Why Your Anxiety About Job Stacking Is Holding You Back
Let’s talk about anxiety. Specifically, your anxiety about Job Stacking.
The logic felt sound: more responsibility, more eyes on you, more accountability. Less freedom. Less room to move. I even wrote about it in the past.
Turns out… that logic is wrong.
Here’s what most employers actually rely on to control workers: low wages and constant monitoring. They need people glued to their desks, wasting enormous amounts of time, just to prove they’re “working.” The goal isn’t productivity — it’s dependency.
But senior and managerial roles don’t work like that. Not necessarily, at least.
If anything, employers hope people in these positions enslave themselves. They count on you to overcommit, overthink, and carry responsibilities you invented for yourself.
I know, because I tried it.
What I found was surprising: less micromanagement, less direct pressure, and certainly no boss yelling in my face. Accountability exists, yes; but it’s outcome-based, not minute-by-minute surveillance.
That makes these roles excellent for Job Stacking.
In the end, we know how it all works. Companies can fire anyone. Any department. Any role. At any time. Seniority is not exempt from that. But it does give you better tools, and it’s something I believe people should take advantage of.
Senior positions are about delegation, communication, and monitoring results. Those are skills in their own right. And they translate incredibly well to managing multiple roles, if you know how to do it correctly.
Oh, right, that’s another thing that makes people anxious:
“What if my team hates me?”
“What if I raise red flags?”
“What if I mess this up?”
Those fears are understandable. But they’re also learnable problems. Not something that should stop you from stacking multiple jobs.
Creating trust. Communicating clearly. Delivering results without burning yourself out. These are systems, and we know how to teach you those systems because that’s our bread and butter.
Here’s the irony: CEOs brag about sitting on multiple boards at once. Investors praise diversification. But when you want optionality, suddenly it’s “unethical” or “risky.”
So what should make you anxious is to be a part of an unjust and outdated system that will not reward you in the long term.
But worrying about how to job stack, how to approach all of this when it’s right there for the taking?
Well, that’s why you’re reading this newsletter, aren’t you?
Hit me up and let’s talk. Let’s put those skills to use.
Until the next time,
Rolf.
