Uptown Bourgeois is an art space for the creative works of freelance writer, editor, author, and content creator Jefferey Spivey.
Shit I Wish Someone Would’ve Told Me, Volume 2

Shit I Wish Someone Would’ve Told Me, Volume 2

Photo by Tarik Carroll Creative

Photo by Tarik Carroll Creative

If you’re considering leaving your cushy corner office to work from home, there’s a lot to learn, and you should probably backtrack to the first installment to get started.  But don’t think you’re done learning once you book your first client.  You need to be agile to make it in the freelance world.  Throughout each day, you’ll experience a mixture of joy, curveballs, sharp turns, about faces, and blind rage—sometimes all at once.  The longer you survive, the more pride you’ll feel when you look back at your accomplishments.  But, unfortunately, it doesn’t get any easier.  Just when you’ve mastered one skill, another challenge pops up to test you or that skill you spent so much time learning becomes obsolete. 

It’s not my intention to scare you away from freelancing but it is my hope to paint a realistic picture of what it’s like.  And I want to share some of my hard-learned lessons so you can avoid the same mistakes.  So, without further ado, here’s volume 2 of the shit I wish someone would’ve told me.

1.   Don’t say yes to everything

It’s amazing what people will say yes to when their checking account is empty.  When I first started out, I happily accepted every job opportunity that came my way.  I’ve written several articles about corset construction, European pop stars I’ve never heard of, and Dragon Ball Z t-shirts.  With a little bit of research, anything is possible.  But just because you can do something doesn’t mean you should.  When you say yes to everything, you fill your schedule to the brim—which makes your passion feel more like a normal job (not fun!).  And it’s hard to focus on your goals.  You’re too busy trying to keep up the pace instead of looking for opportunities that fall in line with your objectives.  It’s tempting to take on every assignment that pops up in your inbox, but don’t let your account balance guide your decision making.  Stay true to your vision now, and it’ll pay off in the end.

2.   There’s no pay on sick days

Freelance life allows you the chance to take off all those holidays you used to work through.  You can take vacations when you want and for as long as you please.  And when you get sick, you can stay in bed without having to answer to anyone.  But, while you’re recouping or living it up in France, you aren’t getting paid.  You’re your own boss, and your company doesn’t offer paid time off or sick days.  So, a day off means less income.  This doesn’t mean you need to work 365 days a year—I surely don’t.  But it does mean you need to budget accordingly for planned time off.  And you might need to pull a long day or two to make up for those days you spent in bed recovering from the flu.

3.   People will ask for free work—tell them no

Just this morning, I had a rather unpleasant exchange with a young “CEO” who wanted me to place backlinks on my site and other sites I write for—for EXPOSURE.  And he was a bit indignant when I told him this service requires a budget.  For some reason, a lot of people, especially startup CEOs, think that writing and content creation services should be free.  They’ve managed to pay a developer to create their app and build their website.  They’ve bought a domain and bandwidth.  They’ve manufactured products and brought employees onboard.  But when it comes to our precious words, they can’t spare a few extra bucks to pay us what we’re worth.

People will ask you to do work for free in exchange for exposure.  Or they’ll use euphemisms like “mutually beneficial partnership” or “great opportunity to grow together”.  These are all code words for “we’re broke”.  They’ll find some sucker out there who’s so desperate to get published, they’ll do this kind of work for free.  Don’t let that sucker be you.  Your words, work, time, and effort come for a price.  And if a potential client isn’t willing to pay you for those things (or pay your full ask), you should walk away.

I don’t know any landlords, grocery stores, or restaurants that take exposure as a form of payment.  Until they do, we all need to get paid.

4.   You can make a ton of money and still feel broke

I book a lot of work through freelance marketplaces like Upwork and Fiverr.  When I complete a job, it takes upwards of two weeks for payments to clear.  I recently worked the highest-grossing week of my freelance career so far, but I found myself charging everything because I didn’t have enough cash.  Sometimes, as you wait for payments to come through or for invoices to be paid, you’ll feel it in your wallet.  Know that the money’s coming, and don’t let it get you down.

5.   Don’t be afraid to raise your rates

If you’ve ever navigated a freelance marketplace, you’ve witnessed the race to the bottom.  A large portion of the freelancers offer their talents for the lowest price possible to book a higher volume of jobs and outrank other freelancers.  You’ll feel compelled to do the same.  I entered the market with ridiculously low prices that were far below market rate.  But once I had enough reviews and repeat clients under my belt, I raised my prices.  Not because I was full of myself but because I felt I was already providing a service that was worth the higher price.  And I’ve continued raising my prices periodically.  In doing so, I’ve attracted a different quality of client, and many of my best clients didn’t object.  When you feel it’s time to raise your rates, do it.  The clients who truly value your work won’t have a problem.  And if they do, it’s probably best you drop them anyway.

Photo by SahedPhotography.com

Photo by SahedPhotography.com

6.   Get the money upfront

I want to believe that every CEO or content manager is trustworthy, and that I can do two weeks of work upfront and invoice later. But clearly, that’s naïve.  Sometimes, invoices go unpaid, and aggressive follow up is needed.  If you’re working through marketplaces like Fiverr, Upwork, or Remote, the client pays the money upfront when you start the job.  The site holds onto the funds and releases them once the job is complete.  So, unless you decided to back out of the job, you get paid.  But if you’re working on your own and getting paid through money-sharing services like PayPal or Venmo, you don’t have that protection.  If you don’t have a rapport established with a client and you’re using one of these apps/sites, ask for some portion of your fee upfront.  Be it half or a quarter, consider this a deposit of goodwill.  It’s a way for both of you to establish trust, and it’s a way to ensure your client means business.

7.   Don’t take offense when people unfollow or unsubscribe

When you run your own business, you take personal stake in every social media post, every email, and every word written on the blog.  Thus, those unfollows and unsubscribes hurt your soul.  They feel like a rebuke of your talents and your mission.  But they’re not.  Get over it!  If someone doesn’t want to be a part of your movement, they don’t have to be.  Fuck ‘em!  There’s only room on your ship for people who want to help steer it forward.  Be grateful for the people who are still there engaging, opening, clicking, and sharing.

8.   Prep your tax payments in advance

You’ll probably make less money on your own than you made at your previous full-time job.  But sometimes it’ll feel like more because you aren’t losing half of it to taxes and deductions.  Though, before you order that second glass of wine at dinner, start calculating your taxes.  At year’s end, you’ll owe taxes on your income.  And that payment can be a doozy if you haven’t been saving.  Funds will seem too tight to save but trust me on this.  The IRS is coming for your money, and you need to pay up.  If you have questions, The Freelancers Union offers the most comprehensive source on the web for freelance taxes.

9.   Build leads BEFORE you launch

Around this time last year, I launched a terribly unsuccessful Patreon campaign.  Patreon is a crowdfunding site where you raise funds continuously.  People can pledge small amounts of money every month to keep your artistic endeavors afloat.  It’s a genius idea but I was unable to convince anyone to help me out.  On top of educating people about the platform, I failed to get pledges before I went live.  So, a big ol’ goose egg sat at the top of my fundraising page until I deleted the campaign in shame.  Whether you’re launching a similar crowdfunding campaign, a new product, an app, or a web site, get some people onboard before you go live.  If other people see some kind of interaction already taking place, they’ll be more likely to join.  Don’t take the Field of Dreams approach.  People will not come just because you’ve built it.

10. Keep learning

When I say ‘learning’, I don’t mean keeping an open mind.  I mean actually learning.  Taking class, conducting research, attending webinars, reading books.  Technology is developing rapidly, and every advancement affects the way we work and get paid.  I’ve encountered so many people who expect others to give them the answers.  I can’t keep count of the number of people who’ve asked me to help them get work.  But those people haven’t even explored the most basic resources to learn the industry.  We live in an age of excessive information.  There’s no excuse to be uninformed about the business in which you’re attempting to make a living.  Keep learning.

I’m only a year and a half into my freelance journey, and I’m sure I’ll have more takeaways in the coming months.  I’ll probably learn more about the business as soon I press ‘publish’ on this piece.  If you’re forging ahead on your own journey, I hope this helps.  Either it motivates you to push forward or convinces you to cling to that 401K.  Whatever response it elicits, I hope it helps you in some way. 

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