Careers are irrational. Or more precisely, linear careers are irrational. There's no reason to dedicate your life to one job, craft, or business.
The beginning of a career is the hardest. You have to learn a lot and get paid a little. The only way to rationalize this stage of your career is "I love my craft, I'm sharpening my knives, and I'm going to spend the rest of my life with this."
This line of thinking numbs helps you get through the shit of it, but lots of people latch onto this belief and stick with it for decades.
People go to college to develop a minimally commercial skillset––enough training to get in the door somewhere––then spend the rest of their working lives scaling that skillset up.
You know, the standard career ladder nonsense: start as an engineering intern, end as a Director of Engineering.
Even if you work at 25 different companies in your career, if you're leveraging the same skillset everywhere, you're essentially just climbing a linear career ladder.
It doesn't make sense that 55 year old me would be a senior software engineer simply because 17 year old me stumbled into programming.
I, for one, don't have one primary interest. As much time as I spend thinking about technology and economics and consumer behavior I spend thinking about fine arts and basketball and hip hop.
Why can't I move to Turkmenistan and start a semi-pro basketball career right now? Or become an anonymous SoundCloud rapper? Throughout my life I'd love to spend at least a few years pursuing each of my interests.
For most people, they can't spontaneously career hop because they're dependent on salaries to survive. Their income stops when they stop working (read more about that here).
Because it takes a while to build a minimally commercial skillset for any career, few can afford to just jump ship and survive off of savings. It's all uncertain: "How long will it take to make money with this?" "How long is my runway?" "Can I go back to my old job if it doesn't work out?"
That's a ton of personal and financial risk to bear with a salary. It's very, very difficult to pull off, and it likely won't work.
Unfortunately, there's no real way to get around that. Even a big savings account doesn't guarantee a successful career hop.
The only way you can guarantee a clear win here is if you don't actually need to be financially successful at this new career. If you've already created sufficient wealth for yourself, you don't need to have huge commercial success in every field you pursue.
Most people don't have sufficient wealth to afford the lives they want to live, so they don't jump ship. But that doesn't mean that they don't really want to. It also doesn't mean that they shouldn't.
Most people are tied up to their careers. Talented people gradually becomes slaves to their craft, and ambitious people to their ambition. If you're dependent on a salary, it's nearly impossible to escape your career.
By mid-career, there is massive short term financial incentive to stay. You don't have to learn anymore, and you're getting paid near peak salary. As long as you stay in the game you can really generate cashflow.
That's important because usually mid-career is when people start families. That's what that extra cashflow is for.
After early career poverty, kids, and college, it's alarmingly easy to end your career without a sliver of wealth. If you're lucky you'll have a seven-figure bank account––but in practice that's really not that valuable. Beyond minimal runway and emergency savings, cash is a waste. It only becomes valuable once it's been deployed into wealth generation.
Many of the most successful career-ists are living a silent tragedy, a siloed, unbalanced, unexplored life.
My point in all this is that, in the long run, linear careers are irrational. While hopping careers is both financially and psychologically difficult, there's no reason why the freedom to do so shouldn't be the goal.
There's no meaningful reason why anyone can't spend their lives exploring every single one of their passions, at any given time, whenever they want. There's no meaningful reason why you have to invest 30 years into one field.
Fuck around, work hard, and choose wealth creation over richness; and at the end of your life you won't have to ignore the gaping holes you have no choice left but to write off as "necessary sacrifices for my career and family."