Do you want to retire together? Avoid common pitfalls with this heartfelt guide!
When Bill and I started thinking seriously about retirement, we thought the biggest decisions would be things like, “Where should we travel first?” or “Should we repaint the kitchen?” But oh boy, we were so wrong. If you had the impression that couple life was complicated before, try to retire together!
As it turns out, the trickiest parts weren’t about paint colors or plane tickets; they were about conversations we hadn’t had, questions we didn’t know to ask, and assumptions we didn’t realize we were making.
Retirement planning as a couple is harder than you might expect, but not impossible. Once again, communication is a must, and we’ve learned it the hard way. Those oh-so-familiar moments of “I thought you were handling that” were present all the time, but if you are patient, you will manage to overcome them.
These are some of the most common mistakes a couple who retire together makes. I experienced them firsthand, and I want to shed some light on what’s going on!

Being overly generous
Making big financial gifts before ensuring your own security can backfire big time, and Bill and I witnessed it directly. When Billie, my daughter-in-law, had her first child with my son Greg, we decided to help them with a nursery makeover. It was a great idea, and we had a lot of fun as we had to travel to Portland, Maine, and do the work ourselves.
As the mother of three, I get it, and I was more than eager to help. But when that cozy surprise became a financial burden, and our heating bill shot through the roof last winter, I got a little bit scared. I still remember Bill asking me, “Did we overdo it?” Yes, we did, but we don’t regret it.
The problem is not that we wanted to help, but that we didn’t plan accordingly. Health expenses, repairs, and Maple’s knee surgery. We didn’t have them in mind, and this affected our finances. So, when you retire together, always speak with your partner, set planned gift budgets, and don’t let generosity blind you to your own needs.
Claiming Social Security without a strategy in mind
My teaching colleague Hazel claimed her Social Security at 62. At first, this seemed like a great idea. She thought that retiring earlier would mean more time for her to spend with the family, but unfortunately, later on, she regretted this decision. She got the money early, but it’s significantly less. If she had waited, she’d receive 75–80% more over her lifetime.
Bill and I decided to discuss our options. Do we go at 62, survive on it, and let Bill’s full benefit kick in at 66? Or wait? We hired a financial advisor, and they told us that when people want to retire together, as a couple, the best thing is to wait. Why? because survivor benefits latch onto the higher earner later.
We chose to wait until 66 for both of us. It meant delaying but gaining peace of mind. Always try to examine your claiming age choices; you’re selling months of retirement income. Talk it through with your partner and try to find something that works for you as a couple.
Only one partner is in charge of all money decisions
In our early marriage, Bill handled the budgets. I trusted him, but later on, I regretted leaving all of this burden on him. When I tried to access our accounts last year, I didn’t even know the passwords. And I really needed the money; it was an emergency. I called him; I called back. It was an adventure. It took a while to sort everything out.
Ladies and gents, knowledge is safety. I didn’t have the knowledge, and this led me into a seriously scary situation when I thought I was about to block our account. It was not fun. You should make an effort and sit together and learn about your pensions, Social Security, investments, IRAs, and health care accounts.
Not taking care of estate planning and beneficiaries
I still remember my mom’s passing. It was a devastating moment, but even in these moments, you need to be careful about the legal aspects.
When it was time to clear her estate, I had to face a legal labyrinth that made my entire situation worse. I was already down because I’ve lost my mother, and now I could not advance the process because the law was constantly putting new obstacles in front of me. This is not a pleasant experience, and anyone who has gone through it knows what I am talking about.
Bill watched me struggle, and he said, “Let’s just do it now.” So we updated our wills, named ourselves as executors, updated beneficiaries, and even made advance-care plans. We didn’t want our kids to go through what I went through, and this is probably one of the best decisions we’ve made since we decided to retire together.
We spoke with Jake, Emma, Greg, and Billie about this, and they were pleased to hear about it. We also made Maple’s vet and care instructions part of the plan, because she’s family too.

Not preparing for health & long-term care
Ok, maybe this might sound like a thing everybody is aware of, but despite this, many people simply ignore it. Do you know how we tend to underestimate the things that are right in front of our eyes? This is exactly what’s happening when people need to prepare for entering health-related retirement.
But let me tell you that nothing jolts you to planning faster than a medical emergency. During his first year of retirement, Bill had a heart scare that came with the full package. The ambulance. The ER. The tests. The anxiety. That’s when I realized that if we want to be happy when we retire together, health is number one.
So, we started to save. Right now, we have some money but not enough to feel completely safe. We met with a specialist, updated our insurance, and talked about assisted living possibilities. This is something I’d pushed off as morbid, but sometimes it is what can make your life better in some aspects.
In the end, planning for this isn’t being morbid. It’s just the reality we all have to confront, whether we like it or not. You’re protecting each other. You’re protecting choices.
When you want to retire together, you need to keep in mind that this is not just a financial milestone but also a relationship one. Bill and I didn’t have all the answers when we started this journey, and honestly, we still don’t. But as soon as you learn how to ask the right questions and where to ask them, things start to look smoother.
Planning together doesn’t mean everything goes perfectly. It just means you’ll face the surprises side by side, with fewer regrets and more peace of mind. But if I were to give you a piece of advice, it would be this: Don’t be afraid to talk! Talk about the uncomfortable stuff, the boring details, and the “what ifs.”
Ready to retire together? Tell me your stories in the comments!
Do you want to learn more about planning in retirement? This book might help?
Have you ever wondered how people managed to survive before Social Security? I’ve studied this phenomenon in this article: How Our Parents Got By Before Social Security?