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Freelancing Lessons Learned From the Author of ‘It’s Always Personal: Emotion in the New Workplace’

If you’re thinking about freelancing, Anne Kreamer has a few words to say about it. And if you’re currently freelancing full-time you’ll probably agree with what she says in a recent Wall Street Journal piece.

After all, the author of It’s Always Personal: Emotion in the New Workplace, reminds us that a recent Intuit study revealed about 40 percent of the workforce will be freelancers by 2020.

Freelancers are becoming more common and there’s more than meets the eye when you become your own boss. Yes, it’s the growing norm but perhaps in an unstable job market, it’s prudent to learn how to become your own boss.

Per the piece, she writes, “In a world where job security is a quaint 20th century artifact, perhaps evolving an independent, freelance career for oneself is a cleverly Darwinian means of survival.”

1. Reality check: It’s expensive. Yes, you’ll have the freedom of a flexible schedule but a price comes with the gift of time. And sure, there will be savings in terms of commuting costs and reduced wardrobe budgets but there are costs to consider.

She writes, “Setting up and operating a home office and business – legal fees (will your corporate self be an S, C or LLC?), bookkeeping and productivity software, computer hardware, website design and hosting, marketing, tax preparation (just to name a few) – costs real money. Don’t overlook the importance of funding retirement accounts or health insurance.”

That’s not all.

She adds, “As for that paycheck, you should know when you go freelance, that you probably won’t earn as much money as you would have had you stayed in your company job.” Did we mention the cyclical checks? Your income could be variable and this is why monthly retainer clients are oh-so-important. Then there’s delayed payment as well. You may not get paid until 90 days after your invoice has been submitted.

Of course, the goal is to have multiple clients and in turn, guess what that breeds? More paperwork! And check chasing.

2. It’s hard work. Keep in mind we’re not trying to dissuade you from freelancing, we’re just presenting the realities per her piece. Rejection becomes “infinitely harder to shake off” and you’ll be wearing several hats. Kreamer quips, “When the internet goes down or the printer jams, you are the IT department; when payments are in arrears, you are Accounts Receivable as well.”

3. You’ll need collaboration. Sometimes you just need to rely on a little help from your network of friends and colleagues. Consider co-working space in order to collaborate or at least have some water cooler buzz to feel less isolated than working independently from home.

4. It can make you happy! Kreamer has freelanced for the past 15 years and per the piece, can’t quite remember what it’s like to work a 9-to-5 job. “The irregular cash flow and diminished income is more than made up by the freedom to choose my work.  I love being wholly responsible for the success or failure of my output, which researchers have identified as a key determinant of workplace happiness.”

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