It Starts Now with Juanita Dillard
It Starts Now, September 9, 2026
It Starts Now with Juanita Dillard Retirement Planning, Funeral Humor, and Choosing the Right Advisor with James Holloway The month of September is where we start fresh. 0n today’s show we are going to do just that. My guest is James Holloway, Esquire to talk about retirement, savings and the one thing you be doing now. Most of us are living longer. Longer than we have anticipated so you don’t wanna miss this show. James Holloway can be reached at: jas.holloway@earthlink.net Juanita Dillard sits down with attorney James Holloway, Esq. for a funny, frank conversation about funerals, Social Security timing, 401(k)s and Roth IRAs, and how to find a financial advisor who actually has your best interest at heart. Setting a Lighthearted Tone for Retirement Talk Juanita Dillard opens the episode by explaining why she started the podcast: she likes to talk, share information, and keep serious subjects light. She frames today's topic, retirement, as something people dread but says she wants to approach it with humor instead of dread. She introduces her guest, James Holloway, Esq., praising his unexpected sense of humor and warning listeners that a Wi-Fi disconnection interrupts the interview partway through, so the conversation will noticeably drop off and then pick back up. Dillard previews the ground she and Holloway plan to cover: what to look for in someone who helps with retirement decisions, what age is a good one to start planning, whether Social Security will still be there, and, only half joking, whether Mama will still be able to eat steak instead of tuna fish. She closes the cold open with the show's tagline before bringing James into the conversation. A Comic Detour Into Funeral Planning Back from the break, Dillard welcomes listeners to what she calls a retirement 101 course and reintroduces James Holloway, Esq. She talks about her sister, whom she calls her shero, who retired in her fifties and inspired Dillard to think about scaling back her own workload, even though she loves what she does. The conversation slides into a long, comic riff on funerals: Dillard says when she dies she wants a proper memorial with food, champagne, and a pastor bragging about her, not a bargain casket people whisper about. Holloway plays along, imagining mourners asking whether that was all she could afford or why there was only one limousine. Dillard recalls that her own mother planned her funeral down to the potato salad, banning raisins on pain of returning to haunt the family. The exchange sets a warm, joking tone before the two turn to the serious business of retirement planning. Why Everyone Needs a Retirement Strategy Asked directly why a retirement plan matters, Holloway tells Dillard that retirement only happens once, so there is no do-over if someone waits too long to start saving. He says the biggest mistake he sees is people failing to build a real strategy, paraphrasing the old line that people do not plan to fail, they fail to plan. Dillard turns the conversation personal, noting she has no children and only her sister to leave anything to, and asks whether she should sell her paid-down house for a low-maintenance condo or keep doing her own yard work. Holloway says the real starting point is always a sit-down conversation about goals, finances, and how long someone can keep working, since some jobs become impossible at a certain age while others allow decades of consulting. He warns that selling a long-held home can trigger capital gains taxes unless the sale is structured carefully, a detail Dillard had not considered before asking. Picking a Trustworthy Fiduciary Advisor Holloway steers the conversation toward how to choose financial help, telling Dillard he has spent thirty years competing against advisors who are really just selling products for a commission. He describes annuities and other instruments dressed up as advice when they actually carry high fees, years-long lockups, and penalties for withdrawing one's own money, and says people rarely read the fine print closely enough to catch it. His advice is to seek a certified financial planner or, more specifically, someone with a fiduciary designation through FINRA, the Financial Industry Regulatory Authority, since a fiduciary is bound to act in the client's best interest rather than their own. He compares it to getting three quotes before hiring a contractor, urging listeners to seek recommendations from people they trust rather than picking an advisor at random. Dillard agrees, noting a friend had told her the same thing after hearing Holloway's advice secondhand, which is part of what convinced her to book him for the show. Retirement Accounts and Social Security Timing After a brief call disconnection that the two joke about on air, Holloway walks through the mechanics of retirement accounts. He urges listeners to max out an employer 401(k), 403(b), or 457 plan, at least up to any employer match, then explains the difference between a traditional IRA, which reduces taxable income now but taxes withdrawals later, and a Roth IRA, named for a former Delaware senator, which taxes contributions up front but lets savings grow and come out completely tax-free with no required withdrawal age. Dillard asks about Social Security, and Holloway explains that benefits shrink for every year someone claims before their full retirement age, historically sixty-seven and a half, while waiting increases the payout, though seventy is when withdrawals become mandatory. When Dillard asks about becoming disabled before retirement, he clarifies that falls under Social Security disability, or SSI, with benefits depending on the specific disability, prompting another round of the pair's running jokes about Capitol Hill and lost minds. Lifestyle Adjustments and a Promise to Return Holloway shares an observation from thirteen years of advising government retirees: almost everyone who retires in their fifties or sixties with a comfortable pension ends up back working within a few years, because even a healthy six-figure nest egg does not stretch as far as their old salary once they keep traveling, golfing, and attending conventions and jazz festivals the way they always did. Dillard laughs that she relates, describing her own swings between feeling flush and eating tuna instead of steak. She jokes about James's astrological sign, noting that Leos, like her own sister, tend to be careful savers unlike herself, then wraps the interview, thanking Holloway and praising his unexpected sense of humor. She promises to bring him back for a second conversation focused on long-term healthcare costs and whether policies like Aflac are worth buying, and he agrees readily. The episode closes with Dillard, speaking as herself, thanking listeners for supporting the show's second season and asking them to share it with friends.
