Year-End Money Checkups, Holiday Spending Plans, and Guilt-Free Boundaries with Chevonne Roman
Steve Sexton talks with money wellness expert Chevonne Roman of Heal Plan Invest about conducting an emotional year-end money checkup, building a realistic holiday spending plan, and avoiding common money traps, before closing with his own warning about long-term bond risk as US debt nears $40 trillion.
Welcoming Chevonne Roman For Year-End Planning
Steve Sexton opens the show by thanking listeners for helping the program pass a million audience members in the United States and nearly 300,000 overseas, then turns to the topic of year-end financial planning before the holidays arrive. He introduces Chevonne Roman, money wellness expert and founder and chief money strategist of Heal Plan Invest, whose work has been featured by Forbes, Yahoo Finance, Nasdaq, CNN, CBS, Fox, Essence and Black Enterprise. Roman explains that after a decade as a financial advisor with a Fortune 100 investment firm, where her job was to make already wealthy families richer, she felt an unshakable pull to leave despite friends telling her she was insane to abandon a stable income. She recalls evenings and weekends spent quietly applying the same planning framework to families who were not wealthy, and describes sitting in advisory meetings where every question was directed at the husband, which convinced her to build a firm centered on women, hearts and money together.
Conducting An Emotional Year-End Money Checkup
Sexton asks Roman to unpack the year-end money checkup she recommends every listener start immediately. She tells him to begin without judgment, reflecting on what happened financially over the past year: which decisions felt strong, which created anxiety, and how the household responded when the refrigerator broke, the dishwasher failed, or a child left for college. Only after that emotional inventory, she says, should anyone move to the numbers, reviewing the budget, net worth and retirement accounts. Roman pushes Sexton to widen the lens beyond money entirely, asking whether every member of the family felt safe and experienced more joy than sadness over the year. She frames the checkup as a reflection of the whole family's life, with money representing just one piece, and insists that starting with feelings rather than spreadsheets is what makes the rest of the planning process actually stick going into the holidays.
Building A Realistic Holiday Spending Plan
After the break, Roman lays out how to build a realistic holiday spending plan that covers meals, travel and gift buying rather than gifts alone, insisting the plan be written down rather than kept in someone's head. She urges listeners to type their situation into ChatGPT or Claude for tailored ideas, and Sexton shares that he asked an AI for gift ideas with a fifty-dollar budget for a forty-two-year-old and got eight strong suggestions, one of which the recipient later called the best gift he had ever received. Roman insists the spending plan include the giver too, whether that means a year-end massage or a staycation. She then turns to the emotional weight of the season, telling Sexton that anyone anticipating difficult family dynamics should consider booking a therapist before the holidays begin. Sexton recalls a friend who scheduled a November therapy session specifically to prepare for a strained in-law relationship and came away far better equipped to handle it.
Avoiding Holiday Money Traps And Setting Boundaries
Roman's next tip is to fund the holidays ahead of time rather than swiping cards impulsively, suggesting a prepaid or secured card, dedicated gift cards, or a single savings account fed by a monthly transfer earmarked for holiday spending. Sexton adds that friends who keep a standing Christmas checking account, contributing roughly ten to twenty percent more each year than the last, arrive at November already funded and interest-free. Turning to guilt, Roman tells listeners to first confirm they have handled the essentials, updated life insurance and 401k beneficiaries, a current will, conversations with aging parents about long-term care, before spending freely on joy without shame. Sexton jokes about the infamous eight-hundred-dollar Christmas sweater bought on a card charging twenty-nine percent interest, and Roman offers a concrete boundary: delay any purchase over one hundred dollars for forty-eight hours, a cooling-off period she says reliably shrinks or eliminates impulsive regret.
Resetting Finances In The Final Quarter
Roman shifts to the last quarter of the year as a reset point rather than waiting for January, urging listeners to check what has gone into their 401k, look for room to max out an IRA or Roth IRA, and confirm their savings actually matches what they had planned. She flags free documents at freewill.com and distinguishes a will, which dictates what happens to belongings and any guardianship of minor children, from an advance directive, which governs medical decisions if someone cannot speak for themselves; she stresses that both need conversations with a spouse about wishes, not just paperwork. Sexton relays a listener question from Susan in Ohio, who wonders why she waits months every year for a tax refund instead of adjusting her withholding. Roman answers that September is the ideal moment, since the IRS and most states publish income-tax calculators that reveal instantly whether a paycheck is over- or under-withheld, giving four months to correct it before filing season.
New Year Confidence And A Closing Bond Warning
As the show closes, Roman tells Sexton that anyone entering January already regretting holiday debt or family friction should simply give themselves permission to correct course rather than carry guilt forward. She encourages listeners to ask AI tools plainly what an appropriate savings rate looks like for their age and retirement goal, calling it a free way to start planning a dream retirement one honest question at a time. Sexton shares that he is a twenty-year colon-cancer survivor and recalls how expensive both treatment and lost income became, reinforcing Roman's point that plans should survive life's shocks. Roman describes her firm, Heal Plan Invest, and its seventeen-person team building roadmaps for people who have handled money their own way for decades and want a second opinion. Sexton then turns solo, warning that with US debt approaching forty trillion dollars, long-term bonds many retirees treat as safe could lose value if yields keep climbing, and urges listeners to ladder short-term holdings and review portfolios calmly rather than panic.
