Ready For Retirement
Ready For Retirement
You Can Retire… But You Might Not Like the Life You Built
Many people retire with enough money — and still feel lost.
James explains why financial readiness alone doesn’t guarantee a fulfilling retirement, and why some of the most financially prepared retirees struggle once work ends. Through a real-life example, he shows how retirement can solve a money problem while leaving a life problem untouched.
The episode explores the hidden challenges that often surprise retirees: losing identity, too much unstructured time, and strained relationships when expectations don’t align. These risks aren’t captured by retirement software, but they shape how retirement actually feels day to day.
The takeaway is simple and powerful: before asking “Can I retire?”, it’s worth asking “Will I like the life I’m building?”
Money matters — but it’s meant to support a meaningful life, not define it.
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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.
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I've worked with a lot of people who have retired successfully. No debt, plenty of money, Social Security dialed in, and they were completely unhappy. Not because they ran out of money, but because retirement solved the financial problem, but did nothing to address a life problem. And the reason for this is pretty simple. Retirement software, planning software can really only answer one question. And that question is: are you prepared to retire? Do you have a high enough probability of success to make the financial side of retirement work? And that is necessary. That's only half the picture. Because while that projection will show you if you can retire, it will never ask you, what are you retiring into? So why does this happen? Well, it happens because for decades, we are trained, either consciously or subconsciously, to focus on the finish line, to focus on the numbers, to focus on saving, to focus on the thing that is very easy to quantify. And that thing is your retirement readiness. But the problem with this is we make the naive assumption that once work ends, life just fills in and everything is good to go. Here's what we don't realize though. Work quietly gives us those things we don't realize that we need. The structure, the relationships, the purpose. Even when you don't fully love what you're doing for work, there's at least this sense of the things that we all need are being checked off in some way. That's not to say there's not a better way to do it. That's not to say you can't do these things in retirement. But what it is to say is if all we do is focus on the finish line and the numbers and the finances, we might be completely set up financially, but have a horrible retirement. Mark's a perfect example of someone this happened to. He retired at 62. He had all of his debt paid off. He had a little more than$2 million in his portfolio. He had a pension that would kick in, a strong Social Security benefit that would kick in. On paper, his plan showed nothing but success. In the reality is the first six months also felt like success. He caught up on rest. He traveled. He did the things he had never been able to do up until that point. But by month seven, things started to change. Days just started blending together. Friends were still working. He didn't really have any purpose, anything that he was excited to do on a daily basis. And that vacation phase, that honeymoon phase, it was great while it lasted, but it never lasts. So nothing went wrong financially. But the real problem was there was nothing to meaningfully replace the gap that was previously filled by work. So this became a classic example of he retired from something, but he didn't know what he was retiring to. That's the challenge with retirement. We're trained because of commercials we see, because of media we see, because of neighbors we think we see. We're trained to think that once you're done working, life magically becomes full. Life magically becomes fun. Life magically becomes an adventure. And that can be true if you proactively prepare for it. But it will not be true by default. The problem is we spend so many of our years working and saving and deferring and planning for this finish line that we don't think of the other scorecards that exist. We don't think of the other things that actually give life purpose. Yes, we focus on the money, but money should be the enabler. Money should not be the sole pursuit. Money should be the thing that supports our ability to maintain the relationships we have. It supports our ability to prioritize health. It supports our ability to do fun things, to do adventurous things. It supports our ability to give and to live purposefully. But if money becomes a thing, well, that's when your retirement is going to be far more disappointing than you ever thought it would be. So what are the three invisible risks that surprise people when they retire with all the money they need to support their goals, but don't actually have any fulfillment in retirement? Well, number one is identity shock. When you're working, you have an answer to who are you and what do you do. When you're retired, you don't. And as much as we might not think that that matters, when you're no longer a doctor or a teacher or a physician or a carpenter, whatever you are, there's a piece of your identity that goes with that. Now there's ways to plan for that, there's ways to prepare for that, there's ways to put your identity into other things. The point here is if we're not mindful about that, or if we're not intentional about that, work becomes a thing that fills that identity that we all seek to have. So the challenge is retirement asks you, who are you now? If you're not prepared for that, you're going to be caught off guard. The second risk is time just becomes heavy. We all think of more time as automatically equating to more freedom. We think of more time as automatically equating to there's more things or more time I can do what I love. But the problem is if you don't have structure, everything just starts to blur together. Everything starts to feel like it's just drifting. Everything just starts to feel like the sea of sameness. And while that's good for a little bit of time, you need to have that structure. You need to have something that gives some structure to the way you spend your days. Because freedom is great, but freedom without direction doesn't actually feel like freedom. Now, here's the thing. I know that some of you are thinking this. Some of you are thinking either I'm retired and I love the unlimited time. I'm retired, I don't have a big purpose, and that's totally fine. And let me be very clear: this is not universal. Everyone is different. Everyone has their own experiences, everyone has their own stories. What I am specifically addressing to tends to be, not always, but tends to be something that people who were most prepared from a financial standpoint are maybe least prepared for an emotional or a psychological standpoint. Those same people who put their identity into saving and growing and put their identity into who they were in terms of what they did, those are the people that typically have the largest amount of money saved for retirement, but also have the greatest inability to enjoy that. But also those are the same people who, in many ways, are the greatest disadvantage when it comes to enjoying all that for retirement. And that's because of the identity piece. It's because of the structure piece. It's because so much of what they place their identity in that actually gave their life this feeling of purpose and momentum that is stripped away and money alone is not going to replace that. So I don't want to pretend this is something that everybody will face, that all of you will face. But there does tend to be a correlation where the people who are most prepared financially for retirement, in many cases, are the same ones who are least likely to actually enjoy retirement. So with that said, the third risk that I see quite a bit is just the relationship risk. If you're married, you might have two spouses retiring into very different visions for what retirement will look like. Do you enjoy being together 24/7? A lot of spouses, they didn't realize how much it was good to have other pursuits, other activities, and they really enjoyed their time together. But now that it's 24-7, you're starting to get on each other's nerves. You're starting to have misaligned expectations of what that would look like. That's starting to lead to conflict. And that's something that catches people off guard. Or maybe you do have two spouses that retire at the same time, but one had visions of travel and adventure, others had a vision of rest and leisure. How do you reconcile those two things, knowing that both of you are different and both of you probably have your own vision for what a successful retirement looks like? So, what should you do? Well, you should stress test this. If you have a financial plan, we're gonna stress test it. We're gonna say, what would happen if there's a major market decline in the first few years of retirement? What will happen if there's a premature death between you and your spouse? What would happen if inflation is much higher or returns are much lower or you fill in the blank? We need to stress this so we have contingencies of what to do in those situations. Well, stress test the personal side too. Imagine get out a piece of paper and just start writing. You're retired today. So the only thing that changes is you no longer have that job that you're spending 40 to 50 hours a week doing. Does life magically become better? What are you waking up excited for? Who are you spending your days with? What does life actually look like for you to be able to look at that period of time and say, yes, this is everything. This is exactly what I was hoping for it to be. Because this doesn't need to be complicated. This doesn't need to be something that becomes a giant project. This just needs to be something that requires some intentionality on your end. Otherwise, you're gonna fall into that same trap of just drifting into an aimless retirement. So, what do you want retirement to look like? Stress test that. Imagine it. What does a day in the life look like? The same thing that you're gonna do on the financial side, do it on the personal side. Because if the finances are fully locked in, but the personal side, there's no plan, you're going to drift and it's not gonna be what it could be. Now, here's the good news. And working with hundreds of retirees, I do find there's some patterns. What are the things that lead to fulfilling retirement? Number one, there's some sense of purpose. Now, purpose isn't just productivity, like maybe it was in the workplace. Purpose is contribution. Is this volunteering? Is this mentoring? Is this teaching? Is this giving of yourself either your financial resources or your time resources? That tends to be the biggest single thing that most people would credit as giving them that sense of purpose in retirement. You have a lifetime of experience. Don't let that fade away. Use that in a way that's meaningful for you and is meaningful for others. Number two, successful retirees tend to have some level of light structure. You don't need to schedule it every single day, but do you have a routine? Do you go to the gym at the same time? Do you go to a group at the same time? Do you go play pickleball at a similar time? Do you have something that gives some structure to your days? What does this do? It stops everything from feeling like it's just one big aimless blob. You don't really have that sense of structure that many of us really need. Number three, there's a level of connection. Now you can get this through the number one and number two that I just mentioned, but make sure that your connection isn't just once a year trips to see family or twice a year trips to see family. Make sure your connection is somewhat regular. This can be people at the gym. This can be people at church. This can be your family. This can be your neighbors. This can be anyone, but make sure it's someone. One thing that work provides that many of us don't think about until we don't have it anymore is you got social interactions there. You had people to talk to there. You had people that whether you like them or not, there is something that we all need as humans in terms of that connection. Even if you're introverted, you do need some level of connection with someone. So who is that going to be? What's that gonna be? Think about that on the front end because the people who enjoy retirement most tend to have connection as a big part of the foundation for that. And then finally, number four is growth. Retirement should not be the finish line. Retirement might be when you wrap up work, but it should not be the end of your growth. This can be learning languages, this can be going to Toastmaster's classes, this can be learning a new instrument, this can be learning how to play a different sport, this can be anything. But are you continuing to push yourself? Are you continuing to grow? Because growth is what's going to lead to a satisfaction with your life. So the more you can continue with that mindset, retirement's not the end, but instead, retirement should be that point at which you are continuing with these things that have given life satisfaction up until now, just doing so without work is part of that picture. So money absolutely still matters, but money is not the point. Money is the support system. And the sooner we can start to shift our focus from making more money to making money more, making money more freedom, making money more time, making money more personal, allowing your money to support the life that you want to live, that's the shift that's gonna turn retirement into an amazing next season of life, as opposed to being something that you just drift into and never really feel a sense of purpose or meaning within. So before you ask, can I retire? First ask yourself will I like what life looks like on the other side? If you enjoyed this video, give it a like, share with someone who you think you might benefit from it. Thank you for watching.
