The Boss of You

Our friend and admired col­league, Michelle Good­man, gra­ciously took the time to do a Q&A with us. Her new book, My So-Called Free­lance Life: How to Sur­vive and Thrive as a Cre­ative Pro­fes­sional for Hire, is chock-full of great advice for entre­pre­neurs of all stripes, whether you fall into the “free­lancer” cat­e­gory or not.

Bonus: Amazon.com has a deal right now where you can pick up Michelle’s two books and a copy of The Boss of You for just over $30! Could there pos­si­bly be a bet­ter hol­i­day gift for the entre­pre­neur­ial gal (or guy) in your life? I think not…

OK, enough sales talk — on with the interview!

So much of the advice in My So-Called Free­lance Life applies to small (and even large) busi­ness own­ers as well as free­lancers. Are there spe­cific chap­ters you would rec­om­mend to non-freelancers who are con­sid­er­ing pick­ing up a copy?

It’s hard to nar­row it down because I agree that most of the book (if not all of it) applies to star­tups of all sizes, but here goes: Chap­ter 1, “Busi­ness Plan to Go,” can help you iden­tify your entre­pre­neur­ial goals. Chap­ter 6, “Name Your Price,” tells you how to estab­lish a fair mar­ket price for your ser­vices or wares. Chap­ter 10, “The Check is Not in the Mail,” tells you when work­ing for free can be worth­while from a mar­ket­ing stand­point — and when it’s most likely a scam you should run far, far away from.

Chap­ters 11 and 12, “Let’s Make a Deal” and “Get It in Writ­ing (But Don’t Sign Blindly),” are two of my favorites because they tell you how to nego­ti­ate rates and con­tracts like a badass. I also really love Chap­ters 13 and 14, “Care and Feed­ing of Your Clients” and “The Client from Hell,” because cus­tomer ser­vice and set­ting bound­aries with would-be blood­suck­ing clients is such a huge part of work­ing for your­self. I’d prob­a­bly list all eigh­teen chap­ters if given the chance, so I’ll stop there.

I hear from a fair num­ber of free­lancers who got into their careers uncon­sciously — it’s like they woke up one morn­ing and real­ized they’d become a free­lancer, with­out nec­es­sar­ily plan­ning it that way. What advice would you give some­one in that situation?

I agree. So many peo­ple find them­selves free­lanc­ing in the wake of a lay­off and before they know it, they’re run­ning a full-fledged busi­ness. If you too are an acci­den­tal free­lancer, take stock of the work you do and the clients you do it for. Are these the types of projects you want to be work­ing on and the types of peo­ple and orga­ni­za­tions you want to be work­ing with? If not, list the kind of free­lance projects that inter­est you most and the names of at least ten orga­ni­za­tions you’d love to work for. Then tap your pro­fes­sional and per­sonal net­works to see if you can find a way in. If you need to acquire any addi­tional skills or port­fo­lio sam­ples to make your­self attrac­tive to these orga­ni­za­tions, get cracking.

Even if you are happy with your clients and work­load, it’s impor­tant to revisit your free­lanc­ing goals –income, cre­ative mile­stones, client wish list, and so on — at least once a year. (Jan­u­ary is a great time for this.) Get too com­fort­able and you’ll quickly get bored, burn out, or start to feel like an employee all over again.

If you had “do-over” priv­i­leges, what’s the one thing you would change about your free­lance journey?

There are so many things I would have changed. I would have taken bet­ter advan­tage of my last staff posi­tion (pub­li­cist at a New York pub­lish­ing com­pany in the early nineties) before going solo. Specif­i­cally, I would have saved up some money to cush­ion my land­ing as a free­lancer, taken on a few more free­lance jour­nal­ism and copy­writ­ing projects to beef up my port­fo­lio, and made more con­tacts in the pub­lish­ing and mag­a­zine indus­tries while I was still in New York. I also would have read a book or taken a class on free­lanc­ing or run­ning a small busi­ness instead of div­ing in head first and spend­ing a cou­ple years fig­ur­ing out how to swim. Plus, I would not have bought a lifetime’s sup­ply of sta­ples and paper­clips like I did six­teen years ago at Office Depot. I’ve barely made a dent in them.

As some­one with a busi­ness part­ner, it’s hard for me to fathom jug­gling all the roles a free­lancer has — sales, mar­ket­ing, invoic­ing, book­keep­ing, etc. etc. — not to men­tion the actual client work. What do you tell peo­ple who worry that one or more of those free­lancer hats won’t fit?

There’s no get­ting around sell­ing your­self to new clients dur­ing your early years. I know a lot of new free­lancers are loathe to do it, but as I promise in the book, it does get eas­ier — dare I even say fun – with prac­tice. Plus, email and social net­work­ing sites make con­tact­ing new prospects so much less painful for you (and less intru­sive for them). So you really have no excuse there.

As for mar­ket­ing, that’s pretty closely tied into sell­ing your ser­vices, but there are many aspects of mar­ket­ing you can farm out to other free­lancers (for cash or trade): you can have a writer fine-tune your pro­mo­tional copy, a web designer set up your blog or web port­fo­lio, a vir­tual assis­tant cre­ate and main­tain a Face­book group or fan page for you, and so on. And there are all sorts of free or low-cost appli­ca­tions that can help you auto­mate your invoic­ing or book­keep­ing. Also, an accoun­tant or tax advi­sor who spe­cial­izes in work­ing with free­lancers in your indus­try is a must; that is one road you don’t want to walk down alone.

While I’ve always advised new­bies not to go over­board spend­ing money on com­puter soft­ware and con­sul­tants, some invest­ments will save you untold cash, hours, and/or headaches in the long run. If given the choice to pay a web designer to tweak my web­site or to try wrestling with the blasted Word­Press code myself (usu­ally results in me swear­ing at the com­puter and tear­ing out clumps of my hair), I’ll gladly pay the designer and use the time saved to make money doing some­thing I actu­ally know how to do.

I think all entre­pre­neurs — even those with staff — can relate to your tips about time man­age­ment and bal­anc­ing “task mis­tress” with “zen mis­tress.” I loved your advice about how to deal with friends and fam­ily who assume that because you’re self-employed, your sched­ule is infi­nitely flex­i­ble. What kinds of tips do you have for those of us who have trou­ble say­ing no to friendly inter­rup­tions in our workdays?

Don’t do social lunches or mid­day cof­fee dates with other self-employed pals, unless you’re meet­ing right around the cor­ner from your office and can be back at your desk within the hour. At least once a week, I get a request from some­one who wants to “meet for lunch down­town — since we’re both work­ing from home.” I’m about 30 to 60 min­utes from down­town Seat­tle, depend­ing on park­ing and traf­fic. Fac­tor in the other per­son deal­ing with park­ing and traf­fic, and my entire afternoon’s shot. Bet­ter to get your work done first, then play.

Also, don’t do laun­dry or turn on the TV while you’re work­ing. Don’t answer or look at your phone just because it’s ring­ing or vibrat­ing, unless you’ve been wait­ing for an urgent call. If you acci­den­tally answer a call from a friend look­ing to shoot the breeze, say, “What’s up?” in your clip­pi­est “I’m busy” voice and tell them you need to call them back after busi­ness hours. Don’t answer the door­bell, unless your neighbor’s house is on fire. If you like to work out dur­ing the day, go at the same time Mon­day through Fri­day so you don’t throw off your work sched­ule. And finally, if you want any chance at get­ting that big project off your plate by mid­night, shut down email, Face­book, IM, and all web browsers until you’re finished.