“I don’t know what my industry looks like in 15 years, and I’m not going to tell my kid to aim for it.”

Hey there,
I had a very nerdy lunch with a friend a couple of weeks ago, even by my “nerdy dad” standards. 
My friend is a lawyer, I’m a software developer, we’ve both been professionals for 20 years. And by the time we were done with our salads and sandwiches, we both admitted we can’t recommend our own career paths to our kids.
We’re not looking to escape – we like our jobs. There was no dramatic speech about robots taking over. It was two guys comparing notes and landing in the same slightly deflating place:
“I don’t know what my industry looks like in 15 years, and I’m not going to tell my kid to aim for it.”
That applies to the majority of work that can be primarily done on a computer these days. It’s not that whole industries will disappear, but they definitely will be reshaped dramatically by the time our kids enter the workforce.
I’ve been coding since I was 12, the same age my son is now. It’s always been both fun and a business for me. In addition to being the CEO here at Innovating with AI, I run a web development firm that does $1mm+ a year in revenue. My friend went to law school and has built an impressive career as a litigator, and he’d be happy on that track until retirement.
Both are high-prestige positions that anyone would have enthusiastically encouraged a teenager to pursue as recently as 2022.
It’s not 2022 anymore.
A “career pivot” used to mean your plan failed. Now it means you’re paying attention.
If two people doing well in their fields at age ~40 can’t confidently recommend those fields to their children, then a career pivot isn’t just a fallback for people whose plans went wrong.
It’s the normal condition now.
And not just for the kids, but for all of us. That may sound a bit bleak written down, but it shouldn’t, and here’s why.
Pivot toward the Four Freedoms, not a new job title
The mistake is thinking a pivot means picking a new thing to be. New job title, new industry, new set of letters after your name, and then hoping that one lasts.
That approach doesn’t work in the AI era.
What actually holds up is pivoting toward what you wanted the job to give you in the first place. Money matters, but it’s one part of a bigger picture of freedom, which, if you zoom in, looks like 4 different kinds of freedom:

⌛ Freedom of time: Being able to choose where and how you spend invest your days – whether that’s working on meaningful things, recharging, trying something new for fun’s sake, or having experiences you’ll look back on for years or decades to come.