Jeff Judge, CFP®, AEP®, ChFC®, CLU®

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Chesapeake Financial Planners Jeff Judge, CFP®, AEP®, ChFC®, CLU®
Forest Hill, MD

Serving Clients Nationwide

Trusted Guide for Busy Professionals Seeking Financial Clarity

14 Certified Advisor Reviews™
5 out of 5 Stars
Jump to Reviews

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

  • 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 goals

We 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

  • 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

FINRA Lookup

View Disclosure

Who 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

Wealthtender® is a trusted, independent financial directory and educational resource governed by our strict Editorial Policy, Integrity Standards, and Terms of Use. While we receive compensation from featured professionals (a natural conflict of interest), we always operate with integrity and transparency to earn your trust. Wealthtender is not a client of these providers. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.

Write a Review


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My advisor with LPL has tailored a retirement plan to fit my specific needs, and completely removed the anxiety I had about my financial future and retirement needs. I could not recommend LPL enough.
Relationship to Financial Advisor: Client as of May 18, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
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David

Chesapeake Financial Planners

✅ Wealthtender Certified Advisor Review™
May 14, 2026
Jeff Judge has been helping me since 2014 with life insurance and retirement investment products. After a bad experience with a big insurance company, I found Mark and I’ve been working with him ever since. I’m successfully retired now and drawing lifetime income. I highly recommend Chesapeake Financial Planners for your retirement planning.
Relationship to Financial Advisor: Client as of May 14, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Mark G
Mark G

Need good advice?

✅ Wealthtender Certified Advisor Review™
May 13, 2026
I'm forever grateful to Jeff Judge for his advice and judgement. I wish I had found him years before. My accounts have grown beyond my hopes. The most amazing is that when I started to take a monthy RMD, my account did not drop. In fact, it actually increased a bit! I did not expect that! I only wish I had heeded his advice and not invested a very small amount in a certain stock on my own. I can be stubborn. From now on I'll heed ANY advice he gives me.
Relationship to Financial Advisor: Client as of May 13, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Patricia Komoroski
Patricia Komoroski

Trusted service

✅ Wealthtender Certified Advisor Review™
May 8, 2026
My husband and I have been customers of Mr. Judge and his employer for many years. Jeff has always been attentive to our needs and has always led with positive guidance. Our trust has never waivered.
Relationship to Financial Advisor: Client as of May 8, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Kimberly Saladini
Kimberly Saladini

Jeff Judge is a great wealth advisor

✅ Wealthtender Certified Advisor Review™
May 8, 2026
Jeff has been managing my retirement accounts for years. He facilitated the consolidation of several retirement accounts for me. That made my life a LOT easier. I trust Jeff. He's a good guy. I highly recommend him.
Relationship to Financial Advisor: Client as of May 8, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for KSW
KSW

5 Stars

✅ Wealthtender Certified Advisor Review™
May 7, 2026
I have been working with Mark and Jeff for 10+ years. I recently asked for a review of my financial plan and was provided outstanding feedback that provided me a much better solution.
Relationship to Financial Advisor: Client as of May 7, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Bob Burris
Bob Burris

5 Stars

✅ Wealthtender Certified Advisor Review™
Apr 7, 2026
I am delighted with LPL. They've stayed with me for years and Jeff Judge has been exceptionally helpful. I've gotten good advice. He's managed my assets professionally and has always been available answer my questions. He helped me consolidate several accounts into one manageable asset. He took the guesswork out of what could have been a complicated process. I trust him to be there and guide me through issues in which I have no expertise. But he does this all the time and has proven to be trustworthy. I do recommend Mr. Judge. You will not be disappointed.
Relationship to Financial Advisor: Client as of Apr 7, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Kim Wright
Kim Wright

5 Stars

✅ Wealthtender Certified Advisor Review™
Apr 7, 2026
My husband and I met Mark and Jeff in 2014 when my husband left his job after 23 years. We met with Mark and Jeff to decide where to invest his retirement money. Before that decision was made, they took their time to understand our entire financial picture and based on that they gave us several options on where we could invest. They were very easy to talk with and made the conversation easy to understand. They are easy to get in touch with if you have questions and provide answers quickly. When it came time for me to retire, I also rolled my retirement investments into accounts managed by Mark and Jeff. We have also setup our estate planning as well as long term health planning based on advice we have had in review meetings in the years following our initial meeting. We have even referred our daughter and son in law to them. Highly satisfied with the investment service and customer service.
Relationship to Financial Advisor: Client as of Apr 7, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Sharon Lewis
Sharon Lewis

5 Stars

✅ Wealthtender Certified Advisor Review™
Mar 25, 2026
I check in with Mark a couple times a year and he always helps me keep my money that he manages growing. He also helps us with general advise regarding the type of places our 401k money should be (growth vs value, etc)
Relationship to Financial Advisor: Client as of Mar 25, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Andrew Benner
Andrew Benner

5 Stars

✅ Wealthtender Certified Advisor Review™
Jan 18, 2026
Jeff has been helping me since 2014 with life insurance and retirement investment products. After a bad experience with a big insurance company, I found Mark and I’ve been working with him ever since. I’m successfully retired now and will begin drawing on my investments this year. I highly recommend Chesapeake Financial Planners for your retirement planning. – Mark G.
Relationship to Financial Advisor: Client as of Jan 18, 2026
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Mark Gray
Mark Gray

5 Stars

✅ Wealthtender Certified Advisor Review™
Dec 21, 2025
Jeff has been my financial advisor/ planner for several years. He has always guided me in the right direction and I have seen my retirement account continuously moving in the right direction. During the current uncertainty of the financial world right now Jeff has given me peace of mind that I continue to be in a safe and secure position with my finances. Jeff is very professional and quick to respond to my emails. As I approach my retirement years it is comforting to know my finances will be there when I need them.
Relationship to Financial Advisor: Client as of Dec 21, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for David Carrington
David Carrington

5 Stars

✅ Wealthtender Certified Advisor Review™
Dec 6, 2025
I have been working with Jeff Judge and Chesapeake Financial Planners for about 3 years. Jeff has provided timely and well considered advice and acted promptly when I've needed access and changes to my portfolio. Highly recommend their services.
Relationship to Financial Advisor: Client as of Dec 6, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Matt Hurson
Matt Hurson

5 Stars

✅ Wealthtender Certified Advisor Review™
Nov 17, 2025
We have worked with Jeff at Chesapeake Financial Planners for over 10 years. Throughout that time he has provided valuable investment and retirement information. Our investments have navigated this turbulent market far better than expected. Thank you Jeff.
Relationship to Financial Advisor: Client as of Nov 17, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for John Komoroski
John Komoroski

5 Stars

✅ Wealthtender Certified Advisor Review™
Nov 14, 2025
I've been working with Chesapeake Financial Planners for a little over six years, and it's been an outstanding experience. They're knowledgeable, responsive, and consistently provide clear, personalized advice that aligns with my financial goals. Their long-term commitment and reliability have given me real peace of mind.
Relationship to Financial Advisor: Client as of Nov 14, 2025
Compensation: This reviewer received no compensation for this review.
Conflicts of Interest: There are no material conflicts of interest.
Avatar for Charles Gaither
Charles Gaither
Get answers to frequently asked questions regarding the services offered by Jeff Judge, CFP®, AEP®, ChFC®, CLU® View Disclosures

FAQs

How do financial planners get paid and what does it cost to hire one in Maryland?
Here’s how we do things at Chesapeake: 1) Flat annual fee for planning: Our comprehensive financial planning and personal oversight ranges from $3,00 to $7,500 per year, depending on the complexity of your situation. 2) Optional investment management: We charge a percentage of assets under management. That starts around 1.3% for smaller portfolios and decreases to as low as 0.35% as your assets grow. We’re also licensed to offer commission-based products (like life insurance), but we only recommend them when they’re in your best interest and we’ll always disclose how we’re compensated. Learn more
Does Jeff Judge offer financial planning services in Harford County, MD to business owners requiring help with exit planning?
Yes. Jeff Judge, CFP® serves business owners in Harford County, MD, including Baltimore County and Baltimore, who need exit planning guidance. As a fiduciary, Jeff is legally obligated to act in your best interest, with no products to push and no hidden agendas. He helps business owners clarify exit options, understand the full tax implications of a sale, and build a comprehensive financial plan that supports life after the business. Whether you're years away from exiting or ready to act now, Chesapeake Financial Planners delivers the clarity, strategy, and accountability you need. Read more on our site
How much money should I have before hiring a financial advisor or financial planner in Maryland?
New client relationships at Chesapeake Financial Planners typically require investable assets of at least $250,000 or household income of at least $200,000 or engagement for annual Financial Management Oversight (financial planning). We work with professionals, business owners, and families across Harford County, Baltimore County, and Baltimore, Maryland navigating retirement, business exits, and major life transitions. As fiduciaries, Jeff Judge, CFP® and the team are legally obligated to act in your best interest. No products to push, just clarity and a tailored plan built around your goals. Find out more
Why do I make a lot of money but still feel behind or like I'm not making progress?
You're not alone, and it's not just in your head. High earners across Harford County, Baltimore County, and Baltimore, MD often feel stuck because income grew but strategy didn't keep pace. Spending scales with salary, decisions pile up without a clear plan, and what worked at $80K doesn't cut it at $300K+. Without a guide, it's easy to miss blind spots, leave taxes on the table, and lose confidence in your next move. As a fiduciary at Chesapeake Financial Planners, Jeff Judge, CFP® helps you go from "I make good money, but..." to "I know exactly where I'm headed, and I like what I see." Get back on the right track
How much money do I need to retire comfortably in Maryland?
There's no single number. Comfort in retirement depends on your lifestyle, spending habits, and what "comfortable" truly means to you. A common benchmark is 25x your expected annual expenses, meaning $100,000/year in spending may require $2.5 million saved. As fiduciaries serving retirees and pre-retirees across Harford County, Baltimore County, and Baltimore, MD, we look beyond the rule of thumb. We factor in your retirement age, Social Security, healthcare costs, taxes, inflation, and your specific goals to build a detailed income plan around your real numbers, not someone else's formula Let's start your next chapter together
What should I do with my company stock options in Maryland?
Company stock options can be one of your biggest wealth-building opportunities, but timing and taxes make the difference between a windfall and a costly mistake. The wrong move can trigger a surprise tax bill, AMT exposure, or leave you dangerously concentrated in one company. At Chesapeake Financial Planners, serving professionals across Harford County, Baltimore County, and Baltimore, MD, we help you evaluate when to exercise, understand ISO versus NSO implications, minimize taxes, and diversify intelligently. As fiduciaries, we build a strategy around your goals, not a generic formula Learn about our approach
What should I do with a large sum of money I suddenly received in Maryland?
Sudden wealth can disappear quickly without a plan. As fiduciary planners serving Harford County and Baltimore County, MD, we help you slow down and think carefully before making any major moves. We secure your financial foundation first: emergency reserve, high-interest debt payoff, updated insurance, and estate plan. Depending on the source, whether an inheritance, business sale, or settlement, your windfall may carry significant tax consequences, and we coordinate with your CPA. Then we invest the remainder based on your goals, timeline, and risk tolerance, not market hype or hot headlines. Let's make a plan
How can I catch up on retirement savings in my 50s in Maryland?
You are not alone, and it is never too late to catch up. As fiduciary planners serving Harford County and Baltimore County, MD, we build personalized strategies for pre-retirees who want to close the retirement savings gap. The IRS has given you real tools: in 2026, those 50 and older can contribute up to $32,500 to a 401(k). If you're between ages 60 and 63, the SECURE 2.0 super catch-up raises that limit to $35,750. We build those contributions into a complete plan covering Roth conversions, Social Security timing, income projections, spending, debt payoff, and long-term healthcare planning. Learn about our approach
What should I do with my 401(k) when I change jobs in Maryland?
When you change jobs, your 401(k) has four main options: leave it with your former employer, roll it into your new employer's plan, roll it into an IRA, or cash it out. Cashing out is rarely the right move. You will owe income taxes plus a 10% early withdrawal penalty if under 59½, which can cost nearly half the balance. As fiduciary advisors in Harford County and Baltimore County, MD, we help you compare your plans by fees, investments, and flexibility. A rollover to an IRA typically offers the broadest investment choices and control, but the right path depends on your full financial picture. Explore your options
What questions should I ask before hiring a financial planner and what are the red flags to look for?
Before hiring a financial planner, ask these questions: Are you a fiduciary? How are you compensated? What credentials do you hold? Who do you typically serve? A fiduciary is legally required to act in your best interest, not just meet a suitability standard. Fee-only and fee-based structures disclose costs transparently, limiting conflicts. Red flags include vague fee disclosures, refusal to confirm fiduciary status in writing, high-pressure tactics, and promises of guaranteed returns. In Harford County and Baltimore County, MD, we welcome and answer every one of these questions freely. Discover how we work

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.