My Most Important Investment Is a Financial Flop
My wife’s grandmother, Mimi, was in a drab hospital room in North Jersey, caught somewhere between her 89th birthday and the end of her life. It was a cold January day, and it didn’t really matter which one came first—the outcome felt the same. She had already lived two decades without her husband, Pop, much of it with failing health and vision. Mimi was ready. Her family stood by her, a testament to the life she’d built. The room was packed with her four children, ten grandchildren, and eight great-grandchildren.
We sang songs, retold old jokes, and shared memories. As I watched and listened to Mimi’s grandchildren, one theme came up again and again: their summers at her cottage in the Adirondack Mountains. It was the place they all treasured. My wife, Ginny, first visited that place in Mimi’s womb and has gone back every summer since. When Mimi and Pop bought the cottage in 1980, they had a clear purpose: to have a place where their family could always gather. And it worked. It became our family’s anchor.
Our own kids have spent part of every single summer of their lives there. It’s where they learned to hike, swim, canoe, and waterski. It’s where they got their first summer jobs as teenagers. Our daughter even met her husband there. But more than anything, the cottage gave us time. It was where conversations happened, values were passed down quietly, and memories were made. We were investing in each other.
The “Why” Behind Investing Money
In the financial world, we spend so much time figuring out to invest. We talk about diversification, low costs, asset allocation, and the magic of compound interest. All of that is crucial. But we don’t spend nearly enough time on we invest in the first place. The “why” is the foundation. A good financial plan isn’t just about numbers; it’s a tool designed to fund the life you want to live, on purpose.
Sticking to a financial plan is often harder than creating one. Life gets in the way. That’s when remembering your purpose becomes so important. When we think about the end of our lives—like Mimi in that hospital bed—it can push us to make better, more meaningful choices today. Our brains are wired for immediate rewards, making it easy to ignore the intangible, long-term investments that truly matter. There’s often a huge gap between the life people say they want and the one they actually live, and it’s usually self-inflicted. If your relationships aren't what you want them to be, it’s often a sign that your priorities are out of order.
Your purpose is personal. Ginny had a great college experience; my parents couldn’t afford to send me. So when it was time for our own kids, paying for their education so they could graduate debt-free was a massive priority for us. Many financial planners would argue that money would have been better spent on our retirement. But we had our “why” sorted out. We willingly accepted the trade-off of potentially working longer to give them that start.
The Best and Worst Investment We Ever Made
Mimi passed away two days after her birthday. Her cottage is still in the family, but with everyone grown, it’s no longer big enough. So that fall, Ginny and I bought our own cottage just five minutes away. From a purely financial standpoint, it’s a terrible decision. We already have significant exposure to the property market from our home in Southern California, so this venture into adds to that. The property taxes are high, the old buildings require constant upkeep, and it’s only usable in the summer.
It’s a lousy investment. But this summer, Ginny will be there for six weeks with our grandkids. We’ll all be there as much as we can. They’ll play in the lake, jump off the dock, pick blueberries, and eat s’mores around a fire. We’ll even put up a tetherball pole. It will be the best time of their lives—until next summer. It is, without a doubt, the most important financial investment we will ever make. It's easy to get lost in the details of , but sometimes the answer is simpler than charts and returns.
I’m reminded of Harry Chapin’s song, “Cat’s in the Cradle.” The lyrics tell the haunting story of a father who is always too busy for his son, only to find that when he’s finally ready, his son has grown up just like him—with no time to spare. That song has always scared me. That fear is part of why we bought the cottage. But the bigger part was love.
Success, like compound interest, is sequential. The best things in life—from our finances to our relationships—build on themselves over time. Generosity compounds. Healthy habits compound. Education compounds. And love is the most powerful compounder of all. While my portfolio is built on practical strategies like low-cost funds and avoiding individual , my life portfolio is built on this principle of compounding love.
We can’t completely control our legacy, but if we invest well—in every sense of the word—it can be profound. Mimi and Pop knew what was important, and they used their resources to bring that purpose to life. That's what we're trying to do, too. In the end, how we invest our time, our talent, and our treasure shows what we truly value. It’s the ultimate benchmark for a life lived on purpose.
