Getting paid to *sit in a chair*
is modern-day torture 🫠

One of the weirdest parts about being your own boss... is undoing the 9-5 conditioning.

My first "real job" as a uni student was in the office at the Quaker Oats factory my dad worked at.

I would wear the button-up shirts and black dress pants, traipse over the aluminum walkway into the plant, and log on to my Windows 95 desktop computer every SINGLE Monday to Friday.

... And have literally NOTHING to do.

This was clearly one of those "they're doing it for the tax break" kinda jobs, and I fkn hated it.

Fast-forward 5 years to my first post-uni "real job" and again... nothing to do.

This one was even more of a mindfk because I got this big promotion and pay raise, so I felt like I should be doing SOMETHING to earn it.

Being forced to sit in a chair just because is so grating 😤

Fast-forward 10 years of working for myself... and I still feel the ol' 9-5 pull.

I still default to subtle panic when I take a day or two off.

Even if I planned for it.

Over the years, I’ve realized that working more will never quiet those voices.

And this kind of conditioning? It takes a lifetime to break, because it was a lifetime to build.

The reality of being a freelancer is that timelines and planning are fluid

Clients don't always respond as quickly as you hoped.

Things outside of your control will trash your task list, and you need to adapt quickly.

That's what I love most about ClickUp.

When everything I need to do is together in one place and I can plan out every hour of my day... I feel in control.

When a client's condo suddenly floods and two projects are delayed by weeks, I feel in control.

When a client refuses to give feedback in Google Docs and it takes 4x longer, I STILL feel in control.

All that work fluidly moves through the week, and my days still don't exceed 5 hours.

I can look at my task list, realize that some of it can't be done and the rest doesn't NEED to be done, and take the afternoon off to start planning my garden. (True story.)

Without the bullshit guilt or panic.

And honestly?

I didn’t start using ClickUp because I love productivity apps.

I started because I was tired of feeling like I had to earn my rest.

Even now, with systems that actually work for how I actually work... those old patterns still whisper, “you should be doing more.”

But now I can hear them, shrug, and close my laptop anyway.

So yeah. I planned my garden that afternoon instead.

And no one died.

I'd love to hear from you:

What was your most painful job before freelancing?

Hit ‘reply’ and share.

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RBH

Robyn Henke

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P.S. whenever you’re ready, here are 2 ways I can help you get organized and reclaim your time:

1. “Time Is Money” — A mini-course that shows you how to earn more without working more. Inside, I’ll teach you a simple system for profit-focused time tracking that shows you exactly where your time goes, when clients become unprofitable, and how to fix it before it tanks your bottom link. Grab it here → ​

2. ClickUp Power Hour — In 60 minutes, we’ll untangle your biggest ClickUp headache, map out a setup that fits how you actually work, and build it together—so you leave with a system you understand and know how to use. Book a Power Hour →​