The question Jeff Judge hears most from Virginia residents at the start of a new planning relationship isn't "What should I invest in?" It's a quieter, more uncomfortable version of the same question: "Where do I even start?"
The answer is almost always the same: you start with the numbers you already have. Not with a perfect financial picture. Not with everything organized. With whatever is currently in front of you.
Online retirement planning in Virginia through TeleWealth at Chesapeake Financial Planners is built to work with clients who are starting from that place—smart people with real financial complexity who haven't had a structured process before now. Here's how to start.
Step 1: Gather What You Already Have
Before your first TeleWealth session, collect whatever you can find on these six categories. You don't need everything. Get what's accessible.
Retirement accounts. 401(k), 403(b), pension, IRA, Roth IRA. Note the institution, the approximate balance, and whether you're still contributing. For Virginia Retirement System (VRS) members, pull your most recent benefit statement, which shows your projected pension benefit at different retirement ages.
Social Security estimate. Create an account at ssa.gov if you don't have one. Your Social Security statement shows your estimated benefit at age 62, at full retirement age (67 for most people), and at 70. These three numbers are foundational to retirement income planning.
Other income sources. Does your spouse have a pension? Do you have rental income? Deferred compensation from a prior employer? Part-time work you plan to continue in retirement?
Debts. Mortgage balance and rate. Any other significant liabilities.
Insurance. Current life insurance coverage, long-term care coverage if any, and health insurance situation (especially if you're planning to retire before Medicare eligibility at 65).
Current income and savings rate. Your gross income and how much you're currently putting toward retirement each year, across all accounts.
You won't have all of this perfectly organized. That's fine. Jeff works with clients who come in with a shoebox worth of accounts and a rough idea of what they want their retirement to look like. Organizing is part of the process.
Step 2: Know Your Contribution Limits
One of the most common and correctable mistakes in retirement planning is leaving contribution capacity on the table. For 2024, the IRS sets the following limits:
401(k) and 403(b): $23,000 per year, with an additional $7,500 catch-up contribution available to those aged 50 and older. Traditional or Roth IRA: $7,000 per year, with an additional $1,000 catch-up for those 50 and older.
Many Virginia clients—especially those who are 50 to 60 and in their peak earning years—are not maxing these out. The reason is usually not financial. It's that nobody has ever told them clearly that this is the priority. "I see clients in their mid-50s who are contributing 6% to their 401(k) and don't realize they could be contributing 30% if they needed to," Jeff says. "The contribution limits are the lever. Most people don't know where it is."
Step 3: Think Through Your Retirement Timeline
You don't need a specific retirement date. You need a range.
Do you want to retire before 65? Between 65 and 70? Work part-time through your late 60s? Each answer has different implications: for health insurance coverage, for Social Security timing, for how much your accounts need to produce, and for whether Roth conversions in the years before retirement make sense.
The R.U.D.D.E.R. Method™ that Jeff uses at Chesapeake Financial Planners starts with Retirement income as the first variable precisely because your timeline shapes every other decision. Knowing when you want to stop working—even roughly—is the input that makes everything else calculable.
Step 4: Identify the Questions That Are Already Bothering You
Most people starting retirement planning come in with at least one or two specific anxieties. Write them down.
Common ones from Virginia clients: "I have a VRS pension but I don't know if it's enough." "I don't know when to take Social Security." "I have old 401(k)s from three former employers that I've never consolidated." "My spouse and I have never really talked about what retirement looks like for us."
These questions are the starting point for a real planning conversation. They're also what a Fit Call is designed to surface.
Step 5: Book a TeleWealth Fit Call
The Fit Call is a 30-minute video meeting with Jeff. You bring whatever you've been able to gather from the steps above. Jeff learns about your situation, your timeline, and what's been on your mind. You ask whatever you want.
If it's a match, the next step is a full financial intake and a formal planning session. If it's not, Jeff will tell you directly.
For Virginia residents specifically, the Fit Call is also the right time to mention any Virginia-specific variables: VRS or FERS pension, military retirement pay, federal job situation, or a recent relocation that's created tax uncertainty.
The online retirement planning process in Virginia doesn't require you to have it all figured out before you start. It requires you to start. Book a TeleWealth Fit Call at www.chesapeakefp.com or call (410) 652-7868.
The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn't guarantee future results. Consult with qualified financial professionals regarding your specific situation.
Securities offered through LPL Financial, Member FINRA/SIPC. Investment advice offered through Great Valley Advisor Group, a registered investment advisor and separate entity from LPL Financial.
Chesapeake Financial Planners | 2402 Scotlon Ct, Forest Hill, MD 21050 | (410) 652-7868 | www.chesapeakefp.com
