DRAFT — When Your Job is Killing You Slowly

My friend is smart, vivacious, funny, driven, talented, passionate, and bubbling over with what the suits of yesteryears called “work ethic.”

And last night, we spent at least an hour going back and forth about her horrible, shitty, no-good very bad boss — hereafter known only as “Crazypants.”

The Ballad of Crazypants

  • Crazypants refuses to pay for services the business needs.
  • Crazypants makes unilateral decisions without consulting the team she’s hired to execute those decisions, who know more about the day-to-day running of the business than Crazypants does.
  • Crazypants likes to take rapid freak turns off the project highway, such as demanding my friend choose a new mailing list service the night before sending out a newsletter.
  • Crazypants takes advantage of her employees’ desire to do good work in order to get away with chaotic management (at best!).
  • Crazypants takes credit for her employees’ ideas — not only to clients and other outsiders, but even inside the company.
  • Crazypants does her damnedest to control and intimidate her employees.

And more.

Now, is Crazypants a bad boss? Yes, clearly. And she’s an excellent example of why employment is such an unholy crapshoot.

The Fundamental Problem with Employment…

is that somebody else has the power to decide how happy you can be. Make no mistake, bad bosses can ruin lives — often temporarily, but sometimes permanently.


When you’re employed, you’re no longer the captain of your own destiny. Someone else is in control of whether you are allowed to do your best work, to feel good about what you do, to have an impact, to grow professionally and personally.

Yup, I said it: Somebody else is in control. Who? Whoever has the power to make your work and your work life suck. (From here on out, I’ll call that person “your boss” but it could equally be an evil coworker or ignorant client.)

Current emo self-help trends say, “Nobody can make you feel bad without your permission.” But how happy campers do you know who can totally laugh off the effects of 8 hours a day under a bad boss?

We humans are social creatures, we need other people, and the other people in our lives have tremendous power to affect our feelings. It’s insulting and unrealistic to imply that if hurtful people doing hurtful things hurt us, it’s our fault.

“You Could Improve the Situation”

Okay, I hear you saying, so Bad Boss is Bad. But you can try to change the situation. That’s true. You sure can try. But when your boss is immune to change, how well does that work?

Then, when your suggestion-ballot-writing and helpful hints fail to create the change you desire, you could take things into your own hands and work covertly, on the down low. Engage in a little on-the-job civil disobedience.

But then, as it turns out, your boss’s attitude is making a dishonest person out of you.

How good can you feel about yourself, your work, and your contribution when you’re forced to rely on subversion and trickery to achieve it?

So, change is out, unless you’re lucky. Then once you eliminate change, there are only two well-worn little numbers left: Denial, and quitting.

Denial comes in two forms. You can deny that anything’s wrong, that it’s not “that bad,” and justify your decision to stay. Or you can accept defeat, pretend you don’t care about doing good work, check out entirely, talk the talk of somebody who is cynical about working for “the man” but who’s willing to fleece “the man,” if the opportunity presents itself. Many talk this talk, but few can walk it, not truly.

And finally, you can quit. Quitting, of course, is the act of ripping yourself away from a huge part of your life — from your work, possibly years of it, and people you’ve spent time with and thought about and maybe even loved a little, from your dreams, your original high expectations, and your trials & triumphs — shredding it to little pieces, and stomping on it. Maybe setting it on fire for good measure.

Do any of these sound healthy to you? Have you done them? How’d that feel?

Pretty Damn Bad, if You Ask Me

Hell, when you combine all the “real” jobs I’ve ever held, I’ve tried ’em all. And they all sucked. I felt like my heart was being stomped on. I felt like my passion and joie de vivre were being sucked out of my chest through a bendy straw.

Then I’d quit, and I’d try a new job (or, finally, consulting), thinking that the next one would be different. I’d be happier; they’d appreciate me more; I wouldn’t feel the slow withering death of passion that comes from the bad marriage between an employee and her company.

Of course, after the honeymoon period, all bets were off. Each new job sucked — in new and different ways, at least, but nevertheless equally. Each one left me disappointed and angry that the people in charge were so incompetent, that I was hamstrung, that, try as I might, it was if all my hard work — in fact my very existence — didn’t even leave a tiny mark on the institution to which I had so naïvely plead my loyalty for 8+ hours a day.

(Don’t get me wrong — I’m not one of those people who always thinks I can do better. I’ve marveled at great bosses I’ve met, and learned a lot from one of them. They were just never my boss.)

Do You Have a Good Boss?

Sadly, caring about your work plus bad boss (or even “okay boss”) equals ennui, frustration, even depression. When you care about your work, and you work for a less-than-stellar boss, it’s well nigh impossible to keep showing up every day and giving your all.

But maybe your boss “isn’t all that bad.” Maybe she “means well.” But you know what? An “okay” boss is a bigger problem than you think. You care about what you do. You want to feel like you’re accomplishing something, and take pride in the results, and share in the rewards.

To do all those things, you need a lot more than a moderate, do-no-bad-or-really-any-good Switzerland of a boss. An okay boss is just as bad as a bad boss, most of the time.

And none of the coping mechanisms leave you happy. Grinning & bearing it, denying that it’s a real problem, telling yourself “it’s just a job,” or quitting… they all hurt, in varying degrees. Eliminating a pain isn’t the same as creating joy.

The bottom line is this: Good, smart, capable people want to feel like their work makes a difference.

When someone else is the one who gets to determine whether we can create value, and feel valued, it hurts; if we can’t make an impact, that hurts too. Continually doing our best for people who don’t appreciate it hurts almost as much as being thwarted. It’s like we don’t matter. Like we don’t even exist.

We want our lives and our work to mean something.

And when our daily work denies us these fundamental needs, we wither.

What we need is personal sovereignty.

Personality Sovereignty: How to Get It

First step: Admit you have a problem. Clichéd, but, well, clichés exist for a reason. If you’re justifying & making excuses for your less-than-lovely job situation, or pretending you don’t care, stop. Excuses don’t help anyone, and they certainly hurt.

Next up, the Big Fix… and I can’t tell you what it is for you. There is no one-size-fits-all solution to the problem of personal sovereignty. What’s right is what makes you happy.

Maybe you have to be employed (or rely on the kindness of others) to have what truly makes you happy. But then again, maybe you don’t.

Me, I quit. I quit my job, then I quit another job, and then I quit one more and became a consultant. Then I quit consulting, for the precise reason that it was very much like having a job.

Now I make & sell products, along with my husband and a team of smart & funny freelancers. We make software together, we teach programming workshops together, we wrote an ebook together, and I teach a class on creating & selling your first paying product.

I get to decide what to work on, when, and how; who to sell to, who to hire. I get to do the cost-benefit analysis for everything I do; I get to buy the things I need, hire the people I need and want. Fire them, too, if I need to.

We have many customers and each one pays a little, so no single customer is too important to lose. No one customer can hold us hostage and force us to do things that don’t fit our vision & our needs. We can simply refund their money and point them in the direction of somebody who fits them better.

In short: Personal sovereignty, I has it. And it feels gooooooooood. We started working on Freckle Time Tracking (our first software product) just under 3 years ago; I quit consulting to work on products full time just under a year and a half ago. Unlike all the jobs I’ve ever held, this one gets better over time.

I highly recommend making & selling your own products, if you’re a maker by trade or spirit, and love doing a wide variety of things, and like to interact directly with people who use the things you make.

That’s What Made ME Happy.

And if you think it’ll make you happy, too, and you’re really ready for a change — like my friend — and you ache to feel satisfied in your work, to serve the people who pay for you directly (not your boss, but your customers), then you might enjoy my summer class on how to make your very first profitable product. It’s called 30×500 and tickets are going on sale very soon.

But maybe being your own boss isn’t what would make you happy. Only you can know.

You’ve got to figure out what it is about work that makes you happy — the work itself? The team? The environment? The schedule? The freedom or the constraints? Working on things that are big and rare, that you can only get access to through certain paths where you must meet the approval of others?

Nobody cares as much about your happiness in your work as you will. Nobody will fight harder for your passion than you will.

A lot of us fall into the trap of waiting — waiting for an opportunity to present itself, waiting for a new job offer to land in our laps, waiting for A Sign™ we should quit and move on, waiting for somebody to talk us into it, waiting for our situation to get better, waiting for somebody to swoop in and save us.

But it’s never going to happen. So if you’re unhappy, stop underrating and undermining your own needs to do great work. Get serious about creating your own happiness — and get off your ass.