If You Want Uncommon Clarity, Ask Yourself Uncommonly Specific Questions

Being successful requires saying no to the wrong things — the wrong money, wrong relationships, and wrong life choices.

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“Life punishes the vague and rewards the specific ask.” —Tim Ferriss

Very few people have true clarity on the most important things in their life — who they are, where they’re going, how they’re getting there. As a result, most people’s lives are often a jumble of priorities and possibilities, with nothing really getting the lion’s share of your attention and focus.

And when everything is a priority, nothing is.

The problem is that people aren’t asking themselves the right questions (or even asking themselves questions at all). And when you ask yourself vague, unhelpful questions, you won’t see any meaningful progress. Your life will reward specific asks — it will also punish vague ones.

The great opera singer Robert Brault once said: “We are kept from our goal not by obstacles but by a clear path to a lesser goal.” In the end, you’ll usually follow the path that is most clear.

Therefore, a little more clarity might lead you to an entirely different destination. The problem isn’t the obstacles; there will always be obstacles to overcome. No — the problem is largely your lack of clarity. And if you want an uncommon level of clarity, you need to start asking yourself uncommonly specific questions.

You Will Follow the Path That is Most Clear

I’ve been going to therapy and counseling for many years. I’ve met many people and heard many stories of how their lives fell apart. One of the most common reasons is simple:

They followed the path that was the most clear — even if it was a terrible path.

Nobody wants to be stuck in a dead-end job with mediocre relationships, low income, and few prospects. But for many people, that was all they knew. They didn’t ask themselves specific questions — they weren’t present — with where their life was going. And when you go on autopilot, there’s no telling where you’ll end up.

I’ve met more people than I can remember who have stayed in horrible jobs for years too long, just because they didn’t really know what else to do. They never asked themselves specific, focused questions. It wasn’t that they weren’t capable or competent — they were just directionless. They followed the path that was the most clear.

You will usually follow the path that is the most clear. It’s on you to make sure it’s a good path that’s taking you in the right direction.

I can relate. I worked a corporate desk job for years, all the while trying to achieve my real goal — to “be a writer.”

The problem was, I never really knew what that meant. Should I be a blogger? Or maybe an author? How do I become a “New York Times best-selling author”? Is that even what I want? I never really answered these questions, so I spent years chasing all kinds of clashing goals. After nearly 5 years of this, I had gotten nowhere.

Finally, I started asking myself uncommonly specific questions — about my work, relationships, and where my life was heading. I got more and more clarity, and doubled down on my work. Success came — in less than 12 months, I built a personal writing business, got a book deal, and quit my job to work for myself.

None of that would’ve happened if I didn’t ask myself specific questions that revealed who I was and what I wanted to be.

You’ll follow the path that is the most clear. Make sure you’re on the right path.

The More Clarity You Have, the Easier It Is to Say No

Being successful requires saying no to the wrong things — the wrong money, wrong relationships, and wrong life choices.

People are unhappy in large part because they are confused about what is valuable,” wrote William Irvine. When you spend most of your time and energy on the “wrong” things, you end up unhappy and unfulfilled.

A lot of people are making the “wrong” kind of money right now.

The wrong money is any money earned while doing tasks that are irrelevant to your Big Goals.

Wrong money is abundant. It’s everywhere. Ironically, it becomes especially abundant when you finally start to take a few steps towards that which matters most.

It’s funny — when I was unemployed and not-funny-anymore-broke for 6 straight months, money was nowhere to be found. I would have done any job for grocery money.

But now that I’m finally making progress in my personal business, wrong money requests come in every day.

I had to freeze my coaching services because I’m getting too many client requests and I want to focus on writing. Magazines, websites, and publishers email me constantly asking if they can pay me. Gigs, jobs, projects, and opportunities are flooding my inbox.

I’ve said no to all of them because it was the wrong money.

The wrong money leads you to mediocrity. And I won’t tolerate mediocrity.

Here’s How to Start Living a Powerfully Fulfilling Life

It’s a funny thing — it actually takes about the same amount of energy to sustain a mediocre life as it does to build an incredibly fulfilling one.

If you want to have a powerfully fulfilling life, you just need to do one thing:

Stop making excuses for your limiting behavior. It’s time to get more specific with what you want, who you are, and where you’re going.

Your choices are extremely powerful. If you make mediocre choices, you’ll get mediocre results. But if you start making world-class choices, you can expect to see world-class success.

Most people waste untold amounts of energy justifying bad behaviors. It’s exhausting constantly ignoring the voice of the real you, sternly reminding you this is not what we’re supposed to be doing.

Best-selling author Darren Hardy once said:

Nothing creates more stress than when our actions and behaviors aren’t congruent with our values.

It’s hard enough to start creating a new, successful life. You can’t keep wasting precious energy practicing negative behaviors that keep you in mediocrity.

If you want to change your life, you need to stop sabotaging yourself by making poor choices — or not even thinking about your choices at all.

Choose to be as clear as you can with your language. Once you’re able to identify what’s truly going on in your life, you can make better decisions and follow better paths.

Ask Yourself “Why” 5 Times

I first about this principle from Mike Maples Jr., a partner at Floodgate, a venture capital firm. When he feels overwhelmed or unfocused, he asks himself “why” 5 times. After the 5th “why,” he can usually pinpoint what’s going on in his life.

I’ve applied this to my own life, with incredible results. For instance: the other day, our little puppy was driving me crazy and I was having a bad day. Then, I applied the “5 Why’s” principle:

Q: Why am I upset?

A: My puppy is driving me crazy.

Q: Why?

A: Maybe she’s tired, or perhaps she’s acting out because of the new medicine we’re giving her.

Q: Why am I still upset?

A: I don’t know. Maybe I’m overreacting. I also didn’t sleep a lot last night, so I’m also very tired.

Q: Why?

A: I traveled this weekend. Maybe I need to take a break from my puppy — we’re both tired, and it’s not productive to be mad. Maybe I need to take a nap.

I only needed 4 why’s to figure out what was going on — I was tired and needed a break. So I put my puppy to bed and I laid down and watched some TV. I felt a lot better. Asking myself those why’s broke the cycle of I’m-angry-and-I-don’t-know-why, and got me to a more productive state (I’m sure my puppy appreciated it, too! …I mean, she better have.)

Get to the bottom of why you’re feeling what you’re feeling.


My 2-year old niece Izzy is the cutest little girl in the whole world. Her mom (my sister) told me that something incredible happens during Izzy’s occasional temper tantrum.

Whenever Izzy is acting out, my sister asks her, “Izzy, what are you feeling?

And then a miracle happens — Izzy identifies why she’s upset.

I’m sad, mommy” she might say. “Mommy, I’m just tired.” Or maybe “Mommy, I’m hungry.

It’s funny how few adults are able to articulate these emotions. They might be acting out — in their relationships, at work, or even home alone — and they don’t recognize the reason for their behavior. They don’t understand it’s because they’re sad, or tired, or even just hungry.

If you want uncommon clarity in your life, it’s time to start asking yourself uncommonly specific questions.