Sometimes you just need a cry. And Eva Cassidy makes me cry... time after time

In partnership with

I’ll admit, the first time I heard the name Eva Cassidy, I thought:
“She sounds like a substitute teacher. Mrs Cassidy will be taking the class today.”

Turns out, she had the voice that changed my life.

So let me ask you: who’s someone you consider has the voice of an angel?
Whitney? Ella? Aretha? Even Taylor Swift?

For me, it was Eva Cassidy.

All beautiful voices. But Eva’s was the one that made me believe things could be okay.

Her name doesn’t usually come up when people talk about the “greatest singers of all time.” She didn’t have the long career or the accolades of the others.

But the first time you hear her? Every hair on your body stands up. And it’s not just goosebumps, it’s warmth.

Like someone you’ve never met is giving you the hug you didn’t realise you needed.

P.S. If this story resonated, I’d love it if you shared it with a friend who might need it too. And if you want to go deeper, you can join the Mental Musician Inner Circle as a paid subscriber. No pressure, but if you do, I’ve got plenty more I’d love to share with you.

I wanted to share when I first discovered Eva Cassidy because the music world feels heavy right now.

Conversations everywhere about AI replicating human voices. Songs churned out to fit algorithmic playlists. The older generation longing for the “glory days.”

So here’s something hopeful. A reminder that there are still voices, past, present, and even future, that cut through the noise.

Eva’s story is one about being yourself, even when the industry tries to make you something else. About respecting the story of a song. About giving people hope without ever knowing them.

And in 2016, I needed that more than ever.

P.S. If this story resonated, I’d love it if you shared it with a friend who might need it too. And if you want to go deeper, you can join the Mental Musician Inner Circle as a paid subscriber. No pressure, but if you do, I’ve got plenty more I’d love to share with you.

Share

That year, I had just finished high school. My mum was in and out of hospital. My dad was stressed to the point of closing one of his shops. I was isolating myself, pretending to be “fine” while being diagnosed with depression.

Music became my escape hatch. Teaching, gigging, recording videos, planning my first “tour” (quotation marks intentional — it was mostly a plan to meet guitar friends across Holland, England, the US and Canada, and play anywhere that would have me).

It was all exciting. But it was also a mask. I’d never been taught how to deal with the other side of life, the part where ambition has to take a backseat.

Maybe you’ve felt that too. That first time where life suddenly felt… uncertain. Like breaking your first guitar string and thinking you’d destroyed the whole instrument. Except 150 times worse.

Then one Saturday afternoon, hanging out with my best friend, I asked his dad what it was like to grow up with Stevie Wonder, Michael Jackson, Prince, Freddie Mercury, Whitney Houston on the radio.

“They’re all great,” he said. “But you have to listen to Eva Cassidy.”

“Who is she?” I asked, genuinely confused.
(And honestly? I thought she sounded like the kind of substitute teacher you’d call Mrs Cassidy.)

“Just listen. You’ll be amazed.”

On the car ride home, I searched her on Spotify and played her Songbird album.

The first track was Time After Time.
I knew the song. Or at least, I thought I did.

The moment she sang the first line — “Lying in my bed, I hear…” — I nearly swerved into a freight truck. Her voice wasn’t just singing at me. It was inside me. Soft. Calming. But also sharp enough to cut straight to the heart.

And when she reached the chorus — “If you’re lost, you can look, and you will find me, time after time” — I believed her. Completely.

Suddenly I thought: maybe Mum will get better. Maybe my friends won’t forget me. Maybe Dad will finally rest. Maybe I’ll have a future.

That’s what her voice did: it gave me hope, line by line.

I went through the entire album: Over the Rainbow, Songbird, I Know You by Heart, What a Wonderful World.

They weren’t “covers.” It was as if the songs finally found their home in her voice.

I needed to know more. When was she playing? Could I see her live?

So I did the one thing you shouldn’t do while driving —I googled her.

And my stomach dropped. Eva Cassidy had died in 1996. Almost exactly 20 years before the night I first heard her.

I pulled the car over. And cried.

Not from pain. Not from sadness. But because for the first time in years, I felt someone — through nothing more than a voice — was telling me: “Things will be okay. Someone will catch you. You’ll be okay in time.”

That night, her songs didn’t just make me cry. They made me believe that things will be okay.

Six months later, I was boarding the first of 15 flights for my “tour.”

Here’s the other thing you should know about me: I had an irrational fear of flying. (Shoutout to all the hours wasted on Air Crash Investigations.)

By the time I got on the plane, I was as pale as the outside of the Boeing 777.

But then I remembered Eva.

So I put on my headphones, hit play on Over the Rainbow, and within a heartbeat, my pulse slowed. The panic drained.

It felt fitting, like going over the rainbow.

Every one of those 15 flights, Eva came with me. Time after time.

Now I’m 27. And every time depression creeps back, in traffic, in silence, in the middle of the night, I still go back to Eva.

She hasn’t cured my depression. She hasn’t erased my panic attacks. But she reminds me every single time that things can be okay.

Sometimes you just need to cry. And when I do, it’s Eva Cassidy who gives me permission.

In Eva I trust.

So I’ll finish with this:

Who is the one singer that makes you cry?
What’s the song that breaks you down and somehow builds you back up?

I’d love to know. Reply to this email or DM me on instagram, linkedin or substack.

Until next week, please take care of yourself.

– Brian, The Mental Musician.

📹 You can also check out my latest YouTube video where I talk more about the impact Eva Cassidy had on me, and give a little performance of Time after time.

Business news doesn’t have to be boring

Morning Brew makes business news way more enjoyable—and way easier to understand. The free newsletter breaks down the latest in business, tech, and finance with smart insights, bold takes, and a tone that actually makes you want to keep reading.

No jargon, no drawn-out analysis, no snooze-fests. Just the stuff you need to know, delivered with a little personality.

Over 4 million people start their day with Morning Brew, and once you try it, you’ll see why.

Plus, it takes just 15 seconds to subscribe—so why not give it a shot?

Check it out