Feeling Guilty for Doing What I Love
On aimlessness, an old Steve Earle song, and learning to serve tea to my guilt
I’ve been doing this Substack for over two years now. Well over fifty posts and a growing podcast.
It’s turned out better than I ever imagined — not just the writing, but the joy and satisfaction it’s brought me. I’ve learned so much along the way, and I’m hoping it’s helped (or at least entertained) other people too.
I think it’s also kept me out of trouble. I’m in my mid-40s, an awkward time of life when people sometimes look for comfort and distraction in the wrong places — convertibles, drugs, affairs, overwork. Pick your poison.
The Guilt
And yet most weeks go the same way. It’s the middle of the day, the house quiet, and I set aside whatever I’m supposed to be doing to write a post or record a podcast.
Almost immediately, the guilt shows up.
The nagging sense that I should be doing something more useful, by society’s measure. I should be out making money, or doing charitable work, or really making a difference. I shouldn’t be tucked away at home on a Tuesday, working on podcasts or posts that only a few people will read.
I figured that as the podcast and the Substack got more established, the feeling would fade. It hasn’t. It’s still there all the time — even now, as I write this.
I know roughly where it comes from. Part of it is the old idea that a man is supposed to provide — to be useful, to bring home something you can measure. But it’s bigger than that. We live in a culture that ties your worth to what you produce. Time is something you turn into money, and anything else feels like time wasted. Even with all the good this creative work brings to my family, to my own life, and maybe even to the world around me.
I’ve wrestled with it for years, and it hasn’t gotten me anywhere. Resistance is funny that way. When we resist something, we just make it bigger. It becomes an arms race: the harder I push the feeling away, the harder it pushes back.
So I’m trying to give up the fight a little. To just let the icky, guilty feelings sit there. I don’t know if they’ll ever let go of me. That’s a sad thought — that I’ll keep grappling with something that undermines my happiness and pulls me away from what gives my life meaning, all because society might not view it as the best use of my time.
Aimlessness & “Enough”
There’s a Buddhist concept called aimlessness. The idea is that everything we need — peace, contentment — already lies within, not out in the world.
But I, like many people in the West, can’t help looking for it outside: a new toy, another post, some number of subscribers to the Substack. And when I get the thing, the bar just moves higher. We hedonically adapt and slip right back into the same cycle.
It’s the same treadmill I write about in investing. Hit your number and the number quietly resets. There’s never a portfolio big enough to finally feel safe, never a return high enough to stop wanting the next one. We tell ourselves we’re chasing security, but the goalpost moves the moment we reach it.
Aimlessness lets me step away from that. It’s the closest thing I’ve found to what investors call “enough” — the recognition that my worth isn’t a line on a brokerage statement, and doesn’t come from playing the role society set out for me. It lies within. Aimlessness is a hard sell, especially to someone wired like me. But I’m slowly coming around to it.
My Old Friend, Guilt
It’s also helped to befriend the guilt. Not to become buddy-buddy with it, but to stop fighting it so hard. Buddhist teacher Noah Rasheta has a great analogy for this: instead of trying to banish a negative emotion from the house, you welcome it to the table and sit it down.
This approach reminds me of a Steve Earle song I love, “My Old Friend the Blues” — the blues as the one companion that never really leaves. My guilt is like that: not a friend I’d have chosen, but a familiar one, always knocking at the door. Maybe it’s something different for you: imposter syndrome, anxiety, anger, restlessness, comparison.
Whatever it is, open the door and let it in. Pull out a chair. Serve it tea and cookies. It’s there with us no matter what, no matter how often we tell it to leave.
So best to make peace with it — and, better yet, use it as fodder for a post like this one.
Take that, guilt.
- The Buddh-ish Investor
The Bottom Line
We live in a culture that ties our worth to productivity, making even meaningful and life-giving pursuits feel indulgent or wasteful.
Instead of fighting guilt, we can acknowledge it, make room for it, and keep doing what matters anyway.
If You’re Looking For More
More Buddh-ish musings on aimlessness:
About as perfect as a country song gets:
