Latest / TaylorMade Retirement with Taylor Demars, CFP® / Retire NOW If You Honestly Answer "YES" to All 5 Questions

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Retire NOW If You Honestly Answer "YES" to All 5 Questions · TaylorMade Retirement with Taylor Demars, CFP®

• 0:00
  SPEAKER_01: Today's content is pulled from Taylor's YouTube channel.
• 0:04
  SPEAKER_01: If you want to watch the video version or catch more great content, subscribe by clicking the link in today's show description.
• 0:13
  SPEAKER_01: Welcome to Taylor Made Retirement, where we explore what it takes to build a retirement that works for your money and your life.
• 0:20
  SPEAKER_01: With third generation certified financial planner Taylor DeMars.
• 0:28
  SPEAKER_00: Most people think the retirement question is, can I retire?
• 0:32
  SPEAKER_00: But after working with hundreds of retirees, I think the better question is, can you retire once?
• 0:37
  SPEAKER_00: Because I've seen both versions.
• 0:39
  SPEAKER_00: I've seen people retire and never look back, and I've seen people retire with enough money only to spend the next year or two second-guessing the timing, reworking the plan, or realizing the retirement they stepped into wasn't the one they actually wanted.
• 0:52
  SPEAKER_00: And the difference between those two outcomes is rarely the portfolio.
• 0:56
  SPEAKER_00: So in this video, I'm going to walk you through the five yeses I look for before I feel someone is ready to make a retirement decision that actually holds.
• 1:04
  SPEAKER_00: By the end of this video, you'll have a clear way to tell whether your retirement hesitation is actually about the money or if it's coming from one of the hidden places these decisions tend to break after the spreadsheet already says yes.
• 1:16
  SPEAKER_00: Because the goal is not just to retire now, the goal is to retire once and get it right the first time.
• 1:22
  SPEAKER_00: But before we get into them, there's one pattern behind all five that's worth naming.
• 1:26
  SPEAKER_00: Because most people who spend 30 years saving don't have a name for what happens when it's time to stop.
• 1:32
  SPEAKER_00: But because we see it so often, we call it the accumulator-to-spender crisis.
• 1:37
  SPEAKER_00: It looks like this a robust retirement nest egg projected to last for decades, and yet the person who built it still can't pull the trigger.
• 1:45
  SPEAKER_00: The math may say go, but your brain says, wait, this 30 years you got really good at saving, yet retirement asks you to do the opposite.
• 1:54
  SPEAKER_00: That's the gap that these five yeses are designed to close.
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  SPEAKER_00: So let's start with the deepest one, because for most people, this is where the pattern first shows up.
• 2:02
  SPEAKER_00: And this is where you've got to know if you've stopped moving the goalposts.
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  SPEAKER_00: You know that number that you've had on your head, the one that you decided long ago would be enough?
• 2:11
  SPEAKER_00: Think about what that was five years ago or three years ago.
• 2:15
  SPEAKER_00: And if that number has crept up, say from 2 million to 2.5 or 3 million, but your lifestyle goal and the retirement you want hasn't really changed, that's the issue.
• 2:24
  SPEAKER_00: It's not a financial calculation, it's a psychological one.
• 2:27
  SPEAKER_00: The number moving up isn't a sign you need more, it's just a sign that you haven't felt ready yet.
• 2:33
  SPEAKER_00: So naturally, you raise the bar.
• 2:35
  SPEAKER_00: Because if the bigger number doesn't feel like enough, maybe the bigger one will.
• 2:39
  SPEAKER_00: But when you get to that number, the feeling still isn't there.
• 2:42
  SPEAKER_00: So the number moves again.
• 2:44
  SPEAKER_00: It's the football field problem.
• 2:46
  SPEAKER_00: You're driving towards the end zone, you hit the 20, and someone moves the goalposts back.
• 2:51
  SPEAKER_00: So you gotta keep trudging forward.
• 2:53
  SPEAKER_00: You hit the 10, they move again.
• 2:54
  SPEAKER_00: And from the outside, it might feel like you're making progress, but it isn't progress if the finish line keeps moving.
• 3:00
  SPEAKER_00: And this is what keeps a lot of people stuck.
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  SPEAKER_00: They're not working for the next paycheck anymore, they're working for the next number.
• 3:06
  SPEAKER_00: And every year that they do that, the version of themselves who actually makes the retirement decision gets a little harder to find.
• 3:13
  SPEAKER_00: So ask yourself honestly: has my number increased over the last three years without my actual lifestyle plans changing?
• 3:21
  SPEAKER_00: And two, if my portfolio rose another 10% next year, would I actually retire or would I just move the number again?
• 3:28
  SPEAKER_00: If those questions make you pause, that's the goalposts moving.
• 3:32
  SPEAKER_00: The point isn't just having the right amount of money, it's about knowing exactly how much you need and realizing the money won't automatically make you feel more ready to retire.
• 3:41
  SPEAKER_00: Because if the number keeps moving, retirement isn't your destination.
• 3:45
  SPEAKER_00: It's a finish line you keep pushing farther away.
• 3:48
  SPEAKER_00: And that's not how you retire once.
• 3:50
  SPEAKER_00: But even if you stopped moving the number, there's a stretch of years right after you can retire that can quietly cost you a lot of money if you don't plan for it.
• 3:57
  SPEAKER_00: And that's yes number two, saying, I know how to keep more of what I saved when I start spending it.
• 4:03
  SPEAKER_00: Most people retire thinking the tax part is mostly handled because they contributed to a 401k for decades and feel like the heavy lifting is done.
• 4:11
  SPEAKER_00: But if you're watching this, you already know that the way that you're taxed while you're working and the way that you're taxed in retirement are two completely different games.
• 4:20
  SPEAKER_00: And the choices you make in the first few retirement years can mean keeping six figures or more of what you saved.
• 4:26
  SPEAKER_00: Here's what I mean.
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  SPEAKER_00: The years between when you retire and when Social Security and then RMDs kick in are usually the lowest income years of your adult life.
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  SPEAKER_00: Your paycheck stopped, and the government hasn't forced you to start pulling money out of your retirement portfolio yet.
• 4:41
  SPEAKER_00: It's that limited window when we can do real tax planning, and you get to make decisions on your own terms before the IRS starts making them for you at age 75.
• 4:50
  SPEAKER_00: A recent client couple, I'll call Mark and Linda are a good example.
• 4:54
  SPEAKER_00: He recently retired from aerospace engineering.
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  SPEAKER_00: Linda was a hospital administrator, and she was planning to retire a few years after him.
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  SPEAKER_00: Most of their savings sat in pre-tax accounts, like 401ks and IRAs.
• 5:07
  SPEAKER_00: Meaning their plan was simple.
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  SPEAKER_00: When they needed money in retirement, they would just pull it from those accounts.
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  SPEAKER_00: And they thought that was a clear income plan.
• 5:14
  SPEAKER_00: But when we look took a deeper look at those years between Mark retiring and Linda retiring, we saw something that most people miss, which is for that period of time, their joint income would drop into the 12% income tax bracket.
• 5:27
  SPEAKER_00: After that, Linda's pension, Social Security, and eventually RMDs would push them into a much higher tax bracket for the rest of their lives.
• 5:36
  SPEAKER_00: So we use that window of time, and that five years felt like a flash sale because for many people, the IRS only charges 12% on every dollar you move from a pre-tax account into a Roth account in early retirement.
• 5:49
  SPEAKER_00: After it ends, those same dollars will cost easily 22% or more on top of state income taxes.
• 5:56
  SPEAKER_00: So each year we did this proactive chunk of money from the pre-tax to the Roth, small enough to keep them within that threshold, but big enough to certainly make a dent.
• 6:04
  SPEAKER_00: So by the time that Linda retired, the strategy was on track to save them potentially six figures in lifetime taxes.
• 6:11
  SPEAKER_00: Missing this isn't necessarily a disaster because your planning can still work.
• 6:15
  SPEAKER_00: It just means it gets more expensive every year for the rest of your life.
• 6:19
  SPEAKER_00: RMDs hit harder, more of your Social Security gets taxed, Medicare premiums go up.
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  SPEAKER_00: It's not a surprise.
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  SPEAKER_00: It's all visible from a decade out, but it just needs to be planned for proactively.
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  SPEAKER_00: So ask yourself, do I know what my taxable income will look like in the year I retire?
• 6:35
  SPEAKER_00: And next, have I walked through whether Roth conversions are worth exploring in my situation?
• 6:41
  SPEAKER_00: If the answer to any of those is no, you may have a planning opportunity sitting right in front of you that won't be there forever.
• 6:47
  SPEAKER_00: So retiring once means making the tax decisions before they get made for you.
• 6:52
  SPEAKER_00: Mark and Linda walked out with a tax strategy, but they walked out with something else too, which brings us to the next yes, meaning your spouse and you are reading the same map.
• 7:02
  SPEAKER_00: Most retirement plans get built around just one person's questions.
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  SPEAKER_00: And it's usually the spouse who is most engaged with the finances.
• 7:09
  SPEAKER_00: But of course, for a couple, retirement happens to two people.
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  SPEAKER_00: And if both of you aren't asking the same questions, the plan doesn't break financially, but the household feels the pressure instead.
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  SPEAKER_00: For example, a recent client couple, I'll call Tom and Janet, were a great example.
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  SPEAKER_00: She was 61, a software engineer, and burnt out.
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  SPEAKER_00: Not just a little tired, but done.
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  SPEAKER_00: The kind of done where she had mentally left work months before our conversation.
• 7:37
  SPEAKER_00: Tom, on the other hand, was a few years younger at 58.
• 7:39
  SPEAKER_00: He was enjoying being a marketing director, and every time retirement came up, he kept saying, Well, why not just wait one more year?
• 7:46
  SPEAKER_00: But Janet was just desperate to know, can we afford to have me stop working now?
• 7:51
  SPEAKER_00: While Tom was asking, Well, what does life look like if you stop working and I keep commuting every day?
• 7:57
  SPEAKER_00: It's the same financial plan, but two completely different questions.
• 8:00
  SPEAKER_00: Once we named that out in the open, the conversation changed where Tom wasn't scared of the math, he was just scared of the asymmetry, where she is at home, but he's still on a 7 a.m.
• 8:12
  SPEAKER_00: commute.
• 8:12
  SPEAKER_00: She's picturing relief, he's picturing imbalance.
• 8:15
  SPEAKER_00: I like to call this imbalance the difference between gardening and grinding, where one couple feels the pressure more than the other.
• 8:23
  SPEAKER_00: Yet no spreadsheet I could build was going to give them the real answer to their question until we had named it.
• 8:29
  SPEAKER_00: And this is where a lot of couples struggle in the gap between one spouse is calculating and what the other one is carrying.
• 8:35
  SPEAKER_00: One person is thinking about income and the other one is about identity.
• 8:38
  SPEAKER_00: It's the same future, just different languages.
• 8:41
  SPEAKER_00: When couples skip the conversation and only one spouse retires, resentment shows up despite the spreadsheet saying everything was fine.
• 8:49
  SPEAKER_00: I can see couples then wanting to redo the plan, except the problem is never financial.
• 8:54
  SPEAKER_00: So it's worth asking yourself and your spouse separately, then comparing notes to say, are we truly pursuing the same retirement goal or are we working towards different visions?
• 9:04
  SPEAKER_00: We're assuming that we're in sync all along.
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  SPEAKER_00: And the second question is, do we both know what the first year of retirement actually looks like?
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  SPEAKER_00: Not the budget, but the actual days.
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  SPEAKER_00: Plans seem to break when the numbers work, but the household hasn't agreed on what the numbers are meant to support.
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  SPEAKER_00: So the third yes isn't just can we afford it?
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  SPEAKER_00: It's can we say yes to the same lifestyle in retirement?
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  SPEAKER_00: Now, Janet and Tom didn't get there alone, and most couples don't.
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  SPEAKER_00: If you and your spouse want to actually be on the same page about retirement, instead of just avoiding the conversation for another year, the link below in the description is to set up a call with me where we can figure out together whether our firm is the right fit to walk you through that.
• 9:41
  SPEAKER_00: At a minimum, you walk out of the call clearer than when you walked in.
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  SPEAKER_00: Now, the next two yeses are about timing.
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  SPEAKER_00: Timing is where the do-over either becomes a real risk or never enters the picture at all.
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  SPEAKER_00: So for yes number four is being able to say, I'm choosing to retire while I can still do what I want to do.
• 10:00
  SPEAKER_00: Because most people plan retirement, assuming that retirement you in the future is the same as today you now.
• 10:07
  SPEAKER_00: But the version of you today who can do everything you've planned to do, like the trips, the trails, the active years with the loved ones and the travel, that version has a window.
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  SPEAKER_00: And that window's deadline is often sooner than most people think.
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  SPEAKER_00: I like to call this your wealth span.
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  SPEAKER_00: It's the limited period where your money, time, and health all overlap.
• 10:27
  SPEAKER_00: And for a lot of people, the financial plan works long before they're emotionally ready to act on it.
• 10:32
  SPEAKER_00: A couple I'll call Bob and Carol came to us when he was 63 and recently retired from manufacturing.
• 10:38
  SPEAKER_00: She was 65 and had retired three years before him.
• 10:42
  SPEAKER_00: They had an impressive portfolio with$4.2 million saved.
• 10:46
  SPEAKER_00: And Bob had unfortunately worked at scene three years longer than he needed to.
• 10:51
  SPEAKER_00: He was one of those one more year kind of guys.
• 10:53
  SPEAKER_00: One more year so he could feel better, let the markets recover.
• 10:57
  SPEAKER_00: But last summer, Bob and Carol finally took the trip to Patagonia that they had been planning since their 50s.
• 11:03
  SPEAKER_00: But just two days in, his knees gave out at altitude.
• 11:07
  SPEAKER_00: They had to cut the trip short.
• 11:08
  SPEAKER_00: And after the trip, Bob lamented to me that he felt like the extra three years were to build the safety he hoped for, yet looking back, they were costing him the life he was ironically trying to protect.
• 11:20
  SPEAKER_00: And that's the part of retirement planning that doesn't always show up on a spreadsheet.
• 11:24
  SPEAKER_00: You can rebuild a portfolio, but you can't rebuild a decade.
• 11:28
  SPEAKER_00: Now, don't get me wrong, I'm not saying you should be reckless, but I'm sharing what I see firsthand that shows me that time isn't a renewable resource.
• 11:37
  SPEAKER_00: Sometimes people wait until the portfolio feels perfect, but by the time it does, the trip they were waiting for requires a different body.
• 11:44
  SPEAKER_00: So ask yourself, what's on my retirement list that's age sensitive?
• 11:48
  SPEAKER_00: If I retire three years from now, am I still physically able to do those things?
• 11:53
  SPEAKER_00: Some of those questions are uncomfortable, and they're meant to be.
• 11:57
  SPEAKER_00: Using your wealth while you have your health is a planning principle in my book, not just a phrase.
• 12:02
  SPEAKER_00: So retiring once means saying yes while the version of you who planned that life can still live it.
• 12:07
  SPEAKER_00: But there's just one more yes, the one that most retirement videos won't say out loud.
• 12:12
  SPEAKER_00: And you need to be able to say you're walking towards something, not just away from work.
• 12:17
  SPEAKER_00: The single biggest predictor I've seen across hundreds of clients of who retires once and one who quietly drifts back towards work isn't financial.
• 12:26
  SPEAKER_00: It's whether they were having a clear direction of walking towards something rather than just running from something.
• 12:32
  SPEAKER_00: Many people retire from something, being their boss, the commute, the meetings, that pit in your stomach on a Sunday night, from that version of life that just doesn't fit anymore.
• 12:42
  SPEAKER_00: And that works for a while, but for the first few months, retirement feels like a long exhale.
• 12:48
  SPEAKER_00: No alarm or inbox or someone asking you for just one more thing.
• 12:52
  SPEAKER_00: But running from something only carries you so far, at some point the absence becomes its own weight.
• 12:59
  SPEAKER_00: Because a vacation from work is maybe what, two weeks?
• 13:03
  SPEAKER_00: A retirement from work is the rest of your life.
• 13:06
  SPEAKER_00: And you simply can't maintain a away from mindset for decades.
• 13:10
  SPEAKER_00: A do-over in this retirement lens is one that most people don't see coming.
• 13:15
  SPEAKER_00: They don't call it that.
• 13:16
  SPEAKER_00: They might call it, oh, I'm just consulting for a few years.
• 13:19
  SPEAKER_00: Oh, I'm taking a board seat to help out.
• 13:21
  SPEAKER_00: And sometimes those are intentional and wonderful things.
• 13:24
  SPEAKER_00: But if they creep in and while you're quietly trying to rebuild the structure you retired away from, it means that you never built a structure you were supposed to retire to.
• 13:34
  SPEAKER_00: So ask yourself, what am I retiring to?
• 13:38
  SPEAKER_00: Is it something you can specifically name and is hopefully already partially alive before you leave work?
• 13:43
  SPEAKER_00: Is it on the calendar or is it just an idea?
• 13:46
  SPEAKER_00: Some things could be spending time with grandchildren or developing that health routine you've been telling yourself you'll do, having a community or faith-based role, or actually finishing the project you've already started.
• 13:57
  SPEAKER_00: It doesn't have to impress anyone, but it just needs to be something that's real enough to pull you forward.
• 14:03
  SPEAKER_00: The happiest retirees I work with have answered this long before they file the paperwork.
• 14:07
  SPEAKER_00: So retiring once here means having a yes on the other side of the no.
• 14:12
  SPEAKER_00: Because if all you have is the no, eventually the no pulls you back to where you came from.
• 14:17
  SPEAKER_00: So these are the five, saying yes to I've stopped moving the goalposts.
• 14:21
  SPEAKER_00: My tax strategy is more than whatever the 401k is doing.
• 14:25
  SPEAKER_00: My spouse and I are reading the same map.
• 14:27
  SPEAKER_00: I'm choosing to retire while I still can do what I plan to do, and I'm walking towards something, not just away from work.
• 14:34
  SPEAKER_00: And if you said yes to most of these, you're probably closer than you think.
• 14:37
  SPEAKER_00: If you said no to a few, that's not a problem, that's just part of the diagnosis.
• 14:41
  SPEAKER_00: And in my opinion, many times a full diagnosis is half of the solution.
• 14:47
  SPEAKER_00: Of course, this is a framework for thinking through your decision, not personal financial advice for your specific situation.
• 14:53
  SPEAKER_00: But if you're on the fence with one or more of these yeses, that's where the Brio planning work begins.
• 14:59
  SPEAKER_00: Because retiring is one decision.
• 15:01
  SPEAKER_00: Retiring once, the kind that holds, the kind that doesn't quietly take you back, is a different decision entirely.
• 15:08
  SPEAKER_00: And that's the one worth making.
• 15:10
  SPEAKER_00: So these five yeses we covered today help you decide if you're ready to retire.
• 15:14
  SPEAKER_00: There are five more I would suggest that matter after the decision is made.
• 15:18
  SPEAKER_00: The ones that show up in years one through five of retirement that can protect the decision once you're there.
• 15:24
  SPEAKER_00: I put those into a free PDF called the Retire Once Guide.
• 15:27
  SPEAKER_00: The link is in the description so you can download it today to see which of the ten you're already saying yes to and which might be still waiting on you.
• 15:36
  SPEAKER_00: If any of the five we covered today is keeping you stuck, that's exactly the type of work we do on our introductory call, where you can click the first link in the description or scan the QR code on screen to get started.
• 15:49
  SPEAKER_00: Whichever yes is the one keeping you up at 11 p.m.
• 15:52
  SPEAKER_00: on a Tuesday night, that's the one worth getting answered.