Five Things I Wish Women Knew Before Retiring
After years of working with women approaching retirement, certain conversations happen again and again. The same questions. The same surprises. The same moments when something clicks and the picture becomes clearer than it was before.
This post is my attempt to share those moments before they become necessary — to put the five things I find myself saying most often in front of women who still have time to act on them.
1. You're probably more ready than you think
The most common thing I hear from women approaching retirement isn't excitement. It's uncertainty. A worry that they haven't saved enough, planned enough, or done enough to feel truly ready.
In most cases that worry is more persistent than it is accurate.
Women who have spent decades saving consistently, paying off debt, and building equity tend to underestimate what they've actually accumulated. They focus on the gap between where they are and some imagined number — rather than on whether what they have is actually sufficient to support the life they want.
One of the most meaningful things I do in early retirement conversations is lay out the complete picture — every account, every income source, every expense — and show what the math actually says. For most women who have been diligent savers, the picture is better than they expected. Not always perfect. But better.
The worry doesn't disappear when you see the numbers. But it becomes grounded in reality rather than fear, and that's a fundamentally different starting point.
2. The first year is harder than people expect — and that's normal
I've written about this in more detail elsewhere, but it bears repeating here because it surprises so many women.
Retirement doesn't feel the way most people imagine it will. The freedom is real — but so is the disorientation. The human desire for structure that work provided doesn't disappear when you retire. It needs to go somewhere. And figuring out where it goes takes longer than most people expect.
The women who navigate the first year most successfully are the ones who retire to something rather than simply from something. Not a rigid schedule, but a handful of activities that give their days shape, purpose, and connection.
If you're approaching retirement and haven't thought seriously about what your week actually looks like without work in it, that's worth doing before your last day — not after.
3. The sequence of your withdrawals matters more than the size of your portfolio
Most people spend their working years focused on one number: how much they've saved. In retirement a different question becomes more important: in what order do you draw it down?
The sequence of withdrawals — which accounts you draw from first, when you take Social Security, how you manage taxable income each year — has a significant impact on how long your money lasts and how much of it goes to taxes rather than to you.
Drawing from a traditional IRA before a Roth IRA might make sense in some years and not others. Taking Social Security at 62 versus 70 can mean a difference of more than a thousand dollars per month for the rest of your life. Converting some traditional IRA money to Roth in the early years of retirement — when your income may be lower — can reduce your tax burden for decades.
None of this is complicated once someone walks through it with you. But it requires looking at your specific situation rather than applying a generic rule. The right sequence for one woman is not necessarily the right sequence for another.
4. Healthcare costs before 65 are manageable — but they need to be in the plan
If you're retiring before 65 and health insurance has been the thing holding you back, I want you to know that it's almost always solvable. I've written a full post on this topic, but the short version is: the options are more manageable than most people fear, and the cost — while real — is a planning consideration rather than a dealbreaker.
What matters is that those costs are actually in your plan rather than estimated vaguely or ignored. A retirement income plan that doesn't account for healthcare costs between retirement and Medicare eligibility isn't a complete plan. One that does — with specific numbers and a specific strategy — gives you a clear picture of what you're actually working with.
5. Retirement is a transition, not a destination
This might be the most important one — and the hardest to convey before someone has experienced it.
Most people spend years working toward retirement as though it's a finish line. Reach it, and you're done. The planning is complete. The work is over.
What retirement actually is, is a beginning. The beginning of a chapter that could last twenty or thirty years. A chapter that requires as much intentionality as the decades of saving that preceded it — just directed at different questions.
What does this chapter look like? What matters most to you now that the constraints of work are gone? What have you been putting off that retirement finally makes possible? What gives your time meaning when a career no longer provides that structure automatically?
My mother worked as a real estate agent well into her 70s — not because she had to, but because she loved what the work gave her. The connections, the rhythm, the sense of purpose. She didn't retire from something. She kept moving toward something that mattered to her.
That's what the best retirements I've seen have in common. Not a specific number in an account. A clear sense of what comes next — and the financial foundation to pursue it without constant worry.
If you're approaching retirement and want to make sure both pieces are in place — the financial foundation and the clarity about what comes next — I'd be glad to help you think it through.
I wrote the Ready to Retire guide specifically for women approaching this transition — covering income planning, Social Security timing, investment positioning, and the personal side of stepping into retirement.
Download Ready to Retire — A Guide to Entering Your Next Season with Confidence
Or if you'd like to talk through your specific retirement picture, you're welcome to schedule a 15-minute intro call.