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There are 10 things in your life right now draining money and energy from your retirement. Selling them could put tens of thousands back in your pocket and give you the extra confidence and freedom during your retirement years. This will be different from the usual retirement advice because most of what you see tells you what you should buy or how much you should save. But after 15 years of helping people retire, I've learned that the happiest retirees didn't get there by saving more or buying more. They got there by letting go of the right things at the right time. By selling these things, you'll be making room for the things and experiences you actually want in this new stage of life. Let's get into it. The stuff you own is either supporting the retirement you want or it's quietly working against it. There's a line I love from best selling author James Clear in his book Atomic Habits that says environment is the invisible hand that shapes human behavior. And I think that preparing for retirement ties directly back into this concept. This isn't about being cheap or being minimalist for its own sake. It's about clearing space physically, financially, mentally, so that when you finally have the time, you're actually free to enjoy it. I'm starting with the most unexpected one, then ranking each one based upon how much they'll add back into your retirement, saving the biggest one for last it's not a strict rulebook. The point is the why behind each of these items. Item number one the treadmill. Now, this might seem absurd because so many of you are thinking, isn't health so important in our retirement years? Yes. But here's the reality. How many times have you seen a treadmill in someone's house and best case scenario goes unused in the corner. Worst case scenario, it turns into extra storage for dirty laundry. Very few people actually use it and it just ends up becoming a laundry rack. The real reason isn't fitness, it's community. If your way of working out in retirement is walking on the treadmill, staring at a blank wall, that's not the best way to do it. What you're missing out on is the opportunity to connect with others, to have structure by going to a gym, by attending a workout class there. Compare these two options. You have a treadmill that maybe you'll use, maybe you won't. You're distracted by the kitchen and the TV and the other things going on in your house versus having a gym where you know, Monday, Wednesday, Friday at 10am you have an exercise class that you're going to go to and you know Bob's going to be there or, you know, Sally's going to be there. It's not just the exercise that it provides. There's also this sense of community that you get when you actually have a class that you go to. I get the appeal of a treadmill. When you're in a hurry, when you need to do something quickly, it's great to have that in your home. But when you're retired, you have the time that you need. You have the time to say, what can I do with my fitness to not only get a better workout, but also to give myself some structure and also to connect with others. There's a very well known Harvard Business School study that shows the quality of all of our lives is largely driven by the quality of our relationships. And I think all the more so in your retirement years. So get that treadmill out of your home. Sell the treadmill, use the proceeds to go purchase a class at your local gym. Your fitness will be better, your structure will be better, in your community, will be better to. The second item to sell in retirement is the cable package. Can imagine this for a second. You finally retire, you're no longer working 40, 50 hours a week. You finally get to relax and what do you do? You plop down in front of the TV and you turn on cable news all day long. What is cable news going to be showing you? Well, if it bleeds, it leads. You're not going to be seeing the positive things happening in this world. You're not going to be seeing the uplifting things happen in this world. You are going to be seeing the things that are intentionally designed to aggravate you. There's 6, 7 billion people in this world. Of course there's always something wrong that's going on. And if you're spending the good part of your retirement sitting in front of the tv, being fed all the things that are bad in this world. That's not a recipe for enjoying your retirement. Now, I'm not saying don't care about things. If you can do something about the problems out there, go do it. But there's a big difference between doing and sitting in front of your TV complaining. So get rid the cable package, watch what you enjoy, watch what you learn from, but be intentional about the environment that you're living within. So the theme here is the same as the theme with the treadmill. What are you doing to design a better environment, One that's going to be conducive to supporting your retirement years? The third thing to sell is your just in Case items. Now, I like to follow the 3030 rule. If you have an item that you know you should probably get rid of, you don't remember the last time you used it, but you think, well, I might need this just in case, ask yourself this. Could I replace this for $30 or less? And within 30 minutes or less, if the answer is yes, and I don't actively use that, I'm throwing it away or I'm donating it. I don't want clutter in my life. And you shouldn't want clutter either. If you can easily replace it, and if you can do so cheaply, get it out of your life. Think of this as the pebble principle. No single pebble is so heavy that it's going to burden you as you're walking with it. But if you're collecting pebbles your entire life, and those pebbles are in your utensil drawers, and those pebbles are in your close, and those pebbles are the mental clutter, at some point, those pebbles start to weigh quite a lot. And the burden that that leaves you with is something that's quite heavy. So get rid of the clutter, especially if it's something that falls within the 3030 principle. The fourth thing to sell is the storage unit. Now, same exact principle as before. None of these individual items by themselves are a serious burden. But what happens when you've spent 40 years accumulating stuff and you feel attached to that stuff? You also forget that stuff even exists until it comes time to, say, time to clean out your storage unit. What you do is, you ask yourself, is this serving my current stage of life? Is this something that's adding to what I want to do? Or is it something that's becoming a burden? So this doesn't just apply to storage units. This applies to the spare room. This applies to the garage. Take that stuff, take that clutter that you think you're attached to, but you're not really, and sell it, donate it, give it away, do something with it. The principle here isn't that by getting rid of it, your life is automatically better, but that we only have so much time. We only only have so much mental bandwidth. Don't fill that bandwidth up with things that are weighing you down. By eliminating some of these things, it's freeing you up to do other things with your time, your attention, and your money. Okay, quick gut check, real quick. You're not meant to sell all 10 of these things. Just as I go through this, think of the ones that are quietly draining you. That's the easy stuff. Cleared from here, the stakes are going to climb. The fifth thing is the lawnmower. Now, here's an interesting thing I think about my father in law when I say this. My father in law loves being outside. He loves mowing the lawn. He loves the gardening. It's a big passion of his. But he's acknowledged that as he's gotten older, this hobby and this passion, it's become a burden. It's become a thing that's taken up his whole Saturday. It's become a thing that's gotten more challenging to continue doing at the level he once did. So ask yourself, is that you? Do you still love mowing your lawn? Do you still love watering the plants and weeding the plants? If so, awesome. Keep doing it. If not, well, then, yes, the feedback is sell the lawnmower. But the real guidance is to buy back your time. You have such limited time. And think about what I said earlier. You might have 25 years of retirement, but only five to seven really good years. Do you want to waste a single one of them doing things you don't enjoy? And heck, even things that become dangerous at a certain point in time. What would you rather be doing with those two, three, four hours? If the answer is gardening, keep doing it. If not, sell the lawnmower. Buy back your time by hiring someone to do that for you and instead prioritize what you actually want to do. The sixth item is expensive toys that have become burdens. This can be the boat, the rv, the Jet Ski, the second car, the third car, things that you once loved. But if you're honest with yourself now, they just sit in the driveway or sit in the garage collecting dust. And not just that, but those insurance premiums continue to go up despite the fact that you're not really using them. So what's the honest test here? Do you actually use it? Don't tell yourself you'll start going to the lake soon. Don't tell yourself at some point you'll make time to drive your third car. Don't tell yourself, don't. Whatever it is, if you're not actually using it, sell it. These aren't irreversible decisions. If you're really concerned that you're going to regret it, well, when you sell it, stick that money in a savings account somewhere. Don't touch that savings for a period of time. And within six months, if that money's still sitting there and you no longer have the urge to go buy back that rv, to go buy back that Jet Ski, then do something else with it. If, on the other hand, you recognize that was a big mistake and you want it back, go buy something. This is not an irreversible decision. But what is something that you can't live with is the burden that that is on your monthly cash flow with the insurance premiums, as well as on your time, your energy, and the biggest thing here, your mental clutter. You want your retirement years to be free, free to travel, free to spend time with who you want, when you want. And the more stuff you have, the more that clutter pulls you away from what you want to do. The seventh item is timeshares. Almost no one's glad they actually kept these unless you're using it every year. You own annual fees and a fixed calendar. That's the opposite of freedom. When do timeshares actually seem attractive? Well, they seem very attractive in the sales pitch, but after that, they become a burden. I can't tell you how many people I've worked with that have actively tried to sell these things, but they feel stuck by it. They can't get out of it. They can't get out of the commitments. So can you avoid them in the first place? But if you do have them, what can you do to start selling these? What can you do to get rid of them and free up your time? Don't limit yourself to one specific place unless, again, you know you're going to travel there and you have actively traveled there, and it's the best place in the world to you. Otherwise, it's so easy to travel, it's so easy to get a hotel, an Airbnb, something else, anywhere you want to go. Why limit yourself unnecessarily like a timeshare might be doing? I've seen this in my own life. My grandma has timeshares, and she never uses them. Now, part of this is, well, I want my grandchildren to have these one day. I want my children to have these one day. We're sitting here saying, grandma, we want to see you live your life. Don't use your money to buy these things that you're not really using. And if you're not really using, family's probably not going to really use them. Use your money for things you want to do. So this is a classic example to me of something that's held onto so tightly that's actually prevented her from being free to use her money and the things that would add to her life. The eighth thing that you want to sell before retiring is your employer's stock. Now, it's okay to have employer stock when you're working, you might have RSUs or stock options or ISOs. All these things can be a fantastic part of a great compensation package. But here's the thing, it's very risky to carry that into retirement. If you retire and still are overly concentrated in your employer stock, that's not a recipe for success. Success. I don't even care if that stock continues to go up over time on average. Because here's the reality. I've worked with many people who have had concentrated stock positions in their portfolio that they refuse to sell even in their retirement years. And those stocks on paper did really well. But here's what's not accounted for on paper. The fact that you're going to be constantly checking your phone. You're going to constantly be checking that stock price. And as much as you want to say, yes, I'm retired and I'm free to do all this, your mental space is going to be glued to what's your stock price doing. And there's this sense that it's going to weigh you down. And even if it's going up, up, there's the anxiety of what's going to happen next. There's the all consuming temptation to feel like you need to know what's going on. Because so much of your retirement portfolio is concentrated in this stock. Now here's the reality. This doesn't just apply to your employer stock. Now, for most people, their employer stock is their single biggest holding because it was a big part of their compensation package. But the principles in general, if you have one stock that makes up more than 5 to 10% of your portfolio, you're getting into a very risky position. Depending of course, on your overall financial plan. Sell that before going into retirement. Retirement is about having the portfolio that will support your lifestyle. If too much of that portfolio is in one stock, you're not going to be able to enjoy that lifestyle because you're going to be so consumed with how's that stock actually performing. The ninth item to sell before retirement is that oversized home. Here's the reality. Think back to when you first graduated, or when you first married, or the first home you owned. How big was that home? Probably was smaller than your home today. Now let me ask you another question. If you think back to some of the happiest moments of your life, how many of them happened in that first home? For a lot of people, they would say almost all of them. A lot of people have enormous homes today, big homes today, fancy homes today, but they will say some of the best memories we ever had were in that small home we had when we were just married or when we just graduated college or whenever they got into their first place. Well, what happened? Started a family, you had more children, you got a dog, you got more vehicles, you got raises. So of course you had to keep up with the Joneses. And before you know it, all of a sudden you have this really big home that served its purpose when you were raising your family, but now it's just empty. And now it just feels like a liability because the cost of upkeep, the cost of property taxes, the cost of all that goes into it, both financially and mentally, is more than you need today. If you downsize that home, you're not just freeing up that mental clutter that's now home equity that you can live on and increase your lifestyle in your retirement years. That's fewer costs that your retirement cash flow needs to cover in those working years. It's also less that you need to keep up with. So those other hobbies that you have, you can prioritize those as opp to having to spending your time and your money keeping up with this big house. Now, this last one isn't clutter, and it really isn't about money. It's the hardest thing on this list to let go of, but also maybe the most important. Stick with me here. The last item is financial support for adult children. Now, there's a fine line here. Helping your children get on their feet, helping them get a head start, that can be good, but there's a point at which that becomes enablement. And if there's endless support, it eliminates their need to make the hard calls, to make the hard decisions, to do the things that are going to stretch them and grow them as children that will actually set them up for a life of success. And not only is it potentially costing your children their future, it might be costing you today. Let me tell you a quick story about a couple of clients who are actually in the same exact position that I worked with. They had their retirement plan. We ran the numbers, we ran the projections. They wanted to travel and do some really cool things. We said, you're good, let's do it. So they retired and they had about six to 12 months of actually being able to enjoy those retirement years. Then what happened is their daughter went through a very difficult time. Daughter went through a divorce, and she had a couple young children. So my client, of course, wanted to step in and help, as they should have, by the way. They had their daughter move in with them. They helped to support with some of the kids needs, some of the schooling, some of the expenses that went along with that. Now that went on for several months and then months turned into years. And at some point we had to look at their plan again and say two things. Number one, the travel and all that stuff that we were doing and that we wanted to do, that's possible, but you can't do that and provide the significant level of support for your daughter. Not just that, but is this actually helping your daughter? And they admitted that this was true, that yes, the support had gone past the point of support and it was now turning into enablement. The drive that they would have wanted to see, the initiative they would have wanted to see. They were past the ugly part, they were past the part of helping her to get back on her feet. But nothing continued from there. And it was because there was this constant lifeline, it was because there was this constant support that was actually holding their daughter back from being able to make the decisions to do what she wanted to continue doing with her career, to support her family. So not just was it holding their daughter back, it was holding them back. They had to make the difficult decision. If we continue doing this and supporting our daughter, we can no longer take the trips that we actually have on our list of trips that we want to take. So what did that support actually cost them? I would argue at the beginning it was an investment. It was an investment, I think, that was most important to them, which was their daughter and their grandchildren. But after about six to 12 months of that, it was no longer an investment. It was quietly, or maybe not even not so quietly, draining their ability to do what they wanted into retirement. And also holding their daughter back from her initiative and her drive with the rest of her life. So that's the fine line that people have to walk with financial support for their children. Now, notice a thread throughout all of these. It wasn't about the boat and it wasn't about the treadmill. It's about your environment. Every burden that you let go of. A physical burden, a financial burden, an emotional burden. Each list clears a little bit more space for the retirement you actually want. You spent decades building towards this. Don't let a garage full of pebbles weigh down the park that's finally supposed to be free. Now, everything here is about clearing the burdens between you and a great retirement. But there's one burden you can't sell on garage sale. The worry about whether your money will actually last. And that's the one worth getting, right? So if this video resonated. The next video you'll want to see is this one called Stop Working for Money youy'll Never Spend. And if you want to see if you're on track for your retirement comment Quiz in the comments below, I'll send you a free link to a quiz that you can take that shows you exactly where you stand.
Host: James Conole, CFP®
Date: June 20, 2026
In this thought-provoking episode, James Conole tackles not what to buy or save for retirement, but—crucially—what to sell before you step into your next chapter. The focus is on releasing the physical, financial, and mental burdens that quietly drain energy and resources in retirement. Drawing on 15 years of retirement planning experience, James argues that happiness in retirement isn’t about accumulation, but purposeful subtraction. He guides listeners through a ranked list of ten specific items (some surprising, some classic), offering not just what to let go, but why—and what it will unlock in your retirement years: confidence, freedom, and peace of mind.
| Timestamp | Highlight / Quote | Speaker | |:----------:|:-----------------------------------------------------------------------------------------------|:-------------| | 01:14 | "Environment is the invisible hand that shapes human behavior." (Quoting James Clear) | James | | 04:43 | "What you're missing out on is the opportunity to connect with others." | James | | 08:08 | "...that's not a recipe for enjoying your retirement." | James | | 10:54 | "No single pebble is so heavy..." | James | | 15:29 | "Do you want to waste a single one of them doing things you don't enjoy?" | James | | 18:11 | "...the biggest thing here, your mental clutter." | James | | 22:20 | "Grandma, we want to see you live your life..." | James | | 25:00 | "...the constant anxiety..." | James | | 28:18 | "...all of a sudden you have this really big home that…just feels like a liability." | James | | 33:35 | "...after about six to 12 months...it was quietly, or maybe not even so quietly, draining..." | James |
This episode is a must-listen for anyone approaching retirement planning—offering not just a checklist, but a mindset shift from accumulation to purposeful simplification for a fulfilling, free retirement.