Meet Jack Phelps,
The Retirement Coach

Back in 1989, a passing 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 registered nurse after I was born.

As everyone knows, 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 receive a football scholarship to attend Holy Cross College. Extremely fortunate because we would never have been able to afford to send me there without that scholarship.

Unfortunately, in the Spring semester of my freshman year, my mother developed an inoperable brain tumor.  After a very long 19-month battle, she passed away at the very young age of 57 during the Fall of 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, one of the issues that really bothered me was that my mother and father got shortchanged.  They really missed out on a lot.

Their lack of financial confidence kept them from doing many of the things they always wanted to do before it was too late.

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 discount, currently being offered, to pre-pay all four years of his son’s tuition!

I remember thinking he was nuts!

What made him believe that he could he afford to do that? How could he be so confident?  My parents never even took a vacation for 26 years, so I can assure you that “pre-paying” all four years of college tuition was never a conversation that took place in our home. 

Well, that one passing comment by that retired school teacher 30 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 discovered some disturbing statistics which revealed that, after a 40-year career, only a tiny percentage of Americans successfully retire independently to a same or improved standard of living. 

That really struck me as sad.  What made that tiny percentage so fortunate?  From that moment on I immersed myself in finding out what those successful retirees were doing differently than everyone else.

My first thought was the “obvious” one: they simply had more money.  But, I was 100% wrong.

Throughout my 5 years working at Prudential, and my 25 years since building and managing The Relaxing Retirement Coaching Program, I’ve met and worked with countless individuals who have a lot of money by most people’s standards. Yet, they faced each morning with enormous anxiety and lived like they might run out of money that night. 

After 30 years of intense study and hands-on work, the key difference I’ve discovered between those who retire successfully and live an exciting and fulfilling life, and everyone else, is their level of financial confidence.

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

There are very specific mindsets and strategies that successful retirees practice every single day that the overwhelming majority of Americans are not taking advantage of.

With the tools, checklists, and systems our Relaxing Retirement Coaching Program provides, we are on a crusade to help individuals and couples implement these mindsets and strategies to develop and maintain the supreme financial confidence they want and need to liberate what they’ve saved and start living the life they’ve earned.

Prior to developing The Relaxing Retirement Coaching Program, Jack spent five years as a registered representative with Prudential Financial Services. In 1989, Jack graduated from Holy Cross College in Worcester, MA with a B.A. in Economics.

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