Living a Legacy: David Foster Wallace on Envy and Endless Wants

October 23, 2023

One of the things we say around here is that wealth is more than money.

We all know that one can have buckets of money and be deeply dissatisfied and that there are those with little money and profound contentment.

Of course, the flip side is also possible. I don’t mean to fall into a simplistic trope.

Being poor is no virtue in and of itself. Money is not the root of all evil, but from it may gush an assortment of corruption and sadness.

We must admit this as wealth managers and all of us need to hear it now and then.

You see there is an incessant demand for growth in investing, and the danger can be that one can slip into a never-ending chase for a number that continues to expand. An investor can get caught up in greed and envy and a hunt for status that swallows up a life.

Author David Foster Wallace in Harper’s magazine wrote about the not-so-subtle problem within human nature that was revealed during a cruise he took on a luxury ship. Wallace describes what happened within him when another luxury cruise line, the Dreamward, pulled up alongside his ship, that he named the Nadir

Because the Dreamward is lined up right next to us, almost porthole to porthole, with its Deck 12’s port rail right up flush against our Deck 12’s starboard rail, the Dreamward’s shore-shunners and I can stand at the rails and check each other out like muscle cars lined up at a stoplight. I can see the Dreamward’s rail-leaners looking the Nadir up and down, their faces shiny with high-SPF sunblock. The Dreamward is blindingly white, white to a degree that seems somehow aggressive and make the Nadir’s white look more like buff or cream. Its snout a little more tapered and aerodynamic-looking than our snout, and its trim is a kind of fluorescent peach, and the beach umbrellas around its Deck 11 pools are also peach, whereas our beach umbrellas are salmon, which has always seemed odd, given the white-and-navy motif of the Nadir, and now seems to me ad hoc and. Shabby. The Dreamward has more pools on Deck 11 than we do, and what looks like a whole other additional pool behind clear glass on Deck 6; and its pools’ blue is that distinctive chlorine-blue, whereas the Nadir’s two small pools are both seawater and kind of icky…

The point is that…I start to feel an almost prurient envy of the Dreamward. I imagine its interior to be cleaner than ours, larger, more lavishly appointed. I imagine the Dreamward’s food being even more varied and punctiliously prepared, its casino less depressing, its stage entertainment less cheesy, its toilets less meaning, its pillow mints bigger. The little private balconies outside the Dreamward’s cabins, in particular, seem far superior to a porthole of bank-teller glass, which now seems suddenly chintzy and sad. 

I am suffering here from a delusion, and I know it’s a delusion, this envy of another ship, but still it’s painful. Its’s also representative of a psychological syndrome that I notice has gotten steadily worse as my Luxury Cruise wears on, a mental list of dissatisfactions that started off picayune but has quickly become despair-grade. I know that the syndrome’s cause is not simply the contempt bred of a week’s familiarity with the poor old Nadir, and the the source of all the dissatisfactions isn’t the Nadir at all but rather that ur-American part of me that craves pampering and passive pleasure: the dissatisfied-infant part of me, that part that always and indiscriminately WANTS.1


No offense to those who enjoy a good cruise…

But there is something wise and terribly true here: the insatiable want for more. The never enoughness of the life we already have.

Our tag line, if you want to call it that, is living and leaving a legacy.

And legacies aren’t built on envy and consumption. They are wrecked by it.

If you live as if nothing is ever enough and with an Ever-Increasing Number, you will miss out on the truly significant and meaningful.

Consider a few suggestions.

  • Combat envy with generosity.
  • Spend your time on things and the people matter.
  • Spend your money with and on those you love and the causes you care about.
  • View life as more of a positive sum game where all can benefit rather than just a few. Replace keeping up with the Joneses with being happy for the successes of others and entering the sadness of other with solidarity.
  • Contest the current cultural pressures toward isolation and tribalism with intentional community and kind honesty.

Your legacy is more than money. It’s not a neon sign blinking lustily for more nor is it the limitless vacuum of consumption and accumulation. Legacy is more resonant with faithful virtue and contented diligence.

Don’t misunderstand. We want our clients’ portfolios to grow—that’s one aim of our job, but—even more—our hope is that worthy financial habits will frame a life that leaves a legacy far richer than dollar bills.



  1. “Shipping Out: On the (nearly lethal) comforts of a luxury cruise”, 51 (1996). Accessed online: