It’s been three long years of procrastination, coming up with every lame excuse to avoid my least-favorite meeting. I’m too busy, I thought. It’s not really important. I’ll get to it after I take care of other things.

Finally, I did it. I survived a visit to the dentist.

When you’re the one in charge, who kicks your butt when fear or procrastination run rampant? Who helps you fire the sweet-yet-unproductive employee? Who insists you meet with an intimidating customer? Who makes you cut loose an unprofitable product line? And who nags you to get a mammogram or go to the dentist? Here’s how you can make sure the right people are bossing the boss.


I really hate going to the dentist. The sound of an ultrasonic cleaning tool or drill causes my panic to rise, and tears as well. The dentist and hygienists were always kind. The problem was the receptionist. Rather than make me more relaxed about the experience, “Dee’s” war-dialing reminders and phony, sadistic smile invoked a visceral reaction. I wanted to smack the smile off her face and tell her to get the hell off my back. So instead of avoiding dentistry altogether, I just needed to make sure I never had to face Dee again.

Lesson: Figure out exactly what needs to change for you to avoiding something you really need to do.

Reach Out

When the going gets tough, enlist a family member, close friend, colleague, mentor or employee to hold your feet to the fire. The bossier the better. Find someone who will keep you accountable and apply the right level of pressure. My employees know about my dental phobia and lovingly send nudges with a healthy dose of humor. When I’m too chicken to make a key business decision, my professional mentor will ask, “So, how’s that working for you?”

Lesson: Trust others to care about you, even when you don’t care enough yourself.


When I decided I did want to keep my teeth, I turned to Yelp to help me find a local dentist who compassionately catered to wimps. I had a wonderful chat with the dentist who patiently listened to my fears. My first cleaning in three years wasn’t nearly as traumatic with her delightful staff and noise-cancelling headphones playing the Bruno Mars Pandora channel.

Lesson: You always have options. Look around, identify a few alternatives, and act on them.


Being the boss is mostly thankless and fraught with fear. When you do step outside your comfort zone and into new territory -- be it a new dentist, an aggressive revenue target or a new business venture -- stop and celebrate. After the successful appointment with the dentist I treated myself to a lovely sushi dinner, ever so grateful I still had my teeth. My company is celebrating a much bigger achievement: After 15 years of profitable growth in a volatile economy, I’m taking my team on a Disney Cruise.

Lesson: Find something that makes you happy and use that as a carrot to move past the crappy. 

Being an entrepreneur requires great focus and relentless dedication. You manage everyone else, making sure they’re healthy and productive, but every boss needs someone bossy to help them when they’re losing perspective.

When tackling the things you hate the most, acknowledge your weaknesses, enlist a friend who cares enough to bug you, find reasonable options and then savor the satisfaction when you finally, finally check it off your list.

Pick one and go. Now!