One of the advantages of being a family financial planner is that I get a front-row seat to how people think about money at every stage of life. Over the years, I’ve worked with young professionals just getting started, retirees settling into a new chapter, and plenty of families somewhere in between. While everyone’s circumstances are different, I’ve noticed something interesting: the same phrase tends to come up over and over again.

“I wish I had”

What’s interesting is that the regret is rarely about one catastrophic decision. Most people aren’t looking back on a single mistake that ruined everything. Instead, they’re reflecting on small opportunities they didn’t recognize at the time, questions they didn’t know to ask, or decisions they simply put off because life got busy. 

Most people don’t lack effort. In fact, most are working incredibly hard. What they often lack is direction and someone helping them connect today’s decisions to tomorrow’s consequences (financial planning advice).

I’ve thought about some of the common “I wish I hads” from different age demographics, as I work with generations up and down the family tree, and here are some of the most frequent I hear:

Financial Planning Advice: In Your 20s: “I Wish I Had Understood Debt Better.”

When people are in their twenties, the most common regrets usually revolve around debt and time. I hear people say they wish they had understood how student loans actually worked before signing the paperwork. Student loans and credit cards all seemed manageable because the monthly payment looked affordable. What wasn’t always obvious was how much interest would accumulate over the years.

In Your 30s: “I Wish I Had Taken the Match.”

By the time people reach their thirties, life often gets more complicated. Careers become more demanding. Homes are purchased, and of course, the children arrive. Money suddenly has more responsibilities than it did a decade earlier – it’s not all fun and games and late nights at the barcade. 

Many 30-somethings tell me they wish they had taken full advantage of their employer’s 401(k) retirement match while life was still relatively simple. Others laugh and admit they had no idea how expensive raising children would actually be. Everyone knows kids cost money. Few people truly understand what that means until they’re writing endless checks. 

In Your 40s: “I Wish I Had a Clearer Plan.”

The conversations I have with people in their forties often sound a little different. By then, many are doing reasonably well. They’re contributing to retirement accounts, paying their bills, and building wealth. But there’s often a lingering feeling that they’re moving forward without a clear roadmap. This is certainly true among my Gen X clients. 

Gen Xers grew up as self-reliant problem-solvers and have spent decades figuring things out on their own. That’s a strength, but it can also create blind spots. One of the most common things I hear is, “I wish I had a clearer plan,” followed closely by, “I wish I had asked for help sooner.”

In Your 50s: “I Wish I Had Taken Advantage of Opportunities Earlier.”

As people enter their fifties, the focus often shifts toward opportunities they wish they had recognized earlier. I’ve met plenty of individuals with seven-figure retirement accounts who simultaneously feel short on cash.

On paper, they’re doing exceptionally well. In reality, much of their wealth is tied up in accounts that aren’t liquid/accessible. That’s when conversations start turning toward liquidity, tax planning, and creating flexibility. The issue isn’t usually a lack of assets; it’s understanding how those assets fit together and support the life they’re trying to live as they edge closer to retirement. 

Financial Planning Advice: In Your 60s: “I Wish I Had Known What Questions to Ask.”

The questions become more personal in the sixties. Many people have spent decades saving, investing, and preparing for retirement, but they still wonder whether they’ve actually done enough.

One of the most common comments I hear is, “I wish I had known exactly how much I needed.” Not enough to retire someday, but enough to retire comfortably. Enough to travel and enough to help children and grandchildren if needed; enough to stop worrying! 

At this stage, clarity often becomes more valuable than accumulation.

In Your 70s: “I Wish I Had Planned for the Tax Bill.”

The seventies bring a different set of lessons; this is when Required Minimum Distributions start becoming a reality, and many retirees discover they have unintentionally built what some advisors call a tax time bomb – these people have been great savers but bad spenders. 

Retirement accounts that grew quietly for decades suddenly begin generating taxable income. I hear people say they wish they had explored Roth conversions sooner or paid more attention to future tax implications while they still had more flexibility. The surprise usually isn’t that taxes exist. It’s how much control they could have exercised years earlier.

In Your 80s: “I Wish I Had Taken the Trip.”

The conversations I have with people in their eighties rarely center around investment performance or account balances. Instead, they often become reflections on experiences, wishing they hadn’t skipped the memories. 

The phrase I hear most frequently isn’t “I wish I had saved more.” It’s “I wish I had taken the trip.” “I wish we had visited the family. I wish we had seen more of the world. I wish we had done it while we still could.”

Those conversations have had a profound impact on how I think about money, because money itself isn’t the issue; it’s a tool, a tool that creates options and opportunities. 

People who seem most satisfied rarely talk about maximizing every dollar. They talk about using their resources intentionally and in ways that align with what matters most to them.

Financial Planning Advice – The Common Thread Across Every Generation

What strikes me most is how these lessons connect across generations. Parents want their children to avoid the mistakes they made. Adult children are trying to learn from their parents’ experiences. Good habits get passed down, and bad habits get passed down, too! Small missed opportunities compound over decades, just as small positive decisions can create tremendous momentum.

Here’s the encouraging news: most of these regrets are preventable. Not through perfection. Not through predicting the future. And certainly not through making every decision exactly right. The best way to avoid saying “I wish I had…” twenty years from now is simply to ask better questions today.

That’s what financial planning really comes down to. It’s not about finding the perfect investment or timing the market flawlessly. It’s about creating enough awareness and direction that your future self has more choices. 

As a financial advisor for parents, grandparents, students, and everywhere in between, I can help you meet your financial goals for the present and the future; let’s take a look together.