Invest in 2026: A Sustainable Financial Plan

In this episode, Motley Fool writers Jason Hall, Jon Quast, and Dan Caplinger explore why many individuals find it challenging to keep their New Year’s resolutions and offer advice on the strategies they’ve developed to succeed.

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A complete transcript is listed below.

Dan Caplingerholds roles at Alphabet, Dollar General, and Nvidia.Jason Hallholds shares in Lemonade, Nvidia, and Shopify.Jon Quasthas roles at Celsius, Dollar General, and Lemonade. The Motley Fool holds positions in and advises on Advanced Micro Devices, Alphabet, Celsius, Lemonade, Nvidia, and Shopify. The Motley Fool has adisclosure policy.

The podcast was captured on January 1, 2026.

Jason Hall:It’s a fresh year, and for countless individuals across the globe, this signifies starting anew. Many of them, perhaps you included, have resolved to make 2026 the year they commit to and maintain an investment strategy. Today is Thursday, January 1. Welcome to Motley Fool Money. I’m your host, Jason Hall. Joining me today are fool analyst Dan Caplinger and the aforementioned Jon Quast. We’ll be discussing our personal investing challenges, achievements, and how we’ve managed to stay committed once the initial excitement fades and the true nature of investing becomes clear. Gentlemen, the hidden truth in the fitness industry is that it relies heavily on January for new members to sign up, only for them to stop coming in February while still paying for their memberships. I may be sounding skeptical here, but the fact remains that we all have stories of significant commitments we made in the past that we failed to follow through on. We won’t be talking about our favorite fitness stocks, though. Instead, we’ll be discussing how we’ve learned from these mistakes and developed investing habits that help us stay consistent. But first, let’s have some fun, mainly at your expense, Jon. What’s an example of a failed resolution you’d like to share, one that you’ve learned from?

Jon Quast:Yeah, I mean, well, it’s not going to be difficult to mock me. This is an easy target. Listen, I don’t make New Year’s resolutions. It’s just not my style. I dislike the concept of waiting for a new year to make a significant change. If there’s something I need to do, let’s do it right away. I try to regularly assess my life and make adjustments when necessary. This includes, of course, adjusting how I invest my money. In the past, in the early stages, I really disliked the idea of investing a small amount in a risky company. I wanted it to be a solid, reliable investment, and I wanted a large stake. I’ve learned, maybe that’s not the best strategy, perhaps a more balanced approach where I invest most of my money in safer options, but also put some into riskier ones, right, Jason?

Jason Hall:Sure, Jon, a barbell approach is something I’ve started using myself for the very reasons you mentioned. Let’s move on to the error. Come on.

Jon Quast:If you decide to invest in a more volatile company, make sure you have a clear investment rationale, explaining why you believe this could be a strong stock. Then, continue investing as your initial reasoning unfolds. As you observe the necessary improvements that transition the company from riskier to more stable, gradually increase your investment. I attempted to protect myself from this situation. However, many companies I invested in, particularly in 2021, began to show signs that my investment rationale was not holding up, and the stock price dropped. At that point, I started ignoring my own guidelines and poured more money into them simply because they seemed so cheap.

Jason Hall:Sure, the well-known investor, Michael Tyson, is recognized for stating that everyone has a plan until the market hits them hard.

Jon Quast:Sure, here’s a paraphrased version of the text: Yeah, the market hit me hard, and I responded by saying, yes, please, give me more? I poured more money into a failing idea. In one instance, it eventually worked out. With lemonade, I was waiting to see if the loss ratio improved before adding more funds. I didn’t actually do that—I added more money before seeing any improvement. Fortunately, things have turned out okay in this case recently. However, some of the companies I doubled down on during 2022 and 2023 are now worth nothing. I do this for a living, and I’ve invested in a company that ended up going bankrupt.

Jason Hall:This is an ideal chance to tease you, but I have a few of those zeros to match yours, so I’m not sure how much I can really expect you to not be that.

Jon Quast:But how many of them did I suggest to you?

Jason Hall:Well, now you’re providing me with material to use here, but I’m not going to. I believe the main idea, and the key lesson for me is that you need to be flexible. When you don’t adapt, that’s when difficulties arise. Dan, could you share a bit on this? Why is it so crucial, especially when people try to improve in areas like investing? What’s a major obstacle they often face that Jon managed to sidestep?

Dan Caplinger:Jason, you might have noticed that when Jon was discussing those zeros, I remained quite quiet because I also have my share of them, and it’s a bit embarrassing. However, it’s something you just need to move past. I believe Jon has an excellent approach regarding the absence of New Year’s resolutions—constantly striving for self-improvement because with resolutions, many people focus too much on the time aspect. With the New Year, it’s like the end of December is this big moment to relax and do the exact opposite of what you plan to change. It’s as if you’re waiting for the apple to fall, and then everything will suddenly be easier, and you’ll stick to your plan perfectly. Well, it rarely turns out that way. Sure, you start off strong. You’ve had some fun before. But once it gets tough, something is bound to go wrong. At that point, if you’ve tied yourself to the idea that you’ll start on January 1 and keep it going all year, and something goes wrong, it’s easy to just say, “Okay, that failed. I’m giving up. I’m returning to my old habits. There’s no point in trying to stick to this plan anymore.” I think the key thing you need to learn is that you won’t achieve perfection. But the good news about investing is that you don’t have to. Being right more often than not is a huge factor in investment success. However, there’s one thing you must do—you have to be resilient. You must accept that you won’t hit a perfect score every time. You have to accept that you’ll make mistakes. You’ll face embarrassing losses. Don’t let that make you quit completely. Just get back up, leave it behind, move on to the next investment idea, and keep going. Don’t wait until 2027. Don’t wait for the next New Year’s resolution period. Just get up from the mat and keep moving forward. That’s the best thing you can do.

Jason Hall:Dan, one of the challenges I’ve faced in the past, and the gym example is a perfect illustration, is that we don’t typically say, “I’m going to go to the gym three times a week.” Instead, we say, “I’m going to get in shape.””I’m going to lose 30 pounds.””I’m going to make some money.””I’m going to invest.””I’m going to succeed.” We concentrate on the end result, and when we face obstacles and see the goal becoming more distant, we quit. However, if we focus on the process and the habits we need to develop, it makes a big difference. In my opinion, this is the underlying theme behind all of this. I won’t tell you how much money I spent at a gym I only visited five times. That’s a different story altogether. We can discuss that another time.

Dan Caplinger:I believe setting measurable objectives is wise, yet I also feel it’s crucial to recognize that you’re gaining knowledge from the journey, even if it doesn’t result in quick achievements. This will prove to be beneficial in the future.

Jon Quast:You mentioned the investor Mike Tyson, but let me reference the investor Rocky Balboa. It’s not about how hard you strike. It’s about how hard you are hit and still continue moving ahead.

Jason Hall:Excellent. Next, we will go beyond those errors. We will discuss the lessons we have learned that have improved us as more reliable and consistent investors. Unlike some of those resolutions, we hope you remain with us.

Welcome back to Motley Fool Money. Dan, you had some fun at each other’s expense. But let’s discuss the lessons we’ve learned and how we can apply them to investing in a way that is sustainable.

Dan Caplinger:I believe one lesson I’ve learned is that one of the most challenging aspects of investing for me is purchasing a stock when I feel I’m slightly behind. It’s too late. I’ve missed the trend and it doesn’t make sense for me to try to join in. Too often, I just say, forget it, I missed my chance, and then the stock continues to rise. After that, I find myself wondering, why did you give up on that? But I realize I just need to work on this. Recently, I made a positive step. I purchased shares ofDollar General, which is Ticker DG. I found myself entering their stores more often than I anticipated because it’s turning out to be a reliable source for discounts on certain items like soft drinks, as grocery stores are applying pricing pressure. They’re keeping absurd profit margins on these products. Dollar General, on the other hand, is more appealing. Dollar General stock hasn’t performed well until recently, although it did well during the 2022 bear market, but then it plummeted. In 2023 and 2024, it couldn’t maintain the growth goals it had set. However, since late 2024, it has doubled from its lowest point, and I’m frustrated that I didn’t recognize the turnaround sooner. That would have completely stopped me from purchasing before. But this time, I’m taking the opposite approach. I’ve recently bought some shares.

Jason Hall:This is somewhat similar to a couple of weeks ago, when the three of us were together, and we discussedAlphabet, and this is one that you recognized the chance to purchase in the past when it was performing poorly. This is a lesson I’ve also learned. With Dollar General, it’s a genuine recovery. The company is truly facing significant challenges. What I’ve come to understand is that sometimes it’s better to arrive late at the recovery than to rush in too soon when the business is still in trouble. Jon, what is a strategy you discovered that has helped you stay persistent?

Jon Quast:Sure, here’s a paraphrased version of your text: I’ve begun to focus on investing in companies that I truly admire or have a strong connection with. I genuinely enjoy the company. I’m not exactly sure when this shift happened, but it was a few years back. When I reviewed my portfolio, I noticed that all the companies I’ve invested in have the potential to grow, but they weren’t necessarily a collection of businesses I was passionate about or excited by. It’s not a purely mathematical approach, but more of a psychological one. Let me explain for a moment. Among companies valued at over $10 billion, four of the top five over the past decade are… Nvidia, AMD,Celsius, and ShopifyEach one has experienced a drop of 30% or more multiple times. Three of them fell by 70% at some point, even while they were among the top five best-performing stocks. Here’s the catch: if you don’t truly like the company or its business model, when it drops that much, you might start questioning whether you really want to hold onto it. That’s when you end up selling at the worst possible moment. I’ve been focusing on investing in companies I believe have strong potential and that I genuinely like, constructing my portfolio around brands I’m committed to holding through all kinds of market conditions. It’s not about numbers—it’s about psychology, and there’s a significant mental aspect to investing.

Dan Caplinger:That’s a really insightful observation, Jon, because when you have faith in the business, there are always people who doubt it and drive the stock price lower. You simply inform those skeptics that they’re mistaken, regardless of how much the decline continues. Naturally, this doesn’t guarantee you’ll be correct all the time. However, when things don’t go as planned, you won’t end up with the added regret of thinking, well, I never liked that company. Why did I ever invest in it to begin with? When the stock recovers, like the ones you mentioned, it feels even more rewarding, especially when you achieve significant profits after going through a long period of difficulty.

Jason Hall:One of the intriguing aspects for me is that beginning with a business perspective definitely offers advantages, particularly when it comes to regret minimization, which can be quite challenging. If you start by genuinely liking the business, as you mentioned, it certainly aids in staying committed during tough times. However, my only warning is that there’s a fine line between being strongly drawn to a business and allowing that attraction to turn into bias, which can make it harder to remain objective when the business faces real difficulties.

Jon Quast:Indeed, it’s definitely a two-sided situation. We must keep a clear and realistic view of the company and its future prospects, as well as its capacity to generate value over time. If you have a strong affection for the company, it might be somewhat more challenging, but there are advantages to this perspective. You’ll end up keeping the stock, and maintaining positions in potential top performers is essential for achieving long-term success in your investment portfolio.

Jason Hall:We’ve discussed some of the things we’ve accomplished, but in the next part, I’d like each of us to talk about a habit we developed that has significantly impacted our personal financial success. Stay with us for that.

Welcome back to Motley Fool Money. To conclude today’s show, let’s each share something we’ve learned that really helps us stay committed over the long haul. I’ll start. The one thing that has made a significant difference for me is postponing my earnings reviews for my core investments. I have numerous professional responsibilities to the Fool and its members regarding several companies I track. However, generally, I don’t go into depth on earnings for most of my personal holdings until we’re weeks past the earnings season. The reason I do this is so I can be entirely on the other side of how the market reacts and what the analysts are saying, allowing me to be more objective. There’s also a humorous aspect to this that plays a big role in my mindset. It also helps me place less emphasis on a single roughly 90-day period of results for companies I hope to own for multiple decades in many cases.

Dan Caplinger:Jason, I can’t tell you how often I’ve witnessed a stock making a significant move after hours following its earnings release. Everyone discusses the reason behind this big movement. Then, overnight passes and regular trading begins. Suddenly, the stock moves in the exact opposite direction. It reverses course, and everyone who was discussing it the previous night is now scrambling to figure out, okay, do I just flip the headline from down to up, or what explanation am I going to come up with for why it’s up when I provided such a solid explanation for why it was down last night. It’s one of those situations where your approach helps avoid that back-and-forth turmoil. All that short-term chaos unfolds, and then you’re left with the real story in a longer-term perspective, which is precisely what you want from the start.

Jon Quast:Jason, I’m interested. For me, time seems to fly by, and I believe there’s a lot of value in your approach of waiting before reviewing the report. However, I came across a company report this morning. I thought they had just released it last week. It turns out it’s already been three months. How do you keep track? What prompts you to revisit it, and how frequently do you do so?

Jason Hall:I probably shouldn’t confess this, but I don’t. After 15 years of actively researching and investing in stocks, I’ve come to realize that if I miss a quarter, there’s likely nothing significant that I’ve overlooked—the hard truth is that it’s not that big of a deal. Part of my process, however, is always reviewing the 10-K. I read the annual report every year. If you know where to focus, you don’t need to go through two or 300 pages. There are maybe 25 pages that are truly important in a company’s annual report. If you do this, you’re unlikely to miss anything crucial, unless you notice the stock has gone up or down significantly since your last check-in. That’s when you should take a closer look at the business, do some research, and figure out what’s happening.

Jon Quast:Wow, I really like that. There’s likely more value in what you just mentioned than what I’m about to say, but I’ve developed a small habit of being open to dollar-cost averaging. This involves purchasing small amounts over time instead of buying everything at once. There are studies out there that show mathematically, it makes sense. If you’re going to invest in a company, just go ahead and invest the amount you plan to. Dollar-cost averaging doesn’t always make the most mathematical sense. However, sometimes I face a big psychological challenge, going back to what Dan was talking about with Dollar General. I often struggle with moving from the sidelines to actually buying a stock, and I found that being willing to dollar-cost average that initial purchase helps me get started. Now I’ve overcome that mental barrier, and I’m ready to invest a larger stake much sooner than I would have if I hadn’t made that first small purchase.

Jason Hall:Sure, here’s a paraphrased version of your text: “Yeah, Ansel Adams is well-known for stating that the best camera to use is the one you have on hand. When it comes to investment strategies, it doesn’t matter how ideal the approach is if it doesn’t align with your situation. This perfectly illustrates how research might suggest one thing, but real-world results can be different. Being open to both averaging up and buying during dips works because if your main focus is on the business itself, you’re more likely to achieve better results, Dan?”

Dan Caplinger:It’s my turn to share. I’m married, and my wife and I. We generally keep our finances separate, particularly when it comes to our investments. However, we do have one major joint stock account that I mostly handle. One interesting observation I’ve made is that I tend to leave this account untouched more effectively than my individual accounts, and as a result, it has performed better. It’s beneficial for me to have my own separate avenues for taking risks on some intriguing trends or more speculative stocks. However, that joint account has been the central part of our portfolio, and I’ve found that having a more balanced and less volatile portfolio has been incredibly helpful—not only because it has done well, but also because it provides the stability that allows me to take on a bit more risk in other areas of my investments.

Jason Hall:As a married individual, I can attest that my partner’s evaluation serves as a great motivation to act more responsibly when it comes to investing. It’s amusing that you brought that up. From my own experience, we have a taxable brokerage account that I tend to interfere with less, and this approach has extended to the educational investments for our son. The same principle applies, and it’s interesting how these accounts have performed quite well simply because of the encouragement to act a bit more thoughtfully.

Jon Quast:Similarly, I’m very appreciative of the Motley Fools’ disclosure policy. All three of us are required to reveal our positions. Everything we do is somewhat public. This has significantly improved my investment results because knowing that if I act in a way that’s not capital F foolish, it will be visible. If I make a mistake or a poor decision, it will be publicly known. It helps keep you more focused on maintaining good investment principles. I agree with what you’re saying, Dan.

Jason Hall:Dan, Jon, I truly value you both for joining and being open about sharing your errors and how they contributed to your achievements. This has been an excellent episode.

Dan Caplinger:You’re welcome, Jason. Have a wonderful New Year.

Jason Hall:Wishing both of you and all our listeners a Happy New Year. I hope you have an extremely successful 2026 and even more so beyond that. Keep in mind, as always, that individuals on the show might have financial interests in the stocks they discuss, and The Motley Fool may have official recommendations for or against them. Therefore, don’t make investment decisions solely based on what you hear. All personal finance content adheres to The Motley Fool’s editorial guidelines and is not endorsed by advertisers. Sponsored content from advertisers is provided for informational purposes only. For our complete advertising disclosure, please refer to our show notes. This is Jason Hall, joining Jon Quass and Dan Caplinger, and the entire Motley Fool Money team. We’ll see you tomorrow.