In San Francisco, we often talk about something called “the trough of sorrow.” This is the sadness that hits after a setback or even after a major victory. When things go wrong, the pressure to bounce back can be overwhelming, especially in a startup where cash and time are tight. But even after big wins, there can be a lingering question: “What now?” and a fear that nothing in the future will measure up to the past success, which can lead to feelings of emptiness and disappointment.
The truth is, these ups and downs are part of a broader pattern in life and work. We often believe that more effort will lead to greater happiness, but the reality is that it can set us up for greater disappointment. Managing our expectations and commitments can help stave off some of this sadness.
I found myself reflecting on this after feeling burnt out from the pandemic and two and a half years of non-stop parenting. Despite my intention to “have more fun,” I ended up working more than ever, especially when the market took a downturn. It felt like I was just running in place, trying to keep up financially for the sake of my family.
The stress wasn’t just from work. Getting back into a scheduled life and dealing with the demands of marketing and live TV appearances added to the anxiety. It’s been ages since I’ve had so many meetings and emails to juggle. Now, finally on a vacation at Lake Tahoe—the first in over a year—I’ve realized much of my drive comes from not wanting to feel guilty, a feeling rooted deeply in my past and the early loss of a friend.
Finding what “good enough” means is essential for personal happiness. My blogging buddy Joe, who retired the same year I did, 2012, commented that having enough to send his kid to college is all he needs. His perspective really made me think about the unnecessary sacrifices we make in pursuit of more money.
My situation is a bit different from Joe’s. My wife doesn’t work, adding more pressure on me to earn, especially living in an expensive city like San Francisco with two kids. But this has forced me to consider what “enough” really looks like and how I might ease my guilt-driven work ethic to find happiness within a more balanced life.
Here’s how I’m tackling the personal “trough of sorrow”: by acknowledging when enough is enough, appreciating the efforts I’ve made, and trying not to overshoot my happiness by overcommitting myself. It’s about finding that balance where you’ve done enough to not feel guilty for stepping back.
One recent challenge has been balancing time between work and being with my children. Marketing my book took precious time away from them, time I usually spent on adventures with them. This struggle culminated in a particularly low moment at a playground with my kids, where they both seemed to prefer their mom over me, despite my efforts to engage with them. It was a stark reminder of the emotional cost of my work.
But a surprising moment with a little girl at the playground, who showed me unexpected kindness, reminded me that I might be doing better than I thought. Her simple gesture of wanting to swing with me lifted my spirits and helped me see that perhaps I am a good enough dad.
Moving forward, if you’re a parent juggling these roles, remember that doing your best is all you can do. Sometimes, that means letting go of trying to be perfect and just being present. And if you find yourself feeling down or empty after achieving your goals, remember you’re not alone in this. It’s a common experience, one that can be managed by setting realistic expectations and finding joy in the journey, not just the destination.
