In partnership with

The Better Veteran

Maximize Your Benefits. Optimize Your Life.

June 4, 2026

A few months after I separated, the calls started.

LinkedIn messages. A cold email. One actual phone call. All some version of the same pitch: "Congrats on your transition, let's hop on a quick call and talk about rolling your TSP into an IRA I can manage for you." Friendly. Professional. This is before the phrase “let’s hop on a quick call” made me want to “hop out of a quick skyscraper”. Corporate world has ruined that phrase. Anywho, it was the grown-up-sounding thing to do with the biggest pile of money most of us have ever had in one place.

I almost did it. It felt responsible. Then I actually ran the numbers, and my stomach dropped.

The TSP charges about $0.35 per $1,000 a year. On a $300,000 balance, that's roughly $105 a year. The "managed" IRA he was pitching? Around 1% which is about $3,000 a year on that same balance. Same money. Same funds, basically. Just thirty times the fee, compounding silently, every single year.

Over 29 years, that gap quietly eats about $538,000 of your retirement. More than half a million dollars for a phone call I almost took because it sounded like the adult thing to do.

That's when it hit me: nobody makes a commission telling a veteran to keep their cheap account and quietly handle it themselves. So nobody tells them. I went looking for a tool that would just lay the decision out honestly whether I should keep it, roll it, convert it but there wasn't one built for us.

So I built it.

Tell it where you are: separating this year, already out for a while, or still drilling in the Guard/Reserve, your balance, your rough income, and your VA rating. It gives you one clear answer and shows its work. No jargon, no upsell. Here's what's underneath that answer.

First: the move with a closing window

Here's the thing almost nobody tells you before it's too late: the year you take off the uniform is probably the last lowest-tax-income year of your entire adult life.

Think about it. A partial year of W-2 pay. Tax-free VA disability that the IRS doesn't even count as income. Maybe some combat-zone pay in the lookback. For one window, your taxable income is low and that's the cheapest time on earth to move money from your Traditional (pre-tax) TSP into a Roth, where it grows and comes out tax-free forever.

Do it that year and you might pay 12% on that conversion. Wait until you're earning a full civilian salary and it's 22%, 24%, or more. Same dollars, double the tax just because of when you moved them.

The tool does this math for you: how much room you have left in your low bracket, the exact dollar amount you can convert before you bump into the next one, and what you'd pay now versus later. If it's worth doing, it even lays out a multi-year ladder — "at $38K/year, you can move your whole $190K Traditional balance to Roth in 5 years."

But it will not push you into a Roth because a Roth isn't always right

Every "Roth vs. Traditional" article you've ever read was quietly selling you the Roth. This tool genuinely isn't.

The honest answer comes down to one question: what tax bracket will you be in during retirement? If it'll be lower than today, converting is a mistake you'd be prepaying tax you'd never have owed. So the tool asks you that up front and gives you a real, two-sided verdict:

  • "Convert — you'll save real money" if you're low now, higher later.

  • "Skip it — Traditional likely wins for you" if your retirement bracket will be lower.

  • "It's basically a wash" when they match and the only edge is tax-free growth.

No rigged default nudging you toward the answer that sounds exciting. Just your numbers.

This is very simple math that seems complicated but is broken down into exactly what you need to see in order to make the best decision.

The $538,000 chart

Remember the fee math from the top of this email? The tool draws it.

Your balance growing in the TSP at 0.035%, versus the same balance in a 1% managed IRA. Two lines, starting at the same place, slowly pulling apart into the hundreds of thousands, then over a million until the gap is its own little fortune.

Once you see those two lines diverge, you cannot unsee it.

It’s a line that will never be able to catch the other in many instances.

One important fairness note the tool keeps front and center: a low-cost self-directed IRA (index funds, ~0.04–0.10%) is nearly as cheap as the TSP and gives you more flexibility. Rolling over to that is a perfectly good move. The trap is specifically the ~1% advisor-managed account. Don't let the chart scare you off a rollover for the right reasons.

Since we’re talking about what to do with your retirement fund, art is a great place to put your money (absolutely not financial advice):

Where to Invest $100,000 Right Now, According to Experts

Investors face a dilemma. When the S&P 500 finished its worst quarter since 2022 last month, diversifiers like bonds and bitcoin fell too.

Even with the turnaround in mid-April, analysts at Goldman Sachs and Vanguard have projected low-single-digit annualized returns from 2024-2034.

Bloomberg asked where experts would personally invest $100,000 for their March monthly edition.

One answer that surfaced for a second time? Art.

It's what billionaires like Bezos and the Rockefellers have privately used to diversify for decades.

Why?

  1. Appreciation. The ArtPrice100 Index outpaced the S&P 500 overall from 2000 to 2025

  2. Low-correlation. The postwar contemporary segment has moved independently of traditional investments like stocks since ‘95.*

  3. Resilience. A scarce, physical, and global asset class with decades of demonstrated demand.

Thanks to the world's premier art investing platform, now anyone can invest in works featuring legends like Banksy, Basquiat, and Picasso, without needing millions.

Shares in new offerings can sell quickly but...

*According to Masterworks data. Investing involves risk. Past performance is not indicative of future returns. See important Reg A disclosures at masterworks.com/cd.

If you live on VA disability, you've got a rare advantage every year

This is the part I haven't seen anyone else point out.

If a big chunk of your income is tax-free VA disability, your taxable income stays low not just your separation year, but potentially every year. Which means you can convert a slice of Traditional TSP to Roth at 10–12% over and over, methodically draining that pre-tax balance at rock-bottom rates while everyone else waits and pays full freight.

And here's the bonus that early-retired civilians would kill for: they have to keep their income low to qualify for ACA health-insurance subsidies, which caps how much they can convert. You don't. On VA health care, TRICARE, or CHAMPVA, you're not chained to that income cliff. You can convert aggressively without blowing up a subsidy you were never relying on.

This isn’t financial advice, but there are better and worse ways to optimize your retirement funds and this is one of them.

Keep, roll, convert, or cash out: the plain-English cards

At the bottom you get a card for each of your four options, with the real pros and cons for your situation. A few calls that catch people off guard:

  • The G Fund is a legit reason to stay. Government-backed, never loses principal, pays a bond-like yield — and there's nothing like it in any IRA. If you value that, the tool tells you not to give it up.

  • The Rule of 55. Separate in or after the year you turn 55 and you can pull from the TSP penalty-free before 59½. Roll to an IRA and you lose that. The tool flags it before you do something you can't take back.

  • Cash out is shown as what it almost always is — a mistake. 20% withheld, ordinary income tax, a 10% penalty under 59½, and decades of tax-free growth gone. It's on the list because it's an option, not because it's a good one.

What this tool won't tell you

I'd rather you trust it than oversell it. The honest limits:

  • It's federal-tax-focused. It doesn't fully model your state income tax, IRMAA Medicare surcharges, or ACA subsidy cliffs (though it flags when the ACA point matters for you). Near any of those edges? Talk to a CPA.

  • It's about where your TSP lives and how it's taxed — not how it's invested. Your fund mix (G / F / C / S / I / L) is a separate decision for another day. This tool won't pick your funds.

  • A conversion is irreversible. Since 2018 you can't undo one. Convert only what you're sure about, and always pay the tax from cash on hand — never from the converted money.

  • It's a planning tool, not advice. Big balance or anything unusual? Run your number here first, then take it to a fee-only fiduciary — one who charges a flat fee, not a slice of your account forever.

Why I built this

I'm a 100% P&T veteran, an MBA student, a husband, and a dad. When I separated, the TSP was the thing I most easily could have ignored, or worse, handed to the friendly guy on the phone without thinking.

The more I dug in, the more it bothered me. The people who show up to "help" with your TSP are very often the ones charging 1% to do it, and 1% doesn't sound like anything until you watch it eat half a million dollars. Meanwhile the actually-valuable move, converting in your low-income years, is something you have to already know about to ever do, because there's no commission in teaching it.

That's the whole reason The Better Veteran exists. The best moves here are free and unglamorous. I'd rather you keep the $538,000 than let someone quietly manage it away from you.

Run your numbers

If you've got a TSP and you've been meaning to "figure it out someday" — someday's cheaper today, especially if you got out recently. Open the tool, drop in your balance and rough income, and look at two things: how much you could convert this year at a low rate, and what a 1% fee would cost you over time.

Two minutes. Might be the highest-value two minutes of your whole transition.

And if you've already got a guy in a nice suit "managing" it for you: run it anyway. Then go look at what you're paying. Hit reply and tell me what you find; I read every one.

Talk soon,

Zak

If you’d like to support the mission of The Better Veteran, you can do so here. If anything I’ve ever shared has opened your eyes on how to take advantage of your benefits, or saved you money, and you feel so inclined to show support. You can do so here:

All tools and resources will remain free, forever, for veterans. This is just a way of saying thanks.

More free tools — one hub:

Scroll to the bottom of each of the tools to see all of the rest of the suite.

Stay informed. Stay empowered. -- The Better Veteran Team

This newsletter is for informational purposes only and does not constitute legal, financial, medical, or benefits advice. All estimates use 2026 federal tax brackets and standard deductions (IRS Rev. Proc. 2025-32, post-OBBBA), published TSP expense ratios (tsp.gov), and 2026 VA compensation rates. This tool is for planning purposes only and is not tax, legal, or financial advice. Roth conversions are irreversible and have tax consequences — consult a CPA or fee-only fiduciary before acting on a large balance.

Keep Reading