Confessions of a Tired Entrepreneur

*stands up* My name is Luvvie and I’m a tired entrepreneur. Everyone: “Hi, Luvvie.”

When I got laid off my gig as a nonprofit Marketing Coordinator in April 2010, I planned on polishing my resumé and getting back in the game. That was almost three years ago and I haven’t had a regular 9-5 since the. By happenstance, here I am. A professional blogger, a social media strategist/trainer and someone running a national nonprofit.

It’s been a DOPE journey getting to where I am today. The glitz and glamour’s been awesome, the perks and prizes are great but the grind and pain to get there has been tough. The hours I’ve put in and the sacrifices I’ve made are numerous.

I love being my own boss. It’s pretty gahtdamb awesome. I get to set my own hours. I can take a long nap through lunch. I don’t have to sit through meetings I don’t want to. Plus my work alphet are pajamas, often with random holes in them because the more pitiful they look, the more comfortable they probably are. And since I’m in the digital space, new gadgets and macbooks are tax write-offs. But a lot of times, I also get stuff sent my way. THREE TABLETS, FTW!

I’ve been to the Academy Awards to do red carpet coverage and I’ve stood in front of a room with Barbara Walters, Anne Hathaway, and Gloria Steinem to accept an award. I’ve appeared in a magazine that I grew up reading. My name is in the Congressional Records of the U.S. House of Representatives recognizing the activism work I do.

BEING MY OWN BOSS! FUCK YEAH. It’s AWESOME. Except when it’s not.

Those lunch time naps I take? They’re because I only slept 3 hours the night before. The new MacBook I had to buy? It’s because my old one crashed since I use it 16-18 hours a day. It basically quit life and I don’t blame it. Too bad it threw a $1,500 wrench in my already too-small budget. OUCH. And when I had the flu right after Christmas? I just had to recover under blankets and avoid WebMD lest they diagnose me with terminal toe cancer in the throat. INSURANCE IS FOR RICH (read: regular) PEOPLE WITH W2s AND 401(k)s. Me? I just sail on a wing and a prayer and hope anything I come down with can be fixed with gulps of Simply Lemonade and almond milk (when I’m feeling fancy).

I’ve been working for myself for almost three years and I’m exhausted.

At least once a week, I’m tempted to #OccupyLinkedIn and look for a job as a Director of Communications or Vice President of Digital Marketing at some company with a nice logo and name and allow them to tempt me with a 6-figure salary that includes full benefits and perks like monthly massages at staff lunches and Bring your Pet to work day, even though I don’t have a pet.

I realize that if I was doing any of the THREE things I do right now (write, social media stuff, or running a nonprofit) on a full-time basis for some company, I’d probably be making three times what I do now. I’d be rocking t-shirts that says “Balling is a habit, get like me.” Instead, I’m spending too much of my time chasing folks who think invoices are “pay when you feel like it” notices. I wish I could send an invoice for the time spent chasing down money from unpaid invoices. Womp!

Working for yourself puts a lot of pressure on your shoulders, and there are times when I want to be able to fail on someone else’s dime.

The fear of failure is what keeps me up at night. Because if I don’t secure clients, how do I eat and pay my bills? While most folks are in bed, I’m up wondering why my to-do list is mostly in red because I’ve missed too many of the deadlines I’ve set for myself. And I’m justifying my staying awake to the fact that I need to finish at least one more task. And then when I go to bed, I’m laying there thinking about more things I DIDN’T do.

And weekends off? HA! You mean I should go Friday through Monday without doing ANY work? HAVE YOU SEEN MY TO-DO LIST? Have you seen that checklist that gives me fake self-importance and more bullet points than a polka dot pattern??? I can do no such thing! Maybe Friday night. And some of Saturday. BUT I MUST DO ALL THE WORK. ALL THE WORK. I have no balance.

It’s an endless cycle of unfulfilled expectations, to-do lists and insomnia. And this is why I walk around with dark circles under my eyes that would make raccoons feel like I’m swagger-jacking. Thank Jesus for the invention of tinted moisturizer because I can do all photoshoots and stuff through Laura Mercier Mocha, which strengthens me and evens my skin tone.

Entrepreneurship is hard.