On Leaving Multi-Six Figures for $35,000/Year

There was a time in my life where I took home well in excess of six figures and worked (roughly) an hour a day to earn it. My bank account was phat fat, I owned had a mortgage on two homes, drove a fly automobile, and never wondered whether my debit card was going to clear at the Whole Foods checkout.
And I was fucking miserable.
After 17 years of living someone else’s Shouldas, I was at my wit’s end. All I could think about doing when I woke up every morning was rushing through my work (that token hour) and spending the next 7 hours in my office writing. Anything.
Have you been there? Staring at a giant pile of money like it’s zero-calorie cake frosting, a delicate sterling silvers spoon resting next to it begging for a good horking. I mean, how do you say no to that shit? IT’S CALORIE-FREE! In my case, it was calorie-free money disguised as a soul-sucking journey through the Shouldas. I was paid (disgustingly) well. And I never went to bed happy.
So one day, I left. Walked out the door of my cushy six-figure gig and into a contract position at a teeny tiny ad agency as a copywriter as a 1099 contractor. I had mortgages, bills, and that pimp ride to get me back and forth.
And while I was over five figures lighter each month when I took home that check from the ad agency, I was finally happy.
Ecstatic, in fact.
That was February of 2008.
In September of 2009, I learned that the startup I’d moved to Denver to team with (and invest in, coincidentally) was out of money. On Thursday I had a job. The following Tuesday, I had a sofa and a minimum of 99 Problems (and yes, they deserved the capital P). And The Bitch (me) was, of course, one.
What would I do? How would I pay my bills? But most importantly, how would I ensure that I never (ever) relied upon anyone else for my professional happiness?
From September of 2009 to year-end 2010, I doubled what I was making at the startup. 2011 doubled that. Today, it’s February-something of 2012 and I’m staring at a national magazine column, the release date for two books, and a community of folks who pick up what I’m putting down at RedheadWriting. I get to wake up every day and love what I do, with whom I do it, and for whom I do it. I get to laugh, travel, write, strategize.
And I know now, three years later, that walking away from a pile of money that only made me miserable was the best choice I’ve ever made. Well, aside from calling off my engagement in 2006 — that was a pretty brilliant decision in its own right. Oh, and getting rid of this hairdo. Primo decision. But I digress.
Book # 1 is coming out soon and Matt Grant over at MarketingProfs recorded a podcast with me about it not so long ago. It’s about why unpopular brands rule. Hell, I should know — I’ve lived my life making vastly unpopular decisions.
But here I am. There’s not a day I wake up and don’t love where I’m at.
Why we jump, why we want to jump…what it takes to really build a business that will survive. We dish about it all. And maybe you’ll discover something in the podcast that reminds you why this thing is important to you. What it takes to make that leap.
So stop by and have a listen — you can stream it right from your desktop. And it’s because of everyone reading this blog post/email that I get to do what I love. Which means I blame you for this. Wholly. (Holy shit)
BONUS PODCAST SPOILER: During the podcast, Matt made me cry. Which isn’t too hard to do. I’m secretly a Weeper.

















