You'll Never Get What You Want If You're Too Scared to Ask for It

Or, the greatest love story I've ever heard

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The woman sat at her kitchen table, staring at the four names laid out in front of her. Her hand was shaking. Despite being 83 years old, her heart raced with the same intensity as it did when she had her first crush as a teenager. 

Months earlier, while walking the Camino de Santiago, a 500-mile trek across northern Spain, the woman met a man. It seemed like your typical friendly encounter with a stranger, one of many she’d had since arriving in the country. The conversation lasted only a few minutes, and when they parted ways, they didn’t even exchange names. 

But after the woman made her way back home to Norway once her walk came to an end, she couldn’t stop thinking about the man. There was something about him. She couldn’t quite put her finger on why his face flashed before her closed eyes as she lay in bed alone at night, but she knew she had to see him again. 

When she’d planned the trip, meeting someone new was the last thing on her mind. She’d decided to go on the walk to come to grips with the passing of her husband a few years prior. It was her way of reentering the world after her paralyzing loss. Yet, again and again, she kept replaying the exchange she had with the comfortable stranger she’d met.

That is until one day she decided to do something about it.

Not knowing where else to turn, she called the office of the Camino de Santiago and shared the whole story. She explained how she met a man during the walk. She said she didn’t have much information about him, but she knew he was from the Netherlands. She laughed when she admitted she didn’t even know the man’s name.

The woman knew the odds were against her as most organizations have strict rules about passing along the personal information of other people. As her luck would have it though, the woman she spoke with had a soft spot for the story. It took some digging, but by the time the call ended, the woman had the names and mailing addresses of four Dutchmen who finished the walk around the same time as her.

All the days she’d spent dreaming about the man had all of a sudden become very real. She couldn’t believe it. “What do I do now?” she asked herself. “What do I even say?” But after pacing her house with the names of the four men in tow for a few days, she hatched a plan. Immediately, she sat down and spent the rest of the evening writing out four identical Christmas cards to each of the men.

Three years later, while my dad was walking the Camino de Santiago to straighten out the twists of a recent big life event of his own, he stopped in a café a few kilometers short of Leon, Spain. He pulled up a seat at the bar. He noticed an elderly couple to his right. He nodded and said hello. After sharing a few glasses of wine, my father asked the two of them how they met. 

The couple smiled.

Then the man explained that one day while going through his mail, he found a letter from a beautiful stranger.

If You Don’t Ask, You Don’t Get

Sometimes when I’m feeling stuck, I imagine the woman in this story, sitting alone at her kitchen table, thinking about the man she’d met. I imagine her picking up the phone and then putting it back down again, wondering if the whole plan was absurd. But then I imagine her thinking, “What have I got to lose?” and slowly dialing the number to the information center and stumbling her way through asking for help. I then envision her writing out the fourth letter with the same level of care as she did the first. I can practically feel her heart pounding in her chest. I can see the lines on her face shifting when she finally looks down at her mail one day and sees the man’s name staring back at her. 

When I think about the woman’s actions on the day she decided to be bold in the moments that matter, I’m reminded of the fact that we’ll never get what we want out of life if we don’t summon the strength to ask for it. 

How many days do we waste living in a state of hesitation because we’re scared of being rejected?

How many times have we sat paralyzed thinking of the countless ways our potential dreams could go wrong?

How many opportunities have passed us by because we chose to give more power to our excuses than our possibilities?

Stories from people like the elderly woman reinforce the notion that I don’t want to live my life in a constant state of hesitation. I want the courage to ask for what I want. And I don’t ever want to stop treating my curiosity like a responsibility.

Everywhere we turn, we are bombarded with advice on how to get the most out of life. All of it is worthless if you don’t make the hard decision to be brave in the moments that matter.

Maybe you’ll have to send out a thousand letters.

Maybe you’ll get rejected, and it will hurt.

Maybe you’ll find out that what you thought you wanted isn’t actually what you want, and you have to change your course.

It’s all part of the deal.

But when you default to asking, you open yourself to opportunities that can bring joy and meaning to your life. Rejection hurts far less than never knowing what could have been.

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If you like this story and struggle to bet on yourself, you may enjoy my book — Shy by Design: 12 Timeless Principles to Quietly Stand Out.

Part III of the book — Quiet Courage — is full of inspiring stories and actionable insights to go after what you want, even when feeling shaky.

“(Thompson) strikes an effective balance between empowering readers to embrace their shyness and encouraging them to venture outside their comfort zones.”
— Publishers Weekly

You can grab your copy or gift it to a friend whose shyness is holding them from going after their goals here.

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Thank you for reading.
My best to you and yours.
— Michael