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The Job Stacking Guidebook

Apr 01, 2026
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How Do I Pick The Right Jobs to Stack?

Last week or so, I came to a conclusion. I finally realized what the ultimate green flag for a company is.

Are you ready to hear it?

Laptops.

That’s it, see you next week.

Alright, fine. I’ll delve deeper. The ultimate green flag is a company that does not have any protocols in place for sending you a company laptop.

People normally get all perky and excited when their employer tells them they’ll send them a shiny MacBook. And sure, I get it: you get all happy that you don’t have to put your own equipment through the wringer (especially if you’re beginning to stack), so you see it as a massive perk.

Hey, maybe you’ve been one of those guys who posts it on LinkedIn and tags the company (please don’t do that anymore).

There’s just one tiny issue with that.

It’s not a gift, and it’s definitely not a perk.

It’s a tracking device.

Last time I mentioned this to someone on my team, they even said their former employer actually told them to their face that they needed to use the company laptop because they needed to track their performance.

Obviously, they didn’t heed that advice, but I think the solution—or the lesson we can take from that—goes deeper than that.

Starting with the now-obvious: the best, most laid-back jobs are the ones that do not send you a company laptop and instead just let you use your own equipment. They don’t care about installing a VPN, activity monitors, keystrokes, or anything else.

This type of company has, in essence, surrendered all control to you. Why? They are most likely a high-trust company.

You see, the job market offers three types of companies: good ones, bad ones, and mediocre ones. But you don’t actually want to apply to the good ones or even the bad ones.

A “good” company is the type you see as the big players or on TV. Think of Industry or Mad Men-level types. These companies normally trust their vetting process and expect nothing short of excellence in your output. They are what I call high-trust, high-expectations companies. You can probably work in one of these if you have the stamina and skills, but you absolutely can’t expect to stack jobs in multiple good companies without burning out.

Next, you have the bad ones. You’ve likely been in one of these. Bad companies fall under the low-trust, high-expectations category. These companies don’t know what they’re doing besides the fact that they prioritize their clientele above the team. You can likely expect to be thrown under the bus when something bad happens, and it’s a pattern that will repeat across all departments. These are the types of companies that will try to track every activity during your workday.

They are managing your time, not your output. You should absolutely stay away from these. Sure, maybe you can find a company that is so bad that they have low trust and also low expectations, but in my experience, these are just transitioning toward being a bad company.

Finally, we have the “mediocre” ones. You can call them middle-of-the-road companies if you think that’s a better term. These ones have high trust and low expectations. A job at a place like this is the type that allows you to have enough autonomy. Maybe they know they don’t have the capacity to engage with clients at the level a “good” company might. Perhaps they feel comfortable with the rate of success they have with their clientele and prefer to keep a good team in place rather than flood them with unnecessary oversight.

It doesn’t matter. What matters is that you must try to focus on finding jobs that allow you a moderate-to-low level of responsibility, where you are trusted to do your job and, in essence, be able to stack multiple jobs during those free hours. These jobs are plentiful, but you must actively look out for them.

A Job Stacker needs an environment that allows them to be judged by the work they put in, that’s it. Zero management, fully asynchronous.

Stop looking for fake perks given to you so you might stay in line. Look for the freedom to operate on your own terms.

 

Until the next time,

Rolf.

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