Roads to Retirement: The Journey Begins

Roads to Retirement: The Journey Begins

Jeffrey H. Snyder

Sat, September 5, 2026 at 5:30 PM GMT+3 8 min read

In Roads to Retirement: Act I – The Journey Begins, Jeff Snyder sets the stage for a thoughtful exploration of what retirement really means by introducing two people whose lives could not look more different. One is an artist in Marin who has chosen a simple, creative life living on a sailboat and staying grounded in what matters most. The other is a Northern California firefighter working hard to build stability and opportunity for his growing family.

Jeffrey Snyder, Broadcast Retirement Network

Hello everyone, I'm Jeff Snyder. I've devoted over two decades of my life helping Americans across this country save and plan for their financial future. I'm starting out on a journey to educate Americans and help get people in this country saving.

Join me as we go on the roads to retirement. Marin County is one of the top five richest counties in the United States, but it's also home to artists, shipbuilders, and tax-free, anchor-out citizens who avoid rent by settling in the open waters of Richardson Bay. Sean here pays his rent and makes a decent home of his 25-foot shoreliner with his loyal first mate and unassuming guard dog, Oscar.

It's really a beautiful location you live at. This marina is wonderful, real serene, quiet.

Sean, an artist

So you went from being an almost professional skateboarder and now you're an artist. I'm a sign painter, sign maker, floral designer. I wear a lot of different hats.

You know, living in SF, I'd probably be sharing a room. I'd be living with five roommates paying like, what, $1,800 a month for a tiny little closet. I got this, you know, 25-foot sailboat and I get to live here alone with Oscar and not have any roommates.

You know, it makes more sense. I do a lot of work on this boat, believe it or not. I've had this about five years now.

It's definitely living within my means, you know. It'd be crazy to have like a huge house and not use any of the rooms, you know, and I use everything in here. It's perfect.

Jeffrey Snyder, Broadcast Retirement Network

Let's talk a little bit about the art, the business that you're in. I mean, you service many of San Francisco's businesses. You're designing art.

Sean, an artist

I do a lot of stuff with restaurants, any type of business. You know, I've done stuff downtown and, you know, office buildings. It's been a pretty fun ride.

It's definitely tough, you know, one man banding it, but it works.

Jeffrey Snyder, Broadcast Retirement Network

I would imagine you have to balance the financial aspect of the business as well or get some personal.

Sean, an artist

It's a feast or famine, you know, to be honest with you. Pretty tough, you know, especially, you know, with rent and everything, you know, in this area, it's very expensive. I've never been really good at like budgeting, you know, when I get it, I spend it, you know, or, you know, help other people out with it or, and then it's next job.

I chose this because it's something I love to do and what's the point of waking up every day and doing something and you're completely unhappy? It doesn't make any sense to me.

Jeffrey Snyder, Broadcast Retirement Network

I think I in the audience can certainly feel the passion that you have for your vocation and obviously they're good at it, you've known for such a long time. The importance of mentorship and learning from others and I had a mentor who told me that life is a learned experience. So one of the things I take away is we need to get people who don't have that luxury investing in themselves both today, so living day to day for today, but also investing in themselves in the future.

Thanks for showing us around your digs and I know we're going to hang out a little bit later on Haight for the tour and kind of check it all out.

Sean, an artist

Thank you for your time.

Jeffrey Snyder, Broadcast Retirement Network

Thank you. Thank you, Oscar. Love you, buddy.

Have you ever met a Coast Guard hero who decided to switch gears and become a financially savvy Northern California firefighter? My guess is you probably haven't since these guys get scooped up pretty quick. I decided to travel upstream to San Rafael where I met with Will and his wife Chelsea to talk about his new home, baby daughter, and their cool dog Leroy.

If you're wondering if dogs are in all of our interviews, you're not entirely wrong. We're in San Rafael and we're talking to Will Fitzsimmons. He's a firefighter, EMT, specialist in the Menlo Park Fire Department.

I just want to start a little bit with your background. You're originally from Jacksonville, Florida and before serving in the Menlo Park Fire Department, you actually worked for the U.S. Coast Guard.

Will Fitzsimmons. Menlo Park Fire Department.

Yeah, I was in the Coast Guard for 10 years, was stationed underneath the Golden Gate Bridge for the last six of my 10 years and met a lot of good firemen, loved the Bay Area, met my wife, so I decided to go to the Coast Guard and become a fireman. What are some of the challenges of doing the job? Some of the challenges are the jobs you go on.

So you could start off the day with cleaning a station and then you get a call and it could be a car wreck, it could be a medical, it could be a fire, it could be a water rescue. The difficult part of the job is how to get your mind ready to respond to that call. It's also the mortality of firemen and police.

Their life expectancy is not nearly as long as a regular civilian.

Jeffrey Snyder, Broadcast Retirement Network

How do you process that kind of thing? I mean, you said you have to get your mind ready, but I'm sure that you've seen some things that you'd rather not.

Will Fitzsimmons. Menlo Park Fire Department.

You just think of it as an actual call and when the call's over, you try to debrief a little bit, but after that, you kind of just work yourself to the next call. How do you kind of de-stress? Spending time with the family is a huge de-stressor.

Jeffrey Snyder, Broadcast Retirement Network

Some people don't think about their retirement until they're in their 40s.

Will Fitzsimmons. Menlo Park Fire Department.

It was always kind of something in the back of the brain. I was always wondering, like, retirement. When I met Chelsea, my wife, and I decided to, you know, start to think about a family and realize that, you know, this is the place that I wanted to be, I could not have survived with the military salary at the retirement of 20 years.

It was a better retirement option, but 2.7% at 57 years old, we'll calculate to be a lot more than the military.

Jeffrey Snyder, Broadcast Retirement Network

So you did the math and you're just like, okay, this is better for me, better for my family, better for the lifestyle. Well, thanks so much for sharing a little bit of your life with the audience and really interesting how you transitioned from serving others in the U.S. Coast Guard to now serving others in the community of Menlo Park. I appreciate that.

Will Fitzsimmons. Menlo Park Fire Department.

Thanks for your time, too. Thank you.

Jeffrey Snyder, Broadcast Retirement Network

I appreciate it. Leroy looks like he needs a little bit of exercise. You think we should go take him for a little bit of a walk?

Will Fitzsimmons. Menlo Park Fire Department.

What do you say? You want to get up, buddy?

Jeffrey Snyder, Broadcast Retirement Network

I really enjoyed my conversations with Sean and Will, who on the surface couldn't seem more different. Sean, a striving artist living paycheck to paycheck, and Will, a firefighter taking risks but also saving for his loving family. But a couple of themes emerged.

Number one, the importance of mentorship and knowing people and working with other people. That collaborative environment leads to great success. And number two, retirement and savings is never far from anyone's mind.

People want to save, want to plan for retirement, but sometimes things get in the way.

This story was originally published by TheStreet on Sep 5, 2026, where it first appeared in the Retirement section. Add TheStreet as a Preferred Source by clicking here.