Between the year you stop working and age 73 (when RMDs are forced under SECURE Act 2.0), you sit in a low marginal bracket the IRS will never give you again. The decisions you make in this window — Roth conversions, capital-gains harvesting, Social Security timing, IRMAA management — determine how much of your retirement you keep and how much the IRS takes from you and your heirs.
This is the Good Deals playbook for that window.
Most pre-retirees have a substantial Traditional IRA / 401(k) balance — built over a 30-year career of deferring tax. The IRS allowed you to defer. But starting at age 73, it forces a percentage of that balance into taxable income every year — at brackets that compound with Social Security, pensions, and IRMAA Medicare surcharges.
Wage income ends at retirement. Social Security can be deferred to 67-70. You may have 5-10 years in the 12-22% federal bracket before RMDs force you into 32-37%+ for the rest of your life. Converting Traditional to Roth during the window pays now at the low rate to avoid the higher one later.
Medicare premiums are tiered on income from 2 years prior. A $1 over a threshold costs $1,000-$6,000/yr per beneficiary. Conversions and gains push you toward cliffs; planning keeps you under them. This is one of the most overlooked retirement-tax issues.
Under SECURE Act, non-spouse heirs of Traditional IRAs must drain the entire balance within 10 years — typically at their peak earning bracket (32-37%). Inherited Roth follows the same 10-year rule but distributions are tax-free. Converting now is often the single biggest gift to your beneficiaries.
Six calculators that map the highest-leverage tax decisions of your pre-retirement and early-retirement years. All free. All cite their sources to IRS / Cornell LII / SSA.
Project lifetime tax savings of converting Traditional → Roth strategically during the retirement-to-73 window. Models do-nothing vs ladder scenarios.
Run the calculator → NewWhere you stand on Medicare premium surcharges, distance to the next cliff, and the annual cost per beneficiary. 2026 estimated tiers.
Run the calculator → NewYear-by-year RMDs from age 73 through 95 with the IRS Uniform Lifetime Table. Plus a side-by-side vs Roth-converted alternative.
Run the calculator → Pre-retirementHead-to-head verdict for the years where you're still contributing. Most pre-retirees in 22-24% benefit from Roth contributions.
Run the calculator → AuditLifetime fee-drag calculator. A 0.5% extra expense ratio on a $2M balance over 20 years is $300K+ lost to fees.
Run the calculator → New 2027The new federal platform launching Jan 2027. How it interacts with existing IRA contributions and conversion plans.
See the guide →Modeled examples, not historical client outcomes. The figures below are projections from the same calculator math you can run above, applied to representative pre-retiree situations. Your numbers will differ based on your specific balances, state, brackets, and timing.
A hypothetical former tech executive retiring at 62 with $4.2M in 401(k) (rolled to IRA) and ~$800K in taxable brokerage. No Roth. Already in a no-state-tax state.
An 11-year conversion ladder modeled here: convert ~$200K/yr to Roth at the 24% bracket (filling but not exceeding), watch the IRMAA cliff and stay just under, harvest LTCG selectively to fund living expenses without pushing AGI. Defer Social Security to 70 for the 8% delayed credit.
A hypothetical software-engineer couple in California, retired Q1 2025, planning to relocate to Austin Q3 2026. $2.8M combined pre-tax balances. CA marginal bracket at 9.3%+ federal 24% = effective 33.3%+ on conversions.
The modeled alternative: do nothing in 2025-2026 (CA tax years), establish TX residency Q3 2026, then aggressive ladder Q4 2026 onward at federal-only rates. State-tax savings alone on a $1.5M total conversion = $140K. Plus standard ladder savings vs RMD bracket.
| Approach | Typical wirehouse / Edward Jones | Robo / DIY | Good Deals |
|---|---|---|---|
| Roth Conversion Ladder modeling | Generic "talk to your CPA" | None | CFA-grade 11-year projection with IRMAA + bracket integration |
| Source-cited advice | Marketing-led | FAQ articles | Every claim links to IRS / Cornell LII / SSA |
| Compensation | Commissions on products | Self-serve fees | Flat fee + transparent AUM. No product commissions |
| Custody | Proprietary platform | Proprietary platform | Altruist (modern independent) — you own the account |
| Annual planning meeting | 30-min review | None | Quarterly review + ad-hoc on tax events |
90 minutes with Andrew + a written report walking your specific situation against the full pre-retiree playbook. Roth Conversion Ladder, IRMAA cliffs, RMD projection, Social Security claiming, asset location, drawdown sequencing, beneficiary audit.
The deal: If we don't surface at least $5,000 of structural retirement savings during the session, your $500 is refunded in full and you keep the written report.
Book the Foundation Review →$500 · 90 minutes · Credited toward an engagement if we work together. Refunded if not a fit.
The Pre-Retiree Tax Playbook PDF covers the full sequence: Roth Conversion Ladder math, IRMAA cliffs, RMD projection, Social Security claiming, QCDs, asset location, and drawdown sequencing. Free. We email it.
Most pre-retirees don't need to switch — they need a second opinion on the highest-leverage move of their lives. The Foundation Review is structured as exactly that: an independent CFA Charterholder walks your situation, surfaces what's missing or under-modeled, and gives you a written report. If your existing advisor is doing the conversion math, the IRMAA management, the asset-location work, you'll know it. If they aren't, you'll have the report to start that conversation.
Yes. By the end of the 90-minute Foundation Review session, if Andrew hasn't surfaced at least $5,000 of structural annual or one-time savings available to your specific situation, your $500 is refunded in full and you keep the written report. No questions asked. The math of pre-retiree planning (compounding bracket arbitrage + IRMAA + state-tax + heir cost) virtually never falls below $5K for someone with $1M+ in pre-tax balances.
The playbook applies to anyone within 5-10 years of retirement with $1M+ in pre-tax retirement accounts. The earlier we model the window, the more flexibility you have on Social Security claim age, capital-gains harvest plan, and conversion sizing.
Yes — Good Deals manages assets via Altruist as our custodian. AUM fee is 100 basis points (1%) of managed assets, billed quarterly. Below the $400K threshold, clients stay on engagement-fee-only. Above that, AUM is optional — many clients prefer to keep assets at their existing brokerage and engage Good Deals on the planning + tax-strategy side only.
Currently registered as an Investment Adviser Representative in Texas. We can engage with clients in other states through the de minimis exemption (limited number of clients per state) and add registrations as engagement clarifies which states matter. Compliance side is real — we don't operate where we're not registered.
If $500 feels like a lot to spend before you know if it fits, start with a free 15-minute Discovery Call. We talk through your situation, you ask questions, and we decide together if the Foundation Review makes sense. No pitch.
Book a free 15-min call →Good Deals is the planning workbook + advisory practice of Andrew Escher, based in Austin, TX. Independent stack: Altruist for investment custody, BackNine for insurance placement, Good Deals for the planning layer that ties them together. We work specifically with pre-retirees, HNW executives, and business owners on structural tax + retirement planning. No product commissions, no proprietary funds, no hidden incentives.