Everyone's a Boss (in the worst way)

Total autonomy.

Yea, that’s we want. No one to tell us what to do. Ever.

No one setting a bar or a deadline, no one telling us when to start and stop work, no one dangling a paycheck in front of our noses like a carrot on a stick beckoning the cart-pulling donkey ever forward yet forever out of reach.

“I wanna be my own boss!” we say. “I wanna set my own schedule! I wanna call my own shots! I wanna be free!”

Mmmm, a delicious series of sentiments…

…what a drag that this fabled “bosslessness” doesn’t exist.

The truth is, in most incarnations of work and life, there will be a “boss”.

There will always be someone (or something) we’re forced answer to.

Let me brace you up front; this post is mostly going to be a series of burst bubbles. I do offer some brief bright sides for reconsideration, and some attitude adjustment advisements. The point is to delivery an honest appraisal of the fantasy jobs so many of us salivate over, and sometimes destroy our lives to pursue.

A pro and a con for all things, eh?

Below are 5 bossful realities of the most commonly mythologized bossless jobs:

1.) Your Client is a Boss

The Dark Side: The first step outside the nest for most of us fledgling freelancers looks like: “I love what I do, but I hate my boss. I’m gonna quit, start my own thing, and be FREE!” Dope plan fam. Foolproof. Flawless. “Oh but wait, I still need to make money. And the clients have the money. And I need to get the clients to give it to me. So I need to do what they say, at least a little bit.” Bam. You got a boss. “Oh shit, now I have a bunch of clients…” Bam. Bunch of bosses. Oops.

The Bright Side:  For those of us who have had some truly awful employers, this is certainly a worthy escape? The benefit of having many bosses (in the form of many clients) is in the diversification of your boss portfolio. Some bosses will perform better than others, both in terms of income and behavior. And just like investments you may rebalance your portfolio in the form of firing one of your client/bosses if the performance tanks. This is certainly a new freedom (the boss firing), but let’s not forget, we have to keep some bosses in the bank if we hope to reap dividends. So, nice bright side, but no total bosslessness in the client services world unfortunately.

2.) Your Customer is a Boss

The Dark Side: After failing to find financial freedom in farming the former format, you may think to yourself: “Ok, to hell with client services. Can’t handle the ‘many boss’ dynamic. Being pulled in a thousand directions, on a thousand projects, with a thousand deadlines…yea, not for me. I want time to focus, and I want to focus one one thing. Eureka! I’ve got it! I should develop a product! Yea, products scale. Make it once, sell it forever. Nice. Figured it out.” And then, upon product launch: “Oh, my customers are actually people. Oh shit, they have wants and needs and demands and gripes and are really good at writing devastating negative reviews when I don’t cater to their every whim. Oh no, there’s so many of them…how on earth will I make them all happy!?” Bam. A million little bosses. Drat.

The Bright Side: The promised land does exist here, but there usually isn’t a shortcut. It is possible to build something once that sells forever. You can create a customer support system that takes really good care of your buyers. And if you do all this reasonably well, you also might find yourself in a position to completely hand the reigns over to someone else and sit back while the ship sails and the biz scales…on autopilot. It is also much easier to sell a product-based company, as the value is in the product, compared to selling a services based company, where the value is either in you or your other service-providing-people.

3.) Your Audience is a Boss

The Dark Side: This model is quite in vogue these days. Everyone wants to be an influencer, or an author, or a celebrity. We all think we have something to say (some of us actually do), and we’d love to be paid for saying it. Hmmm, but what if I say the right thing for a while, and then I say the wrong thing? Shit. Will they all leave? Fuck, probably. What about the other people who start saying what I was saying and my audience starts listening to them but I can’t tell what the hell is different between what I’m saying and they’re saying and it makes no sense that everybody is leaving my platform for theirs? Is it cuz they’re hotter? Smarter? Angrier? Funnier? Skinnier? Ok, I’ll stop eating. Problem solved! Oh, ya, what if I want to preserve some privacy in my personal life? Dealbreaker, huh…guess I’ll have to met the issue head-on and just livestream my whole life via Ring Doorbell cameras in every room of my house.

The Bright Side: The above caricature is perhaps a bit unfair. There are many ways to build an audience, many platforms to do it on, and many ways to be towards your audience. Of course there are healthy and sustainable ways to do this, and sometimes the foundation can become unshakable. Maybe not a sellable business, and maybe fully reliant on you, but certainly a recipe for passive income and compounding residuals. The content itself compounds as well. If the audience is content with your content library, you have truly depressurized your creative process. Go to Greece. Rent a small houseboat to float around in the Mediterranean as you leisurely blog or craft that next novel. No wifi needed, no phone needed, no stress needed. I can imagine the existential crises running rampant in an environment like this (personally). The trick will likely be for US to be content with our content.

4.) Your Donor is a Boss

The Dark Side: Eden. Money for nothing. They give it to us. We’re never accountable for anything. Oh, there are strings attached? Conditions for renewal? You have asks? Small ones? Oh, they’re not actually so small? Hmmm, now I feel like I’m under a thumb, or wrapped around your little finger, or beholden to another demanding digit. You, dear single donor, feel a lot like a client. You all, dear Patreon micro-donors, feel a lot like a fickle audience-customer hybrids. I don’t like any of you anymore. Oh, but I stil have to eat. I guess I’ll trade a moral for supper. Just this once. What’s the harm?

The Bright Side: If we somehow amass recurring donations without making compromises or catering to asks, chances are this is a stable structure. And yes, if we build it this way it has a greater chance of staying this way. “Terms are set. I do what I do. You donate if you find value. Period.” Your authenticity income flow becomes a virtuous circle: you maintain your authenticity, you are rewarded, this reinforces the authenticity, which reinforces the income, and so on. Again, hard to predict where the fickleness will present and difficult to measure the soundness/fragility of the structure. But could be delightful!

5.) Your Inner Critic is a Boss

No dark/light side for this one. This is my conclusion section. So, in conclusion:

Even if you are able to strip your psyche of all emotional accountability felt towards the folks who support your lifestyle (be they clients, customers, an audience, donors, etc.), real or imagined, you still have yourself to face.

Your shitty little self.

That motherfucker between your ears who won’t shut the fuck up sometimes.

“Yea, the book sucks bro. No one will read it. It won’t sell. Oh, and even if it does that’ll be worse. You’ll know it sucks still, and now you’re a fraud. Congratulations asshole.”

This guy ^ for me, is quite the bastard.

He masquerades as a proud perfectionist. An artist who refuses to settle, who believes in real beauty. He definitely likes to build me up and make me feel important for not pushing my babies into the world. Like I’ve done something worthy of praise for not sharing something that might not be a masterpiece. He leads me up the moral hilltop and helps me spew acid on the work of my fellow creatives for having cut a corner here, or being hasty there. I feel real good about myself when I do this. And then I look at the mountain of unfinished work, unrealized dreams, and unshared creations. Then I feel bad about myself.

I am quite beholden to this shitbag.

He doesn’t just employ me, he rules me.

…sometimes…

Other times I’m able to mute the motormouth.

I’m able to get inspired, sit down, and write an article about bosslessness, and the various ways to realize a reality of financial independence, operational autonomy, and emotional fulfillment.

That’s what happened today. That’s this post. This is the post about that stuff. I did the thing I just said sometimes I get to do. I did it. Today.

Hopefully also tomorrow.