From Paychecks to Payouts: How to Make Your Money Work for You in Retirement
“Retirement: it’s nice to get out of the rat race, but you have to learn to get along with less cheese.”
— Comedy writer Gene Perret
Cheeky, but true. Retirement shifts your focus. You’re no longer earning a paycheck—you’re now the one in charge of turning your savings into steady income. In other words, you’re not just making money anymore. You’re making money happen.
It’s a mindset shift, and it’s a crucial one. Nearly half of Americans retiring at 65 risk running out of money in their lifetime. (Source)That’s not a stat you want to gamble on. But with the right plan, you can navigate this new phase with confidence.
Let’s break down what goes into creating a retirement that’s not just stable—but fulfilling, too.
Start With What You Can Control
Retirement planning isn’t about predicting the future. It’s about managing what’s in your control and preparing for what isn’t.
Your Behavior
Money isn’t just math—it’s emotions, habits, and psychology. One of the biggest financial traps retirees fall into is recency bias—overreacting to the latest market swing and forgetting that downturns and upswings are both temporary.
Then there’s the comparison game. Your friend brags about a hot stock pick or a real estate win, and suddenly you’re second-guessing your own plan. Don’t. Your financial journey is your own—and ideally, it’s been thoughtfully built with an advisor who understands your unique goals.
Your Risk Tolerance
Risk in retirement looks different than it did in your working years. You can’t just “wait it out” if the market dips right when you need to draw income.
That’s why your risk strategy needs to match your new reality. A calculated, measured approach is more powerful than swinging for the fences. (Think short, steady plays over Hail Marys.)
Your Diversification
Just like a football team can’t run the same play every time, your investments can’t all point in one direction. Although diversification can’t ensure a profit or protect against loss in a declining market, it can help mitigate the risk of market shocks—because let’s be honest, they will come.
A well-balanced portfolio spreads your risk while still offering opportunities for growth and income. That’s a smart defense and offense.
Prepare for What You Can’t Control
Some challenges are out of your hands—but that doesn’t mean they should catch you off guard.
Medicare
Medicare’s trust fund is expected to run short by 2033 (Source), and that could mean higher premiums or reduced benefits. Translation? Your retirement healthcare budget might need to stretch further than you planned.
Making Money Happen: Practical Ideas
Stretching pennies and using your senior discount only gets you so far. So how do you generate income without clocking into a 9-to-5?
Keep Your Money Invested
Even in retirement, your money can stay invested. A portfolio geared toward income—think dividends, bonds, or annuities—can provide steady cash flow while having less risk than a portfolio focused on growth.
Embrace a Side Hustle
Retirement can be the perfect time to pursue a passion project or part-time gig. Love golf? Work a few shifts at the course and cut down your green fees. Craft enthusiast? Get a job at your favorite store and enjoy the perks. You might even freelance or consult in your former industry.
Think of it as partial retirement—a bridge between full-time work and full-time leisure, with the bonus of income and purpose.
Retirement Is Change—But Change Can Be Good
One day, you’ll pack up your office, take that last elevator ride down, and start a brand-new chapter. It’s a big shift—but with the right mindset and planning, it can be your most rewarding chapter yet.
Retirement success isn’t just about the size of your nest egg. It’s about building a sustainable income plan, staying flexible, and pursuing what wealth really means to you—whether that’s travel, more time with family, or finally buying that fishing boat.
So don’t just retire. Retire with intention. Let’s make your money work as hard in retirement as you did getting there.
Ready to make your money happen?
Let’s talk about how to turn your savings into income, your goals into reality, and your retirement into a season of confidence—not compromise.

Philip Lockwood | Founder + Managing Partner |
Address: 1501 Ingersoll Ave Suite 201 Des Moines, IA 50309 Phone: 515-274-8006 |
Email: Plockwood@parklandrep.com Website: Lockwood Financial Strategies Securities offered through Parkland Securities, LLC, member FINRA (FINRA.org) and SIPC (SIPC.org). Investment Advisory services offered through SPC, a Registered Investment Advisor. Lockwood Financial Strategies, LLC is independent of Parkland Securities, LLC and SPC Securities offered through Parkland Securities, LLC, member FINRA/SIPC. |