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A Conversation with Jack Howley About Finding Direction While Building Career & Personal Success

Jack Howley is an entrepreneur and expert in assisting corporations and individuals in meeting their wealth creation and protection objectives. Jack spends his time between Naples, Florida and Rumson, New Jersey. For over four decades, Jack has been a successful advisor and a leader in his field, representing the top 1% of the industry.  After […]

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Jack Howley is an entrepreneur and expert in assisting corporations and individuals in meeting their wealth creation and protection objectives. Jack spends his time between Naples, Florida and Rumson, New Jersey. For over four decades, Jack has been a successful advisor and a leader in his field, representing the top 1% of the industry.  After college, where he studied finance & marketing, Howley was looking for a career that would provide meaning and fulfillment in his life, but even more importantly, he was looking for a purpose in life.  A fateful meeting with a man named Al Ferrara helped push him towards the insurance and financial services industry.  

Jack opened his own firm in 1986, focusing on a comprehensive approach to protecting families’ finances.  Recognizing that most clients he was meeting with had a set of micromanagers in their lives, including accountants, stockbrokers, bankers, and investment advisers, Howley’s business model was built around integrating all those facets together.  Howley’s firm works with his client’s investment advisers in order to achieve optimal efficiency in meeting the client’s wealth creation and protection, retirement, insurance and estate planning objectives, making the complex world easily understandable and transparent.  He achieves this through a financial model outlining 27 different areas focusing on protection, savings and growth in what he refers to as “an MRI of money”.    The goal is to have their money work as efficiently and effectively as possible, to minimize taxes, and also protect all the wealth that they’ve accumulated against countless wealth-eroding factors.  Howley loves the business that he made his life’s work.  He loves helping people and enjoys the satisfaction of improving others lives through his work.   

In the last few years, what lifestyle, habit, or behavior change has had the biggest positive impact on your life?

Through the years, I’ve learned a lot about people, about myself, and that there are some things you just can’t control.  I think I’ve gained a greater appreciation of spirituality.  You have to give it all to God and just be appreciative of where you are in life.  I know that no one lives a perfect life and you have to overcome challenges and when you deal with them head on and you become a better person as a result of it.

When you feel unfocused, what do you do?

I’m a pretty focused person – unless I’m on vacation – but I try to live a balanced life.  I’m a runner. I like to offset that with other exercises including biking and weight training at a gym, to make my physical activity a sort of blend of those activities.  I like reading and also enjoying time with my family and good friends.  That all helps me retain focus so I can be effective when I’m at work.

What advice would you give a smart and ambitious recent college graduate? What advice should they ignore?

First of all, you should always follow your dreams.  Sometimes as a college graduate you don’t know what your dreams are.  If you’re like I was, you’re looking for something to appear before you and have things fall into place.  But if you’re fortunate enough to know what your dreams are, then follow that with tremendous passion and focus.

I would also develop your contacts to properly network into the profession that you believe would fit into your philosophy, and when you’re comfortable in that profession, I would learn everything I possibly could about that field of endeavor.  Knowledge is power, so learn, learn, learn.  If that’s what you’re going to focus on, you want to be the best at it.  You may or may not be the best, but you want to walk off the field knowing you gave everything you had.

Successful people do what unsuccessful people do not want to do, which is to study and learn.  Most people are going home at 5 o’clock and that’s the end of their day.  The people who excel are there before 9 a.m. and after 5 p.m.  I’ve been working half of the day my whole life, from 8 to 8, and it’s been great.  It takes time and sacrifice and if you don’t do that, then you’ll just be average.

What is one lifestyle trend that excites you?

I think living a balanced life is key.  There are so many people that I’ve met in life that are so focused on professional success, but their home life is in disarray.  Or they become so focused on the career or financial success that when they retire, they’re going to have no identity.  Living a balanced life between your spiritual life, family life, physical life, professional life, and financial life, is key.  You want a true and whole life, where you try to keep everything in balance.  When it’s out of balance, bad things happen.  If you work too much, you’re going to have a bad family life.  If you work too little, you’re going to be unsuccessful.  Having that balance is something that is needed, and I’ve taught that to others throughout my career.

Who has been the biggest influence in your life and why?

My wife would be the biggest influence.  She’s been an amazing support to me.  Right around Valentine’s Day, I was in the store looking for cards and I’m looking at all the different cards and I’m thinking to myself, she epitomizes all of these great things!  I know it sounds so corny.  I know so many unhappy people, but I’ve lived with the greatest woman ever.  She’s smart, beautiful, understanding, hardworking, and has been a great mom to my kids.  She’s awesome.  She’s enjoyed the good parts of life with me and has been incredibly supportive throughout the bad parts.

Professionally, there are a few other influences that are critical to my life:  The person who hired me, Al Ferrara, taught me so much and was a terrific personal mentor.  The economist, Bob Castiglione, really changed my outlook on my professional practice.  He taught me to look at finances in a more macroeconomic and holistic fashion.   There are also several of my business colleagues in the insurance and financial services that are part of my study group, which meets every quarter to continue to learn to better serve our clients and meet their objectives.  Their influence on me has been vast.

What’s one of the biggest life lessons you’ve learned?

God and family is always first.  It’s very easy to lose that focus during the day-to-day hustle and bustle of life.  Also, I want to always be able to help others and become a mentor so I can pay it forward.  You want to know that the people you cross paths with in life are better off, whether it’s professional advice to give your business colleagues, or personal advice that can be given to your friends and family.  I think that is our responsibility as human beings.

Another lesson is to appreciate the “now”.  Let’s appreciate the now, because the past already happened, and you can move on from it. Life happens for you, not to you.

What do you think it is that makes you/someone successful?

There’s no substitute for hard work.  I don’t know anyone who has been successful without working hard.  Focusing on the big picture is so important as well.  I’ve also been told I’m a very good listener.  People like to talk, and I like to listen, which has been a real value for my success.  God gave me two ears and one mouth, so I try to do twice as much listening as talking.  I think you can learn more by listening than speaking, because you are speaking about something you already know.  You’re listening because you’re learning about something you don’t know.

Another area that’s made me successful was being able to relate to various personalities.  I grew up in a blue-collar background where my dad was a mailman.  That’s my life experience, but professionally I also have to deal with attorneys, accountants and many other professionals.  So being able to relate to groups of different people makes you a more well-rounded person.  I am around all kinds of people:  Entrepreneurs, corporate people, professionals, blue collar people, and I appreciate them all for who they are.  Seeing the big picture, being a good listener, relating to different personalities, hard work, the combination of all of that would make anyone successful.  I am grateful that is has made me successful.

How do you stay motivated?

Love and an appreciation of life motivates me.  I wake up and I say, “Wow! How great is this? It’s another great day I can live on this earth.”  Life is short.  We all hear that, but it’s so true.  As you get older and you see some of the people that have been part of your life no longer with you on earth, and your kids start growing up, and you look at the old swing set in the backyard that no one has been on for 25 years, you notice how different life is.

I also stay motivated by learning more about the profession every day.  I’ve been fortunate that the proceeds of our products keep families together, shapes lives, fulfills dreams and prevents nightmares.  I’ve seen it firsthand where people have become disabled or died, and the proceeds of our products have helped them and their families in a very meaningful way.

What legacy do you hope to leave behind?

I think I’ve made so many people’s lives better as a result of my recommendations and advice.  That means so much to me because if they met someone else, the advice would have been different.  Obviously, I don’t think it would have been as good.  I mean, why would I be in the business if I didn’t think I was the best at it?  And their life is better as a result of that.  I’ve had clients pass away and it warms my heart to know that their family can have millions of dollars to be able to continue their lives, educate their children, pay off their mortgage and be able to live in their own world as a result of the decisions they made based on my advice eight, ten, twenty, or thirty years ago.  It makes me feel great that they can retire comfortably despite all the wealth-eroding factors they faced.  No matter what negative events or occurrences they come up against, I’ve helped them build a moat around their castle.  From a legacy standpoint, I feel very good about that.

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