121: Radical Transparency: Diane di Costanzo’s Real Retirement Story
Release Date: 09/30/2025
145: Your Year-End Financial Checklist: 10 Things to Review Before December
Take Back Retirement
“December is probably too late to scramble around and logistically get stuff done.” Our host Stephanie McCullough counts just nine work weeks left in the year, so she and co-host Kevin Gaines walk through a ten-item year-end checklist. Needless to say, these are best tackled months in advance rather than during the December scramble! They cover the year-end deadlines. Contributions to 401(k)s must land by December 31, even though IRA contributions can wait until April 15, and a bonus paid in January counts toward next year. For 2026, the limit is $24,500, with an $8,000 catch-up from...
info_outline
144: We Need to Talk About Inheritance!
Take Back Retirement
“The biggest mistake parents can make is passing down money without communicating the family values that drive your thinking.” Our hosts, Stephanie McCullough and Kevin Gaines, dig into Kiplinger's October cover story on "the great wealth transfer," the slow handoff of an estimated $124 trillion from Baby Boomers to their children and grandchildren. That number is a bit misleading considering more than half of that wealth sits with the richest 2% of households, and a quarter of parents expect to leave less than $100,000. Citing the magazine's survey, roughly two in five families have never...
info_outline
143: Am I Allowed? The Permission Paradox, with Dan Haylett
Take Back Retirement
“The one thing you're guaranteed to run out of is time.” Our hosts, Stephanie McCullough and Kevin Gaines, welcome back financial planner Dan Haylett, founder of Humans vs. Retirement and author of The Retirement You Didn't See Coming, to unpack his viral essay "The Permission Paradox." Digging through his own client conversations for patterns, Dan found the two words that came up most were "permission" and "allowed." The people who have saved diligently for decades are often the ones least able to enjoy it, because permission was always external. For them, a paycheck justified spending,...
info_outline
142: Don’t Wait Until 65: Medicare Planning For Gen X And Beyond with Danielle Kunkle Roberts
Take Back Retirement
“Everything government touches is complicated.” - Danielle Kunkle Roberts Our hosts, Stephanie McCullough and Kevin Gaines, bring on Danielle Kunkle Roberts of Boomer Benefits, and author of 10 Costly Medicare Mistakes You Can't Afford to Make. As the title of her book suggests, Medicare isn't free. Believing otherwise is mistake number one! Premiums, deductibles, and coverage gaps are real costs that blindside retirees, especially anyone who leaves the workforce before 65 and needs an ACA bridge plan to survive the gap. The trickiest wrinkle is the size-of-employer rule. If you work...
info_outline
141: Estimating Spending in Retirement Calculations: Front-end the Fun!
Take Back Retirement
“Spreadsheets are great at math; they suck at flexibility.” Our hosts, Stephanie McCullough and Kevin Gaines, take aim at the assumption that every retiree spends the same inflation-adjusted dollar amount, every year, until death. It's the number your 401(k) statement spits out, the number the 4% rule promises, and it's wrong in two directions at once! First, it ignores life's lumpiness such as the new roof, the wedding, the pandemic-delayed trip to Greece. These are one-off costs that planners can average into projections but never quite eliminate. Second, and more provocatively, it...
info_outline
140: Don't You Dare Call Me Retired: Amy Bernstein on Creativity, Doubt, and Uncoupling Your Worth From Your Paycheck
Take Back Retirement
“You need to uncouple your self-worth from your income.” Amy Bernstein does not like the word “retired”. Our hosts, Stephanie McCullough and Kevin Gaines, aren’t too fond of the word either. A former journalist and federal government communications veteran, she didn’t quit anything cold. She shortened her commute first, then went part-time, then, when the pandemic made her last part-time job untenable, took the final step. What followed was less a plan than experiments guided by whatever sparked joy. These “experiments” included playwriting classes, a first novel written on the...
info_outline
139: What Women Need to Know about Moving Investment Accounts
Take Back Retirement
“As with all things with the IRS, document, document, document.” Our hosts, Stephanie McCullough and Kevin Gaines, explain what actually happens when you move an investment or retirement account from one custodian to another. The mechanics may seem as simple as filling out a form and waiting a few days. But Kevin walks through the fine print that trips up even seasoned advisors. Taxable accounts can usually move without triggering a sale, so cost basis and unrealized gains transfer intact. Retirement accounts are where the real danger lives. There are two ways to move retirement money: a...
info_outline
138: What Women Need to Know about the Estate and Gift Tax System (Rerun)
Take Back Retirement
Today, Stephanie and Kevin cover a topic that can often get confusing for many people: the estate and gift tax system. This is different from the income tax system, and both are federal tax systems that everyone needs to be aware of when planning for retirement. At the end of the day, the IRS is getting paid. The only two questions, then, are: Who pays? and When? Our hosts tackle these questions and more. While today’s discussion is a big picture overview of the estate and gift tax system, it will give you a general grasp of the concepts and vocabulary that will make your next...
info_outline
137: Rethink Retirement: Taking Charge of Your Next Chapter with Andi Simon
Take Back Retirement
“Take charge. Your retirement is your time.” Our hosts, Stephanie McCullough and Kevin Gaines, sit down with Dr. Andi Simon, corporate anthropologist and author of Rethink Retirement, whose research offers a bracing corrective to how most people think about life after work. Andi spent years embedding herself in senior living communities on the west coast, interviewing residents who had done everything "right" financially and still found themselves empty, bored, and stripped of identity. Through it all, she’s concluded that retiring from something is not the same as retiring to something....
info_outline
136: 10 Things To Do When You're 10 Years Out From Retirement
Take Back Retirement
"Don't sit around waiting to feel motivated. You take some little actions, and that often gives you the motivation and the momentum to move forward." Our hosts, Stephanie McCullough and Kevin Gaines, sit down to work through a HerMoney.com list of ten things to do when retirement is a decade away. The meta-lesson turns out to be bigger than any single item on it! The list, from Jean Chatzky's financial information service for women, gives them a useful scaffold, but what they keep returning to is the paralysis that keeps so many people from starting at all. Planning for retirement can feel...
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:
If you like what you’ve been hearing, we invite you to subscribe on your favorite platform and leave us a review. Tell us what you love about this episode! Or better yet, tell us what you want to hear more of in the future. [email protected]
You can find the transcript and more information about this episode at www.takebackretirement.com.
Follow Stephanie on Twitter, Facebook, YouTube and LinkedIn.