Every once in a while, I get caught thinking about how many different careers I’ve had over the years. I’ve swung a hammer, hauled milk, built ropes courses, and helped people build financial plans. Some days I feel like I’ve lived a dozen different lives, each one teaching me something that somehow led to the next.
After college, I worked construction and odd jobs — the kind of work where you learn the value of showing up early, paying attention, and fixing your own mistakes. Later, I worked in the woods as an outdoor adventure and ropes course builder. I loved that job. There was something about creating a space where people could challenge themselves and grow that really resonated with me. But there were also times when things didn’t go as planned — when a bridge had to be rebuilt because it wasn’t right, or when rushing led to someone getting hurt.
In those moments, I had two choices: dwell or draw.
I could have dwelled on the mistake — stewed over what went wrong, beaten myself up, and let it ruin the next job. Or I could have drawn from it — learned something, adjusted my process, and made sure the next bridge was better than the first. Over time, I learned that drawing from the past was a much better use of energy than dwelling on it.
A few years later, when I started driving a tractor trailer for our family business, that lesson came back to me — in a very literal way. I was hauling milk one morning, and if you’ve never driven a half-full milk tanker, let me tell you: it’s an adventure. When the tank isn’t full, that liquid moves like a living thing. As I approached a four-way stop, I started braking and could feel the milk slosh forward. I came to a stop just before the sign — and then a second later, that wave of milk came crashing back, shoving 60,000 pounds of truck straight through the intersection.
Luckily, no one was there. My heart was racing, but I learned something that day. From then on, I approached every stop sign differently — more gently, more deliberately. I didn’t dwell on what could have happened. I drew from it. And I became a better driver because of it.
That idea, the difference between dwelling and drawing, has come up repeatedly in my work as a financial planner and consultant. People make mistakes all the time with money. It’s human. Maybe they spent too much, sold at the wrong time, or didn’t save when they should have. The real challenge isn’t in avoiding every mistake; it’s in deciding what to do with the experience afterward.
When we dwell, we get stuck. We replay decisions, regret them, and sometimes we let that regret cloud every future choice. When we draw from the past, we use it as data, as fuel for better decisions going forward.
I heard a speaker at a conference recently talk about this same idea. He was addressing a group of coaches and athletes, saying that the best teams are the ones that draw from their losses instead of dwelling on them. The teams that fixate on the past — the missed shot, the blown lead, the bad call — tend to stay stuck there. The ones that learn, adjust, and move forward tend to win more often. It’s not that complicated when you think about it, but it’s incredibly hard to practice — in sports, in money, and in life.
Emotion plays a massive role in how we handle mistakes, especially financial ones. I’d argue emotion is more than half the puzzle. We all know the rule: buy low, sell high. But what do most people do? When the market’s hot, they want in. When it’s down, they want out. We dwell on fear and excitement instead of drawing on history and logic. The truth is, whether we’re investing, parenting, or just living, we can’t rewrite the past, but we can learn from it.
So, here’s the takeaway I keep coming back to: when something doesn’t go your way — a mistake at work, a rough season, a missed opportunity — ask yourself if you’re dwelling or drawing. Dwelling keeps you stuck in the problem. Drawing pulls you forward with a lesson in hand.
If you find yourself worrying about what’s next or stuck replaying what’s already happened, maybe shift the mindset a little. Don’t dwell on what could have been — draw from what was. There is power, growth, and peace in that shift, and the good news is, you only have to make it one time to start moving forward again.
Mark J Modzeleski, CFS, CLTC, AIF
President, Legacy Wealth Advisors of NY