Don’t Take The ‘Free’ in Freelancing Too Seriously

As I drove away from my corporate job, I felt a little sad. Should I have left?

And then the sadness shifted to excitement. I’m free! I am — quite literally — free.

No more structure, no more “I’m sorry I’m going to be late” emails, no more dealing with things I simply didn’t want to deal with.

The irony of a successful freelance transition is the exact reason you left your desk job. You think you don’t want structure, but you need it. You think the traditional 9–5 working timeframe is ridiculous, outdated and totalitarian, but being on your own schedule requires just as much (probably more) discipline to be productive. You think not having to check in with your boss will be liberating, but it’s scary.

As I was preparing for my new digital nomad life, everything about it was shiny and bright. The coffee shops! Working out in the middle of the day! Wearing hats! More coffee shops!

After reality of having to actually still work, not just go somewhere, open up my laptop and expect work to be created as I sipped my latte, set in, that feeling of uneasiness returned. Freelancing full-time was harder than I suspected.

Although holding the freelance writer title wasn’t exactly new — I have been dabbling in the journalism field for a few years now — there was now this new, enormous pressure I felt. Because before, I was mainly cranking out articles because I liked it. It was a side gig. I did it because it felt good that people were acknowledging a talent I didn’t really know was a talent. Now, it’s about the money. A part of it was about the money before, but now it’s really about the money. Everything is up to me. I report to me at the end of the day. I hold me accountable. I am responsible for building and sustaining relationships with people in different cities across different time zones. I have to deliver on deadline, every time.

If you’re a freelancer, you can’t afford to have an “off” day. No one may be watching, but not getting anything done for an entire day will set you back. And you can’t be set back if you want to turn your writing career from okay to great, from great to unbelievably lucrative.

While I had promising positions and clients lined up before “taking the corporate leap” as they call it, I still felt like a fraud. Can you believe people are trusting me to be the voice of their brand? Can you believe they are paying me, with real, actual, money? Every month, just like a regular job?

Surely this is not imposter syndrome as I’m not (yet?) famous. Imposter syndrome is for people who have “made it.” I definitely haven’t made it — But I know I’m headed in the right direction.

So I re-convinced myself I was in fact a professional writer with a real job. It was just a different real job now. I got exactly what I wanted — to write from anywhere I wanted while being compensated fairly for it. I’ve got this!

My mentality in the mornings was where it needed to be — excited, determined, focused and motivated to get things accomplished. By early afternoon, that positive outlook wore off. Suddenly I couldn’t focus. I felt distracted and couldn’t get my thoughts streamlined. What is happening?

I spent an entire week bouncing from coffee shop to coffee shop, book store to book store, also throwing in the occasional kitchen counter makeshift office to find my groove, get in the zone, get into that “deep focused state.” But none of it was working. Why can’t I find my groove? Do I need to be put on ADD medication? No, I refuse to add another monthly expense to my already tight budget.

While I adore coffee shops and the community they foster, they are not an ideal place for a writer who needs quiet to produce quality work.

This clearly wasn’t cutting it. I needed some sort of structure. Working from home was too distracting. Working from coffee shops was too distracting.

“I need my OWN office,” I concluded. Perfect. Lexington has some co-working spaces. I’ll check those out. And off I went.

So, I pretended to be an affluent business woman (I pretend this often) and set up *appointments* (very official, grown-up term) with various office renting companies only to find out that renting a private office was more than the rent I paid to live, not work, in Chicago. And they were small. Very small.

The beginning of every appointment was usually the most fun for me. “And what is your company’s name?” They would ask tilting their head, ready to write down what they thought was going to be a company name. “Ashley Alt Incorporated,” I would say as I adjusted my reading glasses. “And how many people will you need to be accommodating for the space?” “It’s just me. I’m a freelance writer.”

Sometimes I would lie to sound more official. “Well I do travel, so I’m not sure I would need to rent by the month.” Because you know, travel is what affluent millennial women do.

Reality comes back again — I can’t afford an office space, and a co-working space would be just as distracting as a coffee shop. Now what? Why was my mind so blocked? What was keeping me from producing quality work?

Mind over matter — “I should be able to work from anywhere” — Carrie Bradshaw didn’t pay for a co-working space. She typed from the comfort of her rent controlled apartment no problem. And she was able to write so effortlessly (most days) because she was ALWAYS experiencing life.

Then it hit me. Maybe my writing wasn’t coming naturally because I was lacking in the life experience department.

So I created an Experience Calendar for the aspiring (key word, aspiring) affluent, millennial business woman.

A day in the life of (an actual) affluent millennial freelancer includes an expensive workout, incredible-yet-overpriced cappuccinos, healthy-yet-expensive lunches, socializing after hours with friends and sparking cocktails- all of this sprinkled in the midst of the workday spent typing on a Mac in an office, a coffee shop or at home.

In place of the expensive workout habit (namely SoulCycle), I went around town snatching up the “first free rides” at cycling studios giving hope to the young men and ladies behind the desk that I would think about my packaging options. When the free rides ran out (along with my dignity), I “cycled” outside, running and doing various HITT workouts from Pinterest. Workout experience — Check.

Instead of meeting with coworkers or friends for happy hour, I spent my evenings at home over a half-glass of red wine FaceTiming about business aspirations with my sister. Socializing experience — Check.

Instead of traveling to Europe on a whim (casual), I dressed as a French woman to meet with my friend for tea in a far away land called Cincinnati. Travel experience — Check.

The one thing I refused to give up from my desperate attempt at affluent business woman status was my weekly trip to Whole Foods. Whole Foods is a place I truly connect with and don’t feel like I’m pretending to be someone I’m not.

Okay, so this is making some serious headway into my Experience Calendar, but what about my focus problem?

Which was when I remembered the incredible discovery of (legal) brain enhancing pills a few months back — Nootropics. Nootropics, if you haven’t yet discovered yourself, are rumored to be the closest thing to NZT, the crazy smart drug that Bradley Cooper takes in Limitless. I found out Nootropics was going to be a buzzy trend of 2018 from the wellness bible designed specifically for health enthusiasts, yogis and colorful smoothie bowl obsessors — Well + Good.

I trust Well + Good the way I trust my intuition to purchase a pair of overpriced designer sunglasses because I will have them and love them for the next 6 years, so of course I was going to trust them when they told me about Nootropics. And not just Nootropics in general (there is an overwhelming amount of different brands), but the popular Rise brand. Rise is a brain-enhancing supplement at $49 a bottle for a 1-month supply of 60 capsules (taking 2 capsules per day is directed).

I headed straight for Amazon to order my first bottle of brain boosting supplements with excitement and a little guilt. It felt like I was getting away with stealing an abundant supply of adderall from a pharmacy given its rave reviews on the intense amount of focus, clarity and memory, not to mention the reduction of anxiety.

And then I remembered my private office dream. I can’t afford Nootropics and a private office. $49 a month is not hefty, but when you’re looking at charts of $1200 monthly private offices, adding an extra 50 bucks to the monthly bill seemed reckless.

So I called my fiance who I knew would bring me back down to earth. A quality I love and loathe about him.

“Don’t you think you should work your way up to that?” He asked when I mentioned my private office showings. I hate how logical he is. Mostly because he is usually right. Knowing this was an irresponsible move in the first place, I pretended to compromise, stating I would now need to transform our home office into a space that is officially MINE. He countered: “As long as you don’t spend any money doing it.” I hung up. He was right about the office renting being too far fetched but I will be damned if I don’t invest in some incredible ball point pens for Ashley Alt Incorporated.

What good came from this, you ask?

I now have a goal to flush in enough income to comfortably rent a private office space. And not just any office space. A chic office with more natural light than one needs with a luxury pink chair and coffee table books for my “clients” to peruse as I finish up emails — Filled with bright green plants, the latest trend in wellness living, compliments from the brilliant Well + Good editors.



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