Some of us just aren’t cut out for that nine-to-five lifestyle. In fact, for me, the mere thought of having to show up at the same place at the same time, Monday through Friday, is enough to trigger an existential crisis that would give Sartre a run for his argent. However, if you’re considering taking the path less (but increasingly often) taken, you should also consider the pluses and minuses of working for numero uno—that’s you. Is having maximum flexibility in your schedule really worth sacrificing things like, I don’t know, a sense of secure healthcare? We talked to real life freelancers to find out what they loved and loathed about working for themselves.


Lindsay Davis, 28, Television Producer

Rose: “The constant hustle to make yourself and prove yourself at each gig can be an addictive rush. I love meeting an entirely new crew, set, and concepts every few months. It keeps me fresh and excited to create, instead of grinding on the same old junk for years.”


Thorn: “Unemployment in all of its uncertainty! The gaps in between gigs are soul-crushing and financially scary. I loathe TV freelancers who regularly use unemployment benefits to supplement their income the day after they wrap on a show. I am a firm believer in saving it for people who really need it. But my weekly rate on a three-month gig can’t get me through three-to-five months of unemployment with car payments, healthcare, rent in NYC, wine…”


Boris Khaykin, 33, Comedian

Rose: “My favorite thing about freelancing is working at whatever time of the day I want to and going to auditions/shows when I need to.”


Thorn: “My least favorite thing about freelancing is having unpredictable streams of income or lack thereof.”


Fergus, 25, Writer

Rose: “I was excited about everything I wrote about because they were topics close to my heart. All the pitching and rejection was hard, but the yeses led to articles I’m still really proud of.”


Thorn: “Chasing down invoice payments made me want to strangle baby animals, but instead I channeled that anger into curt, assertive emails. After a while I made sure I had open lines of communications and, if at all possible, someone in the billing/accounting department.”


Kirsten Reader, 37, Stylist

Rose: “My favorite parts of freelancing are that no day is really ever the same, and that within my job there is lots of variety. I also love that I get to be in charge of my own schedule and have the opportunity to choose what work I want to do.”

Thorn: “The negatives are that it isn’t always very consistent so you don’t always know when your next paycheck is coming. This can be a bit frightening and frustrating. The other is the chasing for payment. So many freelancers have to find the job hustle for the next one while also being the bad guy harassing the clients for overdue payments.”

Tasha Hall, 30, Graphic Designer

Rose: “The freedom to work on my own hours and wherever I want. I’m not confined to sit in an office. I also get to work with diverse groups; it keeps things fresh.”


Thorn:  “Not knowing if I will have a project to work on soon. I also like having a team to work with. Sometimes you feel like you are on an island.”


Adriano Valentini, 31, Director

Rose: “I don’t have to work when I don’t have to.”


Thorn:  “I don’t have to work when I don’t have to.”


Touché, Adriano. Touché.


Julia Reiss (Me), 30 (OMG!), Writer

Rose: I bore easily… in life and in work. Freelancing keeps me on my toes in more ways than one. Sure, there’s the obvious need to clothe and lodge one’s self, but I also get off (so to speak) on jumping from project to project. No gig is ever the same. Each one presents me with a new creative challenge that inspires me to grow as a writer. That, and I love the fact that my home office is pants-optional.


Thorn: Finding ways to stay accountable to myself and structure my time can be an absolute pain in the foot… among other places. As a freelancer, you have to take yourself as seriously as you would the CEO of a company, because you are one, essentially. You have to learn to tell yourself what to do and when to do it, which isn’t always as easy as it sounds.