close up view of an owl

Freelance Career: Owl I Do is Win?


In the past couple of weeks I have had some big wins in my professional life. Two jobs I have been chasing down for a couple of months have become mine. And, it feels just as marvelous as it did the first time I got paid to write an article for a magazine.

Do you note how I said, “chasing down?”

Mmmmhmmm. Even people that have been freelancing forever and eight days have to chase down work. We don’t just sit on our asses and wait for assignments to fall into our laps. We hustle.

Why a Lot of Freelance Careers Fail

One of my best friends, Molly, and I were talking about how many people we have seen go freelance and then tank.

The commonality with all the people we discussed was this one thing: They kind of had this weird sense of entitlement in that they expected people to give them jobs.

Based on talent, based on previous work, based on the fact that once they had a job doing something similar…

And, while talent and previous work does play a huge part in securing more work, you cannot just sit idly by and wait for someone throw work at you.

I Just Got Off the Bus at Hollywood & Vine

This attitude towards freelance work is kind of like the analogy of the fresh faced starlet getting off the bus in Hollywood waiting for someone to discover them.

If there is anything I have learned in my acting, comedy writing, and communications careers it is this: No one discovers you. You have to force yourself in their face and make them look at you. You have to insist on being taken seriously. Especially as a woman. In any industry. It is truth, and fact, at the same time.


I have a lot of philosophies when it comes to freelance work (and, work in general.)

“Don’t ask any subordinate to do something you wouldn’t roll up your sleeves and do along side them.”

“Bring people up the ladder with you.” (I do this all the time, I always look for ways to throw work to my friends, and I actively seek help qualified people I work with get promoted into better gigs.)

“Lead by example.”

The most important one, as it pertains to freelancing and contract work, is “If you’re not thinking about the next job, you’re already failing.”

Why is this so important?

Freelancing is not for complacent people. While you might think that it’s the best option for you, right now, in the midst of massive unemployment numbers and a global pandemic… it might not be your best career choice in the long run.

Look, it’s a rough time right now and you should make money wherever and whenever you can. And, if that means freelancing while you’re furloughed or scrabbling up some 1099 work… by all means do it.

In terms of longterm employment, however, unless you’re willing to put your skin in the game… to quote Hamilton,

“When you got skin in the game, you stay in the game, but you don’t get a win unless you play in the game. Oh, you get love for it, you get hate for it. You get nothing if you wait for it, wait for it, wait for it…”

The Room Where It Happens Lyrics - Leslie Odom, Jr., Lin-Manuel Miranda,  Daveed Diggs, Okieriete Onaodowan & Original Broadway Cast of "Hamilton" |  Genius Lyrics
What do you want, Burr? What do you want Burr? What do stand for… what’ll you fall for?

Another one of my mottos? “Always be pitching.”

Just like an auditioning actor, you have to be casting your net wide to get the business you’ll need to support yourself full time.


I know several people that are close to me that have the anti-hustle. They want a freelance career, but they look down upon hard work and hustle. They expect to work less and get more. And, if you’re independently wealthy, that might be possible. But, the average Joe?

Nope. Not even if you’re going after a traditional 9-5. There is going to be hard work involved. It may not be physical work (or, it might be) but your brain will have to engage and you’ll have to give up time to achieve your goals.

The guy is fucking funny, and talented… albeit slightly lazy.

Personal Experience With This Shit

British Ex-Husband is one of the anti-hustle people I know. For the life of him, he cannot understand why I spend 20 hours per week (at least) pitching for new business, when I do not get paid to do RFPs.

I’m like, “How else am I supposed to get work?”

He thinks I should be able to set up my writing and comms career so that work just falls in my lap and I don’t have to hustle it up.

That’s just not the way it works, bud.

It’s the same thing as when he says, “How did you live in Chicago for 10 years before you met me and not know what the property taxes per neighborhood were?”

Um… because I rented an apartment? Dummy. Unless I’m in the position to buy a property or am researching how to buy a property in Chicago, why would I be thinking about property taxes by neighborhood?

Or, “Why is it that we can’t seem to save any money when I’m working full time?”

Uh… because it’s expensive AF to live in America, we have a kid, and we have to clothe and feed her, and ourselves? Why didn’t you research cost of living in the United States before you moved here, dummy?

Magical Thinking vs. Freelance Career

It’s that magical thinking that people apply to smart people when they have gaps in knowledge. Or, when a smart person reveals one of the tricks to being successful that the other person doesn’t want to do or even hear.

He wanted to be a comedian (standup, improv, sketch.) But he wouldn’t hustle for it. So now, years later, when I have tried to help him in so many ways to achieve his goals… he’s disappointed and unhappy that he doesn’t have a comedy career.

Like so many people who fail in creative/artistic categories and are self-employed, he wasn’t willing to work for it. Talent is not enough, ever. Ya gotta work hard to get what you want.

person holding lighted sparkler during nighttime
Sparkle, sparkle MAGIC! Um, no dude. That’s not how it works. Photo by Matheus Bertelli on


I would honestly love it if I could spend every day playing with my daughter, not spend a buttload on a nanny and cleaner, and work less. But, if I want to achieve my financial goals, that’s just impossible. Trust me, I’ve already tried it. I liked being a stay-at-home mom. But it’s not in the cards for me right now.

I have never gotten anything I wanted in my life for free. That includes everything from material things -to- opportunities to do cool stuff -to- employment -to- having a family -to- having good mental health -to- staying sober.

I have had to work hard for everything I have, ever had, or ever will have.

Being an actor taught me how to hustle. I’ve carried it through my whole life.

If you want a freelance career, but are unable to hustle – and, I mean work HARD – you’re not going to make it.

Just some words of advice.

Leave a Reply