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I want to tell you about a conversation I have probably more than any other in my career as a financial planner. Someone walks in, they're in their late 50s, early 60s, and we see that they saved well, they've invested well. We run the numbers, everything checks out. They could retire today. But then they say the following. I'm going to work for one more year just to be safe. But that one year becomes two, two years becomes three, three years becomes five. And by the time they finally retire, something shifted. And it's not their portfolio balance that shifted, it's them, their health, their energy, their vitality to do the things they actually to do in retirement, in many ways is pass them by. So today I want to actually show you the math of working one more year. So let's compare these two scenarios, because there's not a one size fits all solution. But once you run the numbers for yourself, I think you'll see very clearly whether that one more year truly is worth it or whether today is the time to call it. Let me tell you about a couple that I'm going to call, Mark and Carol. Both Mark and Carol were 60 years old. They had about one and a half million dollars in their combined 401k accounts. And they had another million dollars in a brokerage account that they had saved up bonuses and some stock that invested. He had been in engineering management for the past 30 plus years. She left her career early to care for her aging parents. And they were at the point where both of them were feeling a little worn down, feeling a little tired and ready for that next chapter. Before telling them, of course, whether they could retire or not, we first had to get a very clear sense on what did they want to spend in retirement. We went through all their expenses. We understood what an ideal retirement would look like for them. We understood what travel would look like, what family time would look like. And all that came out to $95,000 per year. When we compared that 95,000 dol thousand dollars to what they were currently spending, it all checked out. So we felt very confident that that was the actual number that would allow them to do what they wanted to do. When I ran their plan, they were in great shape. Everything checked out. But here's the thing. Every year Mark came up with a new reason to stay. Whether it was a market downturn or you know what, let's wait to see what happens in this election cycle. Or you know what, it couldn't hurt to wait around for one more year to get one more bonus. There was always A reason to stay. Sound familiar? Maybe you've experienced that same thing. So here's exactly what I did. I said, mark and Carol, let's work one more year. In fact, let me show the numbers. Let me run the math to show you what that will actually do for you. And as I do that, let's be very clear about one thing. The math for working one more year is very compelling. They were going to be adding another $60,000. Between 401k contributions, 401 matching contributions. Between saving a portion of their bonus, $60,000 was going to be going to their portfolio. 2.5 million. Assume they even just got a 5% growth rate on that. That's another $125,000 that their portfolio would be growing by. So you take those two numbers, and 2.5 million is getting closer to 2.7 million. Not just that. That's one fewer year that they're spending $95,000 from their portfolio. It's one fewer year that their portfolio has to support all their needs until Social Security starts. So you can start to see here how all the numbers made a ton of sense for him to keep working if the numbers were all we cared about. But here's what I said to them. I said, mark Carroll, this looks so much better. Look, your Monte Carlo score is better. Your portfolio has gone up in value. But let me ask you the question that actually matters here. Let's assume by this decision to work one more year, you have an extra $200,000 in your portfolio. What does that translate into? Well, $200,000. One simple way of looking at that is that translates into about 600, 700 extra dollars per month that you can now spend for the rest of your life. That's pretty darn cool. But let's go back to your budget. You have $95,000 here that we've itemized. What would you do with another $600 to $700 per month? Mark and Carol looked at each other. They thought, and they said, you know What? Nothing. That $95,000 that already enables us to do what we want to do. We don't want an incredibly lavish lifestyle. We simply want to be able to spend time together. The stress of Carol caring for her parents and their final days, the stress of Mark being the position he was in, the demands, the pressures. They just wanted to have the freedom to. To enjoy these golden years together. So when I said, there is one more year of work that you can do, and it looks great, but what does that translate to? A higher dollar Value didn't necessarily translate to a better retirement, to more peace of mind. It was just a way of letting fear take control here. Because there's always going to be a benefit of working one more year if all we're looking at is the financial side. So in that moment when they said, you know what? We have enough, this 95,000 is more than enough, no extra dollars are actually going to change what our retirement in a meaningful way based upon what we want to do, that's the moment the conversation changed. Now, here's what I've come to believe. After working with hundreds of people in their transition into retirement, we are very good at calculating the cost of retiring early. We have software for it. We can understand the 4% rule. We understand these rules of thumb that say, here's what you're leaving on the table if you stop working today instead of working one more year. But despite being so acutely aware of that, we are almost completely blind to the cost of leaving too late. So let me try to put some numbers on that side of the ledger. Mark and Carol are 60. They're in relatively good health, but the demands in the stresses of life are starting to get to them. But overall, they eat healthy, they have their health, no major health events. Let's be realistic about what the next couple of decades look like. I asked Carol to think about how many years she and Mark actually had to do, the types of things they wanted to do in retirement. I'm not talking about sitting on the couch or sitting on the front porch. I'm talking about seeing the national parks, being able to play with their grandchildren, being active and able to enjoy their time together. She said, James, 10 to 12 years, maybe that would take them to their early 70s, and that's being optimistic. Research consistently shows that your healthiest years, sometimes you'll refer to these as the go go years. Those start to decline somewhere in your mid to late 60s. So the reality we're working with here is when you run retirement projections based upon taking you to 90 or 95, that's fine to do, but you're missing the picture. I don't care what your life expectancy is. What I really care about here is what is your health expectancy? What's your health span years? Do you actually have to do all the things you shared with me you want to do? So I asked Mark and Carol, let's assume you have 10 more years of good, healthy living. How many of those years do you want to spend continuing to work? They were quiet for a while and Then Mark said, you know, when you put it that way, maybe it's crazy to think that I've already given up three of them over the past three years. So that's the real math. Every year Mark continues to work, they're paying the price of something that can't be measured on a balance sheet. Now, let me be clear here real quick. Some people love their work. If that's you, keep going. If work is adding to your life and not taking away from your ability to do what you want to do, work itself is not the enemy. Work can be an incredible thing that's very meaningful and additive to your life. But we need to look at this realistically. We need to take a sober minded look at this to understand none of us is guaranteed any specific amount of time. And every single thing we say yes to is us saying no to something else. And as it feels responsible to say yes to work and say yes to saving and say yes to growing our portfolio, the real question is, what's it costing you? What's it going to cost you in terms of regret one day when you have more money than you're ever going to spend and you're looking back on your life realizing you gave up a good portion of the best of your golden years simply to save more money that you were never going to spend? So why do people like Mark continue saying one more year even when the numbers look good? In my experience, it's almost never about the money. Even when it feels like it is. Part of it is fear. Yes, there's the fear of running out of money, but there's an even deeper fear, and that fear is the unknown. You've spent 30, 35, 40 years doing something with your life, going to work every day. And now on the other side of that, it's completely unknown. Who are you going to be when you're no longer the engineer or the attorney or the teacher or the business owner? That's a big fear that holds people back. So a big part of this is identity. If your career has been a major part of how you see yourself, it's very difficult just to switch that off when you retire. Because when you do, even if you're financially free, shutting down work can feel like a loss. Even if it's a win for your freedom and your ability to do what you want to do. And the other part of it is this. The financial headlines will always give you a reason to keep working. Whether it's global uncertainty, whether it's inflation, whether it's the impending recession, whether it's the upcoming election. Whether it's you fill in the blank. There will never be a day where you look at a headline and it says, you know what? Now is the perfect time to retire. All is rosy, all is good. Retire and enjoy your golden years. That's not going to happen. That's why it's so important to have a plan. Engineer your plan that says regardless of what happens in the markets or a recession or inflation, you have a plan that shows you, if you're Mark and Carol, how you can spend that $95,000 per year and be okay long term. How does that change if there's a downturn? How does that change if there's inflation? How does that change when Social Security kicks in? You need to have a plan that's specific to you. But until you run that math, both the math of working one more year as well as the math of what you're giving up, by doing so, you're not going to be able to make that confident decision to do what's right for you. So run the numbers. Yes. But also ask the quality of life questions as well. Once you do those two things, you're going to have a very clear picture of what you're giving up in either direction. All that's left at that point is to ask what's holding you back. Because you got to understand, the goal is never just to accumulate the biggest portfolio you possibly can. The goal is to take that portfolio and turn it into something that's going to support your ability to live the life you want to live. If this was helpful to you, please make sure that you like this. Please make sure that you subscribe every week, putting out videos to make sure that you have access to the highest quality financial information that will help you to create the retirement you dreamed about.
Ready For Retirement with James Conole, CFP®
Episode: The Real Math of Working One More Year (It’s Not What You Think)
Date: June 6, 2026
This episode of "Ready For Retirement" tackles the nuanced decision many pre-retirees face: Should you work one more year to "be safe"? Host James Conole walks through both the highly rational mathematical arguments and the equally crucial emotional and experiential considerations that inform this choice. He draws from a real client example to illuminate the often-overlooked costs of staying in the workforce longer when you're already financially prepared for retirement.
Quote:
"By the time they finally retire, something shifted. And it's not their portfolio balance that shifted, it's them, their health, their energy, their vitality to do the things they actually want to do in retirement, in many ways has passed them by.” – James (01:10)
Quote:
"There was always a reason to stay. Sound familiar? Maybe you've experienced that same thing.” – James (03:42)
[06:00 - 09:15]
Conclusion:
From a purely numerical perspective, staying professionally active for one more year made a strong financial case.
Quote:
"So you take those two numbers, and 2.5 million is getting closer to 2.7 million... all the numbers made a ton of sense for him to keep working if the numbers were all we cared about." – James (08:42)
Memorable Moment:
"What would you do with another $600 to $700 per month? Mark and Carol looked at each other... and said, you know what? Nothing. That $95,000 already enables us to do what we want to do." – James (10:10)
[11:00 - 16:30]
Quote:
"We are almost completely blind to the cost of leaving too late... Every year Mark continues to work, they're paying the price of something that can't be measured on a balance sheet." – James (13:47)
[17:00 - 19:00]
Quotes:
"The financial headlines will always give you a reason to keep working... There will never be a day where you look at a headline and it says, you know what? Now is the perfect time to retire." – James (18:31)
"If your career has been a major part of how you see yourself, it's very difficult just to switch that off when you retire." – James (17:44)
[20:00 - end]
Final Takeaway:
Once you’ve run both sets of math—the financial upside of another year of work and the very real cost in lost time or opportunity—you’ll be empowered to make the right call for yourself.
Quote:
"The goal is never just to accumulate the biggest portfolio you possibly can. The goal is to take that portfolio and turn it into something that's going to support your ability to live the life you want to live." – James (21:10)
James Conole’s episode provides an eye-opening perspective on the true implications of working extra years beyond financial readiness. While the numbers often make a compelling case for more savings, the lost opportunities, vitality, and well-being during that time are rarely considered. The ultimate message: Analyze the finances carefully, but place equal weight on your life goals, health, and happiness when deciding if “one more year” is worth it. Make sure your plan supports not just your financial future, but your ability to truly live during your best years.