Planning for the next stage includes a lot of questions and emotions, especially when you're thinking about selling the family home. Here are the questions you have to answer before making any big moves.

29 April 2024

The Big Questions You Have to Answer Before Selling the Family Home

Welcome to the Exploring Your Retirement with Willowfinch Series, where we’ll be going over all of the information, dreams, and numbers that can make your plans for “What’s next?” get you somewhere you actually want to go! Today’s post "How to Round Up Your Retirement Numbers" is the first in the bunch. Keep an eye out for the rest in our upcoming blogs!

Before we get into the whats and how-tos, remember that we’re not financial advisors or giving any specific recommendations or advice here. We’re going through the topics that we’ve found helpful when gathering all of these thoughts and showing how they pair up with your Willowfinch account dashboard to get you the most personalized and helpful data possible with our tools and resources. We always recommend getting insight and advice from financial professionals!


When you start to look at “what’s next?” for your retirement, you have to figure out if, when, and how to sell the family home. It’s a question with a lot of moving pieces, just like any big decision, but it’s a bit more than that, too.

Whether it’s downsizing just down the road, heading to another state to be closer to family, or finally living the dream of moving halfway around the world, it’s a big choice that comes with big shifts in your life. The emotions and memories are wound pretty tightly around all the practical considerations surrounding savings and interest rates.

Get Clear on the Plan

We like to define retirement as “having the ability to earn less,” because there are so many ways to approach this next stage! It’s like being a 23 yr old graduating from college and looking at a whole world of opportunities for what comes next.

As exciting as that is (or maybe isn’t), you really do need a plan. Navigating big financial events like house sales, investment choices, and career changes can get messy and expensive quickly if it’s too haphazard.

We’re going to go over the big questions to get clear on options, make good choices, and outline the important milestones and to-dos along the way.

Don’t forget to have lots of conversations with other people who will be part of this process when it happens! That includes any partner or kids who will be part of the moves, other family and friends impacted, and your advisors. Compare answers, brainstorm, and find solutions that balance everyone’s needs and plans.

The Questions:

1) What are my key financial goals?

What steps are involved and what timelines do I need to follow? This can include:

  • When or if you plan to retire from your current work structure and what you’ll do after that.
  • When it’s best for you to claim social security.
  • What future finances you are expecting or would like to create.
  • What upcoming expenses you have.
  • What assets you have or plan to create.
  • What healthcare you’ll need and which insurance options will be available.
  • What order these things have to happen in and whether there’s anything else that has to happen first.

💡 Important to remember: Your property can often be your biggest asset, but it’s not liquid for most families. Be clear on your mortgage and research the best options for freeing up your liquidity, if you need it. This is a great time to find a financial professional you can trust.

2) What things, spaces, and options do you need to account for practically?

It’s important to get the non-negotiables, but try to include nice-to-haves that make a big impact on your happiness and quality of life, too. This may look like:

  • Space required for hobbies and gear.
  • A place that allows pets.
  • The ability to add accessibility and mobility features in your home.
  • Needing certain professionals or care nearby.
  • Weather that suits your activities and comfort.
  • How much renovation or other work you can or want to take on.
  • Amenities and necessities like local food options, community services, and public transportation.

3) What are the fun or meaningful things that matter to you?

Do you want to have certain spaces, be near certain people, or be able to access particular local places and experiences? List the things most likely to make your days fulfilled and happy:

  • A certain view you’ve always wanted to see every day.
  • Any community space you’d love to be near or have easy access to.
  • A space like a library or workshop and whether it’s something you want already done or to create yourself.
  • What you love that you created in your current space, like gardens you’ve cared for or a kitchen set up exactly how you want.
  • Outdoor or other recreational activities you do. (Or want to start!)
  • Community groups you want to be involved with or support.

4) What do you need to plan or do in your current situation?

Are there special considerations for the home like repairs, other family members who live there or have plans to, or previous obligations you need to keep in mind? Think about:

  • Any repairs that would make a big difference in selling or renting the house.
  • Anything you need to wrap up at home or in your neighborhood.
  • When the best time for living changes will be for everyone involved.
  • Whether you need to do any research or seek any advice about complex or unexpected situations.
  • What a real estate agent or appraiser would recommend addressing to maximize buying price.

5) What are the unexpected or catastrophic things you need to be able to adapt to and how would you need to adapt?

This can run from the personal to the large scale things…a little extra preparation can save a lot of headaches and money later! Everyone’s list will be different, but here are some possible issues to think about:

  • Any decisions by other people that could influence our needs or plans. (Don’t count on this, but get the information you may want to take into account.)
  • Climate changes that could dramatically impact you and your home.
  • Market crashes or other economic shifts that would undermine your planned income or savings.
  • Laws and rights that could change in a harmful way in that area.
  • Health catastrophes or changes in accessibility needs.
  • Family members or friends needing support or care in the future.

💡 An important part of this question is taking the time to think through the order of your plans. Some things may not derail you unless they happen at the worst time. For example, a house buyer falling through isn’t necessarily an emergency…unless you bought a big RV and you were counting on the proceeds to make your monthly loan payments.


Looking at all the details and goals that come from these questions, what’s next? Is your current home the best for your future plans? Or is there an alternative that sounds more promising?

It’s a lot of information, a lot of decision-making, and a lot of best guesses for an unknown future. We know that can be tough! But taking your time to think things through is worth it. Especially if there are other people involved in the same decisions, it’s an essential step to make sure you’re on the same page and understand each other’s hopes and concerns.

Don’t rush yourself. Break things down, brainstorm, seek input and advice from qualified voices, and let yourself get creative with your ideas. Double-check on regulations and your math for the core numbers. And set a calendar reminder every year or so to revisit and update your goals and plans!

Want some help as you work out these answers?

This is an area where Willowfinch can be a huge help! In fact, this situation is exactly what made Willowfinch founder, Andrea, realize how much a tool like this was needed.

The personalized insights, easy-to-understand data, and clear calculations like the affordability number all help you think through the options and find what’s best for you and your goals.

And don’t forget, you can book the VIP Explorer Package if you want customized recommendations and data maps based on your situation and ideal scenarios! The detailed information you’ll tap into can make all the difference in seeing what makes sense for your plans and goals. You can see more about signing up inside your Willowfinch account.

Ready to dive in?

We'd love to talk about how Willowfinch can work for you! Get in touch now!


Catch all of the posts in our Exploring Your Retirement with Willowfinch Series:

How to Round Up Your Retirement Numbers

The Power Behind Your Willowfinch Heat Maps

The Big Questions You Have to Answer Before Selling the Family Home

How to Use "War Gaming" to Make Strategic Housing Plans

And Interview with Andrea: Applying for Social Security

© 2024 Willowfinch | All Rights Reserved | Terms & Conditions | Privacy Policy