The Questions Beneath Our Goals

August 1, 2026 5 Minute Read

In 2018, I wrote that I wanted to “race any car, on any track in the world.” I found the line recently while going through some old newsletters. I had forgotten writing it, but it showed up just at the right time:  HicokFinancial.com/Get-to-Know-Your-Advisor 

It reminded me of David Whyte’s poem, Sometimes, where he writes about the questions that continue asking something of us, “tiny but frightening requests.” Racing is one of mine. 

Racing was there before I knew how to call it a goal. At about ten years old, I tried to build a go-kart on our front porch using whatever materials I could find around the house. The project did not go particularly well.  

Racing was never simply something I wanted to accomplish. It wasn’t a goal to be pursued. It was written into the code. 

In my line of work, we are trained to keep asking, “What are your goals?” We write them down, analyze them, and make recommendations based on them. Good planning includes thoughtful questions, and those questions matter. But even good planning often stops at the goals we already know how to name. What rarely emerges are the “life-changing, course-correcting, comfort zone-crushing goals.” These are often harder to reveal, perhaps because they are less practical and more personal. 

Sometimes the goals we write down are only placeholders for the questions we haven’t yet learned to ask. Nobody walks into your office saying, “David, I think I’ve ignored the thing that makes me feel fully alive for thirty years.” They say, “I’d like to retire in five years.” That’s the language they have. 

Most people tell me they want to retire at 65, buy a second home, travel more, or leave money to their children. Underneath those goals are different questions. Who am I when work ends? What part of me have I ignored? What would make this next chapter feel alive? 

One of those questions has been waiting for me for a long time. In about 60 days, my brother and I are going to Virginia International Raceway for the Skip Barber three-day Formula Racing School.  

I am not physically ready, but I have changed how I eat, stopped drinking, increased my training, and started preparing as seriously as I can. I do not know whether I will reach my weight goal. But I will not arrive unprepared.  Already I feel the changes taking place.

I bought my first race car at 18 and spent my weekends racing on ¼- and 3/8–mile dirt tracks. Actually, the car sort of found me, but that is a story for another time. Later came helping my friend Scott prepare and race a Sports Renault, then came a middleweight superbike effort that ran out of money, and eventually a return to Laguna Seca in a race-prepared Mustang.

We’ve all learned to name conventional goals, but they do not always satisfy desires that feel less practical and more revealing. I have spent much of my life seeking meaningful goals and challenges. Yet racing has never felt like ambition in the usual sense. I do not want to conquer the track, beat an opponent or hoist a trophy. There is no striving, only the desire to arrive prepared and ready to meet the challenge. I want to enter that rare state where time bends, the noise drops away, and I am fully present.

I have played tennis for over 40 years, and the flow state does not come to me as quickly or as assuredly as it does when I get in a race car.  I pull on the 6-point harness so hard that it squeezes my chest.  In that moment, there will be adrenaline, but the second I put the car in gear, let out the clutch, and begin to roll down the track, fear subsides, heart rate settles, breathing becomes rhythmic, and my attention narrows to the point where time slows, things get quiet, and I am here, in the moment.

We spend much of our lives pursuing goals because they are easier to describe than callings. We know how to say we want to retire, travel more, or buy a second home. Harder to admit is the question that has quietly followed us for years, asking us to become a little more ourselves. Those questions are easy to ignore, but they rarely disappear.

My hope is that the work we do helps people make financial decisions that leave room for those questions, because they often point us toward the life we were meant to live.

Less “What should I accomplish?” and more “How should I live?”

Warmly,

David