Many women start our first conversation the same way: “I think we’re okay, but how do I know for sure?” Retirement planning for women at this stage tends to raise the same five questions again and again, so I’m answering them here just like I would if we were sitting across the table from one another.
They are usually great savers, organized to a level most advisors rarely see, and quietly uneasy anyway. They’ve managed the accounts, tracked the details, and carried the mental load for years. And yet, the closer retirement gets, the more the same questions keep swirling back.
1. Do we actually have enough to retire, and how would we know for sure?
“Enough” is different for everyone. It depends on your lifestyle, what you want retirement to look like, and the financial structure you already have in place. That’s why I start with a specific process to define what enough means for you: what you spend, a real retirement date, which accounts you’ll draw from first, what taxes you’ll owe, and how long the money needs to last. A written financial plan then tests your savings against decades of spending, inflation, and market history, so you can see exactly where you stand.
Now, I want to be clear: nobody honest can offer a guarantee, and I certainly can’t. What I can offer is research-based structure, a plan that controls what we can control and prepares for the possibilities we’ve seen play out before. The Thistle Process page walks through exactly how that works. We also explore the question further in this post.
2. Can we maintain our lifestyle in retirement?
If that’s your goal, your financial plan is built around it. The plan either confirms you can do it now, or answers the more useful question: how much longer would you need to work for your standard of living to hold?
A long life, typically 95 or beyond for women, is the assumption I build in from day one. I use the Actuaries Longevity Illustrator, a free tool from the American Academy of Actuaries and the Society of Actuaries. Try it yourself. A few basic health questions will show you how long the actuaries think you might live, and the answer surprises most people. I use your unique answer in all of my plans.
Keep in mind that your spending will change shape during retirement. It’s typically highest right after you retire, slows as you settle into the new rhythm, then ramps back up toward the end to cover healthcare. A plan that survives 30+ years requires flexibility built in: cash set aside so a bad market never forces a bad decision, and room to adjust when conditions change. Structure, not a single magic withdrawal number, is what keeps a lifestyle intact.
3. Which accounts do we withdraw from first, and how do we avoid overpaying taxes?
This depends on your end goals and how you’ve funded your existing accounts. The order matters more than most people expect. Which account you pull from affects your Medicare premiums, what you send to the IRS and to Oregon, and your lifetime tax bill, including what your heirs will pay on whatever is left. Retirement income planning is complicated, and our goal is to help you while not paying more than you should in taxes.
I wish I could give a one-size-fits-all answer, but this one is genuinely unique to your situation. One example: if you plan to leave everything to charity and hold a large traditional IRA, I would never suggest Roth conversions. Charities receive traditional accounts tax-free, so converting would spend real money today to solve a tax problem your charities will never have. Leave those same accounts to your children, though, and they’ll pay ordinary income tax on the withdrawals (within 10 years), which changes the math completely. Same account, different beneficiary, opposite advice.
4. When should we each take Social Security?
For a couple, this is a joint decision, not two individual ones. Benefits grow for each year you wait, up to age 70. And when one spouse dies, the survivor keeps the larger of the two checks, so if one of you earned significantly more, the timing of that claim is an opportunity to protect your spouse.
Women typically outlive our husbands (sorry, men!), so this decision lands hardest on us, and it deserves to be run as a calculation to make sure we are covered. I explore this question in more depth in this post on Social Security timing.
5. What happens to our finances if one of us dies first?
This is the question many couples never ask, and I wish they would. When one of you dies, one Social Security check goes away. The survivor’s tax filing status changes, which often means higher tax rates on less income; this is known as the widow penalty. Some pension payments shrink or stop entirely, depending on elections made years earlier. Income can change dramatically while the expenses mostly stay flat.
It doesn’t have to be so jarring if we plan ahead. How your accounts are titled and who is named as beneficiary determines how smoothly everything transfers. We can build the game plan now, so no one has to figure it out on the fly while also planning a funeral and grieving. I’ve developed a checklist for women covering what comes after the death of a loved one; you can find it here.
Start with whatever question is loudest
These five questions are where most first conversations begin, but they’re rarely where they end. The questions about who you’d actually be working with, whether your situation is the kind I take on, and how to bring your family into the plan deserve their own post, and that one is coming.
You’ve probably already got the spreadsheet. Most of my clients do. They arrive organized, with the accounts tracked and the details handled, looking for an answer the spreadsheet can’t settle: does all of this actually hold up? That’s the question I answer.
If any of these five questions resonate, start with the short form on my contact page. It asks what you’re hoping for, which lets me show up to our first conversation already prepared for you.
This article is for general educational purposes only and is not personalized financial, tax, legal, or investment advice. Your situation is unique and may call for different strategies than those described here. Please consult with a qualified professional who can provide guidance tailored to your specific circumstances. All investing involves risk, including potential loss of principal.
