Why You Can't Retire (Even When the Numbers Say You Can)

Find out if you're working longer than you need to: https://www.demarsfinancial.com/start-here?utm_source=Youtube&utm_medium=Videolink&utm_campaign=46139

If you've done everything right — saved, invested, stayed in when markets crashed, built the kind of number that's supposed to make retirement feel obvious — and you still can't pull the trigger, your problem probably isn't money. It's that you're stuck in a system that was never built to help you actually leave work.
In this episode, Taylor breaks down the two reasons financially-ready people stay stuck in "one more year": the internal one almost no one names, and the structural one almost no advisor will tell you about. He walks through Robert's story (92% confidence, still couldn't retire), Jim's story (one extra working year for $800/month after taxes), and the Purpose-Plan-Portfolio framework we use with clients to actually answer the question a spreadsheet never can.

If your retirement plan stops at the math, you're getting half a plan.

📌 TOPICS COVERED
→ Why a 92% retirement confidence score still leaves people stuck
→ The cultural script that quietly trains high achievers to keep working past "enough"
→ The concept the financial industry never taught you: how to recognize sufficiency
→ Why most advisor meetings end at the math — and what's missing after that
→ How "one more year" can erode 70%+ of its expected value once taxes, IRMAA, and pension quirks stack up
→ The asymmetric risk most retirement plans completely ignore
→ The Purpose → Plan → Portfolio sequence (and why most advisors run it backwards)
→ What permission actually feels like when retirement is built in the right order
→ Why 51% of retirees over 60 wish they'd retired sooner — by an average of 4 years
→ The window for active retirement most people don't realize is closing

00:00 The "One More Year" Trap 
00:38 Robert’s Story: Overqualified but Unconfident 
02:03 The Five Types of Wealth & the "Busy" Trap 
04:23 Reframing "Enough": Is it enough for what? 
05:07 Why the Financial Industry fails at "The Landing" 
06:22 Jim’s Story: The real cost of staying one more year 
08:05 The Risk of Retiring Too Late vs. Too Early 
09:14 The Framework: Purpose, Plan, Portfolio 
11:50 A 50-Year Family Legacy in Financial Planning 
13:33 Why you should believe the math

Resources:

Website:  https://www.demarsfinancial.com/

Phone: (509) 536-9556

Schedule an introduction call with Taylor: https://bit.ly/demarspodcast

Check out Taylor's YouTube Channel: https://www.youtube.com/@TaylorMadeRetirement

Taylor's Newsletter: https://demars-financial-group.kit.com/827c64fe0e

Disclaimer: Since we don't know your specific situation, none of this information should be construed as tax, legal, financial, insurance, financial advice, or other advice and may be outdated or inaccurate. It is your responsibility to verify all information yourself. This content is prepared for entertainment purposes only. If you need advice, please contact a qualified CPA, attorney, insurance agent, financial advisor, or the appropriate professional for the subject you would like help with. Demars Financial Group, LLC or its members cannot be held liable for any use or misuse of this content. Advisory services offered through Demars Financial Group LLC, a Registered Investment Advisor. Demars Financial Group is not affiliated with LPL Financial.

Transcript

SPEAKER_01 0:00

Today's content is pulled from Taylor's YouTube channel. If you want to watch the video version or catch more great content, subscribe by clicking the link in today's show description. Welcome to Taylor Made Retirement, where we explore what it takes to build a retirement that works for your money and your life with third generation certified financial planner Taylor DeMars.

SPEAKER_00 0:28

If you still can't retire, even though the math says you can, it's probably because you're solving the wrong problem. And until you understand what that problem actually is, no spreadsheet is going to give you the confidence to finally leave work. The retirement industry has a framework for building wealth, but almost no framework for helping people leave work. So even financially ready people stay stuck in one more year. I'm a CFP and third generation advisor, and I sat across from hundreds of people in your exact spot. So by the end of this video, you're going to understand why the numbers aren't what's keeping you from retiring, what is and what to do next. Let me show you what I mean. A client of mine, I'll call him Robert, was 59 years old and had done just about everything right. He was 32 years at the same company, 3.4 million saved for retirement, his house was paid off, his wife was still working because she wanted to, not because she had to. And when we ran his retirement plan, his Monte Carlo score projection came back at 92%. In this industry, that's a very strong result, meaning over 920 outcomes of a thousand possible futures, Robert is projected to not run out of money. To many, he wasn't just ready to retire, he was overqualified. Yet, despite seeing that score, he said, I just don't have the confidence to pull the trigger. Earlier in my career, I thought the answer to this sentence was just more math. Show the numbers again, another cleaner chart, just to prove it one more time. But it never worked because the math wasn't the problem. What Robert was describing, and what you might be feeling too, is that retirement isn't just a financial decision, it's an identity decision. And the tools most people are given are only those that are built to measure one of those. So if we're going to untangle this, we have to start upstream of the spreadsheet and start with the real reason people who look ready on paper still can't bring themselves to stop. While most advisor conversations stop at the math, there's a second reason this feels so hard, and it's exactly why so many intelligent and successful people stay stuck for one more year longer than they have to. I recently read the book The Five Types of Wealth by Sahel Bloom, and there's a line that I just have been ringing in my head. He asks, Over the past month, when someone's asked you, How are you doing? How often are you answered, I'm busy? Not good, not great, but saying, I'm busy. And when I read that, it stopped me in my tracks because I say it all the time. And once I started paying attention to this, I started hearing it more and more into the people around me. And here's what I think is really going on underneath that word. Because busy isn't just a status update. Busy is the answer most of us are pre-programmed to deliver because busy means I'm being useful, I'm producing, I'm still climbing towards something. And in our culture, we see that as a signal of that our life has value. But being busy and time poor in order to make more money is something our American society actually applauds, which means for 30 plus years of your career, every time you're saying, I'm busy, the world answers back with some version of good. Every raise, every bonus, every year that the portfolio ticked up, the culture cheered you on, your company did too. Nobody stood up along the way and said, Hey, are you doing too much? Maybe you have enough. You can stop now. And so your identity gets built around this motion and keeping at the grindstone. And now when someone's asking you to stop and walk away from all that, which on paper feels like freedom, but underneath it feels a lot closer to losing a part of yourself. And that's what's happening when you find yourself running the numbers at 11 o'clock at night, again and again. It's not that you're checking the math because the numbers might have been saying yes for a while. You're just trying to figure out how to emotionally relate to a concept that you weren't taught, which is the concept of enough. You've been taught how to build and be rewarded for that in a very quantitative way, but almost nobody talks about how to know or even what to do when you have enough. I see this the most in people who get really good at the work, who show up for 30, 35 years and did well in their career. The same drive that also got them through the 2008 Great Recession, saving diligently and focusing on their long-term goal. Ironically, now that retirement is a short-term goal, the thing that makes you successful is now that might be what's holding you hostage. So here's the reframe. The money was always the tool, but never the point. And the clients I see that perspective clicking with are the ones that stop asking, Do I have enough? and start asking, is it enough for what? And that's the first real conversation most people on the edge of retirement have never had with themselves. This is hitting closer to home than you expected. That's because this conversation almost never gets named. If you want help thinking through it yourself, the link to book a call with me is in the description. But stay with me because there's a second reason this feels so hard, and it has nothing to do with you being irrational. Because the first problem is internal, the second one is structural, where you've been fighting a system that was never built to help you do what you're trying to. Here's what I mean. The financial services industry was built around one question. Can we help people accumulate wealth? And for the last half century, it's done a pretty darn good job at answering it with compound growth, diversification, investing your 401k, and staying the course. An entire profession has been trained around teaching people like you to build the pile. Think about it like flight school, because for half a century, our industry has been teaching people doing the takeoff and doing the cruise, but relatively few are talking about how to nail the landing. That's not an accident. It's a business model. Advisors are largely measured, compensated, and promoted based on revenue and assets under management, which means the system naturally rewards keeping the focus on growing a lot longer than rewarding helping people how to unwind their money and thinking through the landing. And that's what this industry is incentivizing. So when you sit down with most advisors and you ask, can I retire? They've got one tool, the math, to punch in the numbers and then send you on your way. Having the permission is a different question. It's not just a one-meeting question. I find it's often a month-long one. And nobody's having it because our system wasn't built to. Let me show you what this looks like when it actually plays out in a client's life. I'll call him Jim, who's 61, been an engineer for decades, and he's been having the one more year trap for a couple years now, even though his wife had been ready. Between the extra salary he was getting, the 401k matches, the bonus incentives to stay longer, and another year to boost his pension, that felt like real money that he was walking away from. So when he came in to talk with us, we modeled it out. Jim had been expecting around $3,000 in additional retirement income just for doing the additional year of work. But when we actually ran the numbers between a high tax bracket, Medicare surcharges called Irma at his income level, and a quirk on how his pension was calculated in that last year of service, his real net was closer to $800 more per month in retirement income. Now, that's not nothing, but after doing the analysis, Jim just sat there and didn't say anything for a minute. He looked at the screen and his wife, and he said, nobody ever explained the after-tax side. Four months later, he put in his two weeks' notice and retired. And here's why I'm telling you this: the spreadsheet that turned Jim's $3,000 into $800, any decent planner can do that. It's just math. But the meeting after that one, the meeting where Jim had to sit with what he had almost traded another year of his life for, is something that most of the financial industry isn't set up or trained to have. If you've ever been made to feel dramatic for not pulling the trigger despite your numbers, if you've been told some version of you're fine, just relax, they may not be seeing the urgency of getting this decision right because they're looking at the wrong risk. Because most people were asking, what if I retire too early? Almost nobody models the opposite cost. If you retire early and miscalculate, you can adjust. Cut the budget, pick up some part-time consulting, maybe, tighten your travel for a couple of years. Don't get me wrong, it's not fun, but it is recoverable. However, if you retire late and you miscalculate, you cannot get the year that your knee gave out. You cannot get the year your wife got sick. You cannot get the year your granddaughter was four. We as humans adapt to less money pretty quickly, from my first hand experience, but we don't adapt to lost time really at all. These risks are not balanced. They're actually quite lopsided. And our entire industry is obsessed with can you afford to retire? completely missing the question which actually matters, which is how much is this actually costing you? When you see this comparison, you can't unsee it. Our industry is measuring just one side of a two-sided equation. So the real question becomes what does the actual conversation look like that accounts for both sides? And what changes when you finally get to have it? Here's how we like to think about it. The money is the materials, the plan is the architecture, but neither one of them is your house. The house is what gets lived in inside of your retirement plan. So how do you build it? There's an order, a particular order that we need to get right, because most get it backwards. We like to think of it as starting with the purpose, the plan, the portfolio. Three steps only in that sequence. The purpose is asking yourself, what do you actually want the next 30 years to look like? What matters to you? What would make you feel like those years were well spent? We uncover this in our first meeting with clients called the discovery session, asking questions that most people haven't ever considered out loud. They're quiet for a bit, and then things come up like their needs first. The non-negotiables covering the house, healthcare, groceries, gas, the essentials. And then they come up with their wants, the things that make the years feel like their own, the annual trip they want to do, having a place in the summer, having a grandchild's college fund set up. And then some wishes like to come up as well. The big swing stuff, like a six-week Italy trip, getting a boat, a place on the water, the things that you'd love to do if the years keep cooperating. We ask these things about needs, wants, wishes, not because we can promise everything under the moon, but we want to put it on the table and see what's possible. This purpose exercise tells us what good looks like for your specific situation, not the benchmark, not your neighbor or the average retiree for you. So next comes the plan, which becomes a harder question. How does how much does that lifestyle actually cost? And how does your retirement income become dependable for potentially decades to fund it? And essentially, we're asking ourselves what trade-offs are worth making and what aren't. This is where things like taxes come in, Social Security timing, RMD planning. And the plan exists to fulfill the purpose we started with, not the other way around. And then we get to the third part, the portfolio is last. This is how we structure the assets, the savings you've been building up to support the plan. Things like the investment mix, the account types, where exactly your income gets withdrawn from where in each year. For too many, this is where the conversation starts and ends, letting a spreadsheet dictate the retirement timeline and lifestyle, which to me is kind of sad. Confidence doesn't come from a bigger number, it just comes from knowing what your lifestyle costs, what income is dependable, and what are those trade-offs worth making. I want to be transparent about why I feel so strongly about this, because it's not theoretical for me. When I joined this industry, I was fortunate not to start from scratch. My grandfather started this business, Demars Financial Group, back in 1975. He's since retired, but my dad has built on it for decades. And by the time I came on board, I got to step in alongside him, not only working with him, but also with the clients that had been working with our family for years, some of them for decades. Which meant from day one, I wasn't just sitting with people on the verge of retirement. I got to work with people who were 10, 15, 20 plus years into it, seeing how the decisions they made earlier actually played out. I was able to watch how their lives keep evolving long after those decisions had been made. And it taught me something early on that interestingly, the happiest retirees aren't necessarily the richest. They didn't always wait the longest to retire. They usually were the ones who figured out how to stop letting the numbers be the only voice in the room. In fact, a New York Life study found that 51% of retirees over age 60 wish they retired sooner by an average of four years. One of the reasons for feeling that way struck home for me when I had a client where she and her husband had saved for a bucket list trip for years. They kept pushing it out one more year, her husband kept saying. And after a couple of those years, unfortunately, she got a diagnosis. And today, they're never taking the trip. The window for active version of retirement, where you still get your knees, the years your grandkids still think you're cool, where your spouse is still up for getting up on a plane and taking the trip, that window is shorter than you think and if unfortunately doesn't come back. I'll leave you with this. The hardest part of retirement planning isn't the math. It's letting yourself believe the math when it's already said yes. Most people, in my experience, don't need another spreadsheet, just someone to help walk them through the questions they need to answer, like what those next 30 years look like, and what does it actually take to get there? If that's where you are, that's the kind of work we do with clients without asking you to have us manage your investments to do the planning. The link to book a call with me is in the description, or if there's a QR code on screen if that's easier to scan. If you're not ready to see if we're a fit and want to keep thinking, the next video I'd point you to is one I made that talks specifically about the difference between retiring at 55 versus 65 once you run the actual math. You'll see it on screen now.