When Money is No Longer the Issue

Let me pose a hypothetical to you. It’s Christmas Eve in 2025, and you’re swinging through a gas station on the way home from running last-minute holiday errands. You fill up at the pump and decide to grab yourself a quick sweet treat inside. At the register, you decide to buy some scratcher lottery tickets as stocking stuffers and grab yourself a Powerball ticket. You let the machine decide the numbers: 4, 25, 31, 52, 59, and the power play 19. You go about the rest of your evening, spend the holiday with your family, enjoy yourself, and make merry.

A few days later, you read an article about how someone won the $1.82 billion dollar jackpot, and remember that you bought a ticket. You Google the winning numbers while you dig around in the center console of your car for the ticket. The winning numbers on your phone? 4, 25, 31, 52, 59, and 19. Congratulations, you’ve just won $1.82 billion dollars before taxes.

Question. Assuming we skip past all the chaos and logistics that are about to follow, and arrive a year or two into the future, let me ask: are you spending every minute of every day eyeballing your account balance(s)? Are you day trading? Reading articles about options strategies for hedging? Brushing up on your trust and homestead exemption statutes to better understand how to protect this enormous bounty of wealth? Or have you scheduled appointments and hopped on the phone to speak with a tax expert, an estate law and real estate attorney, and a financial planner? Are you filing your taxes personally or letting that expert do it? Did you draft your DAPT yourself and move to Florida to buy a quarter-acre lot? Do you have your assets properly diversified and efficiently tax-allocated to provide for you and your family in both the short and long term?

I ask these questions because I think we rationally understand that if we won the lottery, we’d immediately be out of our depth. We’ve never had a billion dollars, let alone several hundred million, let alone a hundred million, let alone fifty, and probably most readers haven’t had ten, and many haven’t even yet earned one million dollars. Yet, the inverse of behavior is true for too many people. We cling to the very first dollar we earn and hold, and we continue to clutch even as our wealth grows from one to two to three to four to five to six to seven digits and so on. We are swimming and not drowning, and convince ourselves that it must mean that we’re competitive swimmers. It’s only when we find ourselves drowning, dealing with a tax problem, or losing a lot of money on a poor financial decision that we’re suddenly spurred to engage in wiser action.

The question isn’t whether you’ll make a small or large financial mistake, but when. The very first investment I ever made before I was a financial planner was in a fund that was in the 98^th worst percentile of performers because I didn’t know what I was doing. The first time I ever filed my own taxes, I tried to opt in as a  “head of household” because as a single person in charge of his own household, surely that meant I qualified? I did the estate planning package template given to me when I was in the army and thought my affairs were in order, even though I never got it notarized and witnessed, meaning it was functionally useless. All of these were mistakes, but none of them were informed by competent and ethical help. Each of them was done through the auspices of not knowing any better and assuming things were good enough if they were “done.”

So there’s the question of the week: not a deep exploration of an assortment of sub-topics or delving through charts to better visualize what “enough” is or when the “right” time will come. But just a basic acknowledgment: We all recognize that at some point, we will be out of our depth and need help. But like the boiled frog analogy, we can often find ourselves clinging to something well past the point of reason because nothing bad has happened yet. Because we’re okay.

We’re told with great regularity earlier in life that an ounce of prevention is worth a pound of cure. Proper preparation prevents poor performance. Many hands make light work. All the usual idioms and expressions. But many of us delay in the pursuit of our greater interests. We don’t eat well until we dislike what we see in the mirror or on the scale. We don’t exercise as much as we should until we’re embarrassed to be winded at the top of a single flight of stairs. We avoid engaging a contractor when we’re thinking about a home project because we have YouTube on our side, and how hard could it really be?

I used to ask potential new clients during the initial consult, “What does money mean to you?” I’ve since stopped asking, but often the answers came back to one of two major themes. Freedom or Security. The freedom to do what I want, or the security of knowing that I’ll be okay. They’re good objectives. I’d then ask people how they’d know they were free or how they had a true sense of security. Many people struggled to articulate it. I shared that my answer was in the “freedom” category, and that I’d know I’d accomplished it when I had the income to never clean, fix something myself, or otherwise have to engage in any sort of “home project” ever again. In that regard, today I’m metaphorically swimming just fine in all these categories, and only out of a stubborn sense of “good enough” do I still cling to busting out a Swiffer every Saturday morning.

So there’s my suggested food for thought this week. If you look at yourself and find that you truly do have enough, why are you still doing things that no longer require you? Should you be retiring earlier? Should you hire someone to mow the lawn or pull the weeds? Should you be spending more time on trips and less time going into the office? Should you be doing your own bookkeeping or even have a trading app on your phone if you’re not really sure what you’re doing in either books or trading?

If you like it, that’s fine. But as I’ve gotten older and as I’ve hired help around me, I find that the good people I surround myself with are regularly asking me to do less so they can take on more. It’s a challenge to hand off sending an email to someone else when I could just knock it out in a minute at 139 words per minute typing speed. I feel strange “leaving a cup behind” knowing that someone else will pick it up and take care of it. It still feels damn near miraculous that coffee is just magically made in the office every day and shows up on my desk regularly without asking (thank you, Steph and Daniel). But I won’t lie and say that all of it hasn’t made my life a lot better.

So there’s the challenge I lay out to you. If money was no longer the issue or the object, how would you spend your time? I ask this question of people all the time, maybe I’ve even asked you. But given “enough,” whatever that is, would you rebuild your life the same way today as it has become on its own? What are you still doing that doesn’t “spark joy,” as Kondo would put it? What can you give away? What no longer holds the same meaning to you now as it did when you started?

Give it some thought. But more than that: Do something about it.