Why Can’t I Keep My Office Tidy? Confessions of a Constantly Cluttered Desk

From Organised Intentions to Creative Chaos. Some people seem to live in spotless, Instagram-ready offices. Mine, on the other hand, often looks like a stockroom suddenly exploded and then decided to settle in. There are packaging materials all over the floor, leftovers from my last shipping order preparation. Shipping supplies all over the desk, and boxes of stock still waiting for labels I promised to print “tomorrow.” My mobile packing table always has anything other than packing materials on it so I can never seem to use it as intended.

I’m not lazy. In fact, I’d argue I’m one of the busiest people I know. Running a small business means micromanaging everything, orders, stock levels, suppliers, shipping, photos, listings, and somehow still finding time to write about it all. But somewhere between managing customers and chasing couriers, my workspace slowly collapses into creative chaos, in a never ending cycle of mess, tidy, mess.

The idea for this post came from me trying to ignore the mess around my keyboard… and failing miserably. Also, yes, that’s two mugs and a takeaway cup pictured below. I know.....

If you’d like to know more about how I ended up on this road in the first place, I’ve written a post with a little more detail here about why I’m still self-employed. Or how about the continuation story The Madness & Freedom of Working for Yourself. They might be worth a read if you ever wondered about being self-employed yourself.

When You Do Everything, Something Has to Give

I’ll tidy everything, get it looking almost respectable, and then a few days later it’s back to square one. Why? Because every time I sort something, a dozen new jobs appear out of thin air. That’s the curse of self-employment: there’s always another “urgent” thing that knocks organisation down the list.

The worst part isn’t even the mess, it’s the guilt that comes with it. You tell yourself I’ll clean that tomorrow but then tomorrow arrives with a to-do list longer than your arm. Before you know it, you’re searching for the scissors you had five minutes ago, stepping over cardboard boxes, and wondering how on earth you function like this.

Worse still is when you have to bring someone into the office and scramble for a half-hearted excuse like “It was tidy this morning,” or “It’s the cleaner’s day off.”

I think part of my clutter problem comes from the constant flow of deliveries and outgoing shipments. I even did a whole post on how misleading “Delivery in X business days” can be because half the mess on my desk probably arrived late anyway.

The Cycle of Tidy, Mess, Repeat

It’s not just my office either. The same pattern follows me to the stores area and the workshop. I tidy, reorganise, label everything beautifully… and within days, it’s chaos again. It’s as if the mess has a life of its own, slowly creeping back the moment I turn my back. It's a conspiracy I tell you!

Maybe it’s part of how small businesses really run, moments of order between long stretches of controlled chaos. Every time I clear one space, another one fills up, usually because I’m working flat out trying to keep things moving.

The Guilt of the Messy Desk

There’s a strange guilt that comes with a messy workspace, even when you know you’ve been productive. You start comparing yourself to people who seem effortlessly organised, and wonder what you’re doing wrong. But deep down, I know it’s not a lack of discipline, it’s the side effect of trying to do too many things at once.

Sometimes I think the mess just proves that real work is happening. It’s visible evidence of effort, mistakes, and momentum, not the neat, filtered version people like to post online.

Let’s play a game of “Have You Ever.” Have you ever just scooped everything off your desk into a large box or container, only for the same items to mysteriously reappear over the next week — right back to chaos again? My hand is up for that, in case you’re wondering. A lovely clean desk, polish applied, and then the gremlins (or fairies) sneak back in and scatter all that rubbish again when you’re not looking.

Maybe This Is Just How I Work Best

Maybe it’s just how some of us operate, a constant cycle of order, chaos, and eventual redemption. I’ve started to accept that this might be my natural rhythm: creative mess followed by bouts of frustrated tidying. It’s not ideal, but it’s honest.

So yes, I’ll keep trying to be that neatly organised person with everything in its place. But until then, if you drop by and can’t find me, I’m probably just buried somewhere under a pile of bubble wrap wondering where that tool went that was literally in my hand 5 minutes ago.

Running a small business isn’t always pretty, but it’s real — and sometimes a bit of chaos just means you’re getting things done.

I might have to do another post now too with a picture of my workbench which is never clean for more than a day. If you suffer from the same affliction as I do I'd love to hear from you. Leave a comment below where we both can find solace in our unkempt working spaces.

Thanks for Reading,

David

About the Author

I’m David Condon, a writer and small business owner based in Tralee, Co. Kerry. Most of my working life revolves around woodcraft and teaching woodturning, but this blog is where I share thoughts and discoveries from beyond the workshop — from everyday experiences to product reviews and tech finds that make life a little easier.

If you’d like to know more, there’s a link in the Note from the Author section below.

💬 Note from the Author
This post was written specially for David Condon Finds. If you enjoyed it, you might also like my other projects:

Phoenix DVD Blog – where I write about DVDs, Blu-rays, and life as a collector
David Condon Woodcraft – my main site focused on woodturning and handmade Irish pieces

If you’d like to support my writing, you can do so through the Buy Me a Coffee button below. It helps keep these side projects going — thank you!

Like what you're reading? You can buy me a coffee — sure it’s cheaper than a pint!

Search This Blog

David Condon Finds