I’ll feel like a legitimate business owner when…

Bren had been self-employed for three years, but she still didn’t have a website and she rarely told people that she was a freelancer. When we first met, she said she didn’t identify as a freelancer yet. In her mind, she would be able to say she was legitimately self-employed when:

• People came to her with work, rather than her pitching and sending proposals.
• She had enough work to comfortably pay her quarterly taxes without being stressed.
• She opened up an LLC.

In other words, Bren was waiting to feel legitimate. The first hang-up was huge for her: She imagined that eventually, after she’d done good enough work for long enough, people would start to approach her with work. She wouldn’t have to market herself at all. No more pitching! This would mean she had finally made it.

But this hang-up was keeping Bren from showing up as a professional. When people looked her up online, they struggled to figure out what she did. Who was she? What services did she offer? Often, she was losing out on work because people didn’t think she was a legitimate professional. Her doubts had become a self-fulfilling prophecy.

Bren was also waiting for someone else to bestow value onto her. In other words, she felt like eventually, someone else would decide…