Somewhere in your 50s, retirement stops being this fuzzy idea “way down the road” and starts to feel like a very real chapter ahead. Maybe it hits when a good friend announces they’ve retired, or when you get that first email and photo from an ex-colleague who’s moved to their dream house on a beach somewhere. Whenever you begin to really consider it, it’s time to ask yourself: What do I want my retirement to look like and does that align with my partner’s perspective?
Because here’s the thing—retirement isn’t just about the numbers in your 401(k) or the age stamped on your Social Security card. It’s about vision. About lifestyle. About how you and your partner want to spend your time, your energy, and your money once the workday calendar is no longer running the show. And you may be surprised to find that what you believe your retirement looks like (and when it happens) isn’t the same thing as what your partner has been thinking. Getting to alignment means you can both make better decisions going forward and start making more concrete plans. There’s never a better time to start having this conversation than right now.
A retirement conversation isn’t one chat over a glass of wine—it’s an ongoing dialogue. Still, a few core topics can help you get started:
- Timing: Do you both want to retire at the same time? Or is one of you hoping to keep working a bit longer? How long does that leave you?
- Lifestyle: Picture your days—travel, volunteering, family, hobbies, or maybe launching a “second act” career. What excites each of you? Do you envision doing these things together, apart, or a little of each?
- Location: Do you want to stay where you are, move closer to family, downsize, or try living somewhere new? How does where you live mesh with what you envision yourself doing?
- Finances: Will your resources support the lifestyle you’re envisioning? This isn’t just about dollars; it’s about aligning priorities. For example, if you and your partner would like to travel for an extended amount of time, you may consider renting out your home to create some passive income.
- Identity and purpose: Work gives many of us structure and meaning. What will take its place for you? How might that affect your relationship with your partner?
Harvard University’s long-running Study of Adult Development found that “the quality of your relationships is the single strongest predictor of happiness and health.” Having alignment about retirement isn’t just about avoiding conflict down the road—it’s about strengthening the bond now.
Think of this less as a formal summit and more as a series of heart-to-hearts. Pick times when you’re both relaxed—not rushing out the door or preparing dinner. Maybe it’s during a weekend coffee ritual, a long walk, or a dedicated “date night.”
A few tips:
- Start with curiosity. Ask your partner what they’ve always pictured, and really listen to what they tell you without jumping in with your ideas or feedback.
- Share your own ideas and dreams. Even if they feel unrealistic or like a stretch, getting them out in the open is important. So is being clear about what is important to you.
- Revisit regularly. What you want at 52 may shift by 58. Check in annually like you would with a financial planner.
-Stay open. Your partner may have very different ideas than you do about retirement, but that doesn’t make them wrong. By listening and maintaining an open mind, you both may find common ground or even new compromises that neither of you expected.
As author Stephen Covey once wrote: “Begin with the end in mind.” The earlier you start shaping that “end,” the easier it is to align your choices today.
Retirement can be one of life’s biggest transitions. Without a shared vision, couples risk heading into it with unspoken expectations—and that’s where friction can build. One partner wants to travel, the other wants to stay close to family. One pictures mornings on the golf course, the other imagines launching a small business.
But when you do the work of creating a shared vision, two things happen:
1. You improve your relationship today. Dreaming together is bonding. It gives you something to look forward to and often sparks conversations about what you want more of right now.
2. You reduce conflict later. Instead of feeling blindsided, you’ll both feel like co-authors of the same story.
In other words, the conversation about retirement is really a conversation about life design—yours and your partner’s, together. If you’re in your 50s, now is the perfect time to start that dialogue. Not just because it helps with planning, but because imagining your shared future can actually bring you closer today.
Want a checklist to use with your partner to help guide your discussions? Click here to get your copy.