Rejection is not that scary

When I was in college, if you wanted to go out with a girl, you had to ask them in person (this was pre dating apps).

The scariest scenarios were the ones in which you were in a public setting like a bar and didn't know the girl. Just go up to a stranger and introduce yourself and ask them for a number? That is crazy.

Because it was so scary, I didn't do it very much, and when I did, I had a 99% rejection rate. I don't know why 1% of the time it worked but I attribute it to alcohol induced confidence. Otherwise this technique seems to only work for very good looking guys who can overcome the creepiness factor.

However, I had a much better success rate when I asked girls out when I already had some sort of commonality with them. Perhaps a shared class or a mutual friend.

Most importantly, asking them out was less scary because it was no big deal if they said no. The girl would give me some reason that spared my feelings or helped me save face "oh I'm not looking to date right now" or something to that effect.

Going 1099 is more like the latter situation. You're not just going up to random companies and asking them for a 1099 gig. You cultivate relationships over time, have discussions about mutual interests and contacts, and then you "ask them out."

The rejection is usually analogous to the "I'm not looking to date anyone now" rejection. The PM will just say "sorry by policy we only hire W2s" or "we aren't allowed to bring on 1099s."

No big deal.

So if you're very nervous about asking the prime for a 1099 date, I'm here to tell you it's not actually that scary. You'll have lots of chances to establish a "friend" relationship before you ask them out. If they say no, you can still be friends.

Want the full playbook? Check out Going 1099.