When Should You Start Saying “Yes” to Spending in Retirement?

For many successful retirees, the hardest part of retirement isn’t deciding how to invest their money. It’s learning how to spend it.

That may sound strange at first. After all, most people spend decades working, saving, investing, and being disciplined so they can one day enjoy the wealth they’ve built. But once retirement arrives, I often see clients struggle to make the mental shift from accumulation to enjoyment.

They have more than enough. Their financial analysis looks strong. Their investments are still growing. They could take the trip, help their kids, upgrade the house, fly first class, gift more to grandchildren, or give more generously to causes they care about.

Yet they hesitate.

And I understand why. For most people, saving money becomes a habit. It becomes part of their identity. Saying “no” to unnecessary spending has helped them build wealth in the first place. But at some point, continuing to say “no” can create a different problem: They may end up with far more money than they will ever need while missing the opportunity to use it in ways that could bring joy, connection, and impact today.

This is where the message from Bill Perkins’ book Die with Zero is worth thinking about. The book challenges readers to consider whether the goal should always be to maximize the amount of money left at the end or to use money intentionally while they are still alive, healthy, and able to enjoy it.

That does not mean spending recklessly. It means asking a better question: What is all this money actually for?

The Shift from Saving to Spending

When you first retire, it can feel uncomfortable to start drawing from your accounts. You spent your entire working life watching those balances grow. Now, even if your financial analysis says you can afford it, spending from those accounts can feel like you’re doing something wrong.

But retirement is exactly what those dollars were built for.

A well-designed retirement strategy should first help answer the major questions: Do I have enough? Can I maintain my lifestyle? What happens if markets struggle? What if healthcare costs rise? What if I live longer than expected?

Once those concerns are accounted for, the next question becomes just as important: How do I want my wealth to improve my life and the lives of the people I care about?

For some clients, the answer is travel. For others, it’s spending winters somewhere warm, joining a club, remodeling a home, taking the whole family on vacation, or simply enjoying daily life without worrying about every dollar.

The goal is not to spend for the sake of spending. The goal is to stop treating every dollar as if it must be preserved forever.

You May Have More Room Than You Think

One of the most common issues I see in retirement planning is that successful retirees often underestimate how much they can afford to spend.

They may already be living comfortably, but their portfolio continues to grow. Required minimum distributions (RMDs) may force income that they do not need. Their estate projections may show that they are likely to pass away with far more than they ever expected.

Although that is a great problem to have, it is still something worth addressing.

If your financial analysis shows that you are projected to leave behind significantly more than you need, it may be time to ask whether some of that money could be used more meaningfully today. Could you:

• Enjoy more experiences?
• Make life easier for your children?
• Help your grandchildren with education?
• Support a charity while you are alive and able to see the impact?
• Make memories with your family now instead of simply leaving more assets later?

Many clients do not need to choose between spending and leaving a legacy. With the right planning, they can do both.

Saying “Yes” to Experiences

There is a certain window in retirement when your time, health, and financial resources overlap. That window is incredibly valuable.

You may have the money to take the trip at 85, but will you have the same energy? You may be able to pay for the family vacation later, but will everyone’s schedules line up? You may want to create memories with your grandchildren, but they will not be young forever.

This is why I often encourage clients to think about experiences earlier in retirement. If there is a trip you have talked about for years, maybe now is the time. If you want to gather the whole family at the lake house, beach, mountains, or abroad, consider doing it while you are healthy enough to enjoy every minute.

In my opinion, spending money to create memories with the people you love can be one of the best uses of wealth. The return may not appear on an investment statement, but it often shows up in family stories, photos, traditions, and relationships that grow stronger over time.

And that matters.

You worked hard to build this wealth. It is OK to let some of it improve your life.

Gifting While It Matters Most

If you truly do not want to spend more on yourself, it may be time to seriously consider gifting more during your lifetime.

Many people plan to leave money to their children someday. That is thoughtful and generous. But here is the reality: By the time children receive an inheritance, they are often already in their 50s, 60s, or older.

In many cases, they have already bought the house, raised the kids, built their careers, and figured out their financial lives. The inheritance may still be appreciated, of course. But it may not be as life-changing as it would have been 20 or 30 years earlier.

A gift today could help an adult child buy a home, pay down debt, start a business, fund education, manage childcare costs, or simply create breathing room during a very expensive season of life.

For grandchildren, gifting could help with college, a first car, a wedding, a down payment, or another meaningful milestone.

And perhaps most importantly, you get to see the impact.

That is something an inheritance cannot give you.

Giving Can Be More Than Money

Lifetime gifting is not only about transferring dollars. It can also be about transferring values.

When done thoughtfully, gifting gives you the opportunity to explain why you are helping. You can encourage responsibility. You can connect the gift to education, home ownership, family, charitable giving, or entrepreneurship.

That conversation can be just as valuable as the money itself.

For high-net-worth families, lifetime gifting can also be an important part of a larger estate and tax strategy. Depending on your situation, strategies may include annual exclusion gifts, 529 plan contributions, appreciated assets, trust funding, or charitable gifts through donor-advised funds or other vehicles.

The right approach depends on your goals, your estate plan, your tax picture, and the needs of the people you want to support. But the larger point is simple: If you are likely to leave behind far more than you need, gifting during your lifetime may make your wealth more useful, meaningful, and appreciated.

Give Yourself Permission

At the heart of this conversation is something simple: permission.

• Permission to enjoy what you worked hard to build.
• Permission to stop over-saving if your financial analysis clearly shows you have enough.
• Permission to help your family now instead of waiting until the end of your life.
• Permission to fly first class, take the trip, remodel the kitchen, hire help, give generously, or say yes to the family experience you have been putting off.

This does not mean ignoring risk. You still need to account for healthcare, long-term care, inflation, taxes, market volatility, and longevity. But once those risks are addressed, continuing to live far below your means may no longer be financial discipline. It may simply be a habit.

And habits can be hard to break, even when your circumstances have changed.

Final Thoughts

Retirement should not be measured solely by how much money remains at the end. It should also be measured by how well that money was used along the way.

For some people, success means leaving a large inheritance. For others, it means creating memories, helping children and grandchildren at the right time, giving generously, and enjoying the freedom they spent decades building.

Most of the time, the answer is a balance.

If you are newly retired or have been retired for years and still struggle to spend, it may be time to revisit your financial analysis. Not because something is wrong, but because something may be possible.

You may be able to spend more, give more, experience more, and still leave more than enough behind.

At BGM, we help clients understand what their wealth can actually do for them, not just someday, but now. Because the goal is not simply to die with the biggest balance sheet possible. The goal is to live well, give well, and make sure your money serves the people and moments that matter most.