When I left my job in May, the thought cloud afloat above my head was chock full of ideas. The plan: start my own business and continue as an employee communication consultant. My dream scenario was to work remotely. Naturally, this would require getting some regular clients but once those good relationships were established, I’d pack my Goyard tote with my laptop, eyeliner and some flats and go explore the world. It’s a good thing I’m not a psychic because I would be the Dionne Warwick variety.

SO what’s the verdict?

I’ve started not one, but two businesses! I’m eager to talk about the second one but until that trademark application has been accepted, let’s just say that it involves fashion. And the Internet.

SO what’s the verdict?

I’m not good at bookkeeping, never balanced a checkbook (how is this necessary when you can look online everyday?) and generally get bored with details. Did you know as a small business you have to CHASE the money people owe you? They’re often not in any hurry to pay.

I blame Montessori school for this handicap. I spent my first years of school writing stories and readers. Except for the time we had a lesson on hygiene and I was inspired to spend a whole afternoon taking out the 30 tiny braids my grandmother had cornrowed the day before so that I could use the little plastic comb. Just like the other kids. Yes, I looked crazy once I released those braids. Yes, even Bane from Batman wouldn’t have been safe at pickup that afternoon.  And yes, a third of the teeth on that little comb didn’t survive one swipe through my hair. Bottomline, Montessori didn’t make me do math, which dribbles down into it being difficult for me to keep track of who owes me what.

SO what’s the verdict?

I’m flipping between ecstasy and terror. One minute I’m reveling on an especially good writing session. Then the COBRA bill arrives and I freak out wondering how I will pay it and what I’ll do once I’m no longer eligible.

That’s the life of the self-employed. It’s risky and unpredictable. Two things that are SO not me. If you think you can’t do something, don’t underestimate yourself!

When I went to an alumni weekend for the MLT minority leadership program, I felt like a fraud. My nametag wasn’t emblazoned with the name of a well-known company. The title “Principal” was dropped from my repertoire. Plus, I had no corporate sponsor, and had paid my own way.

I wondered how I would share the big change with the executive coach I’d worked with two years ago. I sat in front of him with the same pitiful look I gave my mom that time I’d eaten a whole box of girl scout cookies while she was at work.

I expected him to be surprised or to ask why I would jump off the corporate ladder. His reaction: “You’re an ENTP, I’m not at all surprised.” He was referring to my Meyers-Briggs personality type. Apparently we do well as entrepreneurs.

I told him I was disappointed in myself. I wasn’t a sales junkie and was nowhere near meeting my self-imposed sales goal. I’m happy with my life, but what happened to my business drive?

He looked at me with the expression I give to a cab driver who asks me how to get to the Midtown Tunnel. After two hours with him, I understood that I’d just re-placed that drive — changed its place. And instead of being Lasik-focused on work, I’d now spread that drive out over all parts of my life. The ambition is still there! I’m relieved.

Yet, I can’t say if I’m on the road that’s less travelled because I can’t clearly see the road ahead of me.

SO what’s the verdict? LOVE IT!

LOVE IT!

Go ahead, stare your dreams right in the face. If I can handle it, I KNOW you can.