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 1

Shit I Wish Someone Would’ve Told Me, Volume 1

That look when no one warned you about how crazy entrepreneurship is...   Photo by Tarik Carroll

That look when no one warned you about how crazy entrepreneurship is...  Photo by Tarik Carroll

You’ve had it with your job. You’re tired of pretending to appreciate constructive feedback.  You wouldn’t exactly shed a tear if you never saw another PowerPoint presentation.  But what do you do? Do you just get up and walk out on your lunch break like a badass? I mean, you’ll go down in company infamy as that one person who actually had the balls to stick it to the man.  However, the rent’s still due on the first, and it’s going to be hard to sustain your Seamless habit without a steady income. 

You’ve probably devised a grand scheme to work for yourself.  But before you start picking out art pieces for the wall in your home office, there’s a few things you should know.  When I started working for myself, my days were split equally between pure joy and blood curdling terror.  I was completely broke, aimless and impatient.  All of these things are a recipe for disaster.  So here’s the shit I wish someone would’ve told me before I started navigating the freelance world.

1.    Working for yourself is lonely.

I’m a writer, so I spend 8-10 hours a day with my laptop, cell phone and Bose Bluetooth speaker.  Save for the soulful voice of Amy Winehouse, I don’t hear other human voices the entire day.  The majority of my human interaction takes place via email.  There’s an occasional Skype call but that’s rare.  Even if you’re not a writer, the beginning of your entrepreneurship is going to involve a lot of researching, emailing and planning.  You’re going to spend a lot of time alone.  Prepare yourself so you don’t end up in a strait jacket after your first week.

2.    There’s no such thing as 9 to 5 and weekends off.

Everyone thinks working for yourself is fun because you set your own hours.  If you want to take off the afternoon to go to the movies, who’s stopping you, right? Well, most of the time, you’re going to stop yourself.  When your company is made up of one employee and that employee is you, you never stop working.  There’s always another email to answer, another strategy to research, another idea to write down.  The days of leaving the office at 5 and enjoying the weekend are over until you can afford to pay someone else to run your business.  If anything, you need a plan for work-life balance.

3.    Don’t leave your job without a nest egg.

You want to leave your job badly.  You’re ready to walk away and leave everything behind.  But if your bank account reads $0, you might want to hold off on the speedy departure.  It takes time to make money when you start your own business.  So save plenty of yours before you quit your day job.  And by plenty, I mean enough dough to cover at least 6 months’ worth of expenses.

4.    There’s still someone to answer to.

Instead of a boss, you’ll have clients or customers, who can be just as demanding and annoying as your former boss.  The difference now is they’re paying you to deliver a service.  You’ll just have to grin and bear it until you get the job done.  Unless, of course, there isn’t mutual respect between you and the client.  Be sure to set boundaries and know when to dissolve a client relationship.  There’s a big difference between nitpicky constructive feedback and outright disrespect.

5.    Have more than one revenue stream.

When you work on your own, different responsibilities yield returns at different times.  If you put all your eggs in one basket, you have to wait for that basket to deliver before you can eat.  If it takes 6 months for your eggs to hatch, that means you won’t eat for 6 months.  Find some other ways to generate income that you can cash in in the short term.  Keep in mind these side jobs might not be related to your business, but they’ll pay your bills.

What most days are like... Photo by SahedPhotography.com

6.    Never be afraid to follow up on late payments.

If you’ve delivered satisfactory work, you deserve timely pay.  Nothing is as awkward as asking someone to give you money, but if it’s owed to you, you have every right to ask.  Some clients will pay you promptly while others will drag their asses.  Don’t ever be afraid to ask a client to pay up.  It’s your right as a freelancer to get paid.  If you wait too long, you can end up in some frustrating tug o’ wars to get your money.  Don’t let late payments linger.

7.    Stay organized

Excel, Quickbooks, a day planner-whatever you prefer, use something to keep your daily duties in order.  You’re running a business, and the minute things start to pick up, you need a system to keep it all straight.  I prefer Excel because I love using the formulas to calculate metrics specific to my business.  Use what works for you but don’t wing it.  You never know when you’ll need to access info about your business.  Have it readily available in a place you can find it.  It’ll keep you on track and make you look professional even though you’re a company of 1.

8.    Create a schedule and stick to it.

When you’re just starting out, it’s easy to work whenever you want.  You’ll want to sleep in or take a mid-morning break to watch The View.  But you need a schedule.  If you want your business to succeed, you need to invest a considerable amount of time into it each day.  And you need office hours during which clients can contact you.  If you just work whenever you feel like it, you’ll never get things off the ground.  Show up to work on time every day just as you did for your boss.  It’ll pay off in the long run.

9.    Take your fucking lunch break.

Don’t be a martyr.  Intellectual and creative skills need to be refueled. There’s no one breathing down your neck to get back to work right away.  Take a full hour and enjoy your chicken salad.  You’ll be able to dive back into your afternoon workload with renewed energy, and your day will be more productive.

10.  Remember to celebrate.

Working for yourself gets hard.  There will be days when things suck and you feel like you’re moving nowhere.  You’ll want to quit.  So it’s important to celebrate even the smallest milestones.  You booked your second client or made your first thousand dollars.  Whatever it is, celebrate it.  If you don’t, no one else will.  And it’ll be hard to remember why you’re in this to begin with.  A little gratitude on your own behalf goes a long way.

11.  Establish your values.

Even though your company is really just you, you need company values and culture.  People will test you.  They’ll ask you to do jobs outside of your area of expertise.  They’ll deliver feedback in nasty ways.  They might even work in an unethical manner.  What’s your threshold of tolerance? What are you willing to deal with?  Yes, it’s just you, but you need to establish some ground rules so you can avoid shitty situations. 

If you’re not scared away by these tips, that means you’re ready to work on your own.  And it means you’re crazy.  Good luck out there.  You’re going to make it, and I’m sure you’ll have some incredible stories to share about your journey.  Maybe we can compare notes some day.  But right now, I need to get back to work.  I’ve been writing this during my allotted lunch break.

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