A playbook for asking for things you hadn’t thought to ask for
I was shy and limited in my perspective for the first twenty years of my life. Whether it was college (I only applied to mid-tier institutions within 200 miles) or my dating life (my criteria for women was if they liked me, not if I was attracted to them), I took what I was given and never thought about anything beyond. My worldview left no room for top-tier schools or romantic partners that were not already into me.
My junior year in college, I went to Spain as part of a study abroad program where I was the only student from my school. An epiphany hit me: no one knows me here. What if I reinvented myself? What if I went after what seemed out of reach? If it’s a trainwreck, I’ll never see these people again.
The Experiment
Thus began the experiment. There were two parts: a) do your best impression of a confident person and b) ask for whatever you want. Sure, at first, putting on a confident demeanor felt like wearing clothes that didn’t fit. But within two weeks, I was captain of a basketball team and the most beautiful girl in the program was hitting on me.
I operated outside of my comfort zone and nothing disastrous happened. No one found me out. I would never return to my previous mental state—shy, reserved, and taking what I’d been given.
The Big Ask
MBAs, psychopaths, and natural-born salespeople are experts at making the big ask. A position outside of their experience level, the phone number of someone out of their league, free guac at Chipotle, things that others would never consider possible, they do with aplomb.
In Spain, I became someone who asks for more. This change was the first domino falling towards later wins, from winning over the love of my life, getting paid speaking gigs in four countries, and talking the University of Texas into making me a professor.
This piece is a playbook for people who have never considered asking for more. Don’t worry if you don’t feel ready. You don’t need the right mindset to take action. Rather, taking action propagates the right mindset. You find the right mindset by plowing ahead.
When I started exploring this idea, I lowered the stakes. While I wasn’t excited about getting rejected, I felt much better about it happening in front of no one I knew. Sometimes I would visualize friends and family members who had my back in case an interaction went poorly.
Hearing the word no is the worst thing that can happen. Over time, that word will bounce right off. Eventually, you will reach a point where if you’re not hearing no enough it’s an indicator you have become complacent. The worst L is taking no L’s.
Here are four actionable steps to get the ball rolling:
1. Ask without Words
I have a friend who’s family had a telling tradition. Every five years, her dad dressed the family in rags and drove to the dealership. Dressing every member of the family in shoddy, worn out clothes gave her father ammunition to make a big ask: “Look at my family,” he would say. “You have to take more off of the price.”
2. Ask Nicely
Nobel prize winning researchers Daniel Kahneman and Amos Tversky discovered that as much as we would like to believe we are driven by reason, the chimp-evolved part of our brain is in the driver’s seat.
We are swayed by factors outside of facts-driven analysis: a warm smile, a charismatic voice, a welcoming personality. They all sway big asks closer to a yes. Learning how to convey warmth and friendliness will serve you well.
3. Downplay the Ask
After making hundreds of asks for things I had no business asking for, I have found that prefacing my words with “I know this is a bit much to ask for, but…” increases the chances of getting a yes. It’s a magic phrase that gives you permission to ask for whatever the hell you want.
This preface works because it signals self-awareness. Idiots and uncool people are not self-aware. If you demonstrate self-awareness, you must be in the category of savvy and cool people. And this category tends to get what they ask for.
4. Skip the Ask
A friend of mine asked me to help him draft an email to platinum-selling musician Jack White. Jack’s tour was coming through his town. My friend was asking if they could meet up in hopes of eventually working together.
Ugh.
That’s a terrible ask. Vague. Non-specific. My friend is a badass leather goods maker. He makes stunning leather jackets. I advised him to shift to a strategy to not ask for anything but instead, communicate that he was doing a favor for Jack. He would make a custom jacket and instead of asking for a meeting, let Jack’s people know he wanted to present it to Jack as a thank you for the amazing music he gave the world.
Months later when Jack came through town, Jack wore the jacket during his set. He shouted out my friend’s brand and posted it on instagram. One of Jack’s collaborators inquired about working together (full story here).
Asking is waiting for permission. You don’t always need to ask.
Order Off-menu
When you go to a restaurant, you read the menu and decide what you want. That menu, however, is only a fraction of the things that could come out of that kitchen.
Those chefs could make so many more amazing dishes than what the menu allows. Hell, some of them would enjoy making something new and different.
Ordering off the menu comes down to four things: ask without words, ask nicely, downplay the ask, and skip the ask. Now get out there and see what that kitchen is capable of.
Once you decide you want to ask for more, it’s wise to learn video. An ask made over video beats an email ask every time. Why? because video has facial expressions, voice, and feeling. Learn the art of video in the upcoming cohort of my course Minimum Viable Video.
Thanks to early readers: Jon Vasquez, Steven Foster, Charlie Bleecker, Sarah Jane, Ee Xin Wong, Chris Wong, Latham Turner