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So You’re Leaving the City? “Let’s Buy That One, Dad.”

Blog August 17, 2026By scott
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Every stage of life has a different definition/measurement of success. In my twenties, success meant living in Boston. I loved being able to walk to dinner, catch a Bruins game on a whim, explore new neighborhoods, and enjoy everything city life had to offer. Like so many young professionals, I couldn’t imagine wanting to live anywhere else; that was never going to be for me!

Then my wife and I started thinking about having a family. Almost overnight, our priorities changed. Instead of asking, “Which yoga class should we try, before going to Community Sailing?” we started asking, “Where can we picture raising our kids?” 

It wasn’t about leaving Boston behind (we both had a hard time coming to terms with that), but it was about building a different kind of life that would fit a family’s needs, not the needs of a fun-loving pair of twenty-somethings. 

Financial Planning for Young Families: The Search Wasn’t Easy

Like many young families trying to buy around Greater Boston, we lost house after house. We submitted more than a dozen offers, and “clean offers” seemed to be everywhere. Every weekend brought another open house and, more often than not, another disappointment. We simply could not compete with all-cash bids above asking prices; the market was just too hot and turning too fast for what we could realistically afford. 

Eventually, we realized we weren’t simply shopping for a house; we were choosing the next chapter of our lives, and that chapter eventually led us to Newburyport. Looking back, I’m so grateful it did.

The moment I knew we might actually be ready to leave Boston happened somewhere completely different. We were in Delaware for Memorial Day weekend and parked near a house by the beach with a For Sale sign out front. Finn was three at the time and had been paraded in and out of open houses with us for almost two years. At that age, you never really know how much they understand. He looked at the house and said, “Dad, let’s buy that one.”

I started reminding him about everything he loved back home. What about your preschool? The playgrounds? The Esplanade? The Children’s Museum? He thought about it and told me he liked the beach better.

About a month later, we were on the North Shore at Appleton Farms for their Bluegrass Father’s Day Festival. On the drive home, Finn and Reese fell asleep in the car, so my wife and I started driving around the North Shore. We ended up popping into an open house in Newburyport. What started with a three-year-old pointing at a For Sale sign by the beach in Delaware suddenly felt a little more real.

Your Lifestyle Evolves Along With Your Finances

I still love Boston. There’s something special about spending an afternoon in the North End and making my way through Fenway before a game – it’s bliss.  But today, some of my favorite memories happen somewhere entirely different.

Walking the Rail Trail while Finn, Rhys, Boden and Isla ride their scooters. Spending an afternoon at Appleton Farms in Ipswich and watching the kids grow up with room to run and simply enjoy being kids. I wouldn’t trade those moments for a reservation at a trendy restaurant.

That’s one of the beautiful things about life. Your priorities evolve, and your financial plan should evolve right alongside them. Working as a family financial planner in Newburyport and Boston over the years has offered me the privilege of helping many families navigate that same transition, from city living to raising children on the North Shore and beyond.

Buying the House Is Only the Beginning

Purchasing a first home is one of the biggest financial transitions most families will ever experience. The mortgage is only one piece of the puzzle. Suddenly, there are childcare expenses, home maintenance, insurance, retirement contributions, emergency savings, and, eventually, college planning. The starter home may not be your forever home, but it often becomes the foundation for your family’s long-term financial future.

That’s why I encourage young parents to think beyond simply qualifying for a mortgage. Your home purchase should fit within a larger financial strategy that grows alongside your family. My wife and I went through all of it as Gen X parents, and now I work to help younger parents work their way through it too. 

“All Set” Isn’t Always Optimized

Buying the house can mean you’re all set, but making sure the rest of your financial life evolves with it means you’re optimized. I’ve worked with many families who successfully purchased their dream home but never revisited the rest of their financial strategy. 

There are so many more phases to life after buying the first house and having the first baby. Cash flow changes and insurance needs increase. College savings become more important and retirement timelines shift. Before long, you’re balancing priorities that barely existed a few years earlier. But that’s ok! It’s how life evolves, for the better. Leaving the Beantown proper doesn’t mean you’re giving something up; it means you’re building something new.

I pride myself on being a trusted family financial planner for young families, so if you have questions regarding what your next phase of life is looking like, please reach out! I’ve been there too, and you’re not alone; my door is always open. 


Securities offered through LPL Financial, Member FINRA / SIPC. Investment Advice offered through Flagship Harbor Advisors, a registered investment advisor. Thrive Wealth Strategies and Flagship Harbor Advisors are separate entities from LPL Financial.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

This is a hypothetical situation based on real life examples. Names and circumstances have been changed. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your advisor prior to investing.

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