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Finding Confidence in Myself as a Writer

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.”

Steven Pressfield, The War of Art: Break Through the Blocks and Win Your Inner Creative Battles

Confidence has never been something that has come easily to me, yet there’s no discernible reason why that’s the case.  I suspect that my lack of confidence in myself is a result of the depression I deal with on a constant basis.  One of the funny effects my depression causes is a weird form of doublethink, in which I have two contradictory thoughts that I both believe: one rational, one irrational.  In nearly everything major that I’ve done in life, I’ve excelled and raised the bar for those that followed me, yet in the midst of those experiences, I felt as if I was woefully under-performing.  Only in looking back after the fact did I realize I did a job that I could be proud of.  The confidence was never there for me when I could have used it.

A ginger ale display I put together for Christmas

Two of the past jobs I held were as a merchandiser for a soda company and a bookkeeper at a grocery store.  In both of those roles, I did more than was expected of me because I took pride in my work and wanted to succeed.  I was never written up, nor did I ever receive a complaint about my work.  For all intents and purposes, I should have been confident during the time I held those roles.  Looking back, I can’t find any reasons for myself to not have been confident.  As a merchandiser, all of the stores on my route were immaculate, with full shelves and product lines, beautiful displays, and neat, organized backstock.  As a bookkeeper, I ensured my staff was trained well, maintained 100% accuracy, and passed every audit I was subjected to.


Why did I doubt myself in those roles, then, and in everything I’ve done thus far?  Lack of confidence.

Earlier this week, I began freelance writing and discovered I would need confidence to succeed.

Why I Decided to Begin Freelance Writing

“A professional writer is an amateur who didn’t quit.”

Richard Bach

For as long as I can remember, I’ve always loved writing.  As I’ve gotten older and began to explore different jobs and careers, I never felt truly fulfilled.  I loved some of my past jobs, yes, but they never resonated with me.  I made sure to work hard, put in as much effort as necessary, and strive to do better every day, but my life still felt lacking.  Having finally transitioned to a full-time job in late 2015, I quickly realized that working a repetitive 9-5 with strict rules and the possibility of bad bosses wasn’t a lifestyle I enjoyed, wanted, or synced well with my depression and anxiety issues.  Routine has always been a struggle for me; call it irrational if you like, but I have a fear of getting stuck in a routine or pattern for the rest of my life, where I become complacent and never stray from that path.  I’m sure my issues with depression and anxiety play into that fear, but it’s there all the same, leaving me to find ways to deal with it.

This past December, I found myself needing to part ways with the grocery store I worked at because the work environment became quite hostile.  Despite my best attempts at rectifying the issues, my ideas for solutions fell on deaf ears and my stress levels rose to the stratosphere.  I could either stay at a job I once loved but that was depressing me more by the hour, or leave and find something new.  I wrestled with both options for over a week, making a last-ditch effort at improving conditions there, but was ultimately forced to leave and figure out my next step.

As a newly-unemployed person does, I fired up Indeed, Monster, and LinkedIn in search of job opportunities.  With the realization that I was experiencing the start of a new bout of severe depression, I narrowed my search down to part-time jobs in RI, wanting something flexible that wouldn’t require my full focus upfront.  I’m one of those seemingly rare employees that puts his all into a job: I’ve worked 70-80 hour weeks, 14 hour days, and streaks of 20 days of work without a day off.  I love and enjoy working, but also recognize when my mind needs a break.  Most of the available part-time jobs seemed to be in either retail or customer service, two fields I’d like a break from after spending most of my adult life working in them.  I also tend to prefer and excel in leadership roles in jobs, so I knew I wouldn’t be happy unless I held some supervisory or management position.  There is a lot of stress that comes along with that territory, however, which left me with a difficult situation.

Please stop saying this to cashiers
I heard this “joke” approximately 10,000 times over three years. (source)

So I did what any other reasonable adult does: I had a panic attack or two, a sleepless night, and then budgeted out my expenses.  After moving back home after my last major life mistake, my expenses boiled down to a fairly low number.  (As a side note, I believe in the theory that everything that happens in life happens for a reason.  While I wish I could see the big picture, clearly moving back home worked out for me in the long-term so far.)  If a part-time paycheck could easily pay for my monthly expenses, then I could take a bit of a chance by going all the way and working for myself.

Until this point, one of the sources of my depression had been a lack of a dream to pursue.  For most of my life, I’ve had hopes and goals and dreams that I would work towards.  These dreams kept me moving forward, even if they were never realized.  It’s easier to wake up every morning when you have a clear purpose to do so, a goal you want to fulfill.  Gradually, it felt as if life battered me down to the point where I had begun to give up on my dreams.  Part of why I started to hate the 9-5, I think, is because my fears were starting to come true.  I was waking up only to work, with no end goals to work towards besides collecting my weekly paycheck.  Humans aren’t made to have such a singular focus on the accumulation of wealth without having another purpose to their life.  Gaining wealth for the sole sake of gaining wealth is pointless; money is meant to facilitate the realization of your dreams and goals and hopes.  If you have nothing to work for, there’s really no point to working at all.

Or, you find something that gives you the drive to wake up every morning beyond simply making money.

“Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”

Howard Thurman

What makes me come alive?  Writing.  Writing, for me, brings me comfort.  Putting words to the blank page is like a drug to me.  During one of the worst bouts of depression in my life, I wrote 57,000 words to a novel (that I’ll some day finish and publish).  The keyboard was like a lightning rod and my fingers the stormclouds as I lit the page up with word after word.  Writing makes me feel like my true self, and until now, I never realized how necessary it is to my happiness as a human being.  Yet I feel like I betrayed writing by forgetting the dreams I had of being a professional writer, of one day making a career of my passion.  I never dreamt about being a rockstar writer like Neil Gaiman or GRRM or Ray Bradbury, of selling millions of novels and becoming a household name.  All I ever wanted was to be able to make a respectable and decent living from my writing.

In realizing how unfaithful I had been to my dream, I came to the conclusion that fate, despite its cruel methodology, had brought me to this point, a perfect opportunity in my life to where I had nothing left to lose and everything to gain by committing to my dream and becoming a professional writer.  So over the next few days I pored over website after website after website learning all I could about becoming a freelance writer.  Having delved into the world of freelance a few years ago, I knew I wanted to stay away from “content mills” – sites and companies that pay the bare minimum for you to write filler content that they in turn make much more money off of.  I decided I’d want to search and work for clients directly, or at least on a more one-on-one basis.  My research brought me to Upwork, which connects clients with freelancers and takes a cut of the fees charged.  From all of the information I read, Upwork is a decent stepping stone for new freelancers and a great way to build your portfolio.

A look at my profile on Upwork.

The First Steps

Before announcing the start of my freelance writing career, I knew I’d have to update my website and my various social media accounts, so I made sure to do that.  I also knew I’d need a portfolio of my written work to prove to would-be clients that I had the required skills to work for them.  While this blog does serve as a portfolio of sorts, very few of my posts here are what I’d consider portfolio-worthy.  They’re more opinion pieces or stream-of-consciousness rants that serve better as a journal than a portfolio.  A portfolio needs to be presentable and professional, and I’ve never written for anyone besides myself before.  Problem #1.

I considered writing some example pieces to put in my portfolio, but I struggle with writing anything that’s not authentic.  Doing something like that – writing a press release or some web copy for a fake company, for instance – would read like it’s inauthentic.  Sure, it would be grammatically correct and have no spelling errors, but it would read as if it were forced, and that’s not something I could be proud of stamping my name on.  I would rather spread the word about being available for freelance writing projects and then use that work – real work – in my portfolio.  The risk was that work would come more slowly, but that was a trade-off I was willing to accept.

Problem #2 was something that wound up catching me off-guard and ties into what I wrote about earlier in this post.  Confidence.  I’ve been told before that I’m a good writer, that a story I’ve shared was well-written and interesting, but I have a hard time believing such compliments.  Perhaps it’s a result of comparing myself to writers that I admire and hold in high esteem, from my favorite authors to journalists and bloggers whose work I read on a daily basis.  Despite the fact that such comparisons don’t make sense and aren’t fair to make, I can’t help but to hold my work to similar standards, and I feel I fall short.  I can’t write for pay if I feel my work doesn’t read as if it were written by a professional.

For a few days, I browsed jobs on Upwork to see what I felt qualified for applying to.  Some looked promising, but I still didn’t submit a proposal.  Why?  Lack of confidence.  I’m irrationally worried that I would apply for a job, write to its specifications, and submit my work only to be told my writing wasn’t good.  Not only would I feel like I’ve failed myself, but I would have failed my client as well, and that’s worse.  Personal failure I can accept, but failing someone who put their faith in me is unacceptable.

(source – AZ Quotes)

Finding my Confidence

Before deciding on freelancing, my research lead me to the websites of many freelance writers.  Some were extremely impressive – one writer charged a minimum of $500 an hour and provided services I barely understood, with a portfolio packed with Fortune 500 clients – but the vast majority seemed to be around my level.  What surprised me even more was stumbling upon websites of many freelancers who seemed like they had no business doing so; their websites were chock full of spelling and grammar errors, punctuation was forgotten about, and sentence fragments adorned paragraph after paragraph.  But they had clients and portfolios and were making money writing!

You see, in the freelance world, there’s no bar to entry.  Anyone, at any time, can start freelancing in whatever field they want.  There’s no test or certification; you sign up for a site, build your profile, and throw your name into the wind.  It’s a common complaint on sites like Upwork that many writers aren’t fluent in English but still bid on projects at a low, low rate, driving down the rates freelance writers feel are fair, and taking work from those who would, theoretically, do a better job.  In the end, it’s up to a client to decide who to hire for a project, and many times they will go for the lower bid, regardless of the lower-skilled writer submitting it.

With those two realizations in mind, I sat down and considered my options.  Lesser-skilled writers than myself were making money from freelancing.  They were making money from writing, working my dream job.  They had the confidence to get to work and commit.  If they could do it, why couldn’t I?  My other option would be to give up on my dream again and start filling out job applications once more.  Is that really something I wanted to do?

On one particularly depressing day, I reached out to my long-time friend and supporter Jared.  I first met Jared in 2008 on World of Warcraft, and he’s been one of my most honest and supportive friends.  He understands depression and the challenges it creates.  In talking to him, he mentioned his fiancée Kaylin, a talented writer and owner of her own successful PR firm, Hourglass Omnimedia.  Jared mentioned he would talk to Kaylin and ask her for some advice as to how I should start freelancing.  “She’s been a writer for a really long time, just like you.  I think it’s what you are supposed to do,” he said to me.  Reading that resonated with me.  Jared’s not a friend who would tell me something like that if he didn’t believe it; in the past, when I had stupid ideas, he’d tell me, and I’d do the same for him.  But to have that sort of recognition from someone who’s known me for 10 years?  It forced me to think that freelancing is something I could pull off.  Writing for a living is something I’m supposed to do.

I know I can write.  I know I have acceptable skill at writing.  It’s my passion, something I could easily do for the rest of my life.  And as the above quote says, I’m doomed if I don’t try.

While I’ve been picky with the jobs I’ve submitted proposals for on Upwork, I’m finding my confidence.  I want to write for a living.  And at this juncture in my life, I need to succeed.  Success means working towards my dream and becoming the professional writer I want to be.

Week 1 of freelancing is over now.  I’ve made $0, but that’s okay, because the true payoff from this week is invaluable: I learned I can do this.  And I will.

I don’t have a choice.  Writing is what I’m supposed to do.

What are some challenges you’ve had to overcome in finding your confidence to make your passion into your living?  Let me know in the comments below or on Twitter!

If you’re looking for a freelance writer or editor for a project, please take a look at my Services page or get in touch!

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