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Rolling Over Your Old 401k: A Checklist

By KingPin 9 min read
Rolling Over Your Old 401k: A Checklist

You Left a Job. Now What Happens to That 401k?

You changed jobs, maybe for a 40% raise, maybe because your manager was insufferable, maybe both. Either way, there’s an account sitting at Fidelity or Vanguard or some obscure provider called “Empower” with $47,000 in it and you’ve been ignoring the quarterly statements for eight months.

This is the moment you either handle it correctly and let compound interest do its thing, or you do something dumb and hand 30% of it to the IRS. Let’s go with option one.


The Four Things You Can Do With an Old 401k

You have exactly four options. Here they are, ranked roughly from “fine” to “please don’t.”

Option 1: Leave It in the Old Employer’s Plan

When it makes sense: The old plan has genuinely excellent funds, think institutional-class index funds with expense ratios under 0.05%, and you’re not annoyed by managing a separate account. Some large employers (Google, Microsoft, Amazon) have plans with fund access you literally can’t get in a retail IRA. The Vanguard Institutional Plus share class of the Total Stock Market Index at 0.01% ER is not something you can buy on your own.

When it doesn’t: Fees are high, fund selection is garbage, or the plan charges a “terminated participant fee” (some plans charge $20$50/quarter just to keep your money there). Also: if the balance is under $5,000, the old employer can force a rollover anyway, so leaving it isn’t always your call.

Bottom line: Check the plan’s expense ratios and any maintenance fees first. If you’re paying 0.8%+ in fund expenses, you’re lighting money on fire every year.


Option 2: Roll to Your New Employer’s 401k

When it makes sense: Your new plan accepts incoming rollovers (not all do, check with HR), has good low-cost funds, and you want to consolidate accounts. There’s also a tactical reason to do this: 401k assets have stronger creditor protection than IRAs in many states, and if you ever want to do a backdoor Roth IRA without pro-rata complications, keeping pre-tax money out of IRAs matters.

When it doesn’t: New plan has high-fee funds or a limited menu. If your new employer’s best fund is a 0.60% expense ratio “managed moderate growth” fund, just no.

Checklist item: Before initiating anything, call your new plan’s 401k administrator and confirm they accept rollovers and ask for their preferred rollover form. Some plans are fussy about how the check is made out.


Option 3: Roll to an IRA

This is the right move for most people most of the time.

An IRA at Fidelity, Vanguard, or Schwab gives you access to nearly every fund in existence, zero account maintenance fees, and full control. You can buy VTI, VXUS, BND, or build any three-fund portfolio you want at expense ratios around 0.03 to 0.07%.

Traditional 401k → Traditional IRA (pre-tax stays pre-tax, no tax event). Roth 401k → Roth IRA (after-tax stays after-tax, no tax event).

Don’t mix them up. If you have both in the same old plan, they need to go to separate accounts.

One caveat: if you have pre-existing traditional IRA balances and you plan to do backdoor Roth contributions, rolling pre-tax 401k money into an IRA will trigger the pro-rata rule and make your life complicated. In that case, rolling to the new employer plan keeps your IRA clean.


Option 4: Cash Out

Please don’t do this.

If you cash out a pre-tax 401k, you pay:

On a $50,000 balance, you could walk away with $31,500 after taxes and penalties. You turned $50,000 into $31,500. The IRS thanks you.

The only scenario where cashing out even approaches defensible: you’re in an unusually low tax year, you’re past 55 and left your employer (the Rule of 55 waives the 10% penalty for 401k distributions in some circumstances), and you have a genuine short-term cash need. Even then, think twice.


Direct Rollover vs. Indirect Rollover

This distinction matters and screwing it up is expensive.

Direct Rollover (Do This)

The money goes directly from your old plan to the new account. The check is made payable to “Fidelity FBO Your Name” (or whatever the new custodian is), not to you personally. You never touch the money.

No withholding. No tax event. Nothing to report except a Form 1099-R showing code G (direct rollover). Clean, simple, zero risk.

Indirect Rollover (Be Very Careful)

The old plan cuts a check to you. Here’s the problem: they’re required to withhold 20% for federal taxes automatically. So on a $100,000 balance, you get a check for $80,000.

You now have 60 days to deposit the full $100,000 into the new account, not $80,000. The $20,000 the IRS withheld still counts as “distributed” unless you make up the difference out of your own pocket.

If you only deposit the $80,000 check, the IRS treats the $20,000 as a taxable distribution, plus the 10% penalty if you’re under 59½. That’s $20,000 taxed as income + $2,000 penalty.

You do get the $20,000 back eventually as a tax credit/refund, but you’ve got a cash flow problem in the meantime and you’ve already lost the compounding on that money.

Verdict: Always request a direct rollover. If your old plan insists on cutting a check to you, it can still work, just make sure you have the cash to make up the withholding and meet the 60-day window.


Step-by-Step: Rolling Your 401k to an IRA

Here’s the actual process, demystified:

Step 1: Open the Receiving IRA (if you don’t have one)

Pick a custodian, Fidelity, Vanguard, and Schwab are all fine. Open a Traditional IRA (for pre-tax 401k money). Takes 10 minutes online. Get the account number.

Step 2: Request the Rollover Forms from Your Old Plan

Log into your old 401k portal or call the plan administrator. Look for “rollover” or “distribution” options. You want a direct rollover to an IRA. They’ll ask for:

Step 3: Choose Direct Rollover and Confirm “Zero Withholding”

Explicitly tell them you want a direct rollover to avoid the 20% withholding. Most online forms will have this option. If you’re on the phone, use those exact words.

Step 4: Wait for the Check or Transfer

Some plans wire it electronically. Many still mail a check, to you or directly to the custodian. If the check comes to you, don’t cash it. Mail or deposit it per your new custodian’s instructions within the 60-day window (though with direct rollovers, the clock pressure disappears).

Step 5: Invest the Cash

Once the money lands in your IRA, it sits as cash. You need to actually invest it. This is where people park $60,000 in a money market for two years because they forgot. Log in, buy your target funds, done.

Step 6: Confirm the Form 1099-R

In January, you’ll get a 1099-R from the old plan. For a direct rollover, Box 7 should show distribution code “G.” Your tax software will handle it, it’s a reportable event but not a taxable one.


Checklist: 401k Rollover


The NUA Exception (For People With Employer Stock)

Here’s a niche situation worth knowing: if your 401k holds employer stock with a very low cost basis, there’s a strategy called Net Unrealized Appreciation (NUA) that might beat rolling it into an IRA.

Normally, rolling employer stock to a traditional IRA means future gains get taxed as ordinary income when you withdraw. With NUA, you can instead take a lump-sum distribution of the employer stock, pay ordinary income tax only on the original cost basis (the price your employer paid for the shares), and then sell the stock at long-term capital gains rates on everything above that basis.

Example: You have $200,000 of company stock in your 401k. The plan’s cost basis is $40,000 (what the company paid for those shares over the years). You take an NUA distribution, pay income tax on $40,000, and the remaining $160,000 in appreciation is subject to long-term capital gains rates (0%, 15%, or 20%) instead of ordinary income rates.

If you’re in a high income bracket and have significant employer stock with a low basis, run the numbers before blindly rolling everything to an IRA. The NUA strategy is one of the few places where not rolling over is actually the smarter financial move.


Don’t Overthink the Destination

If you don’t have a strong reason to stay in the old plan or move to the new employer’s plan, just roll to an IRA. Set it up at Fidelity or Vanguard, buy a three-fund portfolio or a target-date fund, and move on with your life.

The best rollover is the one you actually complete before another year goes by with that account earning 0.01% in the default money market fund while your former employer charges you $25/quarter to exist.

The $47,000 version of you from eight months ago is still waiting. Go fix it.


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