Ask people to give you what you want

In December 2009, Patrick McKenzie invited Thomas Ptacek out to coffee in Chicago. This was unusual for Patrick, because he wasn’t comfortable writing cold emails at the time. While Patrick’s original intention was to gossip about Hacker News threads—they were the top two users by karma points—the conversation shifted to Thomas asking Patrick about SEO and content. Patrick writes, “It was, seriously, the most fun I had all year.”

At the end of the conversation, Thomas—who ran a very successful consulting company—said, “Some food for thought: If this hadn’t been a coffee date, but rather a consulting engagement, I’d be writing you a check right now….I got at least $15,000 of value out of this conversation.” Patrick was working as a programmer at a large Japanese company, and he figured that an intermediate programmer might be able to charge $100 per hour—so Thomas’s idea blew his mind. 

Thomas’s co-worker reinforced his claim, saying they would need a write-up for $15,000—but there was probably $5,000 in the petty cash drawer for the session. (Patrick writes that within two weeks, Thomas’s company did make $15,000 on his advice.)

Sometimes, it takes somebody else giving you permission—in this case, Thomas giving permission to Patrick to send a quote—in order to build your confidence up enough to get you to take action. When somebody decides to do this, they are giving you a gift—don’t dismiss the idea, keep it in mind. At least make a simple plan for what you could do with it.

Several months later, Patrick started consulting. He was still wrestling with his confidence issues—“the doubt monster”—and he experienced another breakthrough sending his first quote:

“I typed a number, agonized over it for ten minutes, then typed a number 50% higher, then curled up in the fetal position for a few minutes, then impulsively hit Send and started hyperventilating. Ten minutes later I got an email back and, to my enduring surprise, they did not hate my guts for picking that number that was 50% bigger than a number I was already barely comfortable with.”

While Patrick started off consulting for $100 an hour to gain experience, by the end of his consulting work he was billing $30,000 per week.

Patrick’s greatest realization was that he would experience discomfort, it was very unlikely the other person would dislike him for sending cold emails out to new people or sending a higher quote. He writes, “Get comfortable with sending email to people and asking them to give you what you want…. I still have a ways to go to do it routinely, but it gets easier every time I do it. Definitely explain to them why giving you what you want is in their interest, but ask.” 

When you ask people to give you what you want, you start to realize that your goals may not be as out of your reach as you think. You may not get it right away, or in the way that you wish, but you’ll be making progress. You may realize that you not only are capable of it, but that you and your skills deserve it. Maybe you just need to pick up some additional skills along the way.

If you don’t play, you’ll never win. And if you don’t ask, you’ll never know.

P.S., Patrick has documented his experiences well—a summary of his conversation with Thomas, a couple of conversations about psychology, and a newsletter on the topic

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