I know. This should be obvious.
It should also be as easy as sneezing.
Working without a boss is, after all, what we signed up for.
It’s why we went freelance in the first place. So we wouldn’t have someone leaning into our cubicle all day, telling us what to do.
We wanted to call our own shots. Steer our own canoes. Hold our own forks. Put our fate in our own hands. Mix metaphors willy-nilly as we please.
Ordinarily, that is all very satisfying. It is even fun.
We get to say ‘no’ when we want to. We can decide to work from the couch today if we feel like it. We don’t have to be somewhere by 8:30.
Fact is, though, working without a boss isn’t always as breezy as it sounds.
From what I see, it’s the cause of more angst, and sleepless nights, and early afternoon beers than all that other ‘downsides of freelancingTM’* combined.
When we freelancers stall out, or find ourselves into the weeds, it’s rarely due to some failing with our craft.
It’s not because we suddenly can’t design or translate or write well enough.
It is almost always a ‘management’ problem. We’re tripped up by our blind spots, by tunnel vision, by indecision, or some chronic foibles of ours. We lose the thread.
That’s a hazard of flying solo.
You and me, we don’t have a boss to tell us when we are screwing up, what we are doing wrong, what is not working.
We don’t have a boss to okay our plans, or back up our decisions. Or tell us when that ingenious idea we have is catastrophically stupid. (Not that bosses are ever right about that, though.)
We don’t have a boss setting the overall strategy or detailing the mission for the next three months.
We don’t have a boss dropping work on our desks every day.
Or putting structure into our days, with his Tuesday briefings and status meetings and emails saying, “See me about this.”
We don’t have annual performance reviews (and I thank the heavens for that), and ‘action plans for professional development’.
You and me, we have to get good at making our way in the world without any of this guidance from the corner office.
We have to get good at untangling our own knots. Doing our own troubleshooting and repairs. Putting air in our own tires.
When we run off into a ditch, we have to get out and push. And figure out how stay on the road next time. All without a boss telling us what to do.
Sad to say, some hopeful freelancers never get the hang of all that.
They land a few clients to whom they cling too tightly. They limp along. They struggle. They grow unhappy and discouraged.
Eventually they go back to a regular job. “I really missed the regular paycheck,” they say.
What they often mean, I think, is they missed having a boss. On their own, they felt rudderless and disconnected and uncertain.
I get that. And it’s not a character flaw.
I have have several friends and clients who are VP-level execs at big corporations and fancy agencies. These are smart and ambitious people. They are not risk-averse or lacking in confidence.
But they need a boss like they need oxygen.
With someone to report to, they are energized. They have purpose and direction. Their calendars are shaped by what the boss likes, what the boss wants, how the boss thinks, what they need to say in the quarterly report.
They may bitch endlessly, but they truly thrive in that environment. They literally define themselves by who they report to.
But most freelancers — at least those of us who are mostly unemployable anyway — we chafe at adult supervision. We never miss having a boss. Ever.
(For me, even having to answer to clients is becoming a bit much. I should work on that.)
But as annoying as a boss can be, there are times when it would help to have one. Maybe one day a month, for an hour or so. And they would have to leave right after.
It would be helpful when you’re facing a gnarly decision. Should I take this assignment or not? Should I be chasing agencies, or not? Should I fire this boor of a client, or not? How much should I charge for this?
It would be helpful when business is merely pooping along and we’re not sure why.
When we’re attracting the wrong kind of clients and don’t know what to change.
When we start to hate the work. Or our clients start to hate the work.
When there’s not enough money, or not enough work, or clients don’t seem to get it.
Without bosses to weigh in on all this, or give us to-do list, here’s what my renegade friends and I do instead.
Write it out
Compose an email to an imaginary mentor. Or to some sage and savvy freelancer with a blog.
Detail what you’re struggling with. What’s going wrong? What’s not happening that should be happening? What have you tried so far? Spell it out.
What’s the decision about? Explain the situation. What are your options? Which way are you leaning? Why? What do you think will happen, either way?
I love when I get emails like this from freelancers. Toward the end they say, “I think I just answered my own question.”
That’s because trying to articulate the problem clarifies everything. And spares me the pressure of thinking up a wise response.
Many creatives I know swear by morning pages. Before starting the day, they write three stream-of-conscious pages in a notebook. They write on what they’re thinking about, mad about, or worrying about. About what they hope to do that day. Or how they screwed up yesterday.
It’s like venting to a boss. Or turning in a daily plan. Or justifying a decision. It’s a way of purging the tanks, or figuring out what is really on your mind.
I once thought the idea a bit trendy and self-helpy. But I changed my mind. It is surprisingly useful.
Alice Walker started every chapter of The Color Purple, with “Dear God. . .”
If you hate writing — which I often do — take a brisk walk and record a rant on your smartphone. Or rehearse what you would say about all this on the witness stand. Listen to it an hour later. It will be revealing.
Get another pair of eyes
Managing yourself as a freelancer is a bit like cutting your own hair or doing your own dental work. It’s too hard to see back there.
A freelance friend of mine has been laboring over a proposal for three days. A choice opportunity for a choice client. It is in his wheelhouse. He wanted it.
At midnight he sent me his proposal to look at. In eleven seconds I see he is overpleading his case, begging, going into way too much detail. He is distraught to hear this. Then he says ‘Ah!’ and re-writes it in an hour.
But I’m not so good at spotting the gaping potholes in my own grand plans. More than once I’ve heard from a fellow renegade, “Um, what?” Or, “Kania, do you hear yourself?”
Sometimes the bastards are right.
I was always skeptical of the value of coaches. (Especially ‘life coaches’ who are 27 years old.) If they’re so brilliant why aren’t they doing, instead of coaching? Golfer Lee Trevino said, “When I find a coach who can out-play me, I’ll take a lesson.”
I’m not so skeptical now. I’ve come to think that coaches mostly serve as a fresh pair of eyes. They see things you are blind to, and ask you questions you never thought of. For people in our line of work, I hear Justine Clay is helpful.
Just pick one, already
Making decisions will always be difficult. That’s why they have to pay CEOs 2.4 million of dollars a year: To make 96 hard decisions per day.
Luckily for us, virtually none of the decisions we have to make will result in death or dismemberment, or major crop failure.
At worst we will take a job that we should have turned down, and we will be miserable. Or we will not charge enough, and be miserable. But only for a week or so. Almost nothing we do is permanent or irrevocable. And we always have the right to bail.
(And we don’t have to grovel and explain our bonehead decision to a boss.)
Also, we should try things. If you think of an idea and it still sounds good six days from now, try it. See what happens. You don’t need permission. And if it bombs, keep it to yourself.
Oh, another trick is to distinguish between choices and decisions. (See Seth Godin on this.)
A choice is when you have three options, and they all have merit one way or another. Like which template to use for your website. If all three look good, pull a number out of a hat. Don’t burn more brain cells than you have to. It is not core to your survival. If the choice doesn’t work out, change it.
I wrote this without an editor or a boss looking over my shoulder, which is why it is 1542 words long and occasionally meanders off topic.
But then, I would only be eye-rolling and bristling at their changes anyway.