Meet Jack Phelps, The Retirement Coach

Back in 1989, a mundane comment by a retired school teacher launched me on an avenue of research that changed the course of my professional career forever.

I was the youngest of four children, which was great because I got to learn from everybody else’s mistakes!

My father was a public school teacher and a coach, and my mother became a nurse after I was born.

As you probably know, teachers and nurses are not the highest paid professions in society. Although I have fantastic memories of my childhood, an abundance of money was not something we had. I never felt deprived, but I never noticed the contrast until I went away to college.

In fact, I can vividly remember my parent’s excitement at taking their first vacation after 26 years of marriage. 26 years! Contrast that by today’s standards.

Fortunately for me, I was a pretty disciplined student and just a good enough athlete to get a scholarship to attend Holy Cross College. Extremely fortunate because, without the scholarship, my parents could never have afforded to send me there.

Unfortunately, however, in the spring of my freshman year, my mother developed an inoperable brain tumor. And, after a very long 19-month battle, she passed away at the very young age of 57 during my junior year.

As you can imagine, it was an overwhelming experience to lose my mother, especially at such a young age. It still pains me today because my 2 children, Caroline and Michael, never had the opportunity to meet her.

Over time, what I came to discover is that their lack of financial confidence kept them from doing many of the things they always wanted to do before it was too late.

One of the issues that really bothered me was that my mother and father got shortchanged. They really missed out on a lot.

To contrast that, a few years later, I had a conversation with a gentleman who happened to be a retired school teacher, like my dad.

Without realizing the impact it had on me, he mentioned in passing that he would have jumped at the opportunity to take advantage of the current discount to “pre-pay” all four years of his son’s tuition!

I remember thinking, “Huh”?

What made him believe that he could he afford to do that? What made him so confident? My parents never even took a vacation for 26 years, let alone even remotely consider ‘pre-paying’ all four years of college tuition!”

Well, that one passing comment by that retired school teacher 24 years ago struck me like a lightning bolt! And, it’s the reason why you’re reading this right now.

My insatiable curiosity got the best of me and I began studying everything I could get my hands on that had to do with money and finances.

In doing so, I stumbled across an amazing piece of information:

Take any one hundred people at the start of their working careers. According to the Social Security Administration, forty years later:

  • 1 will be wealthy,
  • 5 will be financially secure,
  • 5 will continue working,
  • 35 will be dead, and
  • 54 will be dependent upon their social security checks, relatives, friends, or even charity for a minimum standard of living!


That means that only 6% of Americans continue their same lifestyle into their retirement years, while the overwhelming majority (94%) of people end up cutting their lifestyles back.

Only 6%!

That really hit home for me, so from that moment on I immersed myself in finding out what those successful retirees, who did continue their exact same lifestyle into their retirement years, were doing differently than everyone else.

Like most people, my first thought was the difference was that they simply had more money, but I was 100% wrong.

Throughout my 5 years working at Prudential, and my 19 years since running this business, what I have discovered is that the difference between the most successful retirees and everyone else is not just more money.

I’ve met and worked with countless people who have a lot of money by most people’s standards, but they lived every day with an enormous amount of anxiety, bordering on misery, as if they were going to run out of money tomorrow.

After 24 years of intense study and hands-on work, the key difference that I’ve discovered between those who retire successfully and everyone else is their level of financial confidence.

The key is that they weren’t born with that financial confidence. They developed it.

What I’ve witnessed is that there are very specific strategies that successful retirees know and use every single day that everyone else is simply not taking advantage of.

I’m completely convinced of that.

So, what my life has been about ever since that infamous day that I stumbled across that incredibly revealing statistic is developing systems and teaching these strategies to help people develop and maintain the financial confidence they need to spend all of their time doing what they really want to do without worrying about money.

Along the way, I meticulously crafted and trademarked The Relaxing Retirement Coaching Program to help hundreds of individuals and couples make a seamless and relaxing transition to their retirement years so they can enjoy what they’ve worked so hard to achieve.

* * *

Prior to developing The Relaxing Retirement Coaching Program back in 1994, Jack spent five years as a registered representative with Prudential Financial Services. In 1992, he received his Chartered Financial Consultant designation from The American College in Bryn Mawr, Pennsylvania. In 1989, Jack graduated from Holy Cross College in Worcester, Massachusetts with a B.A. in Economics.

Jack Phelps

Jack lives in South Natick, MA with his wife, Colleen,
and their two children, Caroline and Michael.

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Listen to Retirement Coach Jack Phelps, ChFC answer your questions on
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