What to Do in Retirement to Be Happy, According to 2,000 Retirees
Every year, I talk with hundreds of people who are right on the edge of retirement, usually around 64 or 65, and almost all of them have the same mix of excitement and nerves. They’re excited about the freedom. They’re nervous about the money. And deep down, a lot of them are wondering: am I actually going to be happy?
So when MassMutual released their 2024 Retirement Happiness Study, a survey of 2,000 Americans either in or near retirement, I was intrigued. And honestly? It confirmed a lot of what I hear from my clients every day, while also surfacing a few things that genuinely surprised me.
Here’s my take on what the data says, and what it actually means if you’re getting close to this chapter of your life.
The good news: most retirees are genuinely happier
Let’s start with the headline finding, because I think it deserves more attention than it usually gets: two thirds of retirees say they are happier in retirement than they were while working. Not kind of happier. Not “I guess it’s fine.” Actually, meaningfully happier.
of retirees feel happier than when working
feel less stressed in retirement
feel more relaxed on a typical day
That last one, 82% feeling more relaxed on a typical day, is the one I want to point out to everyone who’s been losing sleep over this decision. There’s a version of retirement that a lot of people are afraid of, where you wake up feeling purposeless and anxious. For the vast majority of people, that’s just not what happens.
“The happiest retirees invest not just in their financial futures but also in their social circles and physical health long before retirement.” — Paul LaPiana, MassMutual
But here’s the catch: expectations are a little too rosy
Here’s where it gets interesting. While most retirees do end up happier, they’re not quite as happy as they expected to be. Pre-retirees think retirement is going to feel like a permanent vacation. Retirees will tell you it feels more like a really comfortable Tuesday.
| Topic | What Pre-Retirees Expect | What Retirees Report |
|---|---|---|
| Feeling happy | 77% expect to feel happier | 67% actually do |
| Feeling excited | 61% expect to feel excited | 41% report feeling excited |
| Main activity | 79% plan to travel; 71% plan to exercise | 83% say watching TV is their top activity |
| Financial worries | 43% worried about having enough money | Only 14% worry about this in retirement |
That travel vs. TV finding is pretty shocking, but I don’t think it means people are failing at retirement. I think it means that the pace of retirement surprises people. You have 40+ hours of free time a week. That’s a lot of hours. Not all of them will be adventures.
The bigger takeaway from that expectation gap, in my view, is this: if you go into retirement expecting fireworks every day, you might feel disappointed by something that’s actually quite good. Managing expectations isn’t pessimism. It’s how you actually enjoy what you have.
Money worries shrink dramatically, and that matters for my clients
I want to spend a moment on the financial anxiety piece, because it’s directly relevant to a lot of the conversations I have.
Before retirement, 43% of people worry about not having enough money to support themselves or their family. That’s nearly half of pre-retirees carrying that weight. By the time they’re actually in retirement? Only 14% report the same concern. And 78% of retirees say they have about what they need, or more.
That’s not a small shift. That’s the majority of people discovering that their fears about money were bigger than the actual problem.
A note from Jamie
Part of what I do every day is help people understand exactly what their healthcare costs will look like in retirement, because Medicare confusion is one of the biggest sources of financial anxiety I see. When you know what your coverage actually costs and covers, a huge piece of the uncertainty goes away. If you’re within a few years of 65, that clarity is worth a lot.
What actually separates happier retirees from unhappier ones
This was the part of the study I found most useful, because it’s actionable. The happiest retirees weren’t just lucky. They did things differently, often years before they retired.
They paid off their debts
61% of retirees who describe themselves as much happier in retirement had paid off all their debts at least five years before retiring. Less than half of the unhappier group did the same. Heading into retirement without debt hanging over you genuinely changes how secure you feel day to day.
They prioritized their health early
Nearly half (49%) of the happiest retirees had made a point to take care of their health, eating well and exercising, in the years leading up to retirement. Among the less happy group, only 32% had done this. The study found that once you’re in retirement, health concerns become the number one anxiety. Getting ahead of that while you still can is one of the best investments you can make.
They stayed socially connected
This one surprised me the most when I first read it. Nearly half (47%) of retirees who aren’t happy admit that retirement has made them feel lonely at times. Among the happiest retirees? Only 16% say the same. The social structure of work disappears overnight when you retire, and a lot of people don’t realize how much they were relying on it. Happier retirees tended to spend more time with loved ones (76%), pursue hobbies (64%), and travel (62%) compared to their less-happy peers.
The anxiety that doesn’t go away: health
Here’s the honest part. While financial fears tend to ease in retirement, health anxiety doesn’t, and in some ways it grows. Retirees who have been retired for over a decade are nearly twice as likely to report experiencing more illness or disability than expected compared to those who just retired.
That’s not meant to be scary. It’s just real. Your body changes. Having good healthcare coverage that you actually understand, and that you chose intentionally rather than just defaulting to whatever was easiest, makes an enormous difference in how secure you feel when health issues come up.
It’s one of the main reasons I do what I do. The Medicare landscape is genuinely confusing, and most people approaching 65 have no idea how many choices they actually have, or how much those choices will affect their out-of-pocket costs down the road.
My overall read: retirement is good, and preparation makes it great
If I had to summarize this entire study in one sentence for someone sitting across from me in a remote meeting, it would be this: retirement is likely to be better than you fear and a little quieter than you dream, and the people who prepare well are the ones who love it most.
That preparation doesn’t have to be complicated. Pay down debt. Stay active. Keep your friendships alive. And make sure you understand your healthcare options before you need them, not after.
That last one is where I can genuinely help. If you’re turning 65 in the next year or two and you want to walk through your Medicare options in a no-pressure, no-jargon conversation, I’d love to connect. I work with clients remotely, on your schedule, and my only goal is to make sure you feel confident about your coverage going into this next chapter.
*Source: 2024 MassMutual Retirement Happiness Study, conducted by PSB Insights, January-February 2024. Survey of 2,000 Americans aged 40+ with at least $50,000 in savings who are within 15 years of retirement or 15 years into retirement.
Licensed Insurance Agent Specializing in Medicare Coverage
Serving clients nationwide since 2018 | Licensed in 20+ states
I’ve been helping people turning 65 make sense of Medicare since 2018. I’m licensed and certified in multiple states and offer remote meetings to make the process simple and pressure-free, so you can choose a plan with confidence.