The day I left corporate America and never looked back… the first time. Sigh.

When I left corporate America (update: the first time), it was a banner day for me. Primarily because I pretty much had to be escorted from the building.

But we’ll get to that illustrious occasion in a minute. Let me tell you first about what led up to that most excellent moment in my life.

As you may or may not already know, I had been wanting to become self-employed for years prior to the date when it actually happened. But as you all may or may not have already experienced, it can take some tiiiiime to finally rip off that so-called security bandage that we all know and love, called the corporate J.O.B. Some of us sloooooowwwwwwlllllly get out from under it, inch by agonizing hair-pulling inch, while others execute a smoother, more elegant exit from underneath.

Not me. I blew that fucker off with a flame-thrower.

I was in a comfortable situation: well taken care of, I worked around good people, and I generally had an all-around decent, and maybe even enviable, condition. But the single and inescapable downside was that I wanted to ingest cyanide every day as a result of the utter meaninglessness and boredom of my daily life.

A corporate job for closet entrepreneurs is like crack – you know it’s bad for you, and you know it’s addictive – and the only way to break the habit is to go cold turkey.

At least, that’s the way it was for me. I had to burn the city behind me so that I would never be tempted to go back.

So. What really happened?

Well, it developed in two stages: 1) I left my last real corporate job to take a job as an independent contractor, which 2) turned out to be an illegal attempt by my new “employer” to circumvent the IRS laws that state if you want to control the people you work for, you can’t 1099 them, you actually have to W2 them and pay taxes and benefits. But the truth is, I left one corporate job for another, except the latter falsely advertised it as being self-employed.

Leaving the second-to-last job was admittedly, smooth. We had the requisite leaving happy hours, I got presents and cards, and it was an all around kind of sad exit. I liked the people I worked with, and I was sorry at the prospect of not seeing them every day anymore. But I was excited about my new adventure, which was supposed to be a new foray into self-employment, by being the “independent contractor”. I mean, that’s what my contract (and my 1099 form) said, anyway.

Not so much.

The new “job” didn’t start well, especially when they wanted to dictate that I had to be at a certain location, dressed a certain way, by a certain horrifying time of 8.30am. That right there should have raised a red flag, but alas it did not. I am not a morning person, and I far prefer to stay up until 1am and rise at 9am, than… well… anything else. And I certainly wasn’t about to start wearing pantyhose again in this lifetime. And as a newly independent worker, wasn’t I by law required to dictate my own terms?

Um… apparently not, according to my new “boss”. Ohhh, the things I bitterly didn’t know back then.

At any rate, the job started otherwise uneventfully. It didn’t take long for me to realize my situation really hadn’t changed… at all. I still had to barrel through rush hour traffic with everyone else, still had to get through the door using a key card slung around my neck, still had to sit in a dull grey cube for eight+ hours a day, still had to be forced to do boring work that was… boring, and still had to drag my ass through traffic again to get back home. Something smelled…. like… a corporate job.

The only thing different, apparently, was that I was going to have to pay a lot more taxes the following April 15th.

Naturally, over time, these discrepancies in what I had been led to expect of “self-employment” and what I was actually experiencing began to eat at me. I started to resent being told what to do all the time, how to do it, and when to do it. Not to mention, at my last job, I got to wear shorts! At this place, I got written up for wearing leggings, for the love of God. Written UP. I wasn’t even an employee! Something was vastly wrong here. This certainly wasn’t what I signed up for. I signed up for independence! I signed up for freedom! And what I got was… jail. Jail, with the jumpsuit, and all. I could have stayed at my old job with my fun friends and had paid vacation and benefits for all the good this new endeavor was doing me.

Ahhhhh… but it was perfect. If it hadn’t gotten so bad, I wouldn’t be where I am today. Silver lining, folks.

When I was notified only two weeks prior, that the entire place I was contracting at would shut down for a week for fiscal year end and budget revisions, and that I would get NO PAY (because I was an independent contractor, natch!), I still didn’t quit. When my company’s accounting manager miscalculated our pay and notified us that they were intending to erroneously revoke some of our wages, I still didn’t quit (they eventually realized their mistake). Even when my company started “forgetting” to pay us on time at all, I still didn’t quit.

But when my “employer” tried to blame me and my team for not getting something done that she had never actually asked us to do? That was it. That was when I had had enough. I had better be getting voluminous paid vacation time and healthcare to tolerate that familiar brand of crap.

So I dragged her into a conference room and laid waste. Doors shook, windows rattled. I’m sure the entire office could hear the screaming, but I didn’t care. One can only take so much from “corporate America”, and I had reached my limit.

Needless to say, there was a lot of staring and/or looking down at floors when we emerged. Agreements were hastily written up and signed by both parties, terminating the contract immediately. I gathered up my meager things and stalked out, my “employer” hustling to keep up with my pace, apparently fearing I might steal a coveted stapler on my way out the door.

I have acquired enough staplers, thank you. I’ve worked at a lot of places. 😉

The amazing thing is, I liked (and still like) the lady I worked for. She is a decent person, in spite of some business flaws. She is good at what she does. I don’t blame her for everything, because on my part, I should have never taken the position in the first place. I wanted true self-employment, and this job plainly wasn’t that. Not by my definition (or the IRS’, natch), anyway. I was trying to make something be what it wasn’t, and I was trying to be something I was not. It simply wasn’t a match.

Ironically, by the time we made it out to the parking lot to my car, we hugged goodbye. And it was genuine. I truly don’t harbor any ill will, because I am grateful for the experience. If I hadn’t walked out in such a fury, I never would have had the fortitude to forbid myself to go back to a job like that. The memories of that moment, especially in the times of weakness that followed, gave me the strength to say NO.

Anger can be gooooood.

A month later, after a lot of sweating and praying and testing of my faith in a benevolent universe, I met Alan. And that’s when the fun really began.


The bottom line is, when you want a certain kind of life, you have to go for it. You can’t keep trying to fit yourself into a box that is too small for you, or convince yourself that you can keep one foot in your old life and dangle your toes into a new one, all to feed your insecurities. You have to go ALL IN.

Or else you’ll always be split across the two, and neither life will thrive. Clearly.



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