The Business of Starting a Business: Organization Tactics

I have officially been a full time freelancer for three weeks TODAY, and it’s been amazing. I haven’t been working all that hard or all that much over the last three weeks on freelancing. I wanted to take some serious down time to really mentally separate from my nonprofit job, sleep a lot, and figure out what I want from freelancing.

I’ve done that to some degree of success. I mean, I watched all of OINTB season 4, slept a lot, and spent more time outside than I was before I quit. But these last three weeks I was also staying at an AirBnb while foundation work was done on my apartment, and I didn’t feel settled. We moved back in last Sunday, and I finally feel like I’m really starting my freelance business. Or, more importantly, that I am finally organizing my freelance business.

Turns out starting a business of one requires a lot of attention to detail. And, as my mother will tell you anytime, I am not great with detail. I’m a big picture gal through and through.

Freelancing is all in the details. It’s creating, sending and recording invoices. It’s remembering who you pitched, when, and what. It’s writing down ideas when they strike and keeping track of a million pieces of paper. It’s networking events, coffee get togethers, and a full iCalendar.

I love lots of these things, but they play to some of my weaknesses. I’m a messy person, and organization is something I have a love/hate relationship with.

On the one hand, I LOVE organization. I color code my Excel sheets. I have a small filing cabinet that is beautifully arranged. I go through my papers monthly to throw out what I no longer need, and to file away what I want to keep.

On the other hand, the top of my desk is a total disaster 90% of the time. I take notes by hand on anything that’s near me: the back of envelopes, notebook pages, sticky notes, receipts. Then I throw them on my desk, along with books I want to read, magazines I want to comb through for collabs, mail that I mean to open, and pictures that inspire me. And all that stuff stays there until…well, until something happens to make me go on a cleaning binge.

That’s a habit that I absolutely need to break. It will kill me in my freelancing career. So with that in mind, this week I’ve been cleaning, labeling and organizing my desk and office space. Full disclosure: my ‘home office’ is just my desk in a corner of my bedroom. My boyfriend’s amp sits right next to me, and if I turn around and stretch out my legs, I can touch my bed. This is not the Pinterest home office of your dreams y’all.


I’ve invested in a few pieces and snagged some free stuff to help me do so. Here’s what I’ve got:

Small filing cabinet- Technically it’s just a black box with sectionals in it. I got it at Target for about $12.00 three years ago, and I keep all my important papers in it. Writing contracts, leases, or even (ahem) speeding tickets, it’s all in there.

Pencil holder- And dry erase marker/scissors/Sharpie holder. A desk staple that I scored for free when a friend moved.

Whiteboard calendar– A 12×12 whiteboard calendar that I hung above my desk. I got this for free from a different friend when she moved. (Side note to all my friends, stop leaving me.) I use it mostly to keep track of BIG events (I use my iCalendar on my phone for every day things) and to give myself a monthly overview of my life.

Bulletin board- I use this for inspiration and for personal momentos. It hangs just to the right of my desk. I painted it a few months ago to give it that Pinterest perfect look! My boyfriend got this board for free from his office when they did a big cleaning purge.

Assorted desk shelf stuff- I keep all the extra stuff on my shelves. Checkbook, business cards, thumbtacks, stamps, envelopes, etc. A lot of the nitty gritty stuff like the extra pens, markers, and post it notes also came from the boyfriends office purge. I have an adorable clipboard from one of my friends move too, and I feel so official every time I use it.

Paper tray- I picked this up for $14.00 at Marshalls. A paper tray/file holder is a total essential for me. All those freaking hand written notes add up! I don’t completely love this one though, and may switch it out for another one in the near future.

Motivational quote- I love motivational quotes. They are so good for me! I bought this in Washington D.C six years ago and have kept in on my walls ever since. I like looking up and feeling inspired every day! It reads ‘Stay Hungry, Stay Foolish.”


My desk itself is from Ikea. I got it three years ago for around $100. My chair is also from the boyfriend’s office purge. (I really lucked out with that purge!) So all in all, I’ve spent just under $130 on my little home office.

This is where the magic is going to happen from here on out folks! It probably won’t remain this clean for too long, but I really am giving it a go. I don’t want to fall back into the habit of using this area for storage of crap. This is my work space. This is where I earn my living. It’s a roadblock to success to treat it like anything other than that. 

Fellow work at home people, how do you stay organized? Any tips for me?

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15 Replies to “The Business of Starting a Business: Organization Tactics”

  1. Nice setup and especially getting stuff for free or close to it! When Mrs. SSC was in grad school, I remember being there for the end of year dorm move out day. She and I wandered the campus dorm area dumpster diving and got lots of barely used, cool stuff.
    I don’t work at home, but my desk and “office” get totally stacked up until I get some motivation to clean and organize them, so I feel your pain there. I usually know it’s time to organize when my music stand doesn’t want to stay upright because I’ve just put one too many things on it or my hand keeps bumping papers off my desk as I try to use the mouse…

    1. I think my brain sees such a big space and thinks ‘giant shelf!’. I think organization will be a continuous battle. I would love to raid college dorm dumps- people throw away perfectly good things all the time!

  2. I think it’s really cute! Nice job re-purposing things that were not being used by other people. Hope you get settled in soon and get rolling with your brand new freelance career!

    1. Thanks Tonya! It’s taking longer than I imagined to settle back in, but I’m ready and raring to be writing full time soon!

  3. I love your inspirational quote! Mine, which hangs right next to my laptop stand, is “Always say please and thank you.” And I also have a portrait of Julia Child, who inspires me even more. 🙂

    I’m a big fan of electronic tools these days for organization, especially because I end up working from a lot of different places and not just my desk at home — hotel rooms, airports, coffee shops, clients’ offices, you name it. I’m definitely reliant on my Outlook calendar, though will switch to Google calendar when we quit, and I completely love Todoist for my task list (lets you schedule your tasks and code them by project) and Evernote for project statuses and idea lists. Other than that, my best tip is definitely just make sure you keep your desk tidy. When my desk is cluttered, my mind is cluttered, and I get way less done.

    Can’t wait to keep reading more of your freelance pieces! Keep sharing ’em on Twitter. 🙂

    1. I’ve never heard of Todoit but I will definitely be checking it out. I love that you have ‘always say please and thank you’ up. I could use that reminder hanging around me. That’s an attitude I want to use to run my business!

    2. I keep a photo of Julia Child in my bedroom! As soon as I have my own condo, she’ll be back in my kitchen where she belongs. I’m waiting for a print of Ruth Bader Ginsburg as the King of Hearts to join her on my wall.

      1. I love RBG!

  4. My home office is the tiny room attached to my bedroom. It has a comfy chair and wifi and windows for natural light. It’s main attraction is that my roommates have no idea I’m in there since they have no access to this room. There’s a painting I bought on a trip to Hong Kong and a photo print of Kate Hepburn in a hat (I’m a dyke and need fashion inspiration to lift my spirits). Most of my books are in this little room, too. It’s cozy and crowded. I need to clean it.

    1. It’s nice to have a separate room, even if it’s tiny! Cleaning is important, and yet also always at the bottom of my to-do list…

  5. That’s basically all you need Kara 🙂
    Fancier surroundings do not mean bigger productivity or creativity.

    1. Thanks Mariana. The more I work there the more comfortable I feel!

  6. We’re big fans of Trello! Trello replaces all of those sticky notes and whatnot. 🙂

    1. I’ve used Trello a bit and I like it. I am such sticky note person, it is going to be hard to break!

  7. […] right smack in the middle of building my own business right now. I’m building my brand from the ground up, bootstrapping like a son of a gun. […]

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