How a Barista and Losing a Quarter of a Million Bucks Taught Me to Ask for What I Want

Most people do not know what they want.

The other day at Starbucks, I watched the person in front of me get smoothly upsold from a cup of coffee to a $20 tea sampler set.

I’m not saying that the guy was pressured into buying it; he wasn’t. I’m not saying that he got ripped off; he didn’t. On the whole, he looked pretty happy about his purchase as he left.

But he came in for a cup of coffee, and the chances of him seeing and then buying that sampler set were almost nil. Until he was asked.

You have to ask for what you want. And a surprisingly high percentage of the time, you’ll get it. Maybe not high in the sense of 80% or 90% (though you might, depending on the circumstances), but getting what you want 10% of the time is better than getting it 0% of the time, especially when all it took was you asking.

This is similar to the maxim that if you want to date supermodels you need to be where they are. That’s necessary but not sufficient. You also need to ask them out. Talk to any practitioner of “the game” and they’ll tell you it’s a numbers game and if you have zero going into the top of the funnel because you’re not asking, you’ll get zero in return.

Yes, this is kind of a ridiculously simple observation.

And yet we don’t do it. We don’t.

Most people don’t really negotiate for their salary. Do you know how much simply asking for more is worth in this situation? (BTW, here’s a fantastic post on how to do it right).

I did it too; my first job offer out of college was at a large tech company, and I took the salary they offered without pushing back. That was incredibly stupid of me. I could have easily landed 10% more by pushing back a little. As it was, it took me almost a year to wrangle the 10% raise I should have had from the beginning. That’s thousands of dollars of income that is lost, forever. If I had simply asked for more, I would have gotten it. Let’s say I then put that raise into my retirement account (which I was severely underinvesting in at that time). By retirement, that would be worth a quarter of a million dollars.


For not saying the words: “Based on my research, this position is worth closer to $X”.

Decide what you want. And then start asking for it.