To Truly Succeed, Stop Hustling and Start Questioning Yourself Like Tim Ferriss

How knowing yourself is the key to moving forward.


Michael Touchton

2 years ago | 4 min read

Before he was sentenced to death, the philosopher Socrates uttered the now-famous line, “The unexamined life is not worth living.” That’s ancient-speak for… “If you live on autopilot like a zombie, you’ll waste your life.”

Here’s the deal: lots of us are chasing success like zombies — totally unaware that what we’re hustling to find might not actually be success.

But there’s something we can do about it.

Success is about the accomplishment of a purpose.

You can’t find your success if you’re pursuing someone else’s purpose. But often, that’s exactly what we’re doing: chasing some goal that’s really just another version of the same generalized dream of becoming famous, rich, or powerful.

If you want to find the success that will fulfill you, you’ve got to find your purpose — which starts with getting to know yourself.

That sounds silly, I know. But it’s really important. And by overlooking it, we risk wasting a lot of time.

Question Yourself

One of the best ways to get to know yourself is by asking yourself questions. But not just any questions… questions that will strategically cut through the noise of your inner world and help you to recognize the authentic desires and purpose of your heart.

The practice of questioning yourself is one of the simplest, most powerful ways to end the zombie-life and gain clarity about what’s really going on inside.

I’ve included two of these strategic questions here — the kind that encapsulate the impact of 100 questions in 1. They both come from Tim Ferriss and they help us to do two things: open our hearts and find freedom from fear.

These two things help us to connect with that authentic purpose and find the freedom to then practice that purpose. Together, these two questions create a great foundation for learning what success truly means for you.

“What am I unwilling to feel?”

Tim Ferris once mentioned how Tara Brach — the psychologist and Buddhist meditation teacher — asked him this question. Asking yourself, “What am I unwilling to feel?” is about intentionally checking in with your inner-self.

The question made Ferriss contemplate how much energy he was spending blocking out certain feelings. It’s this avoidance of emotion that holds us back and closes us up.

If you’re always keeping busy, it might be because you want to distract yourself from certain emotional realities. Maybe you’re scared of feeling the pain of a loss and it’s keeping you from moving on. Or maybe you’re terrified of feeling out of control, and that’s keeping you from doing that thing you know you should do.

Whatever it is you’re avoiding, it’s not without consequence. As Brian Thompson, writer at Zen Thinking, says,

“We become ensnared by our very resistance — we get stuck in the middle of a twisted and tangled mess with our aversions.”

The things you’re unwilling to feel are often the things you most need to face. And the emotional realities you’re avoiding are the keys to your freedom. You can’t block bad emotions and still let all the good ones through. You either shut the door or open it. Your heart is either in the process of opening or it’s closing.

And if you’re out of touch with your heart, you’ll be out of touch with your purpose. And no purpose means no authentic success.

“What am I afraid to do?”

Like the first question, this one reveals things you’re actively avoiding — but with a focus on actions that frighten you.

Our desire for success — which we normally communicate as ‘goals’— is often sabotaged by our fears before we even take one step forward. This is the topic of Ferriss’ wildly popular TED talk, “Why you should define your fears instead of your goals”.

Writer Patrick Buggy describes Ferriss’s practice as “a structured reflection exercise used to help you see decisions more clearly when fear is holding you back and distorting your thinking.” It’s a way of diving deep into the question, “What am I afraid to do?”

“Everything you want is on the other side of fear.“

-Jack Canfield

Maybe you’re scared to share your art because you’ll be rejected. Or maybe you’re scared to quit your job and start that thing because you might fail, lose all your money, and look stupid.

But why are you scared of those things? Why does succeeding, having money, being accepted, and looking smart mean so much to you? And why do those things mean more to you than sharing your art or starting that thing that’s been on your heart?

Just like question #1, avoiding things you’re afraid to do is also not without consequence. And it’s not just that you won’t ever fulfill your dream of being a paid artist or entrepreneur. It’s that you’ll be a slave to fear, and fear will work to sabotage any chance you have at authentic success.

You’ll try not to think about it, but it’ll always be there taunting you and making you feel a mix of paralyzed and frustrated. Every time you see an art installation or another startup, you’ll feel jealous, sad, and frozen in fear. You’ll never feel happy until you stop avoiding these things and start facing them head-on.

The thing you’re most afraid of doing is exactly the thing you need to do. And it’s not really about the thing; it’s about the fear. Because naming and facing your fears is how you grow, level-up, and find authentic success.

Go Therefore and Question Thyself

Much suffering in life comes from racing around at the speed of the toxic thoughts sweeping our minds — leaving us in danger of never understanding who we are, what brings us joy, and what it means for us to be truly successful.

What will be success for me will be different than it will be for you. And it’s not as simple as money, fame, or power. It never is. If it’s truly authentic, it’ll be shaped into something as unique as your fingerprints.

To overcome this madness, stop hustling and just start questioning yourself in a curious, non-judgmental way. Start by asking yourself,

  1. What am I unwilling to feel?
  2. What am I afraid to do?

Closing our hearts and living in fear block us from our purpose — leaving us to waste our time hustling and chasing some false version of success like zombies.

Slow down and question yourself, and you’ll be on the fast track to finding the kind of success that will truly make you happy.


Created by

Michael Touchton







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