They’re Gonna Hate Me for This…. One Simple Trick to Bother Important People

In my recent post, I talked about my advice addiction and tendency to bug people like Ryan Holiday.
In that post I make it seem shocking that Ryan would reply to me. But, I’m a fraud. It’s actually not difficult at all.
Before you read any further keep this in mind: ADVICE IS NOT THE ANSWER it won’t help you.
When you bother your idols for advice only a few things happen.
1. Once you start you can’t stop (it’s crack).
2. You’ll get information overload and decision fatigue.
3. You’ll piss off and annoy the people you admire.
In J.D. Salinger’s novel, The Catcher in the Rye. Holden Caulfield says this,
“What really knocks me out is a book that, when you’re all done reading it, you wish the author that wrote it was a terrific friend of yours and you could call him up on the phone whenever you felt like it. That doesn’t happen much, though.”
Holden is spot on. This never happens. J.D. Salinger was a known recluse in his own right. So, seriously leave your idols alone.
But if you insist, here’s how you can get in touch with almost anyone.
Just follow these two rules before you even think about flooding the inbox of every author you know.
Rule One: You’re already wasting their time. So if you must reach out to those more important than yourself have good questions.
Don’t ask anything that you could’ve found out using google for an hour. Don’t ask questions they’re not suited to answer. And, don’t ask them more than three questions in any given exchange.
Rule Two: This trick doesn’t work for everyone. Tim Ferriss has written at length about his hatred of Email. If Salinger was still alive he wouldn’t be refreshing his inbox to answer your questions. Pick your battles.
Now that you’ve got it narrowed down to a few candidates you’d like to pester, there’s one simple trick to get a response out of them.
Are you ready?
Sign up for their email lists. It’s dead simple.
When I emailed Ryan Holiday it was right after I saw a tweet about his email list. I signed up for it, he sent out the generic welcome message, and I’ve been bugging him ever since.
He’s not the only one either, which leads me to my next suggestion.
If you’re going to ask a busy person for their advice. If you must dig at them for pearls of wisdom. Do them a favor and act on their advice.
Recently I received my income taxes and couldn’t decide what to do with the sudden extra cash. I wanted to be smart about it so I immediately tracked down an expert. I saw that they had an email list, and pinged them for advice.
I emailed Ramit Sethi, author of I Will Teach You to be Rich.
Me: “Hey, Ramit. I just got my income taxes in and I’m wondering- what’s the best thing to do with 1000 dollars?”
Ramit: “Read my book pls.”
I deserved that answer. I broke rule one. I messaged a money guru before ever reading his book.
I immediately purchased his book on iBooks for about ten bucks. After the first hundred or so pages I decided to pay off a big chunk of my student loans.
There. Now you know how to aggravate high profile celebrities in a matter of minutes. It’s more effective than twitter and as addictive as street drugs.
Sorry guys. I’m an addict.
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My name is Billy and I’m Addicted to Advice … and It Made Me Do Something Crazy.


If AA is for anonymous alcoholics then I should start a new support group. AAA, Advice Addicts Anonymous. I’m not here to poke fun at addiction. I’m truly addicted to advice.
I subscribe to advice riddled podcasts and YouTube channels. I buy a new book that will “change my life”, every week- I’ve even been known to dish out advice from time to time.
The worst part is, I’m incapable of following any of it. Why? Because I’m an addict. I need my fix. If I listen to the sage wisdom of one person and follow through with it, where will I find the time to pester others for help?
I’ve got a handful of mentors, friends, and family that all put up with my constant, “Woe is me, I don’t know what to do” SOSs. I even bother busy people who don’t even know me for advice.
Recently I was wrestling with a personal dilemma; deciding if I should go back to college or pay off the debts of my first failed attempt. So I did something crazy.
I sent an email to Ryan Holiday.
Ryan Holiday is a best-selling author. He wrote The Obstacle is the Way, Ego is the Enemy, Trust Me I’m Lying, and a few other great books. He’s been on the Tim Ferriss Show, The School of Greatness Podcast, and London Real.
What was I thinking? Ryan Holiday wouldn’t reply to me… Except, he did.
First I asked him if I should go back to school for writing and he replied stoically, “Writing programs are generally a waste of time…” and he sent me a link to his article, So You Want to be a Writer? That’s Mistake #1. In which he outlines the idea that you should only write once you have something to say.
I didn’t even take the time to be grateful that he’d replied. Instead, I shot back (somewhat hurt) with another question.
I asked him how to live a life worth writing about.
“Go live an interesting life. Go do stuff.” That was his response, two short sentences that totally rocked my world.
“That’s not an answer!” I thought to myself. “He has to give me real advice!”
I was wrong on both counts. That was real advice, and he didn’t owe me anything. It just wasn’t the advice I wanted to hear. Living an interesting life sounds so impossible. I wanted a quick fix, some life hack, or some book to read that I could use to manipulate my way to success.
After I’d calmed down I thought about some of my own advice I’d dished out months prior on Instagram. “The best advice is never the quick fix, but instead the obvious, yet never easy dose of hard work.”


I’m addicted to advice and I’m terrible at taking it. I couldn’t take Ryan’s advice, I couldn’t even take my own advice on the subject of advice. But I’m trying.
Since my brief conversation with Ryan, I have yet to put writing on hold. I have, however, been trying to “go do things”, by going on more adventures with friends, (we saw the world’s largest fork). I’m also trying to take advice more seriously by putting it into practice.

“If [more] information was the answer, then we’d all be billionaires with perfect abs.”
-Derek Sivers (From Tools of Titans by Tim Ferriss)

It’s safe to say the same thing about advice. If advice was the answer we’d only have to ask for it once.

If you LOVED this post please share it. If you didn’t absolutely love it-tell me why.