What Does Winning the Lottery Have to Do with Your Retirement? – Quite a Lot

Cartier Wealth | Calvin Combs | 6/18/2026

Last month I wrote an article about winning the lottery (you can read that here if you’re interested). As I did my research, I was struck by two things: #1 winning the lottery is not always a good thing. #2 winning the lottery has a lot more to do with retirement than meets the eye.

Executive Summary (TL/DR):

Retirement and winning the lottery may seem worlds apart, but both create the same core challenge: transitioning from earning money to managing it while redefining how you spend your time and live your life. Without a clear plan, this sudden freedom can lead to costly financial mistakes, identity struggles, and unintended stress.

• Sudden increases in time + money often leads to ‘paralyzing freedom’ and decision fatigue.

• You need to prepare for identity shifts and changing relationships

• The fear of running out can be just as damaging as the risk of running out

Everyone has dreamed about winning the lottery at some point in their lives. The thrill and excitement of cashing in your ticket. The endless possibilities in front of you with unlimited time and money.

But is there something else behind all the glamour and wonder? Yes, there is.

In fact, if you’re not careful, both winning the lottery – and retirement – could ruin your life. Here are four key pitfalls that come with winning the lottery and what you can do to avoid them.

Closer Than Meets the Eye

Now I know what you’re thinking, winning the lottery is nothing like retirement. The lottery is a random windfall that you never saw coming, but not retirement. Your retirement has been planned for, anticipated and painstakingly earned over many years. And that’s all true. But you may be surprised that these two things are actually closer than meets the eye. For example, both retirees and lottery winners have suddenly come into a large sum of money. Now I know this isn’t technically the case with a retiree. After all, your retirement nest egg has been yours all along – but that’s not how you’ve been treating it. If you’re like me, you’d sooner get a root canal before dipping into your accounts early. So practically speaking, the day you retire you’ve unlocked quite the treasure chest for yourself. Another overlap is the total freedom that both the retiree and the lottery winner have. The minute you win the lottery and the minute you retire; you have all the time in the world. Suddenly there are no demands on your time and no restrictions for your future. Experiencing this for the first time is exhilarating…and also terrifying (I like to call it a ‘paralyzing freedom’).

Time and money are just the tip of the iceberg. Once you start mapping out the similarities between lottery winners and retirees the overlap is amazing. What you’ll quickly find is that there are commonalities in the challenges, as well as the benefits.

A Whole New World

In my article So, you’ve won the lottery – now what?, you can see that winning the lottery is a complicated mess. In a moment you’re thrust into a world of taxes, trusts, investment portfolios and charitable giving plans. No matter where you turn, there are multi-million-dollar decisions that need to be made. You used to have a simple life and simple goals and now everything is high stakes and confusing.

Does this sound familiar? If it does, you’ve probably just retired.

Moving into retirement is one of the most jarring and life altering transitions in your entire life. The moment you step away from your career, you’re leaving the familiar world of steady paychecks, automatic tax withholdings and a slowly growing 401(k). Instead, you’re confronted with safe withdrawal rates, Roth conversions, RMDs and estate planning considerations. It’s enough to make your head spin. Retirement pushes you into a complicated and time-consuming landscape of decision making. For many people, this is an unfamiliar and unwelcome world.

Identity Crisis on Aisle Four

Coupled with your new job description and decision fatigue is another problem. Retirement (like the lottery) can also bring about a profound shift in your purpose and identity. Without realizing it, many people have their identities wrapped up in their career. When someone asks who you are, it’s easy for your first thought to be “I’m an accountant” or “I’m a teacher”. But when you step away from your job, that identity is no longer yours. Even if you hate your job, it’s hard to fully anticipate the psychological blow of reinventing yourself at age 65. You’ve done it before, but in the past, you’ve been unknowingly aided by lots of forced structure and interaction. When you go to school for the first time, you’re interacting with classmates and teachers. When you start a new job, you have a boss and co-workers. For most working professionals, there’s never been a time when you have to recreate your identity without any outside structure and responsibility. Now of course, this is a massive opportunity. You can be whoever you want to be and do whatever you want to do! But let’s be honest, it’s going to be hard work. And if your new unstructured freedom wasn’t challenging enough, you’re also hit with a shifting relational landscape.

Altered Relationships

A dramatic change in relationships is one of the more unexpected of the risks of retirement. When you win the lottery, everyone expects this. We’ve all heard the stories about long lost relatives and friends reaching out and asking for handouts. But surprisingly, this challenge can hit the retiree as well.

One of the ways that this shows up is if you’re retiring into a different lifestyle than your friends or family. Let’s say you’ve done the right things. You worked hard, saved diligently, and invested for the long-haul. Now retirement is on your doorstep and you’re ready to enjoy some of the fruit of your labor. You want to go on some nice trips, buy that car you’ve been dreaming of, and you feel a little bit freer when it comes to eating out. The problem is that not all of your friends and family are in the same boat. They can’t go on those trips. They are still driving their 2010 Chevy and in some cases, maybe they aren’t even going to retire. This leaves you in a difficult spot. You want to enjoy yourself and do fun things but part of what makes them fun is the people you do them with. Unfortunately, you’ve only planned a retirement for two, not a dozen. Perhaps you’re even plagued with some survivor’s guilt, or you find yourself judging other people who aren’t as prepared as you. All of these thoughts and negative emotions can easily weigh down your golden years. 

Will I Have Enough?

No matter how much you’ve saved or won in the lottery, a universal problem is the risk of running out of money. We’ve all heard the stories of lottery winners who are bankrupt five years after they cash in their big ticket. They go on extravagant trips, buy fancy houses and cars and before they know it, everything they won is gone. In reality, this is actually a lot rarer than you’d think. Most lottery winners play it smart and stay out of the limelight. But it does happen sometimes. And it’s certainly true that some retirees run out of money before they die.

Let me tell you, it’s pretty scary to be in your late 70s or 80s and to have no more money in the bank. At this point, your body is getting weaker, your skills are outdated and your medical costs have begun to climb. Often, the only option for people in this situation is to move back in with their children or become a ward of the state. This dramatic outcome is the scary bogeyman who looms large in every retiree’s closet. It doesn’t matter if you have $1M or $10M, we’re all at least somewhat worried about running out of money. You’re hard wired to worry about the future and if you’re not careful, it can be consuming.

Fortunately, this dramatic outcome is also rarer than you’d think (at least in America). That’s why the fear of running out tends to be a bigger problem than the risk of running out of money. Anxiety is poisonous and it can destroy the joy that you’ve worked for.

Why Even Retire

Have I scared you yet? I haven’t even touched on your increased vulnerability to financial fraud, the complicated tax and legal issues that you’re faced with, and the negative mental and physical impact of having too much time on your hands.

But please, don’t get me wrong. If I could win the lottery or retire today, I would. My point is that more money doesn’t eliminate risk — it just shifts the risks you face.

There are ways to prepare for every one of the retirement risks that I mentioned above. But it’s hard to prepare for something that you don’t know is coming.

The Prize You Actually Earned

Decades of disciplined saving have built something truly remarkable—your own personal jackpot. But transitioning from earning money to managing it is its own unique challenge. Navigating this sudden freedom requires more than just financial math; it takes a clear strategy for your time, your relationships, and your peace of mind.

Let's make sure the fear of running out doesn't steal the joy of what you've built. We are here to help you manage the complexity so you can confidently step into your next chapter.

Schedule a Conversation: www.cartier-wealth.com/contact

With warmth and precision, 

Calvin Combs & the Cartier Wealth Team 

Cheshire, Connecticut