Outfit Inspiration

What to Wear in Chicago this Week. Plus, 7 Rules All Telecommuters Must Follow

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What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

Wake Up! It’s time to Adult

To be a successful telecommuter, one must adhere to 7 rules.

If you’re the type to board a Metra train without a ticket, or sit bare-bum on a Starbucks toilet, perhaps rules and suggestions are synonyms in your life. I want to be clear, these are not suggestions. These are not relative standards at the liberty of preference. They are not recommendations. These are 7 steadfast rules – nay, commandments – to which anyone wishing to competently work-from-home must adhere. They are as follows:

The 7 Commandments of Telecommuting

  1. Always shower before 8 a.m. Bonus points for perfume. Gold star for doing something, anything, to your hair.
  2. Wear shoes each and every day. Preferably, heels.
  3. Avoid televisions before 5 p.m. like every station is running a marathon of The View.
  4. No matter how hard she tries, don’t allow your cat to talk you into a power nap.
  5. No matter how hard she tries, don’t allow your unemployed friend to talk you into a liquid lunch.
  6. If ever you fail at #5, definitely don’t give in to #4.
  7. Stick to a schedule like a politician sticks to their story. Never waiver. Ever.

I had this lifestyle down to a science. That was, until two of my biggest clients decided to pay me like it was their first year out of college and my name was Sallie Mae. Yes, in addition to working from home I was also working freelance. As a writer. Writing, if you don’t know, is what anti-social idealists do for fun. 5% of these people also suffer from unrealistic expectations and an overflowing pool of encouragement, often familial, often from their mothers. That 5% choose to write for a living. Thanks mom.

There I was: No income and no plan. The latter, was completely my fault. I hate searching for clients. I’m also fully aware that a freelancer who avoids acquiring clients is like a cat who hates judging people. That cat is no longer a cat. It’s a dog. And I was no longer a freelancer. I was the unemployed friend talking my friends into taking liquid lunches. Which, don’t get me wrong, is a great way to spend a summer. But it’s not sustainable. Because bills.

what to wear to work

What to Wear to Work in Chicago

Oh, so this is Storytime Now?

My disdain for defaulting customers turned into a hate for freelancing. That hate fueled me to do something I had put off for over 10 years. Creating a LinkedIn profile. LinkedIn is where unemployed people go to let the world know they badly need a job. It’s like the gallows of medieval times, except public humiliation is self-inflicted. I was screaming in the square, “I’m good at stuff! Someone please pay me to do the stuff I’m good at!” A couple months of premium subscription payments, a few temp jobs, and a few anxious interviews later and a nice woman finally had pity on my self-depreciating soul. I am no longer putting the free in freelancer. I’m an employee.

What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

Cool Story, Bro. What Should We Wear in Chicago this Week?

Reinvesting in my retirement (apparently 401k does not refer to my expected annual salary), clocking in from 9 to 5, and having to communicate with people who aren’t my cat has both its perks and challenges.

First, I’m awkward. We’ve talked about this before, but being in an office full of fabulous, poise, beautiful people has only served to remind me daily of my oddness. I feel like a one-legged basketball player, playing with a team for the first time. The leg isn’t a problem until someone runs up on you with the crossover, and down you go… I have a point.

What to Wear to Work in Chicago

What to Wear to Work in Chicago

What to Wear to Work in Chicago

Adjusting to a new situation is easier when dressed appropriately. You may notice that from our telecommuting commandments above, rules on wardrobe are a glaring omission. That’s because I’ve spent weekdays the last year wearing heels and pajamas. Yes, even at coffee shops. The thing is, I’ve got plenty of office apropos dresses, just waiting to be remembered, growing old in the back of my closet. This week I’m dusting these babies off, one by one. A dress a day keeps the awkwardness at bay. I’m hoping.

What to Wear to Work this Week in Chicago

Long story short, wear dresses. They’re awesome.

Kari Herrera is the creator of Chicagoings.com, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

  • Honor

    Haha! I’ll keep this in mind next time I work from home.

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