When is the Best Time to Rollover a 401(k) into an IRA?
- SkyBlue Wealth Advisors
- Jul 14
- 4 min read
So, you've been socking money away in your 401(k)—nice! But now you're wondering: When’s the right time to rollover that cash into an IRA? Whether you're switching jobs, retiring, or just looking for more investment freedom, the timing of a rollover can impact your taxes, fees, and future gains.

Let’s break it all down in plain English—no financial jargon or confusing charts. Just solid advice to help you make a smart move with your hard-earned retirement funds.
What’s the Difference Between a 401(k) and an IRA Anyway?
Before we dive into timing, let’s do a quick refresher on what sets these two retirement accounts apart.
401(k): Offered by employers, often includes matching contributions, limited investment choices.
IRA (Individual Retirement Account): Set up by you, way more investment options, generally lower fees.

The big picture? You get more control with an IRA, but you give up employer perks like matches.
Best Times to Rollover a 401(k) into an IRA
Timing is everything, especially when taxes and retirement goals are on the line. Here are the most strategic times to consider rolling over:
1. When You Leave a Job
Honestly, this is the most common and ideal time to do a rollover.
Why? Your old 401(k) just sits there, unmanaged. By rolling it over, you keep your investments working hard—on your terms.
Benefits:
Avoids keeping track of multiple old accounts
Opens up more investment options
Helps consolidate your retirement planning
Just make sure to do a direct rollover (more on that below) to avoid taxes or penalties.
2. When You Retire
Now’s the time to simplify your financial life.
Why roll it over at retirement? IRAs can offer easier access to your funds and more flexible withdrawal options.

Heads up: If you’re over 59½, you won’t get slapped with an early withdrawal penalty, but you still want to plan withdrawals strategically to minimize taxes.
3. If Your Employer’s Plan Has Limited or High-Fee Options
Let’s face it: not all 401(k)s are created equal. Some come with high management fees or poor investment choices.
Rollover time? You bet.
Why? With an IRA, you can choose low-cost ETFs, stocks, mutual funds—you name it. That means more control and potentially better returns over time.
4. You’re Planning a Roth Conversion
Thinking of converting traditional retirement savings into a Roth IRA? Timing matters here, too.
Why roll over now? Doing a rollover can be your first step before converting to a Roth. Just know that you'll pay taxes on the amount you convert.
Pro tip: Try this in a year when your income is lower to reduce your tax hit.
5. When You’re Managing Required Minimum Distributions (RMDs)
If you're over 73 (or 72, depending on your birth year), you're required to start taking RMDs from traditional 401(k)s.
IRA edge: IRAs offer more flexible RMD management, especially if you have multiple retirement accounts.
How to Do a Rollover the Right Way
Here’s where folks trip up—rollovers need to be done carefully to avoid taxes or penalties.

✅ Direct Rollover (The Smart Way)
Money moves straight from your 401(k) provider to your IRA. No taxes withheld, no penalties.
❌ Indirect Rollover (The Risky Way)
You receive the money and have 60 days to deposit it into an IRA. But 20% is withheld for taxes, and if you miss the deadline—ouch! You could owe taxes and penalties.
Stick with the direct route. It’s clean, fast, and headache-free.
Pros of Rolling Over a 401(k) Into an IRA
Let’s get to the good stuff.
More investment choices: Stocks, bonds, ETFs—you name it.
Lower fees: IRAs usually cost less to manage.
Better control: Choose your own brokerage, tools, and risk level.
Consolidation: Keep your retirement tidy by merging accounts.
Possible Downsides to Consider
Every rose has its thorn, right?
No more employer matching: Once you're out, you're out.
Creditor protection: 401(k)s typically have stronger protection under federal law than IRAs.
Early withdrawal rules: Slightly different rules apply between 401(k)s and IRAs, especially if you’re retiring early (before 59½).
Quick Checklist Before You Rollover
Here’s a little cheat sheet to help you know if now’s the right time:
✅ You’ve left your job
✅ You're not getting employer contributions anymore
✅ You want more investment control
✅ You’re aiming for lower fees
✅ You're consolidating retirement accounts
FAQs
❓ Will I get taxed on a 401(k) rollover to an IRA?
Not if you do a direct rollover. You only get taxed if the money goes to you first (indirect rollover).
❓ Can I roll over into a Roth IRA?
Yes, but you’ll owe taxes on the amount converted if it’s coming from a traditional 401(k).
❓ How long does the rollover process take?
Usually about 5 to 10 business days, depending on your providers.
❓ Is there a limit to how much I can roll over?
Nope! You can rollover your full 401(k) balance.
Wrapping It All Up
Still wondering when’s the best time to rollover a 401(k) into an IRA? Here's the nutshell version: Do it when you leave your job, retire, or want better investment options—just don’t rush. Make sure it's the right move for your goals and tax situation.
Rollover the right way (direct, not indirect), and you could seriously upgrade your retirement game.
Want More? Check These Out:
Still feeling unsure? Schedule a meeting today. Retirement planning doesn't have to be a DIY mission for everyone.

Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through TOP Private Wealth, a registered investment advisor and separate entity from LPL Financial
