ARTICLES
Why Financial Planning Changes When You Start a Business After 55
You’ve stepped into a new chapter—one that blends freedom, purpose, and a little extra income. But here’s what many people don’t expect: starting a business after 55 also changes the way you need to think about money.
As a retiree e...
The End Game Matters—Plan It as Intentionally as You Began
You started your retirement business with passion, purpose, and a vision for freedom. But what happens when it’s time to move on?
Too often, retiree entrepreneurs pour themselves into their business, only to reach a point where they’re uns...
Don’t Let Taxes Derail Your Retirement Business Dreams
Retirement is a time to explore passion projects, build flexible income streams, and enjoy freedom on your terms. But if your side hustle takes off—and many do—you might be in for a surprise come tax season.
Here’s the truth: the IRS treats si...
Budgeting Doesn’t Need to Be Complicated—Just Consistent
Running a business in retirement can be incredibly fulfilling, but if you're not tracking your money, it’s easy to feel out of control.
Most budgeting tools are designed for full-time workers or fully retired folks, not someone juggling free...
Should You Use Retirement Funds to Start a Business?
You’ve built a solid nest egg, and now you’re wondering if it could help launch your second act.
Many retirees and near-retirees exploring entrepreneurship want to avoid debt and don’t want to jump through hoops for a small business loan. Some c...
You Can Work—and Still Collect Benefits (If You Plan Wisely)
You’ve earned your Social Security—but now you’re ready to earn a little more.
Starting a business in retirement can bring purpose, flexibility, and income. However, it can also bring surprising complications if you don’t understand how ...
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✍️ About the Author
Curt Roese is a CPA, entrepreneur, real estate broker, and a graduate student in entrepreneurship at the University of Florida. With over 40 years of experience in finance, small business, and real estate, Curt understands the challenges and opportunities that come with embarking on a new chapter after retirement.
He founded Retirepreneur to help others navigate this transition, offering straightforward tools, honest advice, and practical strategies for launching second-act businesses.
His mission is to empower retirees to live a vibrant, fulfilling, financially secure future!
