A few years ago, author Ryan Holiday received the news he’d been awaiting for years. His book, The Obstacle Is The Way, reached the top spot on the New York Times Bestseller List, nearly five years after it was first published.

Holiday was mowing his lawn when he got the good news from his agent. After a brief moment of euphoria and reflection, Holiday went right back to mowing, his life largely unchanged.

Holiday had the realization many high achievers encounter: hitting a big goal or milestone rarely provides the enduring happiness or feeling of accomplishment one might expect. The reality is that when high achievers reach a goal or milestone, they rarely spend very long enjoying the view from the top—instead, they quickly set a new target and move on.

This same experience often happens when we make a large purchase that represents a new level of financial achievement, such as buying a house or a new car. The high of the purchase tends to wear off within a few months, just as the new car smell does.

We often believe achievements or purchases are what make us happy in life, but this is rarely the case. According to world renowned leadership coach, Marshall Goldsmith, this paradox is what’s called the “Happy When” trap, a concept Goldsmith and I discussed in a recent interview on his new book, The Earned Life.

According to Goldsmith, many of us mistakenly believe our happiness depends upon something external happening or changing in our lives. Consider this—have you or someone you know ever made one of the following statements:

  • I’ll be happy when I get married.
  • I’ll be happy when I get a raise, or a promotion, or both.
  • I’ll be happy when I buy a house.
  • I’ll be happy when I win an award, publish a book, speak at a conference, etc.

It’s always great to set major goals for ourselves. But where the “Happy When” trap arrives is when we believe that simply reaching those goals will fundamentally change our level of happiness or self-worth. Many of the classic “Happy When” achievements provide external validation, without changing our internal feelings about our place in life.

Having worked with some of the highest achievers in the world, Goldsmith believes that clarity of purpose, and not achievement, is what leads to intrinsic happiness. He believes the Western culture of consumerism, and especially mass advertising, has conditioned us from an early age to believe that our happiness is dependent on the things we acquire, rather than something that comes from our unique, personal purpose. When setting goals, it’s important to ensure those goals align with your core values and purpose; otherwise you may find yourself climbing the wrong mountain and feeling hollow at the summit.

While many of us find ourselves in unhealthy, or even dangerous, situations where simply exiting that environment can dramatically improve happiness, a true test of happiness is if we are able to be happy where we are today—by changing internal feelings without changing our external situation. We should focus less on finding the right destination for ourselves—living in a certain city, finding the perfect home or getting our “dream job,” which is often just a professional fantasy—and instead focus on finding more ways to enjoy and bring purpose to our current place each day.

This is a core tenet of the concept of Stoicism, an ancient Greek philosophy that is embraced by many leaders and is the subject of many of Ryan Holiday’s books, including The Obstacle Is The Way. Stoicism holds that all things are governed by unchangeable natural laws, and that the wise are those who live virtuously and accept whatever happens with calm and resilience. Stoics tend to live in the present and focus on what they control, rather than ruminating on the future and worrying about what they can’t control.

Rather than saying “Happy When,” focus on being happy now, each day. Practice being grateful for what you have and finding ways to improve your happiness in place before you look to make external changes that may not have the desired results.

What is an achievement you been telling yourself will make you happy, but may not in reality?

Quote of The Week

“No amount of applause, acclaim or wealth makes you worth more as a human being.”


–Ryan Holiday