The Highs (And Lows) Of Working For Yourself

'Roller Coaster, Knott's Berry Farm, Buena Park, California'
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Sometimes I think to myself that I'm just not tall enough to be on this roller coaster. I snuck on, thinking I was special and the rules wouldn't apply to me. But it turns out I hate roller coasters.

I'm referring, of course, to the extreme highs and lows that characterize the first year (at least) of self-employment. I wrote a couple of weeks ago that for most of the past year, I've alternated between times of panic, because I didn't have any projects on my plate, and times of feeling utterly overwhelmed by all the work I'd managed to score. I chose at that time not to talk about the panic side, so I'm doing that now.

Terrifying reality
It's not all about the plate, though. It's not just about how much work I'm generating, how many paychecks are finding their way to my bank account. It's also about the constant pangs of regret, the self-doubt, the wish that I could just go back to my old job, or a similar job, because it would be so much easier than getting through this period of my life. Yes, it's exciting to strike out on your own. Yes, it's a good exercise in figuring out who you are outside of working for The Man. But after 20 years of good jobs, and knowing at least the outline of what each day would bring, it's also terrifying, and a regular exercise in mental and emotional self-flagellation.

I think it made sense for that to be the case the first few months after I left my job. I was still trying to find the right freelance work, still going on job interviews, still dealing with the immediate consequences of dropping a hefty salary from the household balance sheet. So I was giddy during the flush times when I was hosting radio shows and writing for The New York Times and being approached for all manner of projects. And on the many days when none of that was happening, I stewed in self-pity and rampant remorse.. What the hell was I thinking walking away from that amazing job I had??

Do I want it to be easy?
Slowly, those moments are becoming more infrequent. But they're still there, despite the fact that I am now working on a book and have plenty to keep me occupied. The problem is now I look back on my old job and tend to forget some of the reasons I left, and instead only focus on the fact that it was a whole lot easier than what I'm pushing through now. But do I want it to be easy? My lizard brain says yes.

But I know if I just wanted things to be easy, I would/could have stayed put in my old career, no matter the frustrations and annoyances. And most of the time, I'm glad I took the leap, and I'm proud of myself for doing so. And my life is good! I really don't have much to complain about, and I hope this doesn't come off sounding like a complaint. It's more an exploration of how we deal with change, and how we figure out who we are outside of what we do. That's a process that is still taking some time, even a year after taking that leap.

I wonder if you've had the same feelings about that roller coaster. Do you enjoy it? Do you wish you were taller, so to speak? Share your stories in the comments section below and email me at
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