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Chip’s Tips: Roll Over Like a Pro

March 24, 2026

Chip’s Tips: Roll Over Like a Pro: 401(k) Rollovers and Tax‑Deferred Growth (Without Tripping Over Wires)

So you’ve saved diligently in your 401(k) and now you’re wondering, “What happens when I change jobs or retire?” The answer: you want those hard‑earned dollars to keep growing – and you don’t want Uncle Sam taking an early bite.

In a nutshell, when you roll over a retirement distribution, you don’t have to pay tax on it until you pull the money out. That means your nest egg keeps compounding tax‑deferred. And doing it right can be as smooth as your favorite coffee — just follow the rules:

  • Direct rollover – ask your plan administrator to move your money directly to your new 401(k) or IRA. The IRS explains that no taxes are withheld if the distribution goes straight to your new account. Think of it as your retirement savings taking a limo from one account to another — no pit stops.
  • 60‑day rollover – if they cut the check in your name, you have 60 days to deposit it into a new plan. Taxes will be withheld from the check, so you’ll need to use other funds to roll over the full amount. Miss the deadline and the IRS may send an unwelcome invitation to the tax dance.
  • One‑per‑year rule – you can only do one IRA‑to‑IRA rollover per year. Breaking this rule could leave you with a tax headache — and who needs more of those?

When in doubt, call a fiduciary retirement advisor. Fiduciary plan advisors — those who legally have to act in your best interest — help you pick diversified investments, monitor the markets and stay compliant. Plus, they keep you from accidentally giving yourself a tax bill!