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Tax-Optimized Retirement Withdrawal & Conversion Planner

Automatically model Roth conversions, withdrawal sequences, and early retirement scenarios to minimize lifetime taxes and unlock financial independence before 60.

Added May 15, 2026

Personal Finance

FinTech

Retirement Planning

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The Problem

Investors aged 30-60 struggle to optimize complex retirement decisions like Roth conversions, IRMAA thresholds, withdrawal sequencing, and accessing locked retirement funds before age 59.5. Standard advice assumes a one-size-fits-all timeline ending at 60, leaving disciplined savers without tools to model early retirement, partial conversions during low-income years, or tax-efficient bridges to traditional retirement accounts.

Potential Solution

A SaaS planning tool that ingests account balances, income projections, and life goals to automatically compute optimal multi-year Roth conversion ladders, 72(t) SEPP strategies, and withdrawal sequences. Users get year-by-year action plans showing tax savings, IRMAA impacts, and early-access bridges, with scenario comparisons for retiring at 40, 50, or 60.

Why Now?

Rising interest in FIRE, recent tax law changes (SECURE 2.0, CGT adjustments), and growing distrust of the traditional 40-year retirement timeline are pushing high-earners to seek sophisticated planning tools that financial advisors charge $3K-10K to produce manually.

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Showing 1-4 of 4 signals

RedditMay 15, 2026

Long term holders of assets are often better off under the CGT changes

People are posting a bunch of scenarios that show a huge new tax burden r.e CGT changes, but it seems they deliberately use a shorter time horizon and an outsized return to make the numbers look as scary as possible. Scenarios ran using plausible returns over a longer term (ten plus years) often show a far smaller increase, or even a reduction. For example, take a home bought for $500000. Assume 3% annual inflation and 5.2% annual capital growth (approximately the past ten year average), and assume it's taxed at the maximum 47%. If held for ten years it would be valued at $830094, for a $330094 profit. Under the old system, you'd get your 50% discount and pay $77592 tax. Under the *new* system, your cost base would be adjusted to $671958, for a $158135 profit. Final tax bill at 47%? Only $74324. The new system primarily hits short term asset holders that made a large, sudden windfall. If your shares suddenly double or triple after a year or two or ownership, you will get absolutely slogged. But frankly, I think it's reasonable for most people in that cohort face a higher than historical tax.

RedditMay 15, 2026

Roth Conversions at Age 43?

I was laid off in February and might end up with significantly lower income this year. Should I consider a partial Roth conversion or wait until retirement isn't so far off? - 43 yrs old, single, no kids, rent - Traditional IRA: $550k - Roth IRA: $200k - I have additional cash in taxable brokerage to cover taxes on a potential conversion - State income tax: 5% Questions: 1. Should I consider a Roth conversion for some of the traditional assets this year or is that something to consider when you're closer to retirement? (maybe filling up to the 24% federal tax bracket) 2. I'm probably opening up a can of worms here, but thoughts on future contributions - Roth vs Traditional? Given current asset mix am I creating more of a tax issue for my future self by contributing to traditional?

RedditMay 15, 2026

When to Convert Tradional IRA to ROTH to avoid IRMAA is confusing me

My Wife and I retire in 2027 at age 62. In retirement, we have the following income: $5500 monthly Military Retirement $1300 Monthly Federal Service Retirement $1241 Monthly in Disability Pay (doesn't count for IRMAA) My Wife and I have: 1. $700K in TSP ($400K in Roth, $300K in traditional). I currently place 25% of my $138,000 annual salary to TSP, + an employer match, but that stops when I retire in April 2027. 2. $500K in Ameriprise (all Roth) and I am in the process of moving all funds from Ameriprise to Fidelity because Ameriprise is a rip-off in so many ways (think high fees on everything) Our current tax bracket is 24% and I've run Boldin scenarios and all pretty much have me staying in that tax bracket throughout retirement (assuming they don't change in the future). I am trying to determine how to convert funds in the traditional bucket to Roth without triggering IRMAA penalties at 65. Because Medicaid will look back two years at 65 (2030), that takes me to my age 63 (2028) retirement earning year. I need to stay below the $218,000 in IRMAA bracket in 2028, so I don't role into the next higher bracket. My income from above will total $81,600. Am I correct in that I may convert up to $136K from traditional to Roth in both 2027 and 2028 without moving into the next highest IRMAA bracket? Are there other options you might suggest other than the conversion? Thanks

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