Uptown Bourgeois is an art space for the creative works of freelance writer, editor, author, and content creator Jefferey Spivey.

A Penny For Your Thoughts...Literally

a penny for your thoughts

Starting a new career can be incredibly humbling. 

When it comes to writing, my history is spotty.  I was first published at 16 years old.  I spent my formative years writing and editing school, town, and city newspapers.  But when I graduated from college, I took a momentary professional turn into retail that became a permanent 11-year stay.  During that time, I wrote exactly two freelance articles for my college’s magazine. 

As my tolerance for retail started to wear thin, I started writing for a friend’s blog covering runway shows at New York Fashion Week.  This was a pro bono job of course.  Then, I started my own blog-a fun job that I funneled a lot more money into than I earned.  I wasn’t concerned about profitability at the time because I was preoccupied with my full-time work selling jeans and t-shirts.

I’d thought about jumping back into writing before.  But I’d applied for tons of jobs at magazines and newspapers to no avail.  I was a retail manager with a decade-long gap between writing jobs.  And furthermore, my current experience wasn’t at some major publication owned by Condé Nast.  I was writing for a friend and for myself.  And with my underdeveloped work history as a writer, I clearly wasn’t a trusted authority in the industry.

"Working as an entrepreneur that depends on freelancing is like skating across a melting ice pond and praying you won’t fall through.  Every day."

This year, I’m proud to say that I’m actually writing full-time for other people.  No, I’m not a style correspondent for GQ or a special reporter for Vogue.  I work for me.  Uptown Bourgeois, LLC.  As proud as I am of owning my own business, it’s not an easy road to travel.  Working as an entrepreneur that depends on freelancing is like skating across a melting ice pond and praying you won’t fall through.  Every day.

In the beginning, it was hard to navigate the freelance market.  My first professional writing prospect came from Upwork and offered to pay me less than $2 an article because I didn’t have any reviews on my profile.  Obviously, I turned it down.  I knew I was just getting back into the swing of things, but literally being paid pennies to do something I was talented at seemed offensive.  An online rating outweighed my resume, cover letter, and writing samples in importance. 

I scanned the freelance marketplaces looking for high-paying jobs.  I knew I deserved more than $2 per article.  But I also wasn’t being realistic about where I was professionally.  I was starting over.  Without a recent stream of published work or high-profile gigs under my belt, I couldn’t demand top dollar.  I was being such a stereotypical millennial.  I knew my worth, and I needed to be compensated accordingly.  But I hadn’t paid my dues.  My time as a student journalist didn’t matter anymore.  It was time to make some sacrifices and get to work.

"My business is growing daily, but I never would have gotten to that point if I hadn’t swallowed my pride and took that first $5 job."

It pained me to write my first job on Fiverr.  I didn’t know how I’d ever generate enough income working on jobs that only paid $5 per article.  But once I landed positive feedback from one client, another order rolled in.  Then another.  Then another.  There was repeat business.  There were bigger orders.  My newfound confidence from my work on Fiverr helped me crack the code on Upwork and Outsource.  Now, I’m spending my entire week working on articles and copy for numerous clients.  My business is growing daily, but I never would have gotten to that point if I hadn’t swallowed my pride and took that first $5 job. 

I know my worth, but I also know the reality of my experience.  Before I can raise my price, I have to prove myself.  I deserve more than a penny for my thoughts, but they’re not quite invaluable.  At least not yet.

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