avatarDanny Wolf

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Abstract

e not getting the right answer, ask better questions. Insightful answers begin with insightful questions.</p><p id="5e63">I’ve interviewed a lot of people over the years. Some of them were celebrities, some were average joes. Over the course of several hundred interviews, I’ve gotten good at asking better questions. Here are some of my favorite questions to ask others and myself.</p><p id="89eb">These are not just great questions — they are exceptionally good at pulling out the essential insights about the person in the least amount of time. I call this information density.</p><h1 id="76a4">How do they handle the hard stuff?</h1><p id="4ae2">You can learn the most about how a person operates, thinks, and collaborates by exploring times when things didn’t go as planned. I want to see how they handle pressure, because you don’t really know a person until you’ve seen them struggling.</p><p id="96b5">Find out who they are when their ego gets bruised or challenged.</p><p id="03db">These questions aren’t just meant for interviews. You can use them on your spouse, as icebreakers at the bar and, most importantly, to learn more about the person you should know best: yourself.</p><p id="56b9"><b>What’s the hardest thing you’ve ever done?</b></p><p id="150e">I want to understand what hard means for them personally. I want to understand why it was hard and how they overcame adversity.</p><p id="1d00"><b>What’s the worst thing you’ve ever written?</b></p><p id="e8c4">I’m always looking for people to break this sort of “interview mindset.” Everyone always prepares for interviews, and then their entire conversation is predicting what they think I want them to say. So, I try my best to catch them off-guard.</p><p id="126d">Asking open-ended questions they can’t prepare for allows them to reveal personal truths that would otherwise be obscured by their mental self-defense mechanisms.</p><p id="d0b4"><b>What would you say is the greatest source of conflict in your life?</b></p><p id="272c">Everyone’s fighting for something. Which means they have to be fighting <i>against</i> something. Whether that be an idea, a belief, an obstacle to their success or something more personal like defeating their demons.</p><p id="7f92">What I’m looking for is: What are you willing to go to war over? As humans, we derive most of the meaning in our lives from conflict.</p><p id="e794"><b>What is your greatest fear?</b></p><p id="50ec">Men lie, fear does not. What a man fears is as close a look into his soul as you will get this side of mortality. Because we only fear what threatens the things we care most for. Are his fears selfish or selfless?</p><p id="e232"><b>When was the last time you were offended, and why?</b></p><p id="5a8d">This is a good litmus test of several things at once. It tells me how fragile their ego is, how thick their skin is and what their values are. We only get offended by things that attack what we value or believe in. I want to know what your sacred cows are.</p><p id="9d6b"><b>Who do you have blocked on social media (or Medium)?</b></p><p id="9cc3">What people are uncomfortable with, and why they are is critical to mapping out who they are. It gives me insight into what their barriers are and whether they live in an echo chamber.</p><p id="f62a"><b>What’s an unpopular opinion y

Options

ou hold?</b></p><p id="7eee">There’s no way to answer that question without being genuinely opinionated. Because it starts with ‘What is the thing that you think…?’ When I break that wall, I’m testing: Is this person authentic?</p><p id="54e7"><b><i>*Readers: Leave your answer to your favorite question in the comments.</i></b></p><p id="e42c">I’d like to leave off by paying tribute to some of my fellow scribes whose wit and wisdom have by turns influenced and inspired me. I highly recommend each and every one of them, so please go check them out. I promise you’ll only be disappointed that you hadn’t found them sooner. If you’re brave, go ask them some insightful questions.</p><p id="adf4"><b>For Big Ideas:</b></p><p id="e0a9"><a href="undefined">London Steinbeck</a>, <a href="undefined">Aure's Notes</a> and <a href="undefined">Cory Doctorow</a></p><p id="48c0">These gentlemen have some of the greatest insights to be found on the platform. They stimulate my critical thinking in ways that make for cerebral stories. This is where I go to get the 30,000-foot view.</p><p id="c769"><b>For business:</b></p><p id="7031"><a href="undefined">Michael Lim</a>, <a href="undefined">Evan Kelly</a> and <a href="undefined">Jamie Northrup - Minimalist Hustler</a></p><p id="ceff">If you’re trying to make money online, look no further. These three will teach you the systems and processes to break free from the 9-to-5, using newsletters, side hustles and niche expertise.</p><p id="4d5e"><b>For writing:</b></p><p id="11ea"><a href="undefined">Brandon Springer</a>, <a href="undefined">Cipher Max</a> and <a href="undefined">Ryan Canady</a></p><p id="c912">These men aren’t just some of my favorite writers on Medium, they’re also some of my favorite personalities. They’re the kind of guys I’d want to hang out with in the analog realm. Ryan is a kind soul, always looking for a way to help others. Max and Brandon are smartasses, kindred spirits. Their writing never fails to make me smile or laugh.</p><p id="b98e"><b>To remind me not to do too many drugs:</b></p><p id="0f50"><a href="undefined">Cindy Steinberg</a>, <a href="undefined">Jason Provencio</a> and <a href="undefined">Joe Exotic</a></p><p id="8aa4">I’m not sure if they have a humiliation kink or they’re just addicted to clicks. Sometimes it’s hard to tell if they’re being satirical or if they genuinely believe their own bullshit. Either way, I hope they never stop, because it’s goddamn entertaining.</p><h1 id="a9dd">Like what you’ve read?</h1><p id="be76">Invite the subscribe button out for a duck hunt with Dick Cheney to get all of my creative genius delivered straight to your spam folder.</p><div id="de4f" class="link-block"> <a href="https://medium.com/@danny.wolf/subscribe"> <div> <div> <h2>Get an email whenever Danny Wolf publishes.</h2> <div><h3>Get an email whenever Danny Wolf publishes. By signing up, you will create a Medium account if you don't already have…</h3></div> <div><p>medium.com</p></div> </div> <div> <div style="background-image: url(https://miro.readmedium.com/v2/resize:fit:320/0*MdG5tZdD-N2brjjl)"></div> </div> </div> </a> </div></article></body>

Your Ego is the Secret Ingredient You’ve Been Missing

Credit: Street Art by Hijack

Part of the reason many writers produce uninspired writing is because they try to leave their ego out of it. They force themselves to write using logic and facts alone, not realizing that wisdom is both emotional and intellectual.

Your passions are eternally tied to your ego. To kill one is to kill the other.

You need ego in everything, writing is no different. The key is balance. In all things, balance. An unchecked ego will grow bigger than the room it occupies, but the death of ego is spiritual suicide.

When we’re writing, we’re constantly making decisions. Which words to use, what style, how to segue into the next train of thought, etc. Not every decision has the gift of being subject purely to reason. Most of the important choices we’ll make rely on emotions, instincts and a dose of ego.

Sometimes it’s just about your ego. Sometimes it has to be. And that’s OK. Just recognize it and make sure you’re not being a hypocrite about it. And once you’ve made a decision, stand by it, no matter the consequences. One thing I learned by leading Marines overseas is this:

Outside the wire, there aren’t always good decisions. Just decisions.

If you can’t think of anything to say, get angry

We’re still dealing with the ego, as everything meaningful to you will attract the attention of your ego. Especially the things that can make you mad. Anger is the ego’s preferred weapon.

When you experience writer’s block, I want you to try this out. Think of something that irritates you or pisses you off. Then write about it until you feel better.

Rants come easily, and sometimes they lead to interesting places. I’ve had rants turn into smartass character dialogue or full-blown essays. You can’t be blocked up if you’re angry, just ask the trolls.

Let your inner cynic come out to play. If it makes you mad, it’s important to you. Which means it’s worth writing about. In fact, those are the things you need to be writing about.

A good speech and good writing are crafted much the same way. The thing being said matters less than the delivery. Words, whether written or spoken, only become compelling if they’re expressed with conviction.

The best writing must mean something to you, or it won’t mean anything to the reader. It must be about something you genuinely believe in. Everything else is just trying to sell something, even if the only thing being sold is your soul.

Creativity doesn’t like to be lonely

You have to be constantly engaging with other minds that challenge and inspire you or your creativity will suffer. Surround yourself with other egos that share your passions. One way to do this is to interview other thinkers and writers. But a word of warning here, interviews live and die by the questions asked.

If you’re not getting the right answer, ask better questions. Insightful answers begin with insightful questions.

I’ve interviewed a lot of people over the years. Some of them were celebrities, some were average joes. Over the course of several hundred interviews, I’ve gotten good at asking better questions. Here are some of my favorite questions to ask others and myself.

These are not just great questions — they are exceptionally good at pulling out the essential insights about the person in the least amount of time. I call this information density.

How do they handle the hard stuff?

You can learn the most about how a person operates, thinks, and collaborates by exploring times when things didn’t go as planned. I want to see how they handle pressure, because you don’t really know a person until you’ve seen them struggling.

Find out who they are when their ego gets bruised or challenged.

These questions aren’t just meant for interviews. You can use them on your spouse, as icebreakers at the bar and, most importantly, to learn more about the person you should know best: yourself.

What’s the hardest thing you’ve ever done?

I want to understand what hard means for them personally. I want to understand why it was hard and how they overcame adversity.

What’s the worst thing you’ve ever written?

I’m always looking for people to break this sort of “interview mindset.” Everyone always prepares for interviews, and then their entire conversation is predicting what they think I want them to say. So, I try my best to catch them off-guard.

Asking open-ended questions they can’t prepare for allows them to reveal personal truths that would otherwise be obscured by their mental self-defense mechanisms.

What would you say is the greatest source of conflict in your life?

Everyone’s fighting for something. Which means they have to be fighting against something. Whether that be an idea, a belief, an obstacle to their success or something more personal like defeating their demons.

What I’m looking for is: What are you willing to go to war over? As humans, we derive most of the meaning in our lives from conflict.

What is your greatest fear?

Men lie, fear does not. What a man fears is as close a look into his soul as you will get this side of mortality. Because we only fear what threatens the things we care most for. Are his fears selfish or selfless?

When was the last time you were offended, and why?

This is a good litmus test of several things at once. It tells me how fragile their ego is, how thick their skin is and what their values are. We only get offended by things that attack what we value or believe in. I want to know what your sacred cows are.

Who do you have blocked on social media (or Medium)?

What people are uncomfortable with, and why they are is critical to mapping out who they are. It gives me insight into what their barriers are and whether they live in an echo chamber.

What’s an unpopular opinion you hold?

There’s no way to answer that question without being genuinely opinionated. Because it starts with ‘What is the thing that you think…?’ When I break that wall, I’m testing: Is this person authentic?

*Readers: Leave your answer to your favorite question in the comments.

I’d like to leave off by paying tribute to some of my fellow scribes whose wit and wisdom have by turns influenced and inspired me. I highly recommend each and every one of them, so please go check them out. I promise you’ll only be disappointed that you hadn’t found them sooner. If you’re brave, go ask them some insightful questions.

For Big Ideas:

London Steinbeck, Aure's Notes and Cory Doctorow

These gentlemen have some of the greatest insights to be found on the platform. They stimulate my critical thinking in ways that make for cerebral stories. This is where I go to get the 30,000-foot view.

For business:

Michael Lim, Evan Kelly and Jamie Northrup - Minimalist Hustler

If you’re trying to make money online, look no further. These three will teach you the systems and processes to break free from the 9-to-5, using newsletters, side hustles and niche expertise.

For writing:

Brandon Springer, Cipher Max and Ryan Canady

These men aren’t just some of my favorite writers on Medium, they’re also some of my favorite personalities. They’re the kind of guys I’d want to hang out with in the analog realm. Ryan is a kind soul, always looking for a way to help others. Max and Brandon are smartasses, kindred spirits. Their writing never fails to make me smile or laugh.

To remind me not to do too many drugs:

Cindy Steinberg, Jason Provencio and Joe Exotic

I’m not sure if they have a humiliation kink or they’re just addicted to clicks. Sometimes it’s hard to tell if they’re being satirical or if they genuinely believe their own bullshit. Either way, I hope they never stop, because it’s goddamn entertaining.

Like what you’ve read?

Invite the subscribe button out for a duck hunt with Dick Cheney to get all of my creative genius delivered straight to your spam folder.

Writing
Writing On Medium
Mindset
Ego
Philosophy
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