I was in the middle of a workout video recently when Jillian Michaels said “Pain is fear leaving the body.” I chuckled to myself, thinking about how people wear that on tshirts and how dumb of a thing it is to say. But then, and stick with me here, I realized that that sentence held a whole bunch of wisdom and that it was actually one of the most important lessons I’ve learned as a self-employed person.


I talked a little bit here before about confidence and how the only way to earn true confidence is to do the things in which we feel absolutely no confidence, and survive. When things don’t go as planned (practically always), we feel some pain – disappointment, shame, etc. – but then we look down and find that we’re intact. That is how fear dies. That is how confidence grows. See? Jillian Michaels might not be so silly after all.*

How does this fit into our conversation about money?  I have had countless planning meetings, where I sat down with a notebook and calculator and a business partner (or two) and figured out how we’re finally going to be making enough money for our parents to stop worrying. We’ve restructured and replanned and refocused the business model more times than I even remember and here’s the rub: We’ve never seen the numbers that we wrote down on those notebooks, the ones to give our parents and partners and selves peace of mind.

If I knew when we started that it would take over three years of running a business before I would make any money, then I would have said “Well, I can’t afford to do that.” If I knew when we started that we’d be over five years in and still only making about a half-time salary, I would have said “That sounds awful and I’m going back to corporate America, post haste.”

Here I stand, however, completely intact, having learned so incredibly much, built some of the most meaningful connections in my life, and having a pretty good idea of who I am and exactly what I’m capable of accomplishing. It hasn’t been easy. In fact, it’s been pretty fucking hard, but here’s the point of this whole post:

You are capable of infinitely more than you think you are, and that includes the amount of money that you need to live your life. If you want your own business, if you want to give your dream a try, if you want control of your life and time, but feel like the financial risk is too great, I challenge you to sit down with a calculator and a notebook and find a way that it’s not. Things probably won’t work out exactly as planned, but seeing how it’s possible might just be the permission you need to give it a shot.

*Give her 30 Day Shred a try and then see who’s silly.