Retirement Planning Beyond Finances: The Ultimate Guide

Most retirement planning focuses on one thing: the numbers. And yes, financial security matters. You need that foundation in place. But here’s what most people don’t expect: You could have every financial box checked off and still feel lost, bored, or lonely in retirement. There’s a lot that goes into retirement planning beyond finances.

After years of dreaming about no alarm clocks and endless freedom, many retirees find themselves asking, “Now what?” In fact, nearly half of retirees say they feel bored within their first two years.

Retirement planning beyond finances is about designing a life that feels meaningful and connected. It’s about the things that don’t show up on your balance sheet but absolutely determine whether your golden years feel golden.

From discovering new passions to building lasting connections, here are the five overlooked elements that shape true retirement happiness.

Show Notes: Your Guide to Retirement Planning Beyond Finances

Hey there. Welcome back. Today I want to talk about some of the most overlooked parts of retirement planning, and it goes beyond the numbers. These are the things that actually shape whether your retirement feels meaningful, joyful, and has some connection. Most of the time we focus on the money, and yes, that matters. We’ve covered that a lot. But it’s not the only piece. You could have all the money covered and still feel lost, bored, or maybe lonely.

One of the things looked forward to in retirement is no alarm clocks, no deadlines, and at first it feels like freedom. But after a while, a bigger question shows up: Now what? And that is so common, so let’s get into it.
Discovering New Passions
The first thing I want to talk about is discovering new passions. Here’s something most people don’t expect: Almost half of retirees say they feel bored within the first two years. After all, you can only reorganize the garage or your closets so many times. This is the perfect stage to rediscover old passions or try something new. Maybe it’s painting, volunteering, gardening, or even an encore career.

Here’s my tip: Try a 30-day curiosity challenge. Each week, pick one new thing. Sign up for a cooking class—okay, that’s not me, I can’t stand cooking—but join a walking group, or finally learn to play the guitar sitting in the corner. Think of something that you’ve kind of wanted to dabble in before. Maybe it’s that pottery class. Whatever it is, say yes. The goal isn’t to be good at it. It’s to stay curious. This is about discovering some new passions.

Now, one of the things that fills the passion and purpose for some is helping out family, and that’s so common in our office. Quite often there’s a new endeavor when I talk to people and ask, “How are you spending your time?” And this is once we’re over the hump of the first kind of shock of the first month or two of retirement, and there is a little bit of boredom, and then they find their rhythm. Sometimes it’s just about being able to help take grandkids to their activities or actually being able to volunteer at the school for reading time with them. Whatever it is, it’s about trying it and staying curious.
The Art of Connection
The next thing I want to talk about is the art of connection. One of the biggest predictors of happiness in retirement is not money—it’s relationships. The Harvard Adult Development Study followed people for 80 years. I’ve talked about this study, and it found the number one factor in long-term wellbeing was connection. So how do we nurture that?

For some, it’s deepening relationships with a partner after years of busy work lives. For others, it’s building new friendships, joining clubs, volunteering, simply saying yes to more invitations. And let’s be honest, retirement can also mean loss—losing colleagues or even loved ones. Staying connected takes effort, it takes work, but it’s worth every little bit.

Practice this: Before retirement, have the connections in place ready to go, already built. This is what my husband—he retired in January—and he is a strong introvert. I have to share, I am on that spectrum as well a little bit. I love one-on-one and I can talk and chat, but I definitely have some of that introvertedness. So it’s about practicing and making an effort to continue with connections.

And that’s something that Ian really worked at before he retired in January. We talked about it—it was important having coffees, making sure you stay connected with those friends. And then in retirement, he actually had that. Every week someone was scheduled for a coffee date so that we could avoid those feelings of loss and loneliness. So you have to work at it and have it in place and have it ready to go.
Creating a Healthy Lifestyle
Okay, so there’s a third thing I want to talk about, and it’s about creating a healthy lifestyle. Now you’ve heard the phrase “health is wealth,” and in retirement it couldn’t be more true. Staying active—even just a 30-minute walk a day—reduces chronic illness risk by up to 40%. I looked that up, people. I wanted to give you a stat that shows just by doing a little bit of activity… Now, probably during your working years, you felt like you never had the time. Now you can make this a priority.

And food matters too. You don’t need to overhaul everything at once, but simply swap. Maybe you were doing takeout lunches at work, and now you can actually have some prepared whole foods and go less processed. Don’t forget mental health: gratitude journaling, mindful practices, a little bit of meditation. This helps reduce stress and keeps you grounded during this big life shift.
The Joy in Giving Back
The other thing to talk about is there is a joy in giving back. Here’s something powerful: Giving back doesn’t just help others—it boosts your own sense of purpose. And studies show volunteering lowers depression and increases happiness. I know retirees who coach kids’ sports teams, they mentor young professionals, or volunteer at local shelters. Every one of them says the same thing: It gave their life some energy, and I think there’s that joy in giving back. There’s a sense of purpose. So ask yourself, where can my skills or my time make the most impact? Is there somewhere you can channel that?
Legacy: Building a Legacy of Love and Wisdom
Last thing I want to talk about here is legacy and building a legacy of love and wisdom. When people hear legacy, they usually think of money. I mean, that’s what I talked about in the last episode—I think it was the last one—as we talk about legacy and planning and probate tax and how to save estate tax, you name it.

But this time I want you to think of something other than money. This is that building a legacy of love. The most valuable legacies… I mean, those are sort of important. We check off the box, we’ve taken care of those pieces around the money, but the most valuable piece is stories, values, wisdom, your history.

That might mean writing letters to your grandchildren or family, recording family stories, or even making a photo album with little notes about each memory. These things often mean more than any dollar amount. What I can say is my mom, in retirement, she has embraced this ancestry and she’s been working on the family tree, and she has the time to do it, and that was part of her legacy—now in retirement.
She actually has the time that she can build on this. Here’s a quick exercise for you: Write down three life lessons you’d want people to remember about you. That’s the start of your legacy.

We have our “what if” binder and the CEO binder of everything, and in there you can actually write your own obituary. I know that sounds morbid. I know you guys always hear me talking about death and planning funerals, you name it. But there’s power in there, and so you can actually write down how you want to be remembered.
Legacy Letter Writing Evening – A New Initiative
We have this idea in our office and we’re just working on it. I can’t tell you when it’ll roll out, but it will most definitely this year or into early next year. We really want to make this happen. We’ll have—maybe it’s once a year, we haven’t quite hashed out the details—but it’s where we have our legacy letter writing evening. Maybe it’s in my head, I’m like, I envision a glass of wine and we have these writing prompts, and it’s where you can write letters to your family and you put them away. You tuck it with your will, and maybe it’s once a year and it’s an update so they have something.

This leaving a legacy letter is not something I’ve made up. I listened to such strong stories and podcasts in business planning, especially being advisors. And one of the biggest gifts was this advisor—and he started this company about spreading the word of writing these legacy letters—is that his father had passed away unexpectedly, and he was young at the time. The person—I can’t remember his first name—but he was a young man at the time. And one of the things they found, and it was a surprise, is in the will his dad had wrote a letter to each of them individually. And it’s not because he had known he was gonna die. It was just one of those things: in the moment, I’m gonna stick it in with my will.

And it felt good, and it was so much closure that he never had. And it was actually having that letter of goodbye. And I just—it really hit home. And I thought, what a beautiful gift.
Taking Time for Thoughtful Legacy Building
So that is something, when building a legacy, that might be writing a letter and taking the time. But now you have this time, and legacy is not just about money. This is doing the things of how you want to be remembered. And so actually being thoughtful and putting some time and thought into it.
The Takeaway: Designing Your Life
So here’s the takeaway. All those things I just talked about—there were five of them. Retirement planning isn’t just about finances; it’s about designing a life. Yes, we need the numbers in place, but just as important are the things that don’t show up on a balance sheet: connection, purpose, health, joy, and legacy.

Retirement isn’t the end of the story. It’s the blank pages you finally get to write. So once we get the money picture completed, the focus is: How do I want to live the years I’ve saved for?

Thanks for listening, and if this episode sparked some ideas for your own retirement, share it with a friend who might need to hear it too. Until next time, take care.