This is how I look every day when I write.

IMAGE // Via Wish Wish

Ever since my declaration of career freedom last October, I’ve been curious as to how this whole experiment would pan out. Chiefly: Could I support myself as a freelance writer? What would yoga teacher certification be like? Is it a sign of weak personal character if one abandons pants?

(Clarification: some pants. I still wear pants. Just not adult, going-to-work pants. These days it’s lycra/cotton blends which I justify each morning for yoga/aerial silks, but is it questionable that I wake up in pajama pants, then change into “daytime” pants that are literally made of the exact same material — only tighter? Is this the tippy-top of the slippery slope to wearing sweat pants every day? To calling french fries a “vegetable?” To watching Jerry Springer non-ironically and alienating my husband in lieu of the company of cats — so, so many cats? Reader, I fear the worst.)

Anyway. I’m happy to report that freelance writing is going swimmingly. I have a website! And clients!

What I don’t have is business acumen. I don’t make people sign contracts for my work (mistake), I don’t have a project management system, and I don’t have business cards. All of that should probably change — I just have to overcome my laziness distaste for all that kind of thing.

I know it’s necessary…but I just wanna write! (For proper effect, please pretend you just read that line as: I just wanna dance!)

Still though, I feel compelled to tell any of you who have ever thought about going freelance that it IS possible, and I don’t know why I was so scared to give it a shot. Last month, I officially earned the exact same amount I made working at my former job as a literary publicist, and you know what’s cute? That same company is now one of my writing clients!  The Universe knows what it’s doing.

Making the decision to become self-employed though is (obviously) a big deal, and there are pros and cons to this kind of life. Now that I’ve been here for a little while, let me tell you what those are.


*Getting to wake up whenever you want. It cannot be overstated how glorious this is. My body is like, “Tolly! You care! You really do care! You’re not just pumping caffeine into me and dragging me around places in a zombie-like fashion! I feel so ALIVE!”

*Getting to set your own hours. So you feel like grocery shopping at 11am? Fine. You can make up the work you were supposed to be doing later.In the meantime, Greek yogurt here we come!

*Setting your own rates. I honestly think I started out a teensy bit low here, with the advantage that I filled up my client slots quickly; now my gut tells me that I should raise my rates. Still, I set my hourly rate rate to be more than I was making before. (And don’t worry if you’re reading this, current clients — you are special to me, my inaugural bunch, and I’ll keep you where you are. FOR NOW. Mwuahahahaha!)

*Not having a boss. Some people benefit from the boss relationship, but no matter who’s been my boss in the past (and I had some great ones), it always became stressful for me. Daily, I default-assumed I was disappointing them. And as embarrassing as this is to admit, I cried in front of every last one of them. Which leads me to believe that at this point in my life, I’m cut out to have clients — not a boss.

*Speaking of which: Choosing your clients. Oh my God, my clients are badass. Seriously. I’ve only had one rude person, and after my (very short) project was done for them: Goodbye! It is so important to me to work for people and projects I genuinely like, and would support even if they weren’t paying me. Who’s to say my standards won’t relax when I have kids and mama needs to send her babies to college, but for now, I have a strict No Jerk Policy. I recommend it to everyone.

*Pitching yourself. This is somewhat unique to freelance writers, but maybe other folks can relate to. I still get a rush out of approaching media outlets and pitching them story ideas. I went a little cray-zay at the beginning of this year and pitched a zillion people, but! Four of them bit (Statesman and Tribeza, plus Kirkus Reviews and Austin Monthly: Home — those last two came from client relationships), and now I’ve got a whole slew of stories coming out, which is pretty cool.

…to be realistic though, there are also some freelancing CONS:

*Never knowing if you’re “doing it right.” This feeling is so common to freelancers, whether you’re a writer, a session musician, or an architect. You don’t have the benefit of having a corporate structure in place that rewards you at regular intervals in the form of raises or promotions, so it’s kind of like you have to find your own carrots to dangle in front of your face, and find your own sources of career affirmation.

*Money. I’m now up to my former job level, but money still makes me nervous. What if Mr. X doesn’t pay on time? What if Mrs. X disputes my invoice? These are things you don’t have to worry about with a regular salary.

*Time management. Yow, I struggle here. Without a boss looking over your shoulder, it is incredibly easy to take a bath / play with your cat / go to Starbucks rather than knock out your work, which usually results in panicky, midnight or 1am project completion.

*Taxes. You have to set these aside all by your dang self as a freelancer, and it can be painful.

*Health insurance. I have my fingers and toes crossed for 2014. I really do. As the nation, and my generation in particular, grows with more freelancers and contractors, it seems like the natural progression of things that quality, decent health insurance will stop being yoked to traditional corporate settings and will become much more mobile, just like us. Until then, Ross and I have pricy, dumb private insurance which hardly covers anything.

*Watercooler talk. Even though I’m not exactly an office kinda gal, I miss making coffee in the morning with my coworkers and gabbing about the Oscars or Downton Abbey or whatever. Granted, the office camaraderie we shared back then was often in a plucky, downtrodden, “we’re all…in this…together!” kind of way, but those giggles were still fun.

So! There you have it. Six reasons to be wary of the freelance life, and six more reasons to embrace it with open arms. I can honestly say that the rewards FAR outweigh the drawbacks, and personally, I have never been happier job-wise in my life. Maybe these are just my sweet, early, halcyon days of freelance writing, and that I’ll get burned later on, but then again — maybe not! I feel so damn connected to my work now in a way I never have before, and that I’m not nearly as stressed out a person as I used to be. This was me six months ago.

I’ll update you guys on how yoga teacher training is going later on (I took my certification mid-term yesterday!) and I also have some neat silks updates to share — but. Staying on the subject at hand here, I’d love to hear from you if you’ve gone freelance. How is your experience going?

Also, are you one half of a totally self-employed couple, like Ross and I? I’m thinking of pitching a story on that theme somewhere, so, talk to me. What is it like for you guys?