Let’s be honest, the word “budget” doesn’t exactly spark joy. For many, it brings up feelings of restriction, sacrifice, and penny-pinching. But what if we reframed it? What if a budget wasn't a list of things you have, but a roadmap to getting what you truly want? The reality is, your odds of reaching major financial goals without a plan are pretty slim. It requires some effort, but the payoff is huge.
Brené Brown once wrote, “Owning our story can be hard but not nearly as difficult as spending our lives running from it.” And man, am I tired of running. For most of my life, money has been a topic I’ve run from. It’s been a source of trauma and anxiety, rarely representing anything positive. When it did, it was usually just a temporary illusion I’d built to fool myself.
My childhood home wasn't one of excess. We were on the free lunch program at school, and I have clear memories of huddling around a space heater on cold mornings. This was pretty normal for my neighborhood, so it never felt strange. But we were lucky—our needs were always met, and my parents often gave what little we had to spare to families who had even less. They instilled in me the importance of caring for others, a value I admire more and more as I get older.
My real education in finance came from two people: my father and my first boss, David Swensen. My dad lost his parents young and had to put himself through college and medical school with very little. When some family friends passed, they told him about stocks, and he bought IBM in 1959. Even when life felt like it was taking everything from him, he held onto those shares. He still has them.
It’s one thing to give financial advice, but it’s another to live by it. The way we handle our own money is often a reflection of our earliest experiences, biggest lessons, and personal values. Here’s a look at how two financial professionals, Nina O’Neal and Debbie Freeman, manage their own investments, shaped by their unique life stories.