Are You Retired? Here's How to Drop the Guilt and Spend Your Nest Egg

Transitioning from a lifetime of diligent saving to confidently enjoying your wealth in retirement tends to be riddled with guilt, but it doesn't have to be that way. You cannot take it with you.

By Joe F. Schmitz Jr., CFP®, ChFC®, CKA®

published 31 October 2025

in Features

An older woman smiles while she sits in a shop and looks at her phone.

Most of our clients are who we call Midwestern Millionaires. They are hard workers and live a life of service. They have $1 million or more saved, pensions and a lifetime of discipline behind them, but they still struggle and feel guilty when it comes to spending their hard-earned money.

They are often the best savers and sometimes the worst spenders. They worry if the vacation, home remodel or gift to the grandkids is somehow irresponsible. They are always looking to save money and concerned about running out.

Sound familiar? If so, this article is for you.

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The retirement transition: From accumulation to enjoyment

You have lived your whole life being frugal and saving diligently. You clipped coupons, passed on new cars and packed lunch when others ate out, all to build toward a secure financial future.

Now that your diligent saving has paid off, the hard part isn't how to invest your money but how to enjoy it without fear. One retired couple told me, "We spent 40 years trying to save. Now we're afraid to use any of it."

If this sounds like something you might say, do not worry. This is a common concern, but it does not have to be a permanent one.

About Adviser Intel

The author of this article is a participant in Kiplinger's Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.

Here are the steps you can take to increase your confidence in the future.

Step No. 1: Recognize what you have achieved

If you have a pension and $1 million or more saved, you are in a great spot and rare company. We call this group the 2% Club, because only about 20% of the population has a pension and just 10% of the population has saved $1 million or more for retirement, according to an AARP survey. (I wrote a bestselling book about this group, titled The 2% Club. You can request a free copy.)

When you combine those two percentages, you are left with only 2% of the population.

But here's the thing: Midwestern Millionaires tend not to feel wealthy. Why?

They have never lived extravagantly
They have been surrounded by other frugal, hardworking people
They associate spending with risk
They have felt like they have always lived paycheck to paycheck

But it is important to understand that you didn't get into this position by luck. You got here by discipline.

Step No. 2: Redefine financial security

Financial security in retirement isn't just about not running out of money. It's about knowing your spending is aligned with your plan and your values. You do not need to splurge irresponsibly to enjoy retirement, but you should give yourself permission to:

Travel with your spouse
Help your children and grandchildren get ahead
Tackle the remodeling project you've put off for years, or even decades
Give generously to causes close to your heart

All of this can be part of a healthy, sustainable retirement if it is intentionally built into your plan with purpose.

I always say the clients we work with should be more concerned about running out of life than they should be about running out of money.

Step No. 3: Create a comfortable spending framework

One of the best things you can do is break your spending into three categories:

Paychecks. The essentials such as housing, food, insurance and health care.
Play-checks. The extras that are fun and purposeful, such as travel, home updates, hobbies and gifting to loved ones.
Legacy. The money you may never spend that is left over after accounting for the first two points above. This could include leaving money to children, grandchildren or charities when you pass away.

This helps you see where your money is going and gives you freedom to adjust as your goals evolve.

We also like to create "spending corridors," or target ranges that show how much can be spent safely, along with upper and lower limits, so there is never a feeling of overspending or living too small.

Many of our clients have more in the legacy category than they thought after doing this exercise, giving them permission to spend more money.

When you have run the numbers and put a plan in place, you can shift your mindset from "Will I run out?" to "How can I make the most of it?"

Categorizing can allow you to tap into your money for guilt-free enjoyment. Once you know the rest of your plan is sound, you can uncover the key to confidence.

Step No. 4: Practice the art of mindful spending

Spending in retirement is about intention, not excess. Ask yourself:

Does this purchase bring me joy or peace of mind?
Is this aligned with my values and goals?
Will this memory be worth more than the money?

If the answer is yes, you know it's the right kind of spending. We have seen clients light up after finally taking that Alaskan cruise, retiring early or helping their church build a new youth center.

These are not unreasonable decisions; they are intentional rewards for decades of sacrifice.

We send "Peak Approved" stamps to our clients who have trouble spending their hard-earned money. It started as a fun joke but has quickly become a hit with our clients.

I received an email from one of our clients who always jokes with her husband and me that she loves shoe shopping, and she let me know that she used our Peak Approved stamp to buy a new pair.

You've saved like a Midwestern Millionaire — now it's time to spend/gift/give like one

Retirement is not about hoarding every penny. We always joke with people that you cannot attach a U-Haul behind your hearse.

Retirement is about living with peace of mind, joy and generosity, while knowing you are not putting your future at risk.

If you are a frugal saver who is struggling to feel good about spending, I wrote a book just for you, Midwestern Millionaire: Hardworking. Frugal. Diligent Saver. (You can request it for free here.)

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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Joe F. Schmitz Jr., CFP®, ChFC®, CKA®, is the founder and CEO of Peak Retirement Planning, Inc., which was named the No. 1 fastest-growing private company in Columbus, Ohio, by Inc. 5000 in 2025. His firm focuses on serving those in the 2% Club by providing the 5 Pillars of Pension Planning. Known as a thought leader in the industry, he is featured in TV news segments and has written three bestselling books: I Hate Taxes (request a free copy), Midwestern Millionaire (request a free copy) and The 2% Club (request a free copy).

Investment Advisory Services and Insurance Services are offered through Peak Retirement Planning, Inc., a Securities and Exchange Commission registered investment adviser able to conduct advisory services where it is registered, exempt or excluded from registration.