Jeff Judge, CFP®, AEP®, ChFC®, CLU®
Trusted Guide for Busy Professionals Seeking Financial Clarity
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Serving Clients Nationwide
Trusted Guide for Busy Professionals Seeking Financial Clarity
Areas of Focus
- Business Owners
- Divorce Financial Planning
- Employee Stock Options
- Equity Compensation Options
- Estate Planning
- Exit Planning
- Financial Life Planning
- High Net Worth
- High Net Worth Retirement Planning
- Inherited Wealth
- Investment Management
- Job Loss
- Legacy Planning
- Multi-Generational Wealth
- Retirement Income Planning
- Retirement Planning
- Roth Conversion Strategies
- Social Security Optimization
- Tax-Efficient Planning
- Tax-Smart Distribution Planning
- Taxes
- Withdrawal Sequencing
- Women & Wealth
About Jeff Judge, CFP®, AEP®, ChFC®, CLU®
“You don’t need to do this alone. I help clients cut through the noise, avoid costly mistakes, and make confident decisions even during life’s biggest transitions.”Meet Jeff – Steady Hand in Unsteady Times
Jeff Judge didn’t grow up around wealth. His parents were blue collar and did what they could to make ends meet. When his dad got sick, Jeff worked multiple jobs in high school and college to help the family stay afloat. That experience taught him how stressful money can be when you don’t have the right support and it lit the fire for his career in financial planning.
Today, Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
Credentials You Can Trust
Jeff holds multiple advanced designations that reflect his commitment to excellence:
▪️ CERTIFIED FINANCIAL PLANNER (CFP®)
▪️ Chartered Financial Consultant (ChFC®)
▪️ Chartered Life Underwriter (CLU®)
▪️ Accredited Estate Planner (AEP®)
He’s also a multi-year Five Star Wealth Manager Award recipient (2014, 2017–2026) and has led retirement and financial education workshops for Fortune 500 and mid-sized companies across the Baltimore and DC metro areas.
The Method Behind the Calm
Jeff leads clients through Chesapeake’s R.U.D.D.E.R. Method™, a simple yet powerful process for turning financial chaos into confident action. Whether you’re facing a big life shift or just want to feel in control again, Jeff combines empathy, expertise, and accountability to get you there.
Outside the Office
Jeff lives in Forest Hill, MD with his wife, Courtney, their son, Reed, and their three dogs Ash, Twix, and Blue. He’s a passionate home cook, lover of live music, stand-up comedy, and comic book movie buff who can just as easily be found on the sideline of Reed’s soccer games, watching live sports in person or on TV, or quietly meditating. If you’re a Disney fan or soccer junkie, you already have something to talk about.
Ready to Feel More in Control?
Jeff and the Chesapeake team are here to make your financial life simpler, more strategic, and a whole lot less stressful. Book a Fit Call to see if we’re the right guide for your next chapter.
Professional Designations
- Accredited Estate Planner (AEP)
- CERTIFIED FINANCIAL PLANNER ®
- Chartered Financial Consultant (ChFC)
- Chartered Life Underwriter (CLU)
Affiliations
- BBB Accredited Business
- CFP Board
- Estate Planning Council
- Financial Planning Association
- Financial Services Institute
- National Association of Estate Planners & Councils (NAEPC)
Primary Location
2402 Scotlon Ct, Forest Hill, MD 21050
Additional Locations
📍 9405 Hayloft Drive, Perry Hall, MD 21128
Video
Meeting Options
- Video Conference
- In-Person
- Phone
Compensation Methods
- Annual Retainer
- Commissions
- Fee Based
- Flat Fee
- Package Offers
- Percentage of Assets Managed
What to expect in the first meeting
Click the 'Book Intro Call' button above and book a short “Fit Call” to see if we’re a good fit for another. No pressure, no jargon, just a conversation focused on your goals and whether our approach makes sense for your needs. I look forward to speaking with you.Offers Investment Management
Yes
About Chesapeake Financial Planners
Chesapeake Financial Planners is a fee-based financial planning firm in Forest Hill, Maryland, founded by Jeff Judge, CFP® and Mark Rossbach CPA. Serving Harford County and the greater Baltimore metro, the firm specializes in retirement planning, business-exit and succession planning, equity compensation strategy, tax-aware investing, and estate coordination for executives, business owners, and families in transition. Jeff is a CERTIFIED FINANCIAL PLANNER™ professional, an NAEPC-affiliated estate planning practitioner (#168219), and delivers every engagement through the proprietary R.U.D.D.E.R. Method™ — a structured six-step process for aligning wealth with life goalsWe use our R.U.D.D.E.R.™ method to help you make better decisions, avoid costly missteps, and stay accountable to the life you actually want, not someone else’s script. Our job isn’t to impress you with acronyms. It’s to simplify, clarify, and walk beside you through every major decision, so you can move forward with confidence.
Services
With ongoing oversight, expert investment guidance, and real accountability, you'll finally feel like someone has your back. Because we do.
You’ve built a life, a business, or a career that demands your time and energy. But managing the financial side of it, investments, taxes, major transitions can feel like a full-time job on its own.
You shouldn’t have to become a financial expert to feel confident about your next step. That’s why our clients choose to work with a fiduciary CFP®: to stop second-guessing, start making decisions with clarity, and gain back time for what matters most. You stay in control. You call the shots. And you get a proactive plan that keeps every part of your financial life moving forward, without carrying it all alone.
Investment advice offered through Great Valley Advisor Group, a Registered Investment Advisor. Great Valley Advisor Group and Chesapeake Financial Planners are separate entities from LPL Financial. Securities offered through LPL Financial, Member FINRA/SIPC.
Education
Goucher College, Bachelor's degree
Hobbies and Interests
- Animal Rescue
- Animals
- Baseball
- Beach
- Billiards
- Board Games
- Cars
- Cooking
- Entertaining
- Family
- Fishing
- Football
- Golf
- Grilling
- Movies
- Music
- Reading
- Soccer
- Sports
- Television
- Tequila
- Video Games
- Wine
- Writing
SEC Lookup
View DisclosureFINRA Lookup
View DisclosureWho We Serve
- Accountants
- Attorneys
- Baby Boomers
- Blended Family
- Business Owners
- Content Creators
- Contractors
- Corporate Executives
- Couples
- Data Scientists
- Divorce
- Dual Income Family
- Engineers
- Entrepreneurs
- Families
- Gen X
- Gen Y / Millennials
- Government Employees
- Individuals
- Intergenerational Families
- Investors
- Living in Retirement
- Newly Engaged / Newlywed
- Private Foundations & Organizations
- Sales Professionals
- Scientists
- Single Women
- Specialty Sub-Contractors
- Startup Employees
- Technology Professionals
- Widow
- Women in Transition
- Women Professionals
- Women’s Finance
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Wealthtender Awards
Jeff Judge, CFP®, AEP®, ChFC®, CLU® received the 2026 Wealthtender Voice of the Client Highly Rated Advisor award.
Wealthtender awarded Jeff Judge, CFP®, AEP®, ChFC®, CLU® with its 2026 Voice of the Client Highly Rated Advisor Award on 06-10-26. Rating criteria based on eligible client reviews published on Wealthtender between 07-01-25 and 05-31-26. Although Chesapeake Financial Planners compensates Wealthtender for marketing services (including eligibility to be considered for this award), Wealthtender’s award criteria is objective and not influenced by compensation. This award is not a guarantee of future performance or success and client reviews may not be representative of the experience of all past or future clients. ↗️ View additional award details and FAQs (wt.reviews/awards)
Other Awards
Award Disclosures
This award was issued on 01/01/2026 by Five Star Professional (FSP) for the time period 04/10/2025 through 10/01/2025. Fee paid for use of marketing materials. Self-completed questionnaire was used for rating. This rating is not related to the quality of the investment advice and based solely on the disclosed criteria. 2446 Baltimore-area wealth managers were considered for the award; 217 (9 % of candidates) were named 2026 Five Star Wealth Managers. The following prior year statistics use this format: YEAR: # Considered, # Winners, % of candidates, Issued Date, Research Period. 2025: 2,389, 254, 11%, 1/1/25, 4/10/24 – 10/31/24; 2024: 2,149, 259, 12%, 1/1/24, 4/10/23 – 10/31/23; 2023: 2126, 256, 12%, 1/1/23, 4/18/22 – 10/21/22; 2022: 2078, 260, 13%, 1/1/22, 5/10/21 – 11/12/21; 2021: 2029, 237, 12%, 1/1/21, 4/27/20 – 10/30/20; 2020: 1898, 234, 12%, 1/1/20, 4/1/19 – 11/13/19; 2019: 1865, 265, 14%, 1/1/19, 4/19/18 – 11/7/18; 2018: 1759, 232, 13%, 1/1/18, 4/21/17 – 11/6/17; 2017: 1093, 355, 32%, 12/1/16, 3/26/16 – 11/11/16; 2016: 1215, 356, 29%, 12/1/15, 6/16/15 – 11/9/15; 2015: 1749, 412, 24%, 1/1/15, 6/16/14 – 11/9/14; 2014: 1484, 395, 27%, 1/1/14, 6/16/13 – 11/9/13; 2013: 1490, 448, 30%, 1/1/13, 6/16/12 – 11/9/12; 2012: 1470, 262, 18%, 1/1/12, 6/16/11 – 11/9/11. Wealth managers do not pay a fee to be considered or placed on the final list of Five Star Wealth Managers. The award is based on 10 objective criteria. Eligibility criteria – required: 1. Credentialed as a registered investment adviser (RIA) or a registered investment adviser representative; 2. Actively licensed as a RIA or as a principal of a registered investment adviser firm for a minimum of 5 years; 3. Favorable regulatory and complaint history review (As defined by FSP, the wealth manager has not; A. Been subject to a regulatory action that resulted in a license being suspended or revoked, or payment of a fine; B. Had more than a total of three settled or pending complaints filed against them and/or a total of five settled, pending, dismissed or denied complaints with any regulatory authority or FSP’s consumer complaint process. Unfavorable feedback may have been discovered through a check of complaints registered with a regulatory authority or complaints registered through FSP’s consumer complaint process; feedback may not be representative of any one client’s experience; C. Individually contributed to a financial settlement of a customer complaint; D. Filed for personal bankruptcy within the past 11 years; E. Been terminated from a financial services firm within the past 11 years; F. Been convicted of a felony); 4. Fulfilled their firm review based on internal standards; 5. Accepting new clients. Evaluation criteria – considered: 6. One-year client retention rate; 7. Five-year client retention rate; 8. Non-institutional discretionary and/or non-discretionary client assets administered; 9. Number of client households served; 10. Education and professional designations. FSP does not evaluate quality of services provided to clients. The award is not indicative of the wealth manager’s future performance. Wealth managers may or may not use discretion in their practice and therefore may not manage their clients’ assets. The inclusion of a wealth manager on the Five Star Wealth Manager list should not be construed as an endorsement of the wealth manager by FSP or this publication. Working with a Five Star Wealth Manager or any wealth manager is no guarantee as to future investment success, nor is there any guarantee that the selected wealth managers will be awarded this accomplishment by FSP in the future. Visit www.fivestarprofessional.com.
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FAQ Disclosures
Investment advice offered through Great Valley Advisor Group, a Registered Investment Advisor. Great Valley Advisor Group and Chesapeake Financial Planners are separate entities from LPL Financial. Securities offered through LPL Financial, Member FINRA/SIPC.
FAQ Admin
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