I just bought my first new car in 10 years. It wasn’t supposed to happen this way—I had planned for a deliberate purchase in 2025. But plans don’t always unfold as expected.
For months, my Grand Cherokee had been showing signs of age. The windshield wiper sensors were glitchy, the transmission was fading, and the Bluetooth worked only on alternating days. All indications that a change was coming.
Then, the week before Christmas, we set off for a family ski trip to Upstate New York. We had to take two cars to fit all the gear, so I drove my Jeep with my son keeping me company. Unfortunately, our 5 p.m. Friday departure meant rush-hour traffic. Then, it started to snow.
Soon I found myself driving in the dark, in a snowstorm, in New Jersey, manually operating my windshield wipers for four hours straight. By the time we arrived, I was mentally fried and ready for a new vehicle. And just like that, my decision about buying a new car was no longer theoretical.
Pay Attention to Warning Signs
For too long, I tolerated the issues with my old car. I told myself I could manage, that I didn’t need to make a change. But when conditions worsened, I put myself (and my family) in a tricky spot. I was driving in a treacherous environment, distracted by the conditions, and tinkering with my vehicle the entire way. Maybe I used to feel a bit of pride in thinking “I can handle whatever comes, I don’t need to change vehicles.” The truth was, I should have been prepared with a more appropriate and functional vehicle before a crisis emerged.
The more I think about this situation, the more I find parallels between how I treated buying a new car and how many approach their financial plan, especially at times of increased anxiety or risk. Every day you might get into your vehicle, merge into 65 MPH traffic, and navigate chaotic traffic. The road is full of distractions and other vehicles weaving around you unpredictably.
Similarly, investors face a daily barrage of news headlines, market moves, and perceived risks. It can feel impossible to separate the signal from the noise, yet we are expected to navigate this confusion confidently and reach our financial goals.
A Plan That Fits the Road Ahead
Your financial plan is your vehicle: Choose wisely. For a business owner building wealth or an executive planning for retirement, you need a plan that has the right capabilities for the financial life you want to lead. It needs to help you make progress toward your objectives, provide safety when needed, and be flexible for the unique needs of your family. It requires you to understand the basics of how it works and commit to maintaining it.
Risk is always present: Much like the car you drive daily needs to leave the garage and navigate the busy streets, your financial plan needs to live in the real world of market and economic forces. Risks and opportunities are always present but hiding is not an option. Like driving, we need to be aware of our surroundings, recognize what could impact us, and take the right measures to successfully navigate to our destination.
Don’t just tolerate your plan: You should also think about the status of your plan more often than I thought about my old car. Check in regularly on all aspects of your plan (Yes, that means more than just performance reports). Your advisor should be able to help you ask the right questions and help make changes. Confidence comes from knowing that your plan is appropriate for where you are now and that the parts are still working. Speaking of parts…
Tinkering is not a plan: Note that above I did not say that funds, stocks, or other products are the vehicles for financial success. They are important, but merely as components that need to work together to keep the plan on track. The need to trade or shift strategy frequently might be a sign that your plan is as fragile as my Grand Cherokee’s transmission. If you find that you are regularly tinkering with the parts but still don’t know if the whole is functioning as it should, you might be distracting yourself from the real work of financial planning.
The Best Time to Upgrade? Before You’re Forced To
In the end, I was lucky. I found a vehicle I’m happy with—one that my mechanic had even recommended. But that’s not always how it works. When we’re forced into an upgrade, we don’t always have the luxury of time, options, or careful decision-making. The same goes for financial planning.
Are you waiting for a breakdown to make a change? If so, it may be time to take a proactive approach.
Aggressive Balance is a biweekly e-newsletter authored by Dennis Morton, Co-Founder and Principal of Morton Brown Family Wealth.
A gifted storyteller and financial advisor by trade, Dennis explores topics of leadership, finance, and the human condition in his writing as they relate to curating a life worth living.
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