“Wait a minute!” my friend gasped, looking horrified. “You mean to tell me that month to month, week to week, you don’t know how much money you’re going to make…ever? Every month is just a fresh start, winging it and hoping for enough income?”
I realized he had a point I’d rarely pondered. Despite his high corporate salary and bonuses often exceeding my entire yearly income, he seemed one of the most money-worried guys I knew.
Yet for me, my last job with a guaranteed bi-monthly paycheck was way back in 1998.
When I moved to LA at 24 to pursue acting, I accepted I’d have to patchwork together flexible gigs to stay available for auditions. It started with temping like data entry at Game Show Network, plus cater-waitering and bartending huge events. Then came years transcribing from home using cassette tapes and foot pedals, before eventually transitioning to digital audio.
I also got occasional background acting work on shows like The X-Files, Six Feet Under, The Practice, Grey’s Anatomy and movies such as Magnolia and Catch Me If You Can. Eventually, I built up some steady voiceover clients too.
Somehow, through this freelance hustle, the rent always got paid in expensive LA. No debt collectors ever came knocking, and I even budgeted for some shoestring travel.
They weren’t always fulfilling times, and I constantly questioned if I should find something more stable. As my therapist noted, I likely carried a lot of underlying stress from that perpetual uncertainty of where the next gig would come from.
But in my circle of dreamers making acting/creative sacrifices to stay available, this was just the norm. Not having kids made surviving this freelance lifestyle far easier too – I’m aware of that privilege.
As I neared 50 though, with no retirement fund or benefits, I started considering getting a “real job” with a city, university, or company to finally build some financial security before age discrimination shut me out.
But then I realized – for nearly my entire adult life since 24, I’ve been 100% in charge of my schedule. Every gig acceptance, vacation, creative pursuit – it was all on my terms. That level of time freedom is priceless.
Last year, I discovered a passion for writing. There’s no way I could take a 9-to-5 now and relegate that to just nights and weekends. My creative work has to come first.
I’m not saying anyone should quit their job! Most of you are far better prepared for retirement. I’m just realizing what I’d be giving up after living this way for so long.
More than money, time is our most precious resource. Having full autonomy over my days is the trade-off I’ve made by avoiding a “real job” with steady pay and benefits. It can be stressful not knowing what each month will bring, but it’s also an incredible gift to wake up and create my own routine and embrace every opportunity – writing, voiceover, even last-minute trips.
This nomadic freelance path was perfect training for our current gig economy of content creators and digital nomads. I’ve gotten crucial experience constantly pitching, juggling clients, seizing every opportunity. Those skills will serve me well as I transition to travel writing and location-independent work.
Living off a steady corporate paycheck provides security, sure. But those of you freelancers know – having control over your time and being the boss of your daily schedule is invaluable. After 25+ years, I’ll never trade that freedom, even for stability. Don’t even ask.
