What To Do When Your Kids Don't Know What "Working" Means

Posted the discussion on X, worthy of posting here as well.

Here’s a reflection for fellow dads in similar situations.

We have two boys, 4 and 7. We’re now at the five-year anniversary of when I effectively stopped working a “traditional” career. Even though I left Wall Street formally in early 2021, with COVID, the holidays, and my wife being 8 months pregnant, I wasn’t going into the office from my suburban enclave, nor was I doing much work at all.

They’ve never really experienced having a father who isn’t always.. or at least the vast majority of the time.. home when they wake up and home when they come back from school. There has also never been a special occasion or event I’ve missed… because there’s no HR portal I report to.

That said, while I champion this lifestyle as a net positive, there are some smaller negatives I’m still trying to solve for.

It’s the fact that I fear my boys, who are getting smarter and more observant by the day, are failing to grasp conceptually that I still have to work for our living... and what “working” even means. The lines have always been blurred. Sometimes I’m home and fully present mentally and emotionally. Sometimes I’m home and only present physically, with my head deep in my business. Or I’m literally just hanging out during an hour between client calls and I’m sort of “half present.”

And as our boys get older and start doing more and more stuff, the sheer number of sports, parties, school events, etc., adds up. And even though I’m “free” or “a matrix escapee,” it doesn’t mean I can be present for every one of these things every single time.

But because my boys never really developed any sense of structure around my work-life.. how Dad is running this consulting business with clients in other countries and all this work is virtual.. they’re starting to make comments like I don’t care or I’m not interested in their events or interests.

The emotional algorithm seems to be..

Dad is not here (mentally or physically)→ therefore Dad must not care about this

This is a real problem in the new age of remote/virtual work.

And it’s a major reason I ended up leasing corporate office space a couple miles from home.. to build some of this emotional scaffolding in their brains about how life requires work and there are still sacrifices no matter how “free” you are.