If that headline doesn’t grab you, fair enough. But if you like playing with numbers like I do, you might enjoy Boldin. Having a simulator handy feels like a reliable co-pilot—someone who reminds you to check the fuel gauge and drop the landing gear. Personal finance never runs on autopilot, especially after an early retirement.
Think about the variables: a new tax-and-spend bill from DC (nicknamed “OBBBA”) added a lot of changes—good for some, not so great for many. Boldin keeps up with those updates and adjusts your plan forecasts accordingly.
Boldin now includes OBBBA provisions
There are plenty of factors beyond Washington. For me, a part-time handyman job brings in cash, interesting work, and great clients—no more cubicle life for this guy. I pop into Boldin now and then to update my take-home pay because the work is seasonal. Knowing how much liquid cash you have matters when considering Roth conversions or overall cash flow. Boldin helps you decide which savings buckets to draw from.
I’m one of those people who didn’t think much about the future tax bill from a 401(k) while I was dumping money into it. Don’t get me wrong—a 401(k) with an employer match and low fees is fantastic. You don’t pay tax while it grows. But after early retirement, you see the downside: the bigger your 401(k), the bigger your required minimum distributions (RMDs) at 73. If you’re a 401(k) millionaire at 50, expect annual RMDs of $200K+ at 73, and nearly $600K by 83. Those forced withdrawals get taxed—and often at a much higher bracket.
That’s why Boldin matters to me. I don’t mind paying taxes, but I’d rather do it in a lower bracket—22% or 24% tops. The Boldin Roth Explorer lets me pick a target tax bracket and set an annual limit for how much cash to set aside for Roth conversion taxes.
Setting cash aside for quarterly federal and state tax payments can be tricky, so it’s smart to work with an accountant to plan those payments. It’s all online, so don’t panic.
Example: If I convert $100K from a pre-tax IRA (rolled over from my 401(k) after I quit) to a Roth in January 2026, I’ll do it within my Vanguard account—Vanguard makes conversions straightforward. I’ll then start quarterly tax payments in April. Expecting to land in the 22% bracket, I’d set aside roughly 20% of the conversion for federal taxes and about 6% for Minnesota. The hard part for early retirees is often cash flow.
If you don’t want to tap your 401(k) before 59½, plan other income sources for the “gap years”: rental income, brokerage dividends, or a business doing gigs you enjoy.
You need real cash to make a dent in a pre-tax IRA. If converting just over $100K means paying nearly $25K in taxes, have a cash plan before you hit “convert.” Those are dollars you could’ve spent on trips, home renovations, or speculative ETFs.
Boldin’s Roth Explorer gives options to tailor conversions. You can limit how much of a post-tax brokerage account can be used to pay conversion taxes—why realize capital gains if you don’t have to? You can also set an annual conversion cap—maybe convert $80K or $50K instead. Figuring this out in early retirement is part of the game; I’d rather avoid being forced into a $600K RMD at 83.
Why not just use IRA funds to pay conversion taxes? It’s math. Using IRA dollars eats into money meant to grow and can trigger penalties if you’re under 59½. Boldin shows how much you lose by paying taxes from your IRA and lets you save that scenario to compare with paying out of pocket. Work with an accountant—sometimes paying conversion taxes from the IRA ends up better overall, but you should model it first.
One silver lining of an oversized 401(k) is the ability to make qualified charitable distributions (QCDs) to nonprofits tax-free. I might grumble about a $600K RMD at 83, but I can give away a big chunk tax-free via QCDs—lowering my effective tax rate while supporting causes I care about.
That’s likely where we’ll end up: using pre-tax IRA dollars to seed a donor-advised fund. There will always be causes to support and disasters to respond to as leaders keep kicking the can down the road.