121: Radical Transparency: Diane di Costanzo’s Real Retirement Story
Release Date: 09/30/2025
127: Conversations That Count: Money, Values, and Clarity with Carl Richards
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123: Making Your Own Story: Finding Meaning After 50 with Diane Gansauer
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121: Radical Transparency: Diane di Costanzo’s Real Retirement Story
Take Back Retirement
“Stop stopping. If something is stopping you from doing this thing you know you should do, just stop stopping.” - Diane di Costanzo Former Chief Content Officer and Financial Journalist Diane di Costanzo proves it's never too late to take control of your financial future! Our hosts, Stephanie McCullough and Kevin Gaines, chat with her in this inspiring episode of Take Back Retirement. At 48, she had saved just $28,000 for retirement. It’s a number that felt shamefully inadequate against the backdrop of million-dollar retirement commercials. Yet eighteen years later, she successfully...
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120: Women, Retirement, and the Lessons of Behavioral Finance (rerun)
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118: Reclaiming Life: Lessons from a Gray Divorce Survivor with Pat Fenner
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info_outline“Stop stopping. If something is stopping you from doing this thing you know you should do, just stop stopping.” - Diane di Costanzo
Former Chief Content Officer and Financial Journalist Diane di Costanzo proves it's never too late to take control of your financial future! Our hosts, Stephanie McCullough and Kevin Gaines, chat with her in this inspiring episode of Take Back Retirement.
At 48, she had saved just $28,000 for retirement. It’s a number that felt shamefully inadequate against the backdrop of million-dollar retirement commercials. Yet eighteen years later, she successfully retired and embarked on a four-and-a-half-month adventure across Asia and East Africa.
Diane was awarded Content Marketer of the Year in 2022 by the Content Marketing Institute and served as Chief Content Officer at Foundry 360, part of Dotdash Meredith. Her transformation began with a simple conversation with a financial advisor who reframed her situation: she had no debt and some savings.
Her philosophy of "radical transparency" about money emerged from her work editing Millie, a financial magazine for women, where she discovered that not talking about money perpetuates inequality and ignorance. She practices what she preaches, openly sharing specific numbers about her savings and even publishing her daughter's wedding budget in a magazine article.
The key to her success wasn't complex financial wizardry but consistent action. She maximized employer 401(k) matches, utilized catch-up contributions after 50, and became an evangelist for Health Savings Accounts. This account offers "quadruple tax-free" benefits when contributed through payroll deduction by avoiding federal income tax, FICA taxes, while providing tax-free growth and tax-free withdrawals for medical expenses.
Her mantra "stop stopping," captures the paralysis many feel about retirement planning.
As Diane tells us, small amounts invested consistently over time create meaningful wealth, finding the right financial advisor is about personality fit as much as expertise, and retirement timing isn't always perfect.
Key Topics
- Travel Adventures and Retirement Celebration (04:43)
- Radical Transparency About Money (08:08)
- Starting Retirement Savings at 48 (11:00)
- “Stop Stopping” Philosophy (15:30)
- Health Savings Accounts Benefits (17:08)
- Sequence of Return Risk Discussion (24:11)
- Finding the Right Financial Advisor (29:06)
- Stephanie and Kevin’s Wrap Up (37:06)
Resources:
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