Why you should stop asking busy professionals, “Can I pick your brain?”

If I had a crisp hundred dollar bill for every time someone stumbled uninvited with their muddied-up shoes into my email inbox asking the question “ Can I pick your brain?” I’d be able to close up shop at Honey Copy, retire from copywriting and move to some beach town in California and start a snow cone business.

No. I don’t hate aspiring writers for offering to buy me coffee in exchange for picking my brain — in part, because I once was an aspiring writer asking this same question to absurdly busy professionals who wouldn’t give me the fucking time of day — but this battered, bloodied and over-used question is in need of some serious revisions.

We’ll get to those revisions, here momentarily. But first, let’s discuss why this absurd question comes off entitled, presumptuous and unprofessional.

It’s not all that unlike asking someone if you can pick their nose.

For one, it sounds disgusting.

When someone asks me if they can pick my brain I can’t help but picture a gore-covered surgeon peering over the cracked open skull of a patient, rifling around with a pair of tweezers on a hunt for whatever it is he is hunting for.

You wouldn’t ask me if you could pick my nose, so don’t ask me if you can pick my brain. I’ve worked hard to add a few wrinkles to my brain, I don’t like visualizing others thumbing through it with a pair of white gloves.

You picking someone’s brain costs them moolah.

Asking to pick someone’s brain is a very big ask.

Most professionals you reach out to charge anywhere from $200 — $500 an hour for their time. So, when asking if you can pick their brain in exchange for a cup of coffee, what you’re really asking is… can I buy you a $5 cup of coffee in exchange for $200 — $500 worth of your time?

Does this not sound absolutely ludicrous to you? Because it sounds quite ludicrous to me.

It’s ambiguous and comes across as deceptive.

Picking someone’s brain can literally mean anything.

Do you want to work with me?

Do you want me to take a look at the rash on your thigh?

Do you want me to give you book recommendations?

Do you want me to donate to your charity?

The question is ambiguous and with this ambiguity comes an air of deception — and nobody’s cup of tea is feeling like they’re being deceived.

The vast majority of professional [fill in the blanks] I know prefer when people are upfront with them about their intentions. Don’t ask someone if you can pick their brain, ask them precisely why you are interested in meeting with them.

With that said, here’s how we can be better with the brain pickings.

Show them you’ve put in the time.

When asking for someone’s time, it’s imperative you show them you’ve put in the time and know a thing or two about them.

Over 6,000 people receive an email from me each week called Sticky Notes. Many of them email me and tell me it’s the only newsletter they read.

Do you know why this is?

Because for each email I send out, I invest 2–3 hours of time writing a damn good one. I recognize these 6,000+ people are giving me the most valuable asset in the world, their time… so I give my time too.

When reaching out to a professional, you should show them you’ve put in the time. Reference a podcast you listened to that they were interviewed on or an article they wrote that you very much enjoyed. Show them you’ve taken the time to understand their world and their work

Be specific.

It’s important to be specific.

Think: why, when and where.

Tell them why you’re wanting to meet.

Tell them when you’re wanting to meet.

Tell them where you’re wanting to meet.

“Can I pick your brain?”

That’s ambiguous.

“I’m an aspiring copywriter trying to decide if I should go the agency or freelance route and would love to hear any thoughts you have here.”

That’s not perfect. But, we’re getting somewhere.

Additionally, throw out a place and time you’d like to meet. If they can’t meet at that particular time and place, most of the time they will throw out a time and place they can.

But, simply asking someone if you can buy them coffee feels like a scheduling cluster-fuck.

Offer something of value.

A $5 cup of coffee isn’t valuable, creative or original. Most professionals can afford to buy their own cup of coffee.

Here are a few things that could potentially be a nice, valuable replacement for coffee…

  • If they’re a big reader, buy them a book off Amazon and ask them if you can ship it to them.
  • Offer to give them $100 in exchange for advice. Most professionals will say no, but it shows you value their time.
  • If you know of a highly-listened podcast they could be featured on, figure out a way to make a connection.

Most of the time, if you’re just starting out down a path or career, you don’t have anything of value to offer. So, you have to get clever.

This isn’t hard if you follow the person’s work closely.

For example, I’m a big fan of Noah Kagan and I know he loves street tacos. If I ever wanted to get some time with him, I’d probably have $200 worth of street tacos delivered to App Sumo’s headquarters for his team with a note inquiring about a short phone call.

Build relationships and have multiple conversations.

I’ve become friends (or at the very least acquaintances) with folks who follow Honey Copy.

Generally, the ones I’ve become friends with have emailed me on a handful of occasions with cool articles they think I might like, they’ve shared my work and they’ve even bought my copywriting guide.

They show up over and over again. So, eventually, when they do ask for a coffee hang or a phone call, it’s an easy yes.

So, don’t be afraid to play the long game.

With all that said, here’s an example of an email that I think will work wonders…

A beautiful alternative to “Can I pick your brain?”

I live in Chicago. So, let’s pretend I’m trying to get in touch with Jason Fried, the Founder and CEO of Basecamp. He also lives in Chicago.

Here’s what I know about Jason…

  • He loves watches.
  • He hates wasting time.
  • He wrote an incredible book called Rework.
  • He admires great writing.

Here’s the email I would write to him…

Subject Line:

I’ve sent a thousand watches your way.

Email Body:

Good morning Jason,

I’ve been following your work for the past three years as I’ve built my copywriting agency. Your book, Rework, has been a huge reason I’ve chosen to remain a small one-person shop rather than build something monstrous.

I know you adore watches, celebrate simplicity and admire good writing. That said, I’m sending two books your way.

The Watch Book, a massive beautifully designed book that depicts the world’s most wondrous timepieces.

And, a short simple book Elmore Leonard wrote years ago called 10 Rules of Writing. He was the greatest crime novelist to ever pick up a pen and shares a few gems I imagine you’ll appreciate.

I’ll follow up here in a couple weeks and see how you’re enjoying the reads. But, in the meantime, I have just one question…

Would you be open to me rewriting this landing page for you?

It’d be pretty badass to write for a company that has so deeply inspired my career, life and approach to work.



Fucking A.

Or, you could always just ask, “Can I pick your brain?”

But, I digress.

By Cole Schafer.

You gotta check this out — Sticky Notes is my email list reserved strictly for entrepreneurs and creatives looking to sell like a Florida Snow Cone Vendor on the hottest day of the year.

I write pretty words and sometimes sell things. https://coleschafer.com/subscribe

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