Horowitz esti­mates that 1 in 3 Amer­i­cans now qual­i­fy as free­lancers, a total of 42 mil­lion peo­ple. In her Chica­go talk, she argued that, thanks to a ​“tidal wave of change” in the work­force, hav­ing a reg­u­lar job no longer ensures secu­ri­ty or longevi­ty. While ​“being a free­lancer used to just mean you’re unem­ployed,” she said, now ​“peo­ple are just say­ing I’ll make an affir­ma­tive choice to live” as a freelancer.

Horowitz, recip­i­ent of a MacArthur Foun­da­tion ​“Genius” grant and one of the founders of the New York-based Free­lancers Union , made free­lanc­ing sound enjoy­able indeed — a way to break free of the fet­ters of an author­i­tar­i­an work­place, set one’s own sched­ule, build alliances with like-mind­ed peo­ple and ulti­mate­ly, to pur­sue one’s dreams. She tout­ed a com­plete re-imag­in­ing of work and the work­place, where free­lancers use their inge­nu­ity to shape their careers and build hor­i­zon­tal (rather than ver­ti­cal) net­works with friends in the same indus­tries who can share resources and coop­er­a­tive­ly buy sup­plies, ​“out­sourc­ing” work to each oth­er in boom times and pulling togeth­er in lean times. She described free­lancer friends whose flex­i­ble sched­ules lefe them free to learn a new skill or ded­i­cate time in their day to family.

The set­ting for labor lawyer Sara Horowitz’s recent author talk in Chica­go was itself a fan­tas­tic adver­tise­ment for the free­lanc­ing lifestyle. The Novem­ber 14 event pro­mot­ing Horow­itz’s new book, The Freelancer’s Bible , was held in Ener­space , a cheery, hip, com­mu­nal work­space in the West Loop where free­lancers such as graph­ic design­ers and writ­ers pay to use sleek, col­or­ful cubi­cles while enjoy­ing a sense of camaraderie.

Free­lancers in the audi­ence includ­ed chefs, artists, graph­ic design­ers, writ­ers, trans­la­tors, lawyers and instruc­tors, and they all seemed to be con­verts to Horow­itz’s vision. A free­lancer myself, I, too, appre­ci­at­ed her mes­sage, and I have great admi­ra­tion for what she and the Free­lancers Union have accom­plished. Since its found­ing in the 1990s, the union has cre­at­ed and facil­i­tat­ed myr­i­ad resources for all kinds of free­lancers, includ­ing insur­ance plans, a client rat­ing sys­tem, dis­count offers and net­work­ing oppor­tu­ni­ties. The group, with almost 200,000 mem­bers, also does polit­i­cal lob­by­ing on tax code and oth­er issues that impact freelancers.

But dur­ing the pre­sen­ta­tion I couldn’t help but feel that in cel­e­brat­ing the free­lance life, Horowitz was mak­ing lemon­ade out of lemons. That can be a help­ful process, but atten­tion must also be paid to the high­ly dis­turb­ing and often unjust sys­temic cir­cum­stances that force so many peo­ple to become free­lancers, like it or not.

The hem­or­rhag­ing of staff jobs and the shift to large­ly free­lance-pro­duced work in the jour­nal­ism and pub­lish­ing worlds are well-known. Mean­while, jobs such as graph­ic design, com­put­er pro­gram­ming, trans­la­tion and web design have also long been heav­i­ly reliant on free­lancers, due to the project-based nature of the work. But more and more jobs that wouldn’t have tra­di­tion­al­ly been thought of as ​“free­lance” are being con­tract­ed out: restau­rant work, account­ing, teach­ing, per­son­al train­ing, sewing. Even tem­po­rary man­u­al labor­ers hired through staffing agen­cies, such as work­ers at ware­hous­es or con­struc­tion sites, are essen­tial­ly freelancers.

Count­less sec­tors of our econ­o­my have shift­ed from a direct, full-time employ­ment mod­el to one that relies on con­trac­tors or free­lancers. And the moti­va­tion for that shift is rarely to allow work­ers more flex­i­bil­i­ty and con­trol, but rather to relieve employ­ers of cost­ly oblig­a­tions like pro­vid­ing health insur­ance, paid sick and vaca­tion days, and mak­ing long-term com­mit­ments to employ­ees. And of course, rely­ing on free­lancers or con­trac­tors usu­al­ly frees an employ­er from deal­ing with tra­di­tion­al unions and col­lec­tive bar­gain­ing rights.

Dur­ing her talk Horowitz not­ed that the idea of work­ing eight hours a day or 40 hours a week was not some moral com­mand­ment from on high. Her impli­ca­tion seemed to be that it’s ​“okay” to work few­er hours, which few peo­ple would dis­pute. But the eight-hour-day as opposed to a 12- or 14-hour day was of course a right for which work­ers fought hard — even los­ing their lives—more than a cen­tu­ry ago. And the ​“free­dom” to work less than eight hours a day because you are your own boss might make a return to sit­u­a­tions where peo­ple will work much more than eight hours a day more like­ly, since that’s what it takes to make a living.

Depend­ing on the indus­try, the explo­sion of free­lance work also rais­es the specter of unreg­u­lat­ed, cut-throat com­pe­ti­tion, where some­one is almost always will­ing to do a job for less, allow­ing employ­ers to ulti­mate­ly prof­it by dri­ving labor costs steadi­ly down.

Horowitz described col­le­gial atmos­pheres where free­lancers in the same indus­try help each oth­er out, shar­ing clients, ideas, mate­ri­als and work spaces. That is the ide­al sit­u­a­tion and of course a com­mon one. And there are count­less inspir­ing exam­ples of work­ers cen­ters, domes­tic work­ers coop­er­a­tives, cab dri­ver or bike mes­sen­ger groups and pro­fes­sion­al orga­ni­za­tions where peo­ple with­out actu­al col­lec­tive bar­gain­ing rights do band togeth­er to agree upon cer­tain wages and work­ing con­di­tions that they will all demand from employ­ers. But these agree­ments are rarely actu­al­ly enforce­able when push comes to shove and a skilled com­peti­tor is will­ing to work for less.

There’s a rea­son that in decades past peo­ple often resort­ed to vio­lence, intim­i­da­tion and social iso­la­tion to enforce pick­et lines and pun­ish scabs. Espe­cial­ly when eco­nom­ic times are des­per­ate, feel­ings of cama­raderie and sol­i­dar­i­ty are often not enough to pro­tect wages and ben­e­fits. That’s why unions strug­gled in years past to enshrine col­lec­tive bar­gain­ing rights backed by law. Though sit­u­a­tions may play out dif­fer­ent­ly, such dynam­ics are prob­a­bly as true in ​“white col­lar” work like com­put­er pro­gram­ming, adjunct col­lege teach­ing or copy­edit­ing as in man­u­fac­tur­ing or stevedoring.

Horowitz invoked labor his­to­ry and tra­di­tion­al unions sev­er­al times dur­ing her Chica­go talk, but framed the con­cepts as things we are mov­ing away from, rather than as lega­cies and struc­tures that are still rel­e­vant and impor­tant to sup­port in the mod­ern era.

The idea of design­ing apps for smart phones could at first glance epit­o­mize the excit­ing mod­ern world of free­lance oppor­tu­ni­ties. It’s a way for cre­ative, smart, ener­getic peo­ple with high tech skills to mar­ket their cre­ations with few up-front costs or bar­ri­ers to entry. App design­ers can work at home on their own sched­ules, and increase the odds of suc­cess by lever­ag­ing their social and dig­i­tal net­works and plain old hustling.

But in just one exam­ple of how hard the free­lance life can be, The New York Times recent­ly pro­filed two free­lance app design­ers who sac­ri­ficed near­ly all their sav­ings and oth­er employ­ment oppor­tu­ni­ties in hopes of mak­ing a liv­ing design­ing and mar­ket­ing prof­itable apps. The sto­ry describes Shawn and Stephanie Grimes sell­ing most of their belong­ings, cash­ing in their 401k and rent­ing out their home to finance their long, large­ly unpaid hours design­ing apps for Apple prod­ucts. Though the arti­cle implies the Grimes are good at what they do, they made less than $5,000 a year.

The efforts of such hope­ful free­lancers play an unquan­tifi­able but clear­ly impor­tant role in help­ing to keep iPhones and iPads pop­u­lar and trendy, boost­ing the brand and val­ue of these prod­ucts while Apple needs to offer very lit­tle in return. The Times not­ed that ​“despite the rumors of hordes of hip pro­gram­mers start­ing mil­lion-dol­lar busi­ness­es from their kitchen tables, only a small minor­i­ty of devel­op­ers actu­al­ly make a liv­ing by cre­at­ing their own apps, accord­ing to sur­veys and experts.”

The Grimes tried their hands at apps after Shawn was laid off from anoth­er employ­er, and he bore Apple no ill well, telling the Times: ​“Peo­ple used to expect com­pa­nies to take care of them…Now you’re in charge of your own des­tiny, for bet­ter or worse.”

There is tech­ni­cal­ly a dif­fer­ence between peo­ple start­ing their own busi­ness­es and true free­lancers who work on con­tracts for var­i­ous clients, but it often equates to essen­tial­ly the same sys­tem, in which estab­lished com­pa­nies or employ­ers have their pick of inde­pen­dent strivers who expect and demand only to be paid for each indi­vid­ual job they do, with no sin­gle employ­er ulti­mate­ly respon­si­ble for mak­ing sure that they are able to actu­al­ly make a decent liv­ing and con­tin­ue pro­vid­ing the ser­vices they do.

I have been man­ag­ing — knock on wood — this type of exis­tence and enjoy it, as do Horowitz and count­less oth­er free­lancers. I offer this post not to crit­i­cize her enthu­si­asm or down­play the impor­tance of the Free­lancers Union, which is need­ed now more than ever giv­en cur­rent eco­nom­ic shifts. But I hope that in our will­ing­ness to make the best of the cur­rent sit­u­a­tion, we do not for­get the big­ger pic­ture, the pow­er dynam­ics involved or the lessons of labor history.