Before becoming a freelancer I was in an interview for a full-time remote job. This is what Steven Pressfield in “Turning Pro” would call a shadow career…

I was interviewing for remote work after my partner and I decided we would move west to be closer to his work. He had work in Nashville, but the work that matters to him is out west.

It was meaningful work calling us to move, work that is important to both of us. Aside from a handful loving friends and my stable job, little was holding us in Nashville. 

I knew I didn’t want another 9-5, show up at the office after an icky commute type job. The commute, the politics, all of it, had worn me to my last scrap of tolerance.

I couldn’t go to a fluorescent box for 40+++hrs a week anymore, even though I loved my team.

I thought remote work for a flex-work friendly company was the answer..flexible schedule, safety net with benefits etc..I don’t even want to share how much of a pay cut I was willing to take for that freedom.

I had this interview set up, and it seemed very promising. Interesting projects, cool company etc. We had a great chat, even extending our meeting over the allotted time until my interviewer had another meeting.

Tons in common, great company culture, it seemed at the surface a great, safe bet. Then he dropped a bomb on me when he asked a (perhaps benign to him) question…

“With all your skills, why not start your own company?”


I scrambled to say maybe I would some day, I didn’t know where to start to do that, I came from a family who was not entreprenuerial and wasn’t open to that sort of risk….

Basically, I blew the question. The honest answer to that question would be that I hadn’t started out on my own because I was afraid.

I had allowed myself to be so crippled with fear that it made starting my own business seem out of reach. I (sort of) tried once, but I wasn’t able to see the light at the end of the tunnel, and got sucked right back into my old ways.

I was just too damn comfortable. I should probably have set the audiobook for the War of Art to my morning ringtone…maybe that would have gotten me out of bed with a bit less resistance ha!…actually, i wonder how you do that?

I am so thankful I finally realized what I was doing, as it freed me up to properly pursue a career as a freelancer.

I was terrified, to say the least. The future was uncertain, it was itchy and uncomfortable and I didn’t like that part.

This interaction made me realize what I was hiding from, and made me look my resistance square in the eye. I saw what my lizard brain was doing, and by recognizing it I took it’s power away.

I realized it’s not “what if I can’t”, it’s “what if I won’t”. I can (and did), but that hinged on a much more challenging thing than my own talents. It’s not about skills. It’s about showing up.

April 21, 2017 was my last day working for someone else in a corporate office. From that day on, I turned pro. 


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