Breaking Free from the Optimization Trap: Embracing Life as It Is

Mad Men (partly for enjoyment, but also for a Mad Men rewatch podcast I initiated), and despite nearly all characters showcasing some variation of philandering jerk, it’s difficult not to observe, and feel envious of, how frequently they just seem to drink, joke around, take contemplative strolls, and generally reflect while smoking.

Why can’t we exist more like that, I catch myself pondering.

The evident response is “because we’re not white males in the 1960s” (and additionally don’t wish to sabotage our families and perish from heart-related issues at 51). However, one can’t help but consider whether eliminating the notion of the “smoke break” was solely about persuading individuals to quit smoking or if it also partially concerned preventing workers from taking breaks. There’s an added irony in my vicarious enjoyment of these fictional characters’ frequent “me” moments in a series that I’m essentially viewing as part of a career.

And that’s the catch: many of us have so completely merged the lines between living and working that we’re hardly able to be spontaneous anymore. I feel an uneasy, anxious sensation whenever I engage in something that can’t be monetized.

Certainly, the situation is tougher here in the media sector. Everyone I’m acquainted with, most of us having spent 10, 15, or even 20 years in the field, is now either occupying one of the dwindling staff positions—which typically entails performing tasks that used to require four or five people while trying to satisfy an MBA somewhere who doesn’t truly grasp your work—or attempting to replace the staff position you lost a few years back with five or six semi-regular part-time or freelance roles. In either scenario, there’s a tendency to feel the pressure to occupy all of your time slots with some form of money-making endeavor.

However, I would assert that this trend extends beyond the decaying, struggling entity that is the media industry. For Gen Xers and Millennials like myself (Wikipedia might categorize me as a millennial based on my birth year, but I argue that if you learned to pleasure yourself using analog media, you’re too aged to be a millennial. I owned ska records, damn it, I will not be erased), we were largely brought up to chase our interests. Study diligently and attend a reputable college, they all cried at us. You don’t want to end up digging trenches and flipping burgers!

Now that I’m past 40, I feel as though I have achieved a certain level of success—and yet, managers at In n Out are making significantly more than I am. Their job appears more desirable as well—offering a tangible product, satisfied customers, and relevant success metrics. A friend of mine recently left tech sales to establish a pool-cleaning venture. He seems happier than ever, and not a single person in our group chat isn’t envious of him.