I don't begrudge them, though. If this person ever needs to go back to work "in the real world", they've kept a brand going that proves they have a work ethic. And if they don't, then presumably at least they've found a way to earn enough cash to maintain the lifestyle they want.
One of the things i wrestle with as i get older is meaning. I don't have a partner and don't want a house or kids. I don't have the killer instinct needed to become a corporate bigwig or an entrepreneur. I keep puttering along as a senior dev, quitting when i have enough cash for a sabbatical, then going back to work somewhere else when the savings run out. I'll never have the means to retire and live my perfect life. I'll just die somewhere, poor and aged out of the profession i never really wanted to do anyway. I suppose that's how most humans go out, but it feels a bit pointless.
I envy people who are very driven and have a clear goal in their lives - whether that goal is to be a rockstar desk jockey, to travel blog the world, or to connect with the people around them. It seems life would be much easier that way. I just kinda drift about, mostly having mediocre or boring days, occasionally having good days, and one day i'll die. It's far from a terrible life, but i can't help but wonder if goal-driven types feel that their lives are more rewarding.
Due to hedonic adaptation, the journey of working toward something is usually more rewarding than reaching any particular destination, especially if you're getting lots of feedback along the way.
Also, I've spoken with literally thousands of entrepreneurs, and most don't have what I'd describe as "killer instinct." Many of them gained a purpose through their business, rather than starting their businesses to satisfy some pre-existing purpose. It's a bit like how people find a new mission in life once they have a child.
What we think impacts what we do, but perhaps less obvious is the fact that what we do impacts how we think. Sometimes the first step is to throw yourself into a situation and then allow the motivation to come.
Finally, I'd say I'm an abnormally driven and goal-oriented person, and even I often think about my inevitable death and the purpose of it all. I think it's just part of being human and thoughtful.
I've come to the conclusion that living a good life is largely about being proactive. We like to think that given enough money and freedom we'll all do things that make us happy, but instead we tend to stagnate. It's easy for anyone to settle into simply letting the days pass: whether you're single or in a relationship, an employee or a founder, traveling or stationary, it doesn't matter. You can get into a routine of simply doing the least effortful thing.
For most of us, being proactive about living your life in a fulfilling way requires effort, the same way work does.
I don't hate my job. It's okay. I'm pretty good at it. The pay is fine. If this is as good as it gets - the joy of seeing someone you're mentoring "get it", the pleasure of getting a complex refactoring done, the accomplishment of shipping a cool feature - then i'm already there.
What i find sad is that it's not viable to spend time on idle things that i enjoy more than that workplace success. For me, my happiest times have been when i was doing nothing productive at all. Watching shows. Reading books. Dancing till dawn. Learning a new language. Cooking something nice. Talking to strangers. Wandering around aimlessly. Playing a computer game. Sitting on a bus to anywhere. Getting drunk apropos of nothing. Those are things i love to do because there is no pressure involved. What makes them satisfying is precisely that they are journeys without a destination. If there's a goal, if there's purpose, then it's exactly like work, so what's the point?
I am not sure that given enough money and freedom everyone would stagnate. That may be true of some, but not of others. Having discussed this with retirees it seems like it is a very individual thing. Some people don't do well with retirement - they get antsy and want to keep occupied, so they join social groups and take part in community events. Others gladly enjoy the chance to live an idle lifestyle. It's unfortunate that those who prefer the latter lifestyle have to work 45 years for it, and (depending on circumstance) may even never get the opportunity to enjoy that time.
We have a significant divide between working and living that I personally hope to erase, or at least minimize, in my own life. I've had some success this year, mostly through being more human and less down-to-business in my interactions with coworkers and colleagues. For example, previously I'd always prioritize speed and efficiency at work, which spelled disaster for experiencing real happiness at work. But recently I've begun to do things like having long, meandering 1-on-1 meetings that feel indistinguishable from casual chats with old friends about life, love, and whatever's interesting. Because why not?
Does having a purpose make something exactly like work? Well, if work is something that can be truly enjoyable, then the question is somewhat pointless. So let's imagine it can't. Then I'd posit that enjoyment depends less on having or not having a purpose, and more on what that purpose is. Trying to rush to hit some metric, or prioritizing speed and efficiency above human connection, or always having standards for success or failure, or doing things alone instead of a group… these approaches likely sap a lot of happiness out of spontaneous endeavors. But I don't think there's anything wrong with a purpose such as, "I'd like to have a lot of fun and make memories with my family over the holiday," and using that to guide you to say yes to some activities that you'd ordinarily ditch in favor of the easier choice to be stagnant and do nothing.
I also agree with you that not everyone would stagnate given time and money, by the way. I didn't mean to imply that. Only that many of us do stagnate instead of being as proactive as we should/could be to get the happiness or the lifestyle that we desire.
This, in a nutshell, is why I plan to never retire. "Retirement" for me is finding a business that holds my attention enough to want to do it for the rest of my life. Right now it has to fit into the interstitial bits of time between "day job" and "family time" and "sleep."
BTW: I love your podcast!
A few years back, I took a ~yearlong backpacking trip which gave me a lot of exposure to travel bloggers, both personally and when doing research for my travels. The impression I got from many of them was that they didn't consider the blogging work, but rather a natural outgrowth of the journaling practice that many people do privately anyway, for the ostensible personal benefits. Once they had already gone through the work of framing and articulating their experiences, polishing it and sharing it with others wasn't a lot of marginal work (and added an extra layer of fun).
I'm sure there are people who treat it like a daily grind, but my impression is that, for most travel bloggers, it grows pretty naturally out of something they were doing anyway.
That said, the longing has not gone away. I just know it to be a siren song.
Or, to put it in different terms, they fly free until they turn 2. Get at it.
One thing about traveling in general while children are young is that they become accustomed to it. Getting on a plane this weekend was a nothingburger for us, because it was like our 18th time going into the clouds. Same with 3 hour road trips, it becomes another facet of life
But I wonder if this represents a cautionary tale -- someone who took their non-"desk job" and assiduously commoditized their adventures. The 110% workaholism never stopped.
Click here to buy the book, follow the instagram, subscribe to the YouTube.
Or maybe this is what can happen if you don't indulge your wanderlust in your early 20s. The scariest, hardest and most rewarding thing always turns out to be connecting with the people around you. Instead, "Rabbit, Run"...