Cover of One Retirement Regret We've Never Heard

One Retirement Regret We've Never Heard

One Retirement Regret We've Never Heard

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Summary
 Bill and Andy Bush open with the one regret they've never heard from a retiree: "I saved too much." Drawing on conversations with plan participants, they explore the regrets people do voice — wishing they'd started earlier, stayed invested, or captured more of the company match — and why those missed opportunities can't be recovered once a contribution year lapses. The brothers make the case for balance, weighing Bill Perkins' "Die with Zero" philosophy of enjoying the here-and-now against the risk of shortchanging your future self. Along the way they dig into maximizing the match, the underused 50-plus and 60-to-63 "super" catch-up contributions, the new Roth catch-up rule for high earners, and the triple-tax-advantaged power of the HSA. They close with a mid-year nudge to review your savings rate and a reminder that money should buy choices, not guilt. ⏱ Episode Timeline & Key Topics 00:03 – Welcome & The Regrets We Hear Bill and Andy open the show with the common regrets they hear from plan participants: "I wish I'd saved more," "I wish I'd stayed in the market," "I wish I'd started earlier," and "I wish I'd taken the match longer." 00:53 – The One Regret Nobody Voices Nobody ever says they saved too much. Andy reframes the goal as balance — saving for later without abandoning a reasonable lifestyle now, or vice versa. 01:34 – Why Retirement Feels Too Far Away Bill notes how "retirement feels far away" leads people to defer saving, even though early dollars have the most time to compound. Life gets expensive as competing priorities — marriage, kids, college, car and house payments — crowd out saving. 02:08 – "Die with Zero" and Valuing What Feels Endless Andy shares Bill Perkins' insight from "Die with Zero": when something feels abundant or endless, we don't fully value it — which is exactly the trap with retirement saving that still feels far off. 02:53 – Missed Opportunities, Not Saved Dollars People nearing retirement rarely regret the money they saved; the regret is around opportunities missed. Each year's contribution limit lapses and can't be refilled later. 03:34 – Deathbed Regrets and Living with Balance Andy recalls that the biggest end-of-life regrets are rarely about working harder — they're about relationships, taking risks, and speaking up. The takeaway: plan forward for a long life while keeping balance today. 04:41 – Know How Your Company Match Works Bill urges participants to understand and maximize the match — an instant return, whether dollar-for-dollar or 50 cents on the dollar — and to capture that opportunity every year. 05:06 – When "Just the Match" Isn't Enough Andy raises the flip side: maxing the match may still fall short. The key questions are whether a match exists, what it is, and whether hitting it will actually be enough for your situation. 05:50 – Catch-Up and Super Catch-Up Contributions Bill covers catch-up contributions starting at age 50 and the SECURE 2.0 "super" catch-up for ages 60 to 63. Despite peak earning years, usage is low — roughly 5% of eligible 50-plus savers per the Public Retirement Research Lab, and low teens in Vanguard's How America Saves. 06:49 – Freeing Up Dollars in Your 50s As kids leave home and certain expenses fall away, your 50s can be a window to put more toward retirement — after assessing where you stand on your savings track. 07:39 – The New Roth Catch-Up Rule for High Earners Bill explains the rule rolled out this year: high earners (making $150,000 or more with an employer the prior year) who are 50-plus must make catch-up contributions as Roth. Some savers are balking — even skipping catch-ups entirely — rather than going Roth. 08:19 – Roth vs. Taxable: Why the Rule May Be a Gift Andy points out that money saved outside the plan gets taxed on dividends and gains along the way, while Roth is taxed up front and then grows and distributes tax-free. Bill notes high earners often can't deduct a traditional IRA anyway. 09:16 – The Value of Tax-Advantaged Space and the HSA The brothers highlight the range of tax-advantaged vehicles — 401(k), IRA, and the HSA, the triple-tax-advantaged account tied to a high-deductible health plan that blends the best of Roth and pre-tax. 09:49 – HSAs, Healthcare Costs, and Reimbursing Yourself Later Andy explains why the HSA may be the best retirement vehicle: healthcare becomes a bigger expense with age, and saving receipts now lets you reimburse yourself tax-free years later for big-ticket costs. 11:09 – An HSA Catch-Up Strategy for Couples Bill shares a lesser-known tip: when both spouses are 55-plus, the family contribution plus two catch-ups is allowed — but the second catch-up must go in a separate HSA. IRAs and HSAs can be funded up to the April tax deadline. 11:59 – Planning for Taxes Down the Road Andy notes most people focus only on today's taxes and overlook RMDs and legacy planning. Structuring ...
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