Step #1: Turn that Freelance Dream into Reality!
For whatever reason—you were downsized, your family was upsized, or you grew an ulcer the size of the Astrodome and decided the 9-to-5 life was not for you—now you’re a member of the Gig Economy and hoping to scrape together enough small projects to score a Nut big enough to pay your bills and still have a little left over for a decent vacation (and maybe even retirement!).
If you don’t have quantifiable dream, a strategy and a little self discipline, however, your freelance dreams can turn into nightmares. And I’m not just talking nude-in-public scenarios or amorous ex-girlfriend werewolves, I’m talking real nightmares, like working part-time as a roadie for an English piano rock band that sings about bad dreams:
Yes, if you’re not careful, freelancing can be that bad.

Giganomics (not to be confused with Figanomics) is a red hot trend word right now, even hotter than hot pink trend words like “faboosh,“ and if there’s one thing I know about trends, it’s that they always stay popular, just like Beanie Babies and faux hawks.
Fortunately, however, freelancing has been around a lot longer than giganomics, even longer than Tina Brown’s hairstyle or even Wigganomics, which actually reminds me a great deal of Brown’s hustler definition of the gig economy. In fact, freelancing has been around so long that its not just a trend—it’s an eloquent and (gasp!) legitimate career choice.
Ready to get started? Good, because the only thing worse than an unsuccessful freelance career is an unattempted one!
As I said before I digressed into stuffed animals and the Wu-Tang Clan, you’re going to need a dream, a strategy, and a little bit (ahem, okay, a LOT) of self-discipline if you want to rise above the trend and make enough money to fill your economic and gastronomic needs (not to be confused with your giganomic needs).
Here’s Step #1:
Wake up!
When I started freelancing, I sought fellow freelancers through their bylines. After a few awkward phone calls and dead emails, I met (well, electronically) Kelly Bastone, a successful freelance writer in Steamboat Springs, Colorado. She recommended I take an annual retreat to dream up my goals for the year:
1. Take out the calculator. Tally up all of your expenses. Not just the monthly bills, but the extraneous insurance payment, souvenir salt shaker, and Braille greeting cards for your blind great uncle, too.
2. Put the calculator away. Now go ahead and dream. What do you want to do, what business title do you want to print on your business card? Who are your top target clients? Do you want to gain experience, make money, or live in a van down by the river? Do you want seven weeks of vacation in the Phillipines? Do you want to learn how to fly fish?
3. Bring out the calculator again. Now, add the costs of your dream lifestyle to your original budget. What’s the total? Does it exceed what you dreamt as your ideal annual earnings? Back to the drawing board.
4. Keep tabulating until you find the balance. Bastone reminded me to break down the big goal to see what it takes to make it happen. Want to make $100K per year? That’s $8333.33 per month, $1923.08 per week, and $274.72 per day—if you don’t take a single holiday or weekend or vacation or get sick. Don’t stop clacking on the calculator until you know exactly how much you need to make the dream come true.
5. Put it all in a business plan. You don’t need to hire a former AIG regulator (now freelancing, of course) or Jonathan Carroll to make your dreams become reality, and you don’t need a exceedingly complicated business plan. Just write or type your budget and goals on a piece of paper, tack it on your wall, and follow it. Seven months later, when you’re contemplating writing for Helium.com as some cockamamie experiment or worse yet as a real way to earn money, it will help snap you back into reality—and ironically, back on the path to your dreams.
That’s it for now. Get cracking. And stay tuned for the next installment of Freelance-ology: The Strategy!












That’s almost the exact same advice Kelly James-Enger gives in her freelancing classes as well. (Thanks, Kelly!)