Escaping the “when-then” trap

My friend’s dad always wanted to be a millionaire. As pre-pubescent boys more focused on Magic the Gathering and ollies, his dad would constantly extol the virtues of index investing on Vanguard. He was a gym teacher who lived modestly and found a simple joy in watching his balances creep up with each quarterly statement.

I remember hearing about the day when the balance flipped into seven figures. My friend described how his dad beamed with pride as they logged in to view the majestic balance. An unconventional father-son moment.

When we were home for the summer a bunch of years later I asked my friend how his millionaire dad was doing. “Oh,” he responded somewhat indifferently, “he’s going for two now.”

Decades later, I wonder. What did he think was waiting on the other side? And why did the goal lines shift so swiftly? Had he fallen for the when-then trap?

Harvard Business School professor Michael Norton studies the rich and their money idiosyncrasies. In a recent study referenced by The Atlantic’s Joel Pinkser, Norton described surveying 4,000 millionaires with a simple set of questions:


  • Rank your happiness on a scale of 1 to 10
  • How much more money would you need to get to a 10 out of 10?


The survey says…

Here were the survey responses, by ascending net worth:


  • $1 million dollars: “2 to 3 times”
  • $2 million: “2 to 3 times”
  • $5 million: “2 to 3 times”


All the way up to $10 mm, which could be reduced to:

WHEN I double my money, THEN I’ll be a Happy 10.

And there you have it, the when-then trap. It’s gnarly. And it’s definitely not the exclusive domain of disgruntled deca-millionaires. Countless RadReaders have invested in the promise of the when-then, in the form of promotions, bigger houses, iPad Pros or a luxury vacations. But why does it never deliver?

Sports stars and celebs

It can feel hard to be sympathetic to the sufferings of celebrities and sports stars, but let’s look at a few examples:

Kevin Durant: WHEN I win my first championship, THEN I’ll feel fulfilled.

Steve Nash, a consultant for Golden State remarking on Durant’s despondency: “He thought a championship would change everything and found out it doesn’t. He was not fulfilled.”

Michael Phelps: WHEN I become the greatest swimmer of all time, THEN I’ll be happy.

Phelps described the demons of depression and substance abuse, ” “It’s like we dreamed the biggest dream we could possibly dream and we got there. What do we do now?”

Andre Aggasi: WHEN I win a Grand Slam, THEN I’ll be accepted by my father.

In his incredible memoir Open (affiliate link), Agassi describes the insatiable expectations of his father. After winning the Atlanta Olympics, he reflects on how “fast the surreal becomes the norm. I marvel at how unexciting it is to be famous and how often they hate what they do.”

Mad Men’s Don Draper succinctly captured this trap:

“What is happiness? It’s the moment before you need more happiness.”

What about RadReaders?

I frequently worship the altar of the when-then. The traps can take shape as physical objects like Gazingus Pins or the fallacy of freedom.

For me, it impacts my family:

WHEN I lock down this new gig THEN I’ll be present for my kids.

My marriage:

WHEN the kids get older, THEN we’ll have more time to re-invigorate our marriage.

And my work:

WHEN I hit this many subscribers, THEN I’ll stop caring about subscribers.

And lastly, my personal goals:

WHEN I get a new surfboard, THEN I’ll catch more waves. (NOPE!)

I sent out a call to RadReaders to share their own. Here’s an anonymous document collecting all of their when-then traps:


  • WHEN I stop working, THEN I’ll get a six-pack
  • WHEN I quit my job to travel, THEN I’ll feel present.
  • WHEN I get a new laptop, THEN I’ll be more productive.
  • WHEN I get a new Kindle, THEN I’ll read more.
  • WHEN it’s less busy at my company, THEN I’ll work on marketing my company.
  • WHEN I get a promotion, THEN I’ll sleep more.
  • WHEN I stop working, THEN I’ll get a six pack
  • WHEN I get this unplug box, THEN I’ll get off my phone in front of my kids
  • WHEN I [have clarity around the project outcome], THEN [I’ll feel confident making the first move].


What’s yours? In 2020, we’ll look at strategies to shift this mindset. Have a great holiday!

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