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IRA Rollovers Cornerstone Guide

The 401(k) Rollover Guide

Leaving a job means deciding what to do with your 401(k). Here are your options and the mistakes to avoid.

Updated June 8, 2026 9 min readIRA Rollovers
Original infographic in development: The 401(k) Rollover Guide

When you change jobs or retire, you have several choices for your old 401(k) — and the right one depends on your goals.

This guide walks through your options and how to move the money without unnecessary taxes or penalties.

Your four main options

Leave it, roll to a new plan, roll to an IRA, or cash out — and the trade-offs of each.

Why cashing out is usually costly

The taxes and penalties that can come from taking the money directly.

Rolling into an IRA

How an IRA can offer more investment and income options.

Avoiding rollover mistakes

Using a direct rollover to sidestep withholding and deadlines.

Positioning the money for retirement

How rolled-over funds can support growth or guaranteed income.

This guide is for general educational purposes only and is not financial, tax, or legal advice. Tim Hartle is an independent insurance professional. Annuity guarantees are subject to the claims-paying ability of the issuing insurance company and are not FDIC insured. Rules and product features vary by situation and by state. Please consult a qualified advisor about your own circumstances.

Frequently Asked

What should I do with my old 401(k)?

Common options are leaving it, rolling it into a new employer's plan, or rolling it into an IRA. Cashing out usually triggers taxes and penalties.

Is rolling a 401(k) into an IRA taxable?

A direct rollover to a traditional IRA is generally not taxable. A Roth conversion would be taxable in the year you convert.

Can I roll over my 401(k) while still working?

Sometimes, depending on your plan's rules. Many people roll over after leaving the employer or retiring.

Apply This to Your Own Plan

Schedule your complimentary, no-pressure Retirement Income Review with Tim. Call (727) 692-5866 or book below.

Annuities are insurance contracts. Guarantees, including guaranteed lifetime income benefits where available, are subject to the claims-paying ability of the issuing insurance company. Product features, fees, withdrawal restrictions, and surrender charges vary by contract.