By George P. Jackson, MBA, CPA, CFA, CFP®, CMT, CLU, ChFC
A 401(k) rollover is a meaningful financial decision that can influence taxes, fees, and the flexibility you have with your investments. Understanding your options helps you decide whether shifting your retirement savings to a more personalized structure aligns with your goals.
Why Retirees Consider 401(k) Rollovers
As you enter retirement, your 401(k) may represent decades of work and discipline. Many retirees look to roll their savings into an IRA managed by their advisory team because it often provides:
- Broader investment flexibility
- A coordinated strategy across all accounts
- Streamlined retirement income planning
- Ongoing monitoring and guidance tailored to their situation
If you’re seeking a more unified approach or prefer a relationship-driven investment strategy, a 401(k) rollover may be an attractive next step.
Step 1: Evaluate Your Current 401(k) Options
Before initiating a rollover, it can be helpful to review:
- Your plan’s current investment menu
- Administrative or underlying fund costs
- Withdrawal flexibility
- Coordination with your broader retirement goals
Clients frequently tell us this comparison clarifies how an IRA under our management may offer greater adaptability and long-term planning advantages.
If you’d like us to run this comparison for your specific plan, we’re happy to do so.
Step 2: Choose Where the Rollover Will Go
Most retirees move their balance to a traditional IRA for long-term management. Others explore Roth planning or consolidation into one coordinated account.
If you’re working with our team, we can help you evaluate:
- The type of IRA that fits your retirement income plan
- How your 401(k) investments translate into an IRA strategy
- Whether consolidating multiple accounts simplifies your required distributions
Clients often find that a single, professionally managed IRA brings clarity and organization to their financial lives.
Step 3: Request a Direct 401(k) Rollover
A direct rollover keeps the process clean and avoids unnecessary withholding. We guide many clients through this step each year, and we can walk you through the phone call or handle the custodian coordination with you.
Most plans follow this process:
- You contact your 401(k) plan or initiate an online request.
- The plan transfers funds directly to your IRA custodian.
- We step in to invest and allocate the funds according to your personalized retirement strategy.
If you’d like assistance with this step, our team is ready to facilitate the transfer.
Step 4: Set Up Your Retirement Investment Strategy
Once the funds arrive, the real value of a 401(k) rollover begins. With a professionally managed IRA, we can design an investment plan aligned with:
- Your income needs
- Risk tolerance
- Tax considerations
- Long-term goals
- Required minimum distributions
The expanded investment universe available in an IRA gives us the ability to create a strategy that reflects your full financial picture, not just the options within one employer plan.
If you’d like us to map out what your retirement income plan could look like post-rollover, we can prepare a detailed illustration.
Step 5: Confirm Withdrawal and Tax Settings
In retirement, comfort comes from knowing your income arrives reliably and your tax settings match your expectations.
We help clients set up:
- Monthly or quarterly withdrawals
- Federal and state withholding preferences
- RMD schedules
- Coordination between IRAs, brokerage accounts, and Social Security
A rollover often gives you more flexibility in how and when your retirement income is received. We can walk through these options together.
Common 401(k) Rollover Mistakes to Avoid
1. Accidentally triggering taxes
Taking the distribution as a check payable to yourself can result in mandatory withholding. A direct 401(k) rollover avoids this complication entirely.
2. Moving funds without a strategy
A 401(k) rollover is most effective when it’s part of a coordinated retirement plan. Clients often rely on us to build the investment and withdrawal framework before the funds arrive.
3. Staying in a plan that no longer fits your goals
Some employer plans are excellent, but many retirees find that an IRA provides more flexibility and hands-on guidance.
If you’d like an objective comparison of “stay vs. roll over,” we can prepare that for you.
When Staying in the 401(k) May Be Reasonable
There are situations where keeping funds in the employer plan aligns with the client’s goals, such as unusually low-cost institutional funds or active employment past age 73. Even then, it’s valuable to review how an IRA might support your broader planning needs.
We routinely evaluate these tradeoffs with clients and can walk you through the same review.
Making Confident Decisions About Your 401(k) Rollover
More than a transaction, a 401(k) rollover shapes how your investments are managed, how your income is structured, and how your long-term plan is executed. Many retirees appreciate having one advisory team overseeing the entire process and coordinating their retirement strategy year after year.
If you’re considering a rollover, or would like a personalized analysis of your 401(k) versus an IRA, Jackson Wealth Management, LLC is here to help. Our team can evaluate your options, outline the potential advantages, and guide you through each step at a pace that feels comfortable.
If you’d like us to prepare a 401(k) rollover comparison or begin the transfer process, we would be glad to get started. To get in touch, schedule a consultation today or calling (407) 585-0235, emailing gj@jacksonwm.com, or booking online.
Frequently Asked Questions
What is a 401(k) rollover, and why do retirees consider one?
A 401(k) rollover is the process of moving retirement savings from an employer-sponsored plan into an IRA or another qualified account. Retirees often consider 401(k) rollovers to gain broader investment choices, consolidate accounts, coordinate income planning, and receive ongoing, personalized guidance that better aligns with their retirement goals.
What are the tax implications of 401(k) rollovers?
When done correctly as a direct rollover, 401(k) rollovers are generally not taxable and avoid mandatory withholding. Taxes may apply later when distributions are taken, depending on the account type and withdrawal strategy. Working with an advisor can help ensure the rollover supports tax efficiency and avoids costly mistakes.
How can Jackson Wealth Management help with 401(k) rollovers?
Jackson Wealth Management helps clients evaluate whether a 401(k) rollover makes sense by comparing plan costs, investment options, and income flexibility. For clients who proceed, the team coordinates the rollover, builds a personalized IRA investment strategy, and integrates withdrawals, taxes, and required minimum distributions into a comprehensive retirement plan.
About George
George P. Jackson is the CEO and CIO of Jackson Wealth Management, LLC, based in Lake Mary, Florida. With over 33 years of experience in the financial services industry, George is passionate about making a meaningful difference in his clients’ lives through comprehensive, integrated wealth management. He specializes in helping clients make confident financial decisions by serving as their trusted “one-stop shop” for anything money related, from investments and retirement planning to taxes and estate strategies.
George obtained his Bachelor of Business Administration as well as his Master of Business Administration (with an emphasis in quantitative analysis) from University of Cincinnati. His designations include Certified Public Accountant (CPA), Chartered Financial Analyst®, CERTIFIED FINANCIAL PLANNER®, Chartered Market Technician®, Chartered Life Underwriter®, and Chartered Financial Consultant®. Outside the office, he enjoys tennis, flying airplanes, traveling, spending time with his adult children, Christina and Matthew, and anything to do with the ocean. To learn more about George, connect with him on LinkedIn.
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