Blogging is not my first venture into entrepreneurship.

From the occasional lemonade stand set up as a kid to a brief stint as a personal trainer as a young adult I’ve had a slew of entrepreneurial endeavors that failed due to one common weakness… I suck at selling.

I can’t decide which is worse- the interruptive approach, the pushy pitch or that awkward moment after finally spitting out price, standing there in silence, nervously awaiting a response.

In theory, I have nothing wrong with selling. It’s necessary and fair for people to be compensated for the services they provide. I just don’t want to do it.

As a wannabe power entrepreneur though, I knew I was going to have to get over my self-consciousness and fear of “the sell” if I wanted to succeed.

Why I Suck at Selling

In reflecting on what made me so uncomfortable in pitching products and services, I realized what was giving me that oh so awkward feeling that made me want to jump out of my own skin. It wasn’t a lack of value or belief in what I was providing, it was an understanding and empathy for the reality of the limited resources of the people to whom I was selling.

The product and services I was pitching were certainly worth $20 or $40, but knowing how much of a difference that $20 or $40 could make in someone’s budget made me feel guilty about denying them any penny of it.

I know the mega sellers out there probably read that and cringe, seeing as it goes against every “you’re worth it” credo in the book- but being honest with myself about how much I hated and sucked at selling is what allowed me to find a new model of entrepreneurship where I could confidently ask for what I was worth.

Finding Success

Recognizing that my biggest hang up in successful selling was the guilt I felt over asking for a small piece of limited individual resources, I started adjusting my model to target those with bigger resource pools- corporations. And it worked. My anxiety over pitching and selling practically vanished overnight.

To confidently ask for what I wanted, I had to find an audience that both needed my services and could more than afford to compensate me for them. When I made that adjustment I found that not only did my anxiety over pitching disappear, I felt empowered to negotiate too- doubling, tripling, even quadrupling my rates in record time without hesitation or any semblance of guilt.

Rather than beating myself up over sucking at selling or continuing to make myself feel uncomfortable on a daily basis, I adjusted my approach to find a model of entrepreneurship that worked for me. Turns out, I’m actually pretty awesome at selling, but only to the right audience.

Selling in Progress

I still feel uncomfortable selling products to individuals (like my book, even though I know people get way more value out of it than the negligible list price). So I’m working on it- learning to say $10 or $20 aloud without apologizing for myself. (Let me practice… buy my book!)

In the meantime, I’ve found a system for the bread and butter of my business that’s working for me- affording me the chance to flex my entrepreneurial muscles through freelance writing, while continuing to provide value to everyone who made it possible free of charge.