In his book, Just Keep Buying, Nick Maggiulli, narrates the startling story of Jack Whittaker. 

It’s CHRISTMAS DAY 2002 and across the state of West Virginia people are spending money like it’s going out of style. But instead of gifts or eggnog, what are they buying?

Lottery tickets.

At 3:26 PM the ticket buying frenzy peaks with 15 people buying a ticket EVERY.SINGLE.SECOND. Tick. Tick. Tick. 45 new hopefuls catch the lottery fever. 

Jack Whittaker was one of these hopefuls. He doesn’t play the lottery normally, but with $100 million at stake, how can he say no? Jack buys his ticket and heads home to see Jewell, his wife of 40 years. 

At 11 PM that night the winning powerball numbers were announced. Jewell wakes up Jack who had fallen asleep. It’s a miracle. They got four out of the five numbers correct. It’s not the jackpot, but they both know a six-figure payday awaits them as they head to bed.

The next morning Jacks turns on the TV before heading to work and makes a startling discovery. One of the numbers from last night’s draw was announced incorrectly. Jack checks his ticket against the correct numbers and is speechless.

He has just won the largest single ticket lottery jackpot in American history – $314 Million. Jack decides to take the money immediately and receives $113 Million after taxes.

But you already know this doesn’t end well, don’t you?

Within two years of taking the $113Million lump sum, Jack’s granddaughter is found dead (likely from a drug overdose), his wife is estranged, and Jack divides his time between high roller gambling, propositioning women to have sex for money, and driving intoxicated. Jack would eventually lose all his winnings. 

Well, there’s one small detail I left out about Jack Whittaker – he was already rich.

That’s right. Jack had a net worth greater than $17million before he ever bought the ticket that would change his life forever. How did he get wealthy? He was a successful businessman as the president of Diversified Enterprise Construction, a contracting firm in West Virginia.

Like myself, you are wondering why a person who was already well off would find meaning in chasing lottery winnings.

But this happens to all of us, across all levels of income.

More Money, More Problems?

Like I have written before, When you start making more money, things change pretty quick. The house you live in starts looking small and unhealthy to live in, the clothes you wear start looking cheap and unfashionable, the food you eat tastes blunt, your car looks old and creaky, and you think the economy class is unfit for humans while traveling.

In other words, your previous luxuries become necessities, and lifestyle creep walks in.

Like most people, making more money means upgrading our lifestyles and aiming for more money, more opportunities, and oftentimes taking up more risks.

And there is no problem with that, as we work hard to make more money that should help us lead better lives at the very least.

The problem comes when in the pursuit of the more that we want, we end up losing the little we had but never appreciated..

And I have seen examples of this in all levels of income.

It’s the recent employed graduate, who takes out a loan to get his first car, only to end up overwhelmed by the loan repayments. 

It’s the investor who enters into real estate highly leveraged only to end up auctioned by the bank as the rental income from his real estate can’t help him meet the monthly installments to clear his loan.

In the Psychology of Money, Morgan Housel writes,

“if expectations rise with results, there is no logic in striving for more because you’ll feel the same after putting in extra effort.. 

It gets dangerous when the taste of having more – more money, more power, more prestige- increases ambition faster than satisfaction. 

In that case, one step forward pushes the goal post two steps ahead. You feel as if you’re falling behind, and the only way to catch up is to take greater and greater amounts of risk.”

Don’t lose what you need in pursuit of what you want!

Jack Whittaker was already a millionaire before he bought his lottery winning ticket. He lost everything since he never appreciated the little he had. Having more money increased his ambition faster than satisfaction. He ended up losing the life he needed in pursuit of the life he wanted.

The paradox of personal finance is that we never realize how well we are doing when we are on an upward trajectory. When our incomes are growing and lifestyles are upgrading, we don’t realize how well we are doing. It’s only when tables turn, and we lose what we took for granted, that we appreciate what we had.