Dear 24-year-old Tom,
I know that living in your in-laws’ basement sucks. It’s not quite the way you thought you’d spend your first few months as a newlywed, is it?
Hang in there. It’s going to be tough finding an internship with your graduate degree in Public and International Affairs, especially now that going abroad is off the table. All the networking you did in grad school? It’s not going to work out for you.
But things will get better.
Keep interviewing. The job market in 1994 isn’t the best, but you’ll have dodged a big mess when Enron doesn’t call you back. The boiler room opportunity that John Hancock is offering — the one where you’d be selling long-term care insurance — doesn’t sound like your dream job, but it’s your ticket for a future you can hardly imagine.
The first few months of cold calling are going to be terrible. There’s a reason the senior agents don’t bother learning any of the rookies’ names: Most people don’t stick around for long.
Your wife, Beth, can’t provide for the two of you on her teacher’s salary. So you have a choice: more cold calls or keep living in the basement.
Thirty years later, you’re still going to remember that call script. It’s a miserable job, I know, and you’re going to deal with a lot of rejection, but it’ll be good for your professional stamina.
Along the way, you’re going to learn how to listen. You’re going to discover that the best way to sell long-term care insurance is to get people talking. The conversations you’re going to have aren’t comfortable. They touch on topics we don’t like to address: frailty, cognitive issues, and caring for a loved one who can’t care for themselves. But the question you’ll start asking prospects in your mid-20s will be true decades later, “When you’re taking care of someone, who’s going to take care of you?”
Your superpower is your mix of empathy and curiosity. Just ignore the other guys in the office when they start calling you the “One-Legger Appointment-Closer” as you schedule follow-ups with senior couples where only one of the two spouses is insurable.
You’re going to talk with a lot of family caregivers. Hundreds every year. Trust your instinct. There’s a future here.
That’s because there’s no guidance for these people. No one is offering them advice. In many cases, no one even wants to talk with them. These conversations are icky. They’re messy. But you’re going to see that this is actually a huge opportunity. Everyone else’s blind spot will be your path to success. These are people who need help, and they’re willing to pay for the help, as long as they understand that it’ll improve their situation.
Your employer will eventually recognize you as a Hall of Fame producer, but it’s only the beginning. If you can get the insurance side of the business to support your entry into financial planning and asset management, you’ll really be able to make a difference in the lives of your clients while catapulting your career forward at the same time.
People are going to think you’re a little bit crazy.
Just ignore anyone who doesn’t understand. If they can’t figure out why helping millions of people who are affected by cognitive issues is worthwhile, that’s their problem. Stay confident. Stay persistent. Keep pulling the string.
You’re going to cross paths with people who will help you in ways you never expected. One of them is Betty, the community services director at the Northern Virginia Alzheimer’s Association. Betty’s skeptical of your motivations, so she’ll insist that you co-host a support group at a local church, where you’ll discuss the topics of death, dying, and grief around the holidays for people affected by dementia.
It’s heavy stuff, but it’s going to teach you about the social isolation and limited bandwidth of caregivers. You’re also going to see how important it is to stay involved in this community, and you’ll eventually serve on the board of the Alzheimer’s Association.
Trust that there’s a viable business opportunity here. It’s bigger than long-term care insurance. When your colleagues in insurance question whether you should get your investment licenses and start working with investments, don’t let them clip your wings. While everyone else is focused on the accumulation phase of a person’s life, they’re ignoring that people need help unwinding their portfolios.
And when you’re ready to start scaling the business you’ve built, remember the importance of empathy. Surround yourself with people who will expand the breadth and depth of your abilities. Find people who will bond and build, because you’re going to need a lot of help for all the bespoke planning and portfolio management you’ll be doing. All the while, don’t forget that if the portfolio is the tail, the planning is the dog. Keep your priorities straight.
It might seem impossible to you as you sit in your in-laws’ basement, dreaming about the future, but in three decades, you will have $1 billion in assets under management.* You will have built a career by helping people that others turned away from. You’ll be motivated to improve the standard of care for your clients. It’s OK to be a little pissed off when you look at how lazy others get and how they treat folks in the later stages of life.
At the same time, understand that change is natural. The financial and intellectual satisfaction that are so important for you today are going to change. It’s going to be a fun ride. Stay curious. Stay empathetic. Keep having fun and keep helping others.
*As of December 2025
Signature Estate & Investment Advisors, LLC and TradePMR are unaffiliated companies.