it’s going to end up being a successful retirement transition. And, what happens is as well is, choosing your own direction and your own path, you also are subject to people saying, well, I, I don’t think I would want to do that. And you’re like, you have your own boundaries. Okay, that’s your opinion. My choices, my way. And I want to know (make sure) that, people are just taking a little bit of time to proactively craft the vision of their specific retirement. And as I said before, the couples, they’ve might each have their own independent path, but it does weave back and forth to intersect. And those are really, positive encounters.

RWS:  Yep. Perfect. That’s great information, Mary. I really appreciate you sharing some of the potholes on the road to retirement. Is there anything else you’d like to mention, either about the book or your chapter, or anything else before we end our meeting today?

MB: Yes, Reid. One thing. The one takeaway I would like for people to understand, and I’ve mentioned a few times here, but specifically in my practice, I’ve seen this over and over again. If there’s much better success at avoiding these potholes and also having a happier retirement transition. If you start the process of crafting your vision three to five years before you retire, and I know some people are like what, that’s so far ahead. But what I’ve found is as you get closer to the finish line or the end of when you plan on retiring, there is a narrowing of vision or possibilities and I think that’s human nature.

But the good news is if you start three to five years out, you have the wide view of all the possibilities of what you might try and do. And you can start practicing, practicing good communication with your family and work, coworkers. Practice some kind of connection that you’re going to regularly maintain.

MB: The other thing about starting that way, out three to five years, is that it feels safer and less risky to take chances to consider (options). Maybe we’ll relocate or things like that. As you get closer, there’s the squeezing down or pressure of I want to do it right and I don’t want to make the mistake. But, you know, with a little distance to go, it’s fine. And I always say, if people are having trouble with this, they should seek out a retirement coach. It can be just even a slight interaction can really change. Make the difference about the happiness in retirement.

RWS: Good points. Thank you, Mary. To learn more about the other potholes Mary discusses, along with 24 other chapters, get your copy of the book, The Retirement Challenge on Amazon. Thank you everybody for watching and listening. We’ll see you next time.