The Happiness Trap
Yesterday I was standing in the middle of a noisy arcade surrounded by flashing lights, claw machines, and overstimulated children when my phone started ringing from an unknown number.
We had been on a trip to a lake for the weekend, but the weather had turned cold and rainy, so Middle Son and I decided to take my seven-year-old to the arcade in an attempt to salvage the day.
The first time the phone rang, I rejected the call without much thought. Then it rang again. And again. And again.
By the fourth call, a text message followed the ring.
“This is Oldest Son. I’m not in trouble, but I need you to answer.”
My heart dropped immediately.
Oldest is currently thousands of miles from home training for his summer job as a wilderness therapy field guide. He’s been in the wilderness for days without access to his phone, so it never even occurred to me that the unknown number might be him. The second I saw the text, even though it was reassuring, my nervous system lit up because history has trained me to brace first when it comes to Oldest.
Years ago, our family went through an incredibly difficult period during which Oldest spiraled emotionally and eventually spent over a year away from home, moving from wilderness therapy to a residential treatment center. Even though he has been doing well for years now, some part of my body still associates unexpected phone calls from him with crisis. Before I even answered, I had already convinced myself something was wrong.
My body traveled immediately back to older versions of both of us, back to years when every unexpected phone call carried the potential to change the emotional temperature of the entire house.
The moment I heard his voice, though, I knew I was wrong.
The reason he had called turned out to be entirely mundane. The friend he had traveled to wilderness with had decided the job wasn’t for him and had accidentally left the program with some of my son’s belongings. Since my son did not have access to his phone, he needed me to contact his friend before he left the area with all of my son’s stuff.
The actual request took less than two minutes, but the conversation lingered.
As Oldest and I talked, he began telling me about the training. He talked excitedly about reconnecting with wilderness skills he had learned years ago, about practicing bow drilling, learning Dialectical Behavior Therapy concepts, preparing to work with struggling teenage boys, and beginning to bond with the other guides. His voice carried excitement, curiosity, pride, and purpose. He sounded challenged in a way that seemed to be building him up rather than defeating him.
My son was happy, yes, but there was something deeper underneath the happiness. Oldest sounded connected to the people around him, invested in what he was learning, and proud of the role he was growing into.
After we hung up, I found myself thinking about my oldest son, once my little boy, and about how differently I understood parenting when he was younger.
Back then, I genuinely believed happiness was the goal. I thought that if my children felt emotionally safe, generally happy, and able to enjoy their lives, then I was probably getting parenting mostly right.
Of course I still want my kids to experience joy. I still want fun afternoons at arcades and ice cream on summer nights and moments where life simply feels light. There is absolutely nothing wrong with wanting happiness for the people we love.
Happiness, though, is slippery. It rises and falls depending on circumstances, moods, relationships, disappointments, luck, weather, and a thousand other forces we can’t control.
Over time, and particularly during the years when Oldest was struggling, I learned something much harder and far less intuitive about chasing happiness. Trying to remove discomfort and maximize pleasure didn’t help my son build a deeper sense of purpose, capability, or connection. In fact, many of the experiences that helped him grow the most were not pleasurable at all.
Wilderness certainly did not make him happy in the traditional sense. Much of it was physically exhausting, emotionally uncomfortable, and relentlessly challenging. Yet it gave him something deeply meaningful and far more sustainable than temporary happiness ever could. It gave him competence, responsibility, connection, and a growing sense that he was capable of hard things. It gave him opportunities to contribute to a group, to be depended upon, to struggle, to adapt, and eventually to discover he could survive difficulty while remaining connected to himself and the people around him.
After we hung up, I stood there for a moment in the middle of the arcade hearing the sounds around me differently: machines flashing, children shouting, electronic games chiming while my youngest son ran happily toward another game.
The irony was not lost on me that while I was standing in the middle of an arcade trying to create a little happiness for my youngest son, my oldest son was reminding me of something wilderness had already taught me years ago: the things that fill us up most deeply are rarely the things that make us happiest in the moment.


This is beautiful, and I can't wait to hear you two talking on the Substack live 😀
It is 3:30 AM here in California and I shouldn’t be awake. But I got up to use the bathroom and I couldn’t go back to sleep. So I sat down in my study and wondered what to do…go back to sleep…or start my work for the day…or…Then your post came in and I thought, “Perfect!”
And yes, once again your post came at the perfect time and had a perfect message for me. Because I’m right smack in the middle of one of those deeply meaningful times. Not the crazy happy times. But not the sad and lonely times either. Just a time when I am feeling highly connected to people and when my heart is feeling a strange peace amidst the noise and chaos.
Let me explain. This past month, my mom-in-law passed away. Then I had major surgery, removing my thyroid gland. And currently, I’m watching two close friends die of cancer. Yeah. Hard stuff. (And always in the back of my head, knowing I have a daughter who has always struggled with mental issues who hasn’t talked to me in almost four years. So I can sorta relate to your story regarding you and oldest son.)
Two days ago though, we had a memorial for my mom-in-law here at home and I saw relatives and long lost friends I hadn’t seen in years and it was such a powerful time of reconnection. I had deep conversations with 2 nephews of my husband who used to be kids and are now 20-somethings, inquisitive, curious and spiritually searching. My kind of connections. Meanwhile, screaming kids (not mine) are running all around our yard which in the past drove me crazy but now they just make me smile and remind me of the “good old days.”
In two weeks, I return to the Philippines and I get to see the under-resourced kids at the school we’ve built there, now in its fifth year of operations. Those kids always fill my heart. We also get to expand on our work with our safe house for abused women and children. I get to meet up with the staff we have been training and building up since last year. I also get to scuba dive at our dive resort…a sport I just started two years ago at 58 and am now thoroughly obsessed with! (The dive resort provides funds and ready employment for the girls at our safe house.)
Finally, I’ve had long and wonderful discussions lately with my two sons (who love and adore me…thank God) and my husband who is missing his mom but is bravely going through the stages of grief and bringing me along with him (as opposed to shutting me out like he used to).
A full life. A very good life. Not always “happy.” But one that I get to move through with purpose and dignity. One that I created with God. And one that fills my heart with gratitude even on days when I get up at 3 AM and can’t go back to sleep.