You hear plenty about the virtues of retirement, but rarely about what happens when it goes wrong. But the bad cases, the ones where things don't work out, are the ones you learn the most from. The biggest lesson I ever learned was actually from one of the first clients I worked with as a financial planner. And what happened to them completely changed my perspective on the realities of retirement, the risks that people don't see until they're in it. This was a particularly extreme case, but I want to tell you about it because it's a pattern I see in almost every retiree to a lesser degree. Small cracks that go unnoticed because in the run-up to retirement, most people are focused on entirely the wrong things. He was in his mid-70s when we first started working together, and I honestly would never have guessed that he'd actually initially struggled with retirement until he told me about it. Before he retired, he'd worked at this company for like 20 years. I can't remember exactly what they did, but he joined when it was just him and the two original founders. And by the end of it, it had grown into a small but pretty successful business, and he was part of the senior management team. And he knew he'd known for quite some time that the founders wanted to sell up at some point, but he had shares in the company, so it was something that they were all working towards. They had a couple of false starts, so when they actually managed to find a serious buyer, it seemed like a golden opportunity. And at this time, he was in his early 60s, so in the back of his mind, he knew that he would probably retire once this deal was done. But because they were all just so focused on getting this deal done and obviously not wanting to count their chickens, he'd not actually given that much thought to what's going to come afterwards. The deal did eventually go through, not quite for the price that they were looking for, but it was good enough that it left them in a position where he could comfortably afford to retire. And he told me that at first, retirement was everything he imagined it would be. They went traveling for several months. I think it was South America and then some place after that. But the thing that he could remember is absolutely loving it. The freedom of it, not needing to be on call. He didn't realize how much stress he'd actually been under until you know he was out from it. And they basically came back feeling uh good, feeling lighter, full of stories, looking forwards to getting back into a new life at home and reconnecting with people that he'd not have the time to. And he said that if for a time life felt good, like it felt really full. But then after a few weeks things started to settle down and this is when things started to drift for him. That started off as just this feeling on like a random Tuesday or Wednesday afternoon where you've got no place to be, no one expecting him. Things that you would normally, you know, you think that's a good thing, right? But suddenly having all of this time in the world so many things that he could be doing, it felt disorientating. He felt unanchored. He felt listless. And he told me and this is the bit that stuck with me because he kept coming back to this. But he said I didn't realize how much I needed Mondays. It wasn't the work he missed exactly, but it was the rhythm, the structure, having a reason to get up, to be somewhere with people expecting you. Then at the end of the day or the week, that feeling, that satisfaction you get when you know you've worked really hard and you've done a good job. But now at the end of the day he'd just been left with this sort of slightly guilty feeling that he probably should have done more with it. By the time I met him he'd had years to make sense of everything that had happened. So he could talk about what had gone wrong almost clinically as if it had happened to somebody else. And he said looking back he didn't realize quite how much of his identity was tied to his job. Work had been a huge part of his life and although it was stressful at times but was very good at it. He was the person that everyone turned to when things went wrong, someone people looked up to. And he didn't realize how much of his self-worth was tied up in just being good at something, being valued for that, just being useful, or how much of his social life was actually just all built around work. He was a really social guy, and work enabled him to maintain a huge number of social connections with relatively little effort. He assumed that those friendships, or at least some of those friendships, would last beyond the workplace. But most of them didn't. People had their own lives, had their own friends, and once that shared context of work had gone, they just drifted apart. And he'd now sometimes go a day or two without having a proper conversation with anyone. And he hadn't realized how much he needed that, how important that was, until it was gone. And he said, "You know, you might think, well, why don't you just pick up the phone? You've got all these old friends just a call away. " But he said that when you're in it, it's not that easy. On one hand, we're now more connected than ever, but on the other, actually connecting it's sometimes so much harder. What hurt him perhaps even more was that the old him would have had no problem just picking up the phone, you know, getting stuff done, ticking things off. But now, he's just sitting there thinking about it. He said that the first time he really admitted to himself that things weren't good was about 3 months after they got back from traveling. His cousin, I think, had come to stay. It was somebody who'd recently retired themselves, and at some point, the conversation got on to exactly that. And the cousin said, "It's the best decision I've ever made, and I've never looked back. " It's what — you hear everybody say. And my client nodded and said, "Yeah, me, too. " But in that very moment, realizing that he didn't feel that way at all. You know, he wasn't finding it easy. He was doubting his decision. He'd even thought about going back to work, but he knew that the company would have moved on and it wouldn't be the same. Although, the thing that made him sit up and think, "Okay, this is bad. I need to sort myself out. " was when his son said, "Dad, are you all right? You just don't seem quite like yourself at the moment. " It wasn't said in like an aggressive way or even overly concerned. It was just an observation. But, it was the first time someone else had said that out loud, which made it just feel that much more real. Made him actually stop, take a look at himself, and think how much he had changed, how much he'd been letting himself go, the weight he'd put on, caring less about what he's wearing, shaving inconsistently. He could see that he was not the same. He was not all right, and the thing was that other people could tell, too. But, before he could really do anything about it, and I think this is the part that shocked him into action more than anything. I mean, it'd shock anyone into action, is that unfortunately he was diagnosed with prostate cancer. One in eight men in the UK will get this disease. It's a highly prevalent disease. But, what seems mad to me is how often this seems to happen right after people retire. I think it's perhaps a real pattern where you're running flat out, you're still working, the body holds itself together, even if you're not living the healthiest lifestyle. But, the moment you stop, it's when all of these health issues suddenly catch up with you. Now, for him, fortunately, they caught it early. He had treatment, it was successful, and he went into remission. But, that period from the diagnosis to not knowing gave him the perspective that, you know, he might not have as much time as he just seems. Made him realize just how much he'd been letting himself go, his health, his relationships, his reasons for living, and that needed to change. Now, before I tell you what he did to turn his life around, I want to take a step back for a minute because this is a pattern I see in almost every retiree, but just to a lesser degree.