Jack’s Approach
Jack Phelps
Managing Partner / Financial Advisor / Member Owner
Overview
Jack Phelps is a managing partner and financial advisor in Savant’s Wellesley, Massachusetts, office. Involved in the financial services industry since 1989, Jack is a passionate advocate and guide for dedicated savers navigating the complex transition from a lifetime of working and saving to spending and enjoying what they’ve built.
He founded The Relaxing Retirement Coach, Inc., where he developed a retirement coaching program designed to help individuals and couples make calm, educated decisions during significant inflection points in their lives. Jack began working at Savant in 2023 when The Relaxing Retirement Coach, Inc. joined the firm. Earlier in his career, he worked as a registered representative with a national financial services firm.
Jack is the author of The Relaxing Retirement Formula: For the Confidence to Liberate What You’ve Saved and Start Living the Life You’ve Earned, a book that reflects his commitment to helping people navigate their retirement transition with confidence and clarity.
He earned a bachelor’s degree in economics from Holy Cross College in Worcester, Massachusetts.
Jack and his wife, Colleen, live in Dedham and North Chatham, Massachusetts. Their daughter, Caroline, and son, Michael, live and work in Boston. In his free time, Jack enjoys golfing, boating, and traveling with family and friends.
Areas of Focus
Comprehensive Wealth Management
Integrated guidance for your full financial life, bringing together investment, tax, estate, and retirement planning to support your goals.
Financial Planning
Our planning process helps you evaluate key areas of your financial life, uncover opportunities, and make decisions aligned with your goals.
Investment Management
Evidence-based investing designed to help you stay focused on long-term goals while navigating changing market conditions.
Estate Planning & Wealth Transfer
Thoughtful estate planning guidance to help organize your affairs, support your wishes, and prepare for future generations.
Trust Services
Comprehensive trust administration supported by integrated investment, tax, estate, charitable, and business succession planning services.
Education
- Holy Cross College
Bachelor of Arts in Economics
Insights & Perspectives
Thought leadership on wealth management, tax strategy, and financial planning.
Before You Make That Charitable Donation This Fall
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Don’t Wait for a Crisis to Get Moving
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All Insights by Jack Phelps
56 insights
Before You Make That Charitable Donation This Fall
Before you write that check: donating appreciated shares or making a QCD may give charities more and possibly…
Retirement Is More Than a Number
In this episode of The Real Return, Zach Ivey, chief investment and advice officer, sits down with Christine…
This Labor Day Can Mean Different Things to Different People
Are you still working because you want to, or because you believe you have to? A Labor Day…
Don’t Wait for a Crisis to Get Moving
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Thinking About Selling Your Home? Read This First
Thinking about selling your home? Learn how capital gains taxes work for primary and vacation homes, plus strategies…
Why Did the Stock Market Fall Today?
Market swings can feel unsettling. Learn why short-term market moves can be unpredictable and why discipline matters.
Celebrate Independence Day with a Financial Confidence Quiz
As a retirement coach, I've seen firsthand how a lack of financial confidence can steal the very independence…
Stock Market Corrections: Do You Have Time to Make it Back?
When markets drop, many investors feel like they've run out of time. But if you're 60, your investment…
Questions to Ask Before Helping Your Grown Children During Retirement
It can be difficult to manage the anxiety about providing financial help your adult children. You have to…
Social Security: Two Underestimated Factors Before You Automatically Delay Until Age 70
Delaying Social Security can help increase monthly income, but hidden tradeoffs and policy risks may shift the optimal…
How to Evaluate Buying vs. Renting Your Vacation Home
Deciding whether to buy or rent a vacation home? Explore key trade-offs, costs, and lifestyle factors to help…
Inheriting Your IRA: The Phone Call That Could Result in Significantly Higher Taxes for Your Kids
Inheriting an IRA can potentially trigger unexpected taxes. Learn how one decision might raise heirs’ tax costs and…
Why You Invest — And Why It Matters More Than Ever Right Now
Inflation quietly erodes savings over time. Learn why investing is about helping to protect purchasing power, especially before…
Taxes: Your Silent Partner
Explore how taxes affect investment results and why coordinating investments and tax planning can matter over time.
Should I Stop Spending Because the Market is Down?
When markets fall, spending fears can rise. Learn why a solid withdrawal plan can help retirees stay on…
When You Transition to Retirement – Remember the Lid is No Longer on the Jar
Retirement habits can limit joy long after work ends. Learn why old perceptions hold you back and how…
Before Reacting to Recent Market Volatility, Look at These Three Long-Term Reality Checks
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Before You Put Your Home on the Market: One Step That May Help Protect Your Sale
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Identity Protection and Fraud Prevention
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What Nick Saban and Andy Grove Can Teach Us About Successful Investing
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Should You Pay Off Your Mortgage Before You Retire?
Explore key factors to decide if paying off your mortgage before retirement is the right move for you.
Market Timing vs. Putting it in a Drawer
Market timing sounds logical but rarely works. Learn why a steady, long-term approach beats chasing perfect entry and…
Strategic Tax Decisions Before You Make Charitable Donations
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What Investors Can Learn from Racecar Drivers
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Why You Must Consider a Revocable Living Trust – with Two Warnings
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A Potentially Costly Investing Bias Created by the Verbs We Use
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Implement a “Portfolio Life” Mindset Before You Retire
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Independence Day Habits for Your Children and Grandchildren
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Key Milestones on Your Road to Retirement [On-Demand Webinar]
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Insurance Claims: Two Potential Strategies to Help You Get What You’re Entitled To
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Protect Yourself From This Potential Catastrophe
Life can change in an instant. One distracted moment behind the wheel can lead to a tragic accident…
How to Help Your Grandchildren Pay for College
Helping your grandchildren pay for college can be a rewarding way to support their future. By designing a…
Building a Marathon Investing Mindset
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A Common Investing Rule of Thumb That Can Be Dangerous
I recently spoke with a thoughtful couple preparing for retirement after 31 years of work. They were curious…
3 Questions to Answer to Determine If You Still Need Life Insurance
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With Stocks in Turmoil, Pretend You’re a McDonald’s Franchise Owner
During periods of market volatility, it’s easy to feel anxious about your investments. However, stepping back and viewing…
The Range of Possible Outcomes You Must Know
Many investors fall short of market-level returns because of a misunderstanding of the relationship between risk and return….
Before You Help Your Grown Children
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Reaffirm Your Investing Goals and Guiding Philosophy
Reaffirming your investing goals and guiding philosophy is essential, especially after consecutive strong market years. It’s easy to…
3 Traps to Avoid as We Enter 2025
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This Holiday Season, Give Your Family the Gift of Clarity and Peace of Mind
This holiday season, take time to ensure your family isn’t left guessing. By organizing your estate plan, updating…
The Mayonnaise Jar and Two Cups of Coffee
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Reasons to Have a Mortgage After You’ve Stopped Working
While traditional wisdom suggests you should be debt-free before retirement, this belief isn’t universally applicable. Under the right…
What NOT to Invest
Investing in retirement is different from investing during your working years. A key strategy is knowing which part…
What You Must Know Before Investing
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Know Your Numbers
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3 Answers You Must Have to Free Yourself from Dependence on Your Paycheck
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How Will You Buy Your Next Car?
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A Better Way to Define Retirement
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But I Don’t Have Time to Make it Back
Market corrections can be unnerving, especially as you approach retirement. But remember, your investment time horizon is likely…
Don’t Let It Take a Crisis
We've all heard the phrase, "Don't wait for a crisis in your life to motivate you to prioritize…
Election Season Fears vs. Market Reality
Elections have the ability to stir up emotions like nothing else, and even at this early stage in…
What Will You Do When You Retire?
With all the turmoil in the news right now, let’s take a well-deserved break from inflation, interest rates,…
When You Transition to Retirement, Remember the Lid is No Longer on the Jar
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Do You Still Need Life Insurance When You Transition to Retirement?
Are you still paying premiums for life insurance? If so, are you sure you still need to? That…
How to Confidently Spend in Retirement
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