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What I Would Tell the Younger Me

As we approach our new stages of life, we review, replay and reflect on the many momentous events, milestones and memories that helped shape our lives. I know who I was and where I came from. I also know where I am and where I am going when my journey ends and beyond.

With Wisdom Comes Experience

In my early years, I met our founder, Bill Tillotson, after making a cold call to him. Actually, it was the younger me that made the call. Would the more mature me have made the call or done it differently? The younger me had intense fire because of the will to succeed. I was looking for every single opportunity, and when you’re younger, that’s when exceptional ambition emerges. 

The younger me had a lot of margin, so I was looking to fill my time proactively, whereas the older me is protecting my time. I am more selective with igniting that ambitious fire because I protect my margin. I will make the calls, but much more selectively. If you’re in business and you’re not serving new clients, attrition is going to get a hold of you.

Could I Manage Me?

If I were my manager, I would give me a long leash.  It’s a bit risky to give a long leash to a 20-something, but, looking back, that’s one of the reasons why I am very grateful to still be part of the Hefren-Tillotson family today.  The firm let me, and continues to let me, try-fail-succeed.

The younger me was living paycheck to paycheck and I just needed to survive. When I was cold calling on Wall Street, I had an order for a stock that I bought for this individual and he didn’t pay for it; he reneged. The stock went down and I had to pay for it through my firm. That was the only sale I made that month.

Payday came and I received a paycheck. I was so happy! “This company really has a heart!” I said. That is, until I looked at it and saw, “Jay Simon $0.00.” I look back on that day and I am still somewhat upset.  I was so ambitious, but over trusting. You must build good relationships first. 

Learn to Live in the Moment

Let’s face it, nobody knows you better than you. Trust your instincts. Trust yourself. Trust your inner spirit. I always knew I wasn’t going to build a family in New York City. One weekend, I flew home to attend my high school reunion. That’s where I connected with Jennifer.

We never dated in high school, but something magical happened that evening.  I knew I was going to marry her that night. After that weekend, I planned to fly in on the following weekend. I called to surprise Jenn about my plans. Her mom answered the phone. “Jenn, do you know a Jay Simon?” So, I left Wall Street for Pittsburgh to get married.  It worked out; we’ve been married for 30 years.

Don’t Be Disappointed by What You Didn’t Do

As we speak, I am at a point where vision came to fruition. I am still very young in many respects so I want to leave a legacy, not strictly financial, but more wisdom and experience, to the next generation and, of course, to my children, Justine, Jonah, Jayne and their families.

I figured out which Jay honestly savors this journey. My younger self was under way too much pressure. Of course, some of it was self-inflicted.

I’m not in a race, and I’ve been so focused that I want to use more margin to enjoy the world in simple ways. And retirement? I’m like Mr. Tillotson. I’ll never retire. He was still working at 82.

What I’ll do is backfill the business by having younger people working with me.  Sure, one day I’ll work less hours.  We’ll travel.  Technology will permit me to work remotely more and still provide exceptional client service.  I am really looking forward to the day when we rent a vacation house and our kids and grandkids come to have a super time for a week’s vacation.

Don’t Be Disappointed by What You Did Do

I have concentrated on building long-lasting relationships with professional athletes, executives, entrepreneurs and retired individuals and helping them, their friends and families through the years.

My youngest daughter asked me, “Dad, why are all your friends your clients?” That’s what happens. They are part of my life and my journey. We’re not in retail where a customer comes in, buys something and walks out the door. We are friends and confidants with our clients.

If you know me, you know faith is huge to me. Every morning I meditate on God’s Word. I think it’s very important for people to reflect and slow down. As young 20 somethings, it is so easy to get ahead of themselves.

I am not being a good steward of the blessing of a relationship with Christ if it is not deliberate. I’ve always had a good relationship with God. In the early years, I had it but didn’t own it. But through God’s grace, I do now.

DISCLAIMER: Past performance does not predict future results. This report is based on data obtained from sources we believe to be reliable. Hefren-Tillotson does not, nor any other party, guarantee the accuracy or completeness of this report or make any warranties regarding results obtained from its usage. All opinions and estimates included in this report constitute the firms judgment as of the date of this report and are subject to change without notice. This report is for informational purposes only and is not intended as an offer or solicitation to buy or sell the securities herein mentioned.

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