The Best Retirement Spending Stories I've Heard This Year

Are You Spending Your Money on What Truly Matters?

A few weeks ago, I challenged you to do the most important thing you can with your money this year—not Roth conversions, not optimizing Social Security, but something far more impactful: aligning your spending with what truly brings you joy. I asked you to write down one thing you've always wanted to do or buy but haven't, set a date to make it happen, and identify where the funds would come from.

In today’s episode, I’m sharing some of the incredible responses I received—stories of travel, family experiences, and meaningful purchases that turned dreams into reality. These stories serve as a reminder: financial planning isn’t just about growing wealth; it’s about using it to create a life you love.

If you haven’t already, take that step. Don’t wait for "someday." Let’s make sure we’re spending in a way that truly reflects what we value most.

Questions answered:
1. Why is it important to align your spending with what you truly value?

2. How can you take action to ensure your money is being spent in a way that brings you joy?

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Timestamps:
0:00 - Reviewing the challenge
1:42 - Ice fishing and family trips
2:46 - Urgency
4:19 - Diving the Red Sea, family cruise
5:35 - Pets and optimizing travel plans
7:28 - Uncertainty and urgency
8:53 - Values, purpose, and happiness

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Chapters

• 0:00 Introduction: Setting the Stage for Meaningful Spending
• 8:29 The Core Question: What’s Your "Must
• 21:07 Inspiring Listener Stories: Aligning Spending with Values

Transcript

Speaker 1: 0:00

A few weeks back, I issued on this podcast encouragement you might even call it a challenge to do the most important thing you can do this year with your money. And no, that has nothing to do with Roth conversions or investing or the way that you're pulling money out in retirement. It had everything to do with how you're spending money. And today's a follow-up episode to that, because in that episode I asked you this question. I asked the simple question of what's one thing you've always wanted to do or buy but, for whatever reason, haven't gotten around to doing it. And by the end of that episode here was the challenge I asked you to write that thing down, whatever it was, on a scrap of paper by the time that the episode was over. I then asked you to write down a date by which you would make that purchase or do that thing, as well as write down where exactly funds would come from, whether it's bonus, stock sale, cash flow, whatever the case might be and by the end of that I asked you to share with me. I said please email me your responses to this question, and I got some really incredible responses.

Speaker 1: 0:58

This is another episode of Ready for Retirement. I'm your host, james Canole, and I'm here to teach you how to get the most out of life with your money. And now on to the episode. So what I want to do in this video is actually share some of the responses you all shared, because the most important thing we can do with our money is align it in the way it's actually being spent. As I mentioned before, it does not matter how impactful your tax strategy is, it doesn't matter how much your portfolio grows. It doesn't matter how much your portfolio grows. It doesn't matter if you've optimized social security, if you can't actually get to a position where you're using this success. You're using this strategy to enhance your quality of life, to enhance the things that you value, by spending money on the right things. So what I'm going to do is I want to share with you some feedback that I got. Go back and listen to that episode if you haven't already, but here are some responses that you all shared with me Thank you for doing so that I now want to share with the audience so we can get some inspiration on what are those things that we can do to align our spending, align our money with the things that we actually value. This was a YouTube comment. Daryl says James, I think this is the most powerful video you've ever done.

Speaker 1: 1:59

I recently retired and I just spent a month ice fishing with my son. The memories made while staying with him in northern Wisconsin are priceless. Love that example. Thank you, daryl. Another comment said this my wife and I traveled with our son from Arizona to see our first home Washington Commanders football game in October of 2024. We're huge fans. The game was on our son's 21st birthday. What a way to celebrate. I can commit to another trip in October of 2025, where the three of us will again travel to see our favorite team play another home game. The memories from the 2024 trip are priceless. I love that sentiment because how many of us have ever taken a trip with family or with friends and regretted it? Very few occasions that actually happening. It's very easy to put off those trips because of the cost, because of schedules, because we're busy, because we have to coordinate, but very seldom do we actually regret taking those trips, because the memories made there, the experience we have there, is the reason that we ultimately save and invest and put ourselves in a position to be able to do the things that we want to do.

Speaker 1: 2:59

This next story speaks to the urgency that all of us should have when it comes to doing the things today to take advantage of the time that we have together. This is a YouTube comment and this individual says I am starting my third year of retirement. My wife and I are taking many bucket list trips every year. We are currently booking two to three trips per year into 2027. My brother-in-law was recently diagnosed with brain cancer and my brother with Parkinson's. You never know what your next doctor appointment might find. We're exploring the world and visiting with our grandchildren at every opportunity. How easy is it to get in the trap of working one more year, waiting for one more bonus, hitting one more milestone when it comes to your portfolio value, only to realize that one day we have a health event, a family member has a health event, a friend has a health event, and we're never going to get to create those experiences, those memories that we would have had we taken the time to do what we wanted to do when the time was right to do it. So I really appreciate that comment coming through.

Speaker 1: 3:53

This next story comes from Ron. Ron says I had always dreamed that we would host a family vacation for our adult kids and my mother when I retire in 2028. However, my mom is nearing age 80 and I'm fully aware that we only have so many opportunities left. So we upped our family vacation to March of 2026 at our family timeshare in Puerto Vallarta. The funds will come through savings and working overtime. In our discussions with family, everyone is so excited to do this and we'd look forward to repeating it in 2028 as well. So perfect example of saying yes, it's easy enough to plan that in three years, but can we do it earlier, when mom's here, when family's here, when people are healthy to do it? So, ron, thank you very much for submitting that.

Speaker 1: 4:31

This next one comes from Harvey. Harvey says amazing timing, James. Last month, a dive buddy asked if I wanted to go on an adventure. Last week I booked the trip and today I booked the flights. Where am I going? I'm going to Egypt to dive the Red Sea for a week and to visit the pyramids in Cairo Museum this May, at 72, to answer some of your questions, the time is now so great example of getting on it and doing that thing as opposed to pushing it down the road.

Speaker 1: 4:55

This next comment comes from Jerry and, just as a reminder. These are the comments I'm getting of asking people please tell me, share with me the things that you're committed to doing today, the things where you're spending your money on things that align with your values. These are the responses that I'm getting, and this next one comes from Jerry. Jerry says this year we're taking our immediate family on an eight-night cruise all 12 of us. Plans are made and tickets are purchased. We also started sharing our two sons' inheritances with them early, about six years ago. We give each of them about $15,000 per year and we enjoy watching them use it. So another wonderful example what are your values? If that's family, what does that look like? Looks like for Jerry. That's both time with family as well. If there's going to be an inheritance, if there's going to be some financial money left to the children at the end of it, why not accelerate some of that today? Why not enjoy getting to see them use those funds to do whatever they're doing with them? So, jerry, thank you for sharing that.

Speaker 1: 5:48

This next one comes from Lois, and this is more of something that she did previous year, but she said I thought you'd be interested in knowing what I did this past year. I bought a puppy. I knew it was going to be expensive between accessories, doggy daycare, food and vet bills and I'm still trying to save for retirement. But I went for it and it completely changed my life. Walking her and snuggling with her on the couch has been so rewarding. Below is a picture of me with Lulu. She included a picture, of course, for dog Lulu, who just turned one years old. So this is a great example. We can get so caught up and I need to save for retirement. I'll do this when I have the funds, I'll do this when I have the resources and, of course, there's a balance here because we can't spend recklessly. But what price tag would Lois put on that puppy? What price tag would Lois put on her experiences with Lulu in just the first 12 months together? Lois, great example there.

Speaker 1: 6:33

This next example comes from Lee. Lee says this is our first year in retirement and we had budgeted and we were planning to travel quite a bit. The one thing we hadn't really considered was how exactly to optimize that travel. But after a little thought, we wanted to put more focus on trips with our grandchildren, who are now four and seven years old. With that in mind, we just got back from taking them to Disney World last week, and it was an unforgettable week filled with smiles and with laughter. In our next adventure, we've booked a Disney cruise in July, which we think is something they should also really enjoy. Our grandkids are only at this age for such a short time, so making the most of it is the one thing we're doing this year to make it special.

Speaker 1: 7:08

What I like about this comment that Lee submitted is he had mentioned that this is our first year of retirement and we had budgeted and were planning to travel quite a bit, so that was already something that's part of the plan. But he went one level deeper. He said how do we optimize that travel? Sure, travel is great. Everyone wants to travel, most people want to travel, but can we do something different to make it as special as it possibly can? And it sounds like Lee and his wife they thought about this and said well, how do we do this in a way that aligns with our other value, which is spending time with grandchildren? So it'll be very cool there. Thank you for sharing that.

Speaker 1: 7:40

Now here's the final story that I want to share with you, the final response that I want to share with you, because I fully recognize. We can still hear this and say that's great, but I'm going to do this later. I'm going to do this at another time. This comment came from a YouTube listener and this individual says this video made me cry. My wife and I were making plans for a retirement when she passed. Even though she was very sick, we still thought we had time. I've been implementing our plan, but I wish she was here to enjoy the plan with me.

Speaker 1: 8:09

Now we have no idea how long we have, how long our spouse has, how long our family has, and if we know we have a long time, how much of that time are we going to have our full health, our full energy, our full vitality? So as we do this, this isn't just some nice thing that we should be doing. There should be an urgency with a message like this, an urgency that we are not promised anything. And if you were to pass tomorrow, what would you look back on and regret having not done? My guess is, for so many of these listeners that are submitting these questions if tomorrow they were to know that was our last day, they would look back on some of these things they shared, on some of these football games on some of these cruises, on this time with grandchildren, they would look back on these things as some of the fondest memories of their life. We don't ever want to be in that position where we're caught looking back on our lives saying what do we all do it for? We have the money, we have the tax strategy, we have all that good stuff financially, but we miss out on these things along the way that actually matter.

Speaker 1: 9:06

So as we wrap up, I want you to understand the key difference here. There's a very big difference between just believing that making more money and spending more money is automatically going to make you happy. That is not true. However, if you can identify what you value most, what's most important to you, and then spend money in a way that aligns with that and supports that, that is where that true joy and contentment and purpose in retirement comes into play. So, to all of you who submitted responses to that previous episode, thank you very much. I did not get a chance to review all of them or go over all of them on this episode, but I did want to share some of these responses, both to encourage you, to give you a sense of what this could look like as well as to caution you of we're not promised tomorrow, and as that listener shared again, I'll read it one more time. My wife and I were planning to make plans for our retirement and then she passed. We need to make sure that we're enjoying what we've saved and what we've worked for today, as well as playing prudently for the future. So I hope this is helpful for those of you looking to align your spending with what you value most. Thank you for all of you who submitted these stories. Thank you for listening and I'll see you all next time.

Speaker 1: 10:13

Not provided any compensation for and has not influenced the content of any testimonials and endorsements shown. Any testimonials and endorsements shown have been invited, have been shared with each individual's permission and are not necessarily representative of the experience of other clients. To our knowledge, no other conflicts of interest exist regarding these testimonials and endorsements. Hey, everyone, it's me again for the disclaimer. Please be smart about this.

Speaker 1: 10:33

Before doing anything, please be sure to consult with your tax planner or financial planner. Nothing in this podcast should be construed as investment, tax, legal or other financial advice. It is for informational purposes only. Thank you for listening to another episode of the Ready for Retirement podcast If you want to see how Root Financial can help you implement the techniques I discussed in this podcast, then go to rootfinancialpartnerscom and click start here, where you can schedule a call with one of our advisors. We work with clients all over the country and we love the opportunity to speak with you about your goals and how we might be able to help. And please remember nothing we discuss in this podcast is intended to serve as advice. You should always consult a financial, legal or tax professional who's familiar with your unique circumstances before making any financial decisions.