Donning the Boss Hat

Originally published in the July/August 2017 issue of Quill, the bimonthly magazine of the Society of Professional Journalists 

Autonomy is part of the appeal of freelancing. As independent journalists, we work with editors as our clients, not our supervisors. We choose our projects and set our own schedules. We may or may not work in our pajamas, or from a lawn chair in the backyard. We’re our own bosses.

But sometimes, that means bossing yourself around.

The joy of working on what you want, when you want to doesn’t always translate into getting done what needs doing; autonomy can also be a pitfall. Successful freelancing, as much as it offers freedom, requires self-discipline.

And sometimes, self-discipline requires a Jedi mind trick — a particularly artful maneuver when you must play both the tricked and the trickster.

As freelancers, we try to take on only work we like. But even great projects often involve tedious phases. Other assignments may serve merely as stepping stones or financial necessities more than they fuel our passions. And aside from reporting, there’s networking, negotiating, public appearances, accounting. Even if you love running your own business, that doesn’t mean you’ll always feel like doing what work requires of you.

This is when I put on the “boss hat” — my term for the ruse I employ to get out of my own skin and into the mindset of a business owner.

Technically, I do play both roles: I am both the sole shareholder and the sole employee of my business. As an employee, I earn a salary. As the shareholder, I may get a bonus if my employee performs well throughout the year. I set up this legal and financial arrangement on the advice of my accountant, and I’ve noticed it facilitates the Jedi mind trick rather well, too.

But you don’t need to engineer a complete internal bureaucracy in order to don the boss hat. Here are a few techniques from my own experience, as well as members of SPJ’s online Freelance Community:

Develop company policies: Rebecca Weber, a full-time freelance writer and writing coach based in South Africa, says she channels most business and marketing decisions through a paradigm of “company policies.” With her business hat on, she instituted certain rules, which now she just has to follow, rather than reconsider perennial issues every time they arise.

“For example, as a norm I ask for more money on the first assignment,” Weber says. “I’m not naturally inclined to negotiation, so knowing ahead of time that I’m going to ask means that I can skip the stage of deciding if I should ask or not. These policies increase my income AND eliminate a lot of stress around money.”

Sign out of social media: This is one of my techniques for keeping procrastination at bay — especially for Facebook, which I find to be the strongest vortex.

I use a password manager and make a point not to learn my password for Facebook. I log out every time I close the website, and therefore have to jump through a couple hoops every time I want to log back in. Even when I choose to engage with that platform in the course of my workday, the added steps make it a more deliberate diversion.  

Pre-set your schedule: This was Hazel Becker’s strategy when she began freelancing full-time after 29 years as a staff reporter and editor. Now semi-retired and chair of SPJ’s Freelance Community, Becker says she would start every workday reading up on her beats, then scouring websites for gigs. She aimed to to send at least one query every day. She spent most Fridays taking care of business, marketing and learning new technology.

The routine came easy, she says. “In those days I had to use the Jedi mind tricks to get in my workout every day. Now that’s my day-starting routine, and actually looking for gigs is what I have to convince myself to do.”

Becker’s role reversal is instructive. As you explore and deepen your sense of yourself as your own boss, remember to be a good one, and also to stick up for yourself as an employee. Consider negotiating a late start time, or a long lunch break for exercise, for example.

Because no matter who the boss is, a happy, healthy employee makes for good business.