a man and a woman sitting next to each other

The Nail in Your Head

Bob Ewing
March 17, 2023
a man and a woman sitting next to each other

Talking Big Ideas.

“All life is problem solving.”
~ Karl Popper

A decade ago the writer Jason Headley made a brilliant video that went viral.  

There’s a couple sitting together on a couch. A woman explains that she’s experiencing “all this pressure . . . I can literally feel it in my head and it’s relentless . . . that’s the thing that scares me the most . . . I don’t know if it’s ever going to stop.” 

The camera pans out and we see she has a nail sticking out of her forehead. Her partner calmly says, “Yeah, you do have a nail in your head.” She gets frustrated: “It’s not about the nail!” The clip is short and worth watching in full: 

I was this woman last year. I decided to finally get good at sleep, so I read several books, bought an Oura ring sleep tracker, TheraICE gel eye mask, fancy ear plugs, an expensive pillow, Plackers, mouth tape, and more. 

Then I’d stay up until 2am and wake up groggy the next day. 

Maryrose didn’t get any of my sleep gadgets. But she would go to bed around 9pm and wake up refreshed each morning. 

Occasionally, she would politely point out if I just went to sleep at a reasonable hour my sleep would improve. It took me a comically long time to realize this and finally “remove the nail.” (Which, to be honest, is still a work in progress.) 

Everyone has at least one big thing that stands in the way of their success. Find yours and deal with it . . . you will hugely improve your life. 

Let’s call this the “nail in your head” phenomenon. It’s the obvious, painful problem you are ignoring that is holding you back – and likely has a simple fix. Not necessarily easy, but simple. 

Elvis Presley suffered from terrible foot pain. He loved to wear cheap pointy shoes that “were murder on his feet” but resisted buying quality shoes that fit. 

Elizabeth Taylor refused for years to acknowledge the tremendous stress her drinking caused. Barack Obama has long prided himself on being healthy, yet he still smoked upwards of 8 cigarettes a day while President. 

The Nail in Your Head: the obvious, painful problem you are ignoring that is holding you back – and likely has a simple fix.
The Nail in Your Head: the obvious, painful problem you are ignoring that is holding you back – and likely has a simple fix.

If you’re being honest with yourself, can you admit to a problem you are currently ignoring that’s holding you back? Perhaps related to health, love, or work? 

Sometimes they’re obvious to us and sometimes they’re hidden. When we examine our lives closely enough, though, they begin to emerge. 

Here are five ways to help identify and remove the nails from our head:

#1. Sweep Your Mind

Imagine a pile of rocks tumbling around inside a dryer.

That’s what a typical person’s mind is like. We have thoughts and feelings constantly bubbling up. There’s a stream of content coming at us from glowing rectangles everywhere. All this stuff mashes together and swirls around inside our heads.

Most of us never take a moment to stop the dryer and get all the rocks out. A mindsweep is the simple act of doing just that. 

A good sweep takes 15-20 minutes. You set a timer and begin writing individual thoughts on little pieces of paper. Simply capture whatever has your attention.

Really dig around to get all the rocks out of the dryer. And then review a Trigger List to help discover even more rocks lurking in the shadows.

Here’s a picture of our kitchen table after Maryrose and I did a mindsweep together:

Blue is for everything that’s giving us anxiety. Green is for everything making us excited.

Emptying your mind will make you feel like you “got that thing off your chest.” Most anxieties you unearth will point to problems you can control. Give each a tiny action item to make progress towards a solution.

For more on mindsweeps, see my essay Sweep Prime Focus

#2. Travel to Neverland

According to Jonathan Gottschall, author of the delightful book The Storytelling Animal, we constantly travel back in time and reimagine our past. He says we “visit Neverland” about 2,000 times every day. If each flashback lasts about 14 seconds, it adds up to almost half our waking lives!

To what end?

So we can learn. And make our lives better.

When I work with clients on a presentation or speech, I always have them do self-assessments before I offer feedback. And whenever they go on stage I ask them to do a self-assessment shortly after they finish and save it. 

I encourage you to do the same. Visit and review the moments of your life that matter. Be honest with yourself. What did you do well? What problems do you see? Notice what causes you anxiety and regret. Capture your thoughts, insights, and lessons learned. 

Look backward to help you solve problems and move forward. 

#3. Journal Your Anxieties

Anxiety is not a problem. 

Rather, anxiety is like a giant blinking light trying to focus our awareness on our problems. But we often ignore it and so problems fester. This builds more anxiety and creates a vicious cycle. 

The author Charlotte Lieberman writes in Harvard Business Review, “if we listen to our anxiety — rather than try to shut it up — we give ourselves an opening to break the vicious cycle.” 

Perhaps the simplest way to do this is journaling.

Ethan Kross, one of the world’s leading experts on how our minds work, explains that “getting the anxieties out of our head and onto the paper makes us feel better, visit the doctor less, and have a healthier immune function.”

Maryrose has a daily journaling habit that’s helped her uncover and solve numerous problems, including core insights into how to improve and grow our business. 

Make time to listen to yourself and give voice to your anxieties in writing. They’ll help you discover hidden problems and how to solve them. 

#4. Embrace Feedback 

Meryl Streep playing Florence Foster Jenkins in a 2016 biopic.

Florence Foster Jenkins was born rich and sheltered her entire life. She loved to sing but didn’t get honest feedback from people on how she sounded or how she could meaningfully improve. 

Her performance at Carnegie Hall is legendary. She was crucified by critics and dubbed the “world’s worst opera singer.”

We all have numerous biases and self deceptions, so without regular feedback from others we may suffer Jenkins’ fate. Seek out feedback often from friends and colleagues. Ask them to be specific, honest, and compassionate

You will quickly discover any problems that may be lurking in the shadows – and get guidance on how to solve them. 

#5. Hire a Coach

Coaches help us solve problems. 

They provide accountability, structure, and perspective to process our experiences. They help us chart and begin to take new paths forward. 

Maryrose and I stressed for years over how to clarify our business pricing. Then this fall Maryrose hired a business coach, and within a few weeks she solved our pricing problem. The anxiety surrounding it disappeared. 

Last year I hired a running coach and a chess coach. This month I hired two business coaches to help me find and dig various nails out of my head. 

The neuroscientist Eric Hoel shows in his fascinating three-part series how one-on-one mentorship is the timeless path to excellence. Any problems that you are struggling with right now can almost assuredly be fixed with a coach. 


We all have problems. 

But with effort and attention we can solve them. As the physicist David Deutsch says, even massive problems are solvable – anything that doesn’t violate the laws of physics is possible. 

This applies to whatever is currently standing in the way of your success. 

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