Awkward 1099 situations

When I was converting my job into a 1099 gig, there were multiple situations that came up where I felt awkward or a little embarrassed.

Announcing my desire to become a 1099

Since I was converting my job, I had to tell my boss I wanted to go 1099. I e-mailed him to set up a meeting and then said something like "my career goals have shifted and I'd like to explore the option of going 1099." Not terrible, but when he said the inevitable "let's revisit this in a month" I said "okay" and then had to awkwardly pester him for the follow up every few weeks. Their stalling made me feel weird.

Negotiating

I pitched maybe $95/hour initially and they came back with $75. We settled on $85 but I awkwardly blurted out I'd like to take Fridays off. It was a weird thing to say because it still made me look like an employee. I could have been more tactful or smooth about it. I still got Fridays off, but it was a little cringe.

Admin ignorance

There were several times when I had to ask the sub-contract administrator at the company what basic administrative things were. I didn't know what the various types of business insurance were or how to format an invoice or understand their role in maintaining my security clearance. As someone who hates looking dumb, it was uncomfortable. This was all in my head though. They didn't care and I got my admin ducks in a row.

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You're going to feel awkward or uncomfortable many times in your pursuit of a 1099 gig. The fear of being awkward though is worse than the actual experience. Don't let it prevent you going 1099 and improving your life.

Want the full playbook? Check out Going 1099.