The Decisions That Matter Most in Retirement Aren’t Spreadsheet Decisions
As we head into the final stretch of Tax Season 2026, I imagine many folks are organizing statements and spreadsheets, receipts and reports, all the data that represents the last year of your financial life.
Many seniors might also be looking at all those charts and numbers for some help with one of life's most complicated decisions:
Is it finally time to retire?
But in my experience, the most consequential choices folks make around retirement aren't mathematical. And many don't have one "right" or "wrong" answer.
A successful retirement transition often comes down to making judgment calls that weigh tradeoffs, unavoidable uncertainty, and what matters the most to each individual.
Here's how Keen Wealth can help you look beyond your numbers and make four decisions that could have a lasting impact on your Golden Years.
1. When Is “Enough” Actually Enough?
If we're just talking about your accounts and amounts, then the best time to retire is ...
Never!
There's always another paycheck to collect, another number to hit that will raise your bottom line and make your spreadsheets look a little more solid.
For some folks, that bigger number becomes the driving force of all their financial planning. Their spreadsheets might practically be screaming, "You will never have to worry about money again!" But they put off retirement for "one more year," or longer.
Why?
Because they're still asking themselves, "Can I afford to retire?" and avoiding a far more complicated and, I would argue, more important question:
“Am I ready to stop trading my time for money?”
During your working years, much of your identity and purpose has been tied to the work you do and how that work provides for your family's basic needs. Once you don't need to trade your time for money anymore -- once you've reached financial independence -- you might experience a loss of identity, a lack of purpose.
Your hard work and your financial plan have largely solved financial risks. Now, it's time to start leveraging your assets and your plan to solve lifestyle risks as well. Folks who don't plan ahead for that random Tuesday afternoon when they need a doubles partner or someone to grab a cup of coffee with often keep delaying retirement until "someday."
And, while the paychecks may keep rolling in, that "someday" when you're finally free to spend your time doing the things you love the most might never arrive.
2. How Much Risk Can You Emotionally Absorb?
Today's financial planning software can analyze the health of your portfolio against a limitless number of potential withdrawal rates, market turns, and longevity scenarios. At Keen Wealth, we run sophisticated Monte Carlo Simulations that assign "probability of success" figures for retirement plans.
But while a projection might be able to show you what your numbers will look like if you withdraw 4% every year, that projection can't tell you how you're going to feel if the markets drop 30% in your very first year of retirement.
Today's soon-to-be retirees have worked, saved, and invested through a lot, from Black Monday and the Dotcom Bubble through 9/11, the Great Recession, and COVID. But as you faced those challenges, you had the safety net of continuing to work and earn. Without that next paycheck, your risk tolerance might feel very different if the same account you're using to buy groceries and pay your mortgage is lower because of an earthquake or a war.
A computer model that projects smooth sailing for 30+ years is also assuming that you will behave rationally during a downturn and stick by the principles of your financial plan: diversification, rebalancing, and sequential withdrawals. You have to be able to trust that plan even when the headlines and red lines are a little scary. That emotional durability around money doesn't come from numbers; it comes from experience, long-term perspective, and the guidance of your financial team.
3. How Flexible Do You Want Your Retirement to Be?
In the pursuit of a "perfect" spreadsheet, folks might be tempted to optimize every single dollar. To be sure, a large part of Keen Wealth's retirement transition process involves segmenting your assets into buckets (emergency, travel, health care, etc.) and analyzing lifetime tax liability and market projections to determine the most advantageous uses for your accounts.
However, "optimization" should not come at the expense of flexibility, especially when you're considering how a senior's needs typically change over 30+ years of retirement.
For example, allocating more of your portfolio to long-term stock investments might be the best way to keep driving up your numbers. But what if you need cash earlier in retirement for a relocation goal? What if you or your spouse suffers an accident and Medicare won't fully cover the bills? What if you decide you want to open a 529 for your new grandchild? Pulling money out of long-term investments to cover these needs might trigger penalties or tax liability that could threaten your plan's stability.
Numbers can be optimized. Life can't. Resilience and flexibility are often far more important to a 30-year retirement than "perfection." As comforting as high ROI projections might look on paper, it can be even more comforting to know that your plan will help you adapt, follow your bliss, and change your mind.
4. What Tradeoffs Are You Willing to Live With?
Almost every major financial decision in retirement comes with a "Yes ... But..."
Yes, you can take Social Security early to help you fund an early retirement goal. But if you delay, your benefits will keep growing. You might need that extra cash later in retirement as your health care needs rise.
Sure, you can make aggressive Roth conversions to boost your long-term wealth projections. But if you don't game out the tax implications and your current liquidity needs, you might be sacrificing too much of your current comforts.
Absolutely, you can give cash gifts to your kids and grandkids. But will that giving make it harder to fund some of your retirement goals? And if you have money problems in a decade or two, who is going to help you?
In these and so many more retirement scenarios, tradeoffs have to be aligned with your priorities. Even if your numbers say "Yes ...", you might find yourself regretting the "But ..."
Helping You Decide.
Financial planning software can map out scenarios.
But it can’t assign meaning to those scenarios and help you decide which path forward will be the most fulfilling.
It can't weigh priorities.
It can’t help a husband and wife reconcile two very different visions for retirement.
And software can't give you the calm perspective you'll need to make difficult decisions when the path forward feels uncertain.
At Keen Wealth, we don't just want to help you save and invest. We want to be your trusted decision partner. Make an appointment to visit our offices and let’s start working out the right choices for your dream retirement.
About Bill
Bill Keen is a financial advisor with over 30 years of industry experience. As the founder and CEO of Keen Wealth Advisors, a registered investment advisory firm, he focuses on providing personalized retirement planning designed to help people thrive before and during their retirement years. With a passion for educating others, Bill regularly blogs about retirement planning, hosts the podcast Keen on Retirement, and has contributed to Forbes, U.S. News and World Report, Reuters, Wall Street Journal’s Market Watch, Yahoo Finance, and other publications. Based in Overland Park, Kansas, Bill and his team work with clients throughout the greater Kansas City area and across the nation. To learn more, connect with him on LinkedIn or visit www.keenwealthadvisors.com.
KWMG, LLC’s dba Keen Wealth Advisors (“company”) is an SEC Registered Investment Advisor located in Overland Park, KS. The company and its representatives may only conduct business in those states where registered or where excluded/exempt or from licensure. For registration information, please contact the SEC or the state securities regulators for the states where the company is notice filed. A copy of the company ADV is available upon request. Advisory services are only offered to clients or prospective clients where the company and its representatives are properly licensed or exempt from licensure. No advice may be rendered by the company unless a client service agreement is in place. This information is not intended to be investment advice or construed as a recommendation or endorsement of any particular investment or investment strategy and is for illustrative purposes only. Clients and prospective clients must consider all relevant risk factors involved with each strategy, including costs or fees, and their own personal financial situations before trading.
The views outlined in the book, Keen on Retirement Engineering the Second Half of Your Life, are those of the author and should not be construed as individualized or personalized investment advice. Any economic and/or performance information cited is historical and not indicative of future results. Economic forecasts set forth may not develop as predicted.
The Amazon Best Seller ranking listed on marketing materials is specifically referring to Best Seller rankings for the Kindle Top 100 Paid Lists under the subcategories of: Budgeting and Financial Risk Management, based on data as of September 5, 2019 and the second edition under Financial Risk Management on October 26, 2022. Amazon rankings although relevant on how a product is selling overall doesn’t necessarily indicate how well an item is selling among other similar items or similar item categories. Amazon may choose the most popular categories or subcategories within which an item has a high ranking to determine its best seller rankings. These rankings are updated hourly and as a result, should be expected to fluctuate as such. Keen Wealth Advisors and Amazon are not affiliated entities.
The Steve Sanduski Advisor Network, Belay Advisor, LLC and other third-party contributors to our blogs and podcasts are not affiliated with Keen Wealth Advisors.
For additional details on Keen Wealth Advisors, please visit https://www.keenwealthadvisors.com/important-disclosures.
20260304-5271245-16621307