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?

  • Leigh Ann

    Oh, pitching. This is where I struggle. Part of me thinks I don’t have the brainpower to think of anything substantial, and the other part of me says, “Woman! You have to WORK your brain to get these ideas!” Then the third part of me is secretly terrified that someone will actually like the idea and then I’ll have to do the work, thus disappointing them greatly.

    • Tolly Moseley

      Yeah…hate to say it Leigh Ann, but you’re smarter than that. Those self-defeating thoughts, I mean.

      I think it’s all about being honest with yourself. If writing for the public/an editor is too stressful, DON’T DO IT. My silks teacher always says that climbing 20 ft above concrete and performing tricks is not necessary. You should only do these things if you want to.

      But, having read your blog myself, I’d venture to say that you *are* ready. You’ve got enough relationships in town, enough rad/interesting life experience, and enough sharp writing skills to pitch legitimate outlets. Working with an editor can be humbling, but oh my God, I’m so grateful for the ones I’ve had over the years. It’s NOT disappointing to them when they have to polish / tweak your piece, bc if they didn’t, editors wouldn’t have a job. ;) So just keep in mind that what editors literally do for a living is take drafts and make them better, and that no matter what you turn in, it’s probably a shining jewel compared to some of the hot-mess manuscripts they’ve seen before.

      You’re good enough, you’re smart enough, and doggone it people like you!! ;) So if this is a fear thing Leigh Ann, just say, “hey fear! I appreciate you trying to protect me, but I’m going to go for this anyway.” And then just go pitch people.

  • Rose

    As a 9-5 (er, 9-7) writer/editor who dreams of someday going freelance, this was a really useful read! Thank you.

    Tolly, do you have any tips on how you dabbled in freelancing while still doing your day job? I’d like to start building those relationships now, but it’s tough to make it happen while tied to the office.

    • Tolly Moseley

      9-7! Damn girl. You dedicated.

      This is controversial advice, but I reached out to a local magazine as soon as I got to Austin, and offered to write for free. (This being the now-shuttered local Austin culture rag, Rare Magazine.) I did that simply to build up my clips, because I didn’t have any yet. I interviewed people and wrote my stories on the weekend.

      YOU, however, probably have lots of clips, since you already do this for a living! So you likely don’t have to write for free. I think it’s all about having your best, shiniest, most awesome clips in a singular location (like a website), then simply reaching out to X outlet and asking if they have a need for contributors. Include a link to your clips, and in the email body, mention the 2-3 places that have published your work. Don’t worry if you haven’t written for anyone big yet. Amy Haley, the music contributor here, just reached out to, and shared a link to the posts/playlists she’s created for Austin Eavesdropper. They wrote her back asking if she’d like to do the same for them.

      So that’s what I would suggest. Have your clips in a centralized place, then just start reaching out. It also helps greatly if you know someone at x publication who can facilitate an e-intro between you and the editor, even if it’s just the IT guy.

      • Rose

        Thanks! That’s excellent advice. By the way, we’re always looking for new freelancers around here (at the UT alumni magazine), and I promise we’re a friendly bunch.

  • KT Feingersh

    Very well-written piece on transitioning to a freelance career! Helpful for me as I embark on my own journey in the working world. I often wonder if I would be better off if I had experience in an office setting before embarking on my own freelance journey.
    Take care :)

    • Tolly Moseley

      KT!!! Hey Intern! Miss ya. :)

      So I think that’s a personal question for everyone (office first, or freelance first). Like Lindsay wrote above — there are definitely perks to the office life. And maybe you don’t have to choose just one. I actually office 1x/week with a real-life company: They’re one of my clients, and thought it was important that I absorb the company culture, so I’m there regularly.

      Office-ing can be cool because it educates you on how business WORKS on a larger scale than what you can accomplish all by yourself. Also, sometimes (but only sometimes), I get nostalgic about dressing up and striding into an office each day, heels clacking down the linoleum. There was a real sense of, “ok, the work day has BEGUN!” every time I sat down at my desk.

      I say you try several things out in your 20s. Before Ross did what he did now, he was a teacher at a private school (as you know), but he also tended bar, waited tables, was an accompanist for the UT dance department, and even worked at Texas School for the Blind. I think rather than it being an office/no office question, dabble in several things that sound interesting (like you’re doing now). Not only will your resume be rich, you’ll always have good small talk fodder at parties. ;)

  • Rachael Genson

    Thanks for posting this Tolly! Though I’m certainly not looking to quit my job, and start freelance writing full time, I have been seriously considering doing some freelance side work. I’d love to get together with you one day over coffee/tea (my treat) and talk more about the nitty gritty of the entire process. Plus, that means we’ll actually get to meet face-to-face instead of just over the Internet (though that has been fun too…)

    • Tolly Moseley

      Hey Rachael! Yeah! Let’s catch up after SX (or maybe during SX, if you’ll be near the convention center…I’m presenting on a Sunday, I think!)

      • Rachael Genson

        Sounds great! And I’ll try and make your panel – I went to the one you moderated last year and LOVED it, so there is definitely some room to add another one to my schedule.

  • Lindsay

    As a person who just went the other direction, from freelance to full-time, I would add that another con of freelancing is not having a team to support you. Every aspect of your work – from finding clients to getting paid – is all on you. No one picks up your slack if you’re out sick for a day, nor do you have anyone to turn to if accounting or marketing or whatever isn’t your greatest strength. Co-workers have more benefits than water cooler chatter.

    Being back in the office world I feel grateful to have meetings, something I’d never thought I’d say. True, it’s great to have the ultimate say and have no one disagree with your opinion ever, but all that responsibility starts to take its toll. It is great to work out problems with other people – even if they involve some tense disagreements. I got really tired of everything being on me all the time – it was more stressful than freeing. Yes, I feel freed in a 9 – 5 now. Weird.

    Also another con: Never feeling like I had a weekend. I could always be doing more work. That’s a time management thing, but it’s extremely common for people who work for themselves.

    The grass is always greener on the other side, I guess. I’m trying to straddle the fence now by still running my own business, but looking for less work.

    • Tolly Moseley


      So, your response is one of my favorites. I think it’s so important to do *what serves you* job-wise, and offer folks a different perspective on this. I can totally relate to wishing I had an accountant to take care of my contracts / taxes / admin stuff, as that is a skill set that does NOT come naturally to me.

      Also, with your line of work, I can see how one might have to devote weekend time, when interview sources have more availability. My husband is a music teacher who works from home, and he works a TON on the weekend (but he makes up for it by having some freer weekdays). I tend to totally avoid the computer on the weekends…but once or twice, I’ve had to grudgingly crank it open on Sunday to meet a deadline. ;)

      PS, where are you working now?!? I got on your website but couldn’t figure out your new digs! Tell me! :)

      • Lindsay

        I found myself working “on” the business during the week, and “in” the business during the weekend. Meaning I would do all the networking/marketing/accounting/emailing/pitching/and on and on during other peoples’ business hours, and log the actual production time on the weekends. I actually didn’t mind interviewing on the weekends when that happened, because interviewing still doesn’t feel like work.

        I’m now working at a company run by one of my biggest life story clients, doing video and other content production. Trying not to advertise the new job too much because I’m still available for life story work and hopefully freelancing if I can manage it.

  • Chelle Lynn

    So glad that self employment is (mostly) everything you dreamed it would be! I am currently in the throes of a George Michael face-first-on-the-floor exhaustion/re-examination of my life, but hey, I’ve got a couple years till my self-imposed By the Time I’m 30 deadline.

    • Tolly Moseley

      Chelle! Well, I think so much of the “what am I supposed to do??” question is necessarily a process of elimination, trying out different things in your 20s (and 30s, and 40s, and 50s…) and exhausting yourself along the way. I think you’re doing it right. (Unlike the person the other day who was “using Twitter to get pregnant.” ;)

      When I was 24, I had this one year where I was going to class for my master’s degree, writing my master’s thesis, working at a magazine, and teaching freshman composition. My diet consisted of Honey Bunches of Oats and coffee, and I slept a few nights in the magazine office. Also, I started doing that neck scratchy thing that you and I are so fond of, and made myself bleed once or twice. It was a weird time.

      BUT – and this is a big but – several revelations came out of that year:

      *I loved writing for magazines,
      *I did not love academia,
      *I loved teaching,
      *Friends/family/people you love are 80x more important than work.

      In every arena – the teaching, the magazine, etc. – I made the most amazing friends, people that I still love, cherish, and talk to regularly. That was helpful, because it made me realize that whatever line of work I have, I need the time to nurture relationships. A high-powered magazine job at Vogue or something would get old extremely fast if I didn’t have time for my buds. (Or, my man.)

      I think we’re so trained to view success in the West as being at the PINNACLE of our respective field, but at what cost? No time for friends? Your health? Your family? No thank you.

      This is all to say that your current exhaustion/re-examination of your life is a sign, I think, that you are laying the groundwork for something Chelle-tastic (yep, I said it) in the future. Lama Surya Das is a Buddhist teacher who says, “the biggest breakthroughs usually come after the biggest struggles.” I don’t know if you’re struggling right now or not, but if so, I’ll repeat what I said earlier — I think you’re doing it right. :)

  • Amy Lynch

    Ah, the pants. I’m right there with you on the pants. We should start a support group, no? Or just go somewhere awesome (and soon!) to celebrate your officially successful transition into freelancing badassery whilst wearing said pants.

    I vote B, by the way.