Over the years, I've sat across the table from a lot of retirees. Some recently retired, some five or ten years in, some looking back on decisions made decades ago. At some point in almost every one of those conversations, a version of the same question comes up: knowing what you know now, what do you wish you'd understood before you retired?

I've started paying closer attention to the answers. Not formally, not as a study, just as a planner with an English degree, taking notes, then reviewing the notes, and then seeing some common recurring themes surfacing again and again across very different people, different incomes, different careers: teachers, small business owners, executives, landscapers, and more. People who'd saved diligently and people who'd saved less than they'd hoped.

The specifics vary, but the patterns don't. Here are some that came up the most, and seemed like they could be the most helpful for others to know.

1. "I Wish I'd Understood How Much Control I Actually Had Over Taxes"

This is the one I hear so often now, almost always with a note of frustration. People discover, usually a year or two into retirement, that the tax bill on their withdrawals could have been meaningfully smaller if they'd made different decisions in the years right before they stopped working. The problem with being in this profession for ten years is that I wasn't in this profession twelve years ago. Similarly, the problem with serving a new client this year is that I wasn't working with them five years ago.

Retirement income isn't taxed automatically the same way a paycheck is. There are choices: which accounts to draw from first, whether to do Roth conversions in lower-income years, how to time the sale of an asset (like a rental property, or that recent endeavor into crypto). The retirees who felt good about their tax situation were almost always the ones who'd had that conversation early, while they still had years to act on it. The ones who felt blindsided usually hadn't thought about it until a few years into retirement, when it was increasingly too late to enact meaningful change.

2. "I Wish Someone Had Told Me Retirement Isn't One Phase"

People plan for "retirement" as if it's a single steady state: the finish line Retirement is not the finish line. Instead, it's more like a milestone on your path. The first few years of retirement often look different from the middle years, which look different again from later retirement. Spending tends to be higher early on, when energy and health allow for travel and activity (referred to as "go-go years"). It often drops in the middle years (the "slow-go years"). It can rise again later if healthcare needs increase (the expensive "no-go" years).

Several retirees, and their family members, mentioned feeling unprepared for how expensive healthcare and homecare are, wishing their original plan had accounted for that instead of assuming relatively flat monthly spending for the rest of their life/lives.

3. "I Wish I'd Made Peace With Spending the Money"

This one is kind of surprising, and I do see it a lot. A meaningful number of retirees, especially the ones who'd been disciplined savers their whole working lives, struggled to actually spend the money they'd saved. The habit of saving doesn't switch off the day you retire. For some people, it took years to feel comfortable using the resources they'd built specifically to use. Scarcity mindset is real, and it's very hard to ignore in retirement.

The retirees who seemed most at peace with this were the ones who had a clear, specific plan for their money. Not just knowing the account balances and having an awareness of their spending habits. These people have a real understanding of what their money is for and a structure that makes spending feel safe instead of reckless. Without that clarity, money sitting in an account can feel more like an emergency fund than a permission to live the life it was meant to support.

4. "I Wish I'd Talked to My Spouse About This Sooner"

Several conversations touched on a more somber theme: spouses who had very different pictures of what retirement was supposed to look like, and didn't realize it until they were already in it. One wanted to travel constantly. The other wanted a slower, quieter life close to home. One assumed they'd relocate, while the other assumed they'd remain close to their kids.

These aren't conflicts about money exactly. They're differences in expectations that had never been fully fleshed out in dialogue. The retirees who'd had those conversations early, even imperfectly, tended to navigate the transition with a lot less friction than the ones who discovered the expectations gap later.

5. "I Wish I'd Known How Fast the First Few Years Go"

Confession time: life goes fast. We all feel it, we all talk about, we're still looking for a way to pump the brakes. People who'd spent years anticipating retirement, counting down, planning for it, often found the early years moved faster than expected. Yes, even after leaving the job that was consuming so much of their time, it seemed there still wasn't enough time! Some described feeling like they were still adjusting to the rhythm of retirement just as the best remaining physically active years were starting to pass.

It wasn't regret exactly. Instead, it was more of a sense that they wished they'd front-loaded some of the bigger experiences instead of saving everything for "later," when "later" assumed a level of health and energy that isn't guaranteed.

What Do These Retirement Themes Have in Common?

The commonality is the desire for clarity. None of these are really about money, in the narrow sense. The retirees who felt most at ease, regardless of how much they'd saved, were the ones who'd thought through these things ahead of time: the tax decisions, the changing phases, the permission to spend, the conversations with a spouse, the pacing of the years.

The ones who carried more regret weren't necessarily the ones with less money. Nope. They were the ones who hadn't had these conversations until retirement was already underway, when some of the more useful decisions had an increasingly narrow pathway.

Twenty conversations isn't a scientific sample. And, honestly, it's roughly 22-30 conversations, but who's really counting? The consistency of these themes, across people with very different financial pictures, is worth noting. If any of them sound familiar, even a little, consider a conversation before retirement arrives (rather than after).

Remember, it's not about having the smartest financial advisor, the most money saved, or the highest probability of retirement success. The perfect retirement plan for you is the one you act on!