5 Mental Traps That Keep You From Retiring (Even When You’re Ready)
Ready For Retirement
James Conole, CFP®
4.8 • 793 Ratings
🗓️ 12 April 2026
⏱️ 8 minutes
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| 0:00.0 | As you get close to retirement, something strange is going to happen. |
| 0:02.8 | And it's not the markets, it's not math, it's not even your portfolio. It's your mindset. Even when the numbers say you're ready, you're going to start hesitating. That's why today I want to talk to the five mental traps that you are going to experience before you transition into retirement and what you can do to get through each of them. The first one is the am I really ready? As retirement gets closer, you're going to start asking yourself, should I really be doing this? Am I actually ready? Have I done everything I need to to prepare for what's next? You can keep working, but the right question is should you? What's the real tradeoff here? Because the way you're going to think about it is this. One more year of work, it's one more year of my portfolio growing. It's one more year of my portfolio growing. It's one fewer year that I have to take money out of my portfolio. So you're going to start using this rational justification for a very emotional decision. And the emotional decisions, you're going to want to keep working simply because it's putting off the hard part about this. Are you really ready? |
| 0:54.7 | And all that goes into that mentally. |
| 0:56.3 | But here's the reality. |
| 0:57.6 | That rational decision is wrong. |
| 1:00.2 | Yes, it's more dollars in your portfolio. |
| 1:02.8 | But what's it costing you in terms of your health, in terms of your relationships, in terms of your time left here on this earth? |
| 1:09.0 | When all you're looking at is the |
| 1:10.8 | portfolio projections, of course it's going to feel better to keep working. Of course, you're going to |
| 1:15.9 | feel like maybe a year from now or two years from now, I'll be a little bit more confident because |
| 1:19.1 | look how much more money I have my portfolio. The invisible part of your Monte Carlo analysis |
| 1:23.9 | is how many healthy years do you have left? How many years do you have where both you and your |
| 1:30.3 | spouse and those closest to you are all living? How many years do you have to spend this time with |
| 1:36.1 | your grandchildren at the ages that they are today? How many years do you have with this health and this |
| 1:40.8 | vitality to golf, to travel, to be active. When all you're doing is focusing |
| 1:45.5 | on the Monte Carlo analysis, you're missing out on what actually matters. So understand this. |
| 1:50.2 | Doubt before a major life decision, especially one as big as retirement, is not a sign that |
| 1:56.3 | you're making the wrong decision. In fact, many times the harder the decision should be a signal |
| 2:00.7 | that it's the decision we be a signal that it's the |
| 2:01.4 | decision we need to make. There's something better waiting for you on the other side. There's |
| 2:06.3 | something better waiting for you that's not to say you're not going to feel this discomfort |
| 2:10.0 | actually making the decision to retire. So big decisions create discomfort. That's completely |
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