The "I'll be happy when..." trap

"Be content with what you have; rejoice in the way things are. When you realize there is nothing lacking, the whole world belongs to you." —Philosopher Lao Tzu

I’ve written before about my client Tony, who’s in his late 20s, very bright, but led a sheltered life growing up. As a result, he’s experienced circumstances, challenges, and new emotions a little later in life than many of us.

Tony works for a video game company and, for the past 18 months, has worked tirelessly on developing a new game. This has required 7-day work weeks, trips to China, and plenty of late-night Zoom meetings. Fortunately, his hard work has been recognized, and he recently got promoted.

When he arrived for his training session last week, he asked me a question I wasn’t expecting—” Are you happy with your life?” The last time someone asked me that, they were offering me “an exclusive and exciting ground-floor opportunity” to invest in a multi-level marketing pyramid scheme.

I told him that, like everyone, I have ups and downs, but there are many things I’m grateful for, including him and my other clients, and I'm pretty content. Now, I was curious to learn, “Why do you ask?”

Tony said he was feeling confused. Despite having a job he likes, a promotion, and a pay raise, he wonders if he should be happier than he is. “If you told me five years ago that I would be the senior project developer at this company, I would have been crazy excited. I’m wondering if there’s something wrong with me because, now that I have it, I don’t feel that way.”

I told him that this isn’t unusual in our society, explaining how people will often envision themselves as highly satisfied and happy with their lives once they’ve reached a particular benchmark. When their experience doesn’t match their expectations, they move the goal post and aim for the next achievement, the next dollar amount, or the next new toy because “then I’ll be happy.”

In my career, I’ve worked with many clients in the corporate world. Among several, I observed that despite impressive accomplishments, they rarely celebrated them or acknowledged their efforts. Instead, they were immediately planning for their next venture. When I asked one of them about this, he said, “You have to keep moving. If you waste time patting yourself on the back, the other guy can catch up to you.”

To me, the real waste was not taking a moment to appreciate one’s hard work and dedication, and hurriedly moving on to whatever comes next.

Relaying this story, Tony listened intently and said my perspective made sense. He admitted, however, that he’d been thinking about what should come next despite his brand new promotion.

I told him he should feel proud of himself and what he’d achieved; that he’d demonstrated his high value to the company and, importantly, learned a lot about what he’s capable of. “In my opinion, Tony from five years ago had the right perspective. Try to honor yourself by feeling the fullness of your achievement and avoid the ‘I’ll be happy when’ trap.”

I could see the wheels turning in his head. “It feels like I’d be disrespecting that younger version of me by not trying what you suggest.” Though he still had a lot to think about, he left our session with more clarity than he’d arrived with.

When I got home, I reflected on the advice I gave Tony, and it struck me that I’d fallen into the same trap. I was nursing my own version of “I’ll be happy when…” by telling myself I’d feel more joy when my life is free of stress, and all I’ve dreamed of finally comes to pass. But I was ignoring the downside to such a mindset.

Focusing on my imagined perfect future had been fraying my connection to things going really well in my life, casting shade on it, and subtly draining my energy. My good health and that of my parents, and a job where I make a positive impact on people’s lives, are worthy of my daily appreciation and can help my worries feel a bit smaller.

While journaling before bed, I felt gratified in paying fuller attention to my blessings, including my conversation with Tony.

Have you experienced the “I'll be happy when…” trap? I'd love to hear what you learned from it and how you escaped.