On several freelance gigs over the years, I’ve had no “boss” – no project manager, no supervisor, no approval system, nobody clearly in charge.

Having nobody to report to sounds pretty good, right? One pictures a halcyon workflow, all birdsong and sunlit-meadows and easy, flexible scheduling. What could be better than absolute autonomy?

Sometimes this situation can be great: it offers a lot of flexibility and creative freedom! Problems only arose when I ran up into the manifold eccentricities of a particularly irritating supervisor: myself.

When you’re reporting to yourself, it can be easy to be the best/worst boss in the world. The best, because you’re an endlessly understanding and accommodating supervisor – sure, self, you can take the day off to go play in the park! The worst, because the temptation to let deadlines slide is always looming; because it becomes easy to procrastinate and tarry, eventually creating chaos for yourself.

So how do you work effectively as an unsupervised freelancer?

1.) Create accountability

Listen, the client may not care how you get your work done. But YOU need to decide, freelance friend, for your own sanity. Create accountability for (and to) yourself, if the client won’t.

Set deadlines. Create a schedule. Determine your normal working hours – since you’re your own boss, that can be from midnight to 3 AM if you choose (although my extensive experimentation in this arena has indicated this may make you a crazy-eyed, translucent-skinned Night Creature).

Allow yourself some flexibility, but not UNLIMITED flexibility – that way procrastination lies. Commit to some level of responsibility beyond I-have-to-do-this-now-or-I-will-have-no-money-and-starve.

2.) Communicate accountability

If you’re without a direct supervisor, your client may not be particularly interested in the shape of your workflow – but communicating with them will help YOU commit, and odds are they won’t mind.

That doesn’t mean that they want to know the minutiae of your schedule – only your Mama is interested in what time you eat every day – but no client will object to a working outline of when/how they’ll get their deliverables. This can be as easy as an email:

Hey, [Client]! I know your schedule is flexible, but I just wanted to let you know I’ll send you the edits by Friday the 4th, EOD. My working hours, if you’d like another revision after that, are Monday-Friday, 10-5. I’ll email an invoice to you and accounting within one week of the edits being completed. Thanks!

In one email, you’ve set a deadline, established your working hours, and alerted them to be on the look-out for your invoice. That’s three pieces of self-imposed structure, and even if you don’t get much of a response (in these kinds of gigs, I often got a “Sure” or radio silence), you’ll be much more motivated to get the job done when the client is expecting concrete results.


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3.) Get into the accountability groove

So you’ve been doing steps 1 and 2 and noticing a difference? Heyyyy, look at you, all autonomous and productive! You’re not procrastinating nearly as much, and odds are your life is a bit easier for it. Congratulations!

Now you can use those skills to become a better self-motivator in the long run.

Start building in structure for yourself and your freelance business – refocusing your energy on things you’re really passionate about. If you can build an efficient structure for yourself (and it takes practice -- I’m always still figuring it out myself), you can often set short-term and long-term goals and ACTUALLY ACHIEVE THEM. Make yourself reportable to your merciless self, and communicate your deadlines to others. Turn “accountability” into a good thing – something you owe to yourself, for yourself.

Once you have a working self-imposed structure in the short-term and long-term, you can take advantage of all of that vaunted flexibility and autonomy – actually enjoying the freedom and self-reliance that comes with working independently. These unsupervised gigs can be great practice for life… which, if you’re very lucky, is the ultimate unsupervised choose-your-own-adventure.

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.