Ask Anyway

The message you don’t send costs more than the one that gets ignored

“What the hell did I just send?”

I stared at the screen after hitting send. Read the email again and again. Looking for the flaws and phrases that’d make them think I was wasting their time.

The email was to a pioneer with over thirty years of experience in the storytelling industry. Someone I admired from a distance, but never spoke to. All I was asking for was a conversation. But that ask alone seemed enormous.

It took me an hour to come up with those two hundred words. I rewrote the opening four times, deleted several paragraphs because it felt too forward, and even after all that, I shut my laptop convinced I’d made a mistake.

I know the principles behind reaching out to someone new. I’ve studied them, written about them, and even helped others apply them.

In my experience, connection is at the core of creativity. Sharing ideas with someone, having conversations that open up new perspectives and opportunities to geek out on topics without ever feeling judged — that’s energising in ways I can’t describe and one of the many reasons I love doing what I do.

Yet, knowing all this didn’t make me press send any faster.

There’s a gap between understanding how connection works and being the one who initiates it. You can internalize every framework, every mindset shift. But when it’s your turn to reach out, especially to someone more experienced, more established, and further along the path you want to travel yourself, all that knowledge fades away and a different voice takes over.

“Who are you to reach out to them?”

“They’re obviously going to look at your work and see right through it.”

“You’re disturbing them.”

“This isn’t the right time.”

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I’ve avoided sending countless messages over the years.

Sometimes, it’s been to someone whose work I deeply admire. I have thoughts, observations, and often ideas that could help. I’ll take a note of that person. Draft a message in my head. Think about what to say, how to say it, and why it might matter to them.

And then… nothing.

No draft written, and no message sent.

I’ve thought about this a lot since the turn of the year, trying to figure out the root cause behind it all. Is it a fear of being ignored? Being judged?

I don’t have the perfect answer just yet, but I think it comes down to a belief that reaching out is “taking” something from somebody else. Time. Attention. Something I hadn’t earned the right to ask.

There have been many times I’ve subconsciously overcome that belief and reached out regardless. But I’ve noticed my instinct is to write in isolation instead of building relationships with people whose ideas and work I care about — waiting for introductions instead of asking for them, and hoping people would find me rather than putting myself in front of them.

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A few weeks ago, I asked one of my mentors if he could connect me with that storytelling pioneer. He made the introduction, and I got the green light to reach out.

It was my turn to act.

Still, there was a part of me that was convinced I should wait. That I “needed to prepare” some more before I reached out.

But I wrote the email as best I could and sent it anyway.

He responded graciously, and we got on a call a few days later.

In just sixty minutes of conversation, new ideas emerged, new patterns came to life, and my perspective on the craft completely shifted.

That same week, I put together a pitch deck for a startup founder I admire. I’d been a huge fan of his work and recently noticed some gaps and how I could help fill them. The old version of me would have kept those ideas to myself. But this time, I condensed everything I had in mind onto a few slides and hit send.

Sending both those emails came down to a different way of seeing what I was doing.

Reaching out isn’t taking. It’s offering.

When you enjoy someone’s work and notice aspects that resonate or have ideas you think could make it even better — that’s valuable, and sharing it isn’t an imposition.

“Hey! I noticed x about your project, thought it was interesting for y reason, and had an idea about z.”

That’s it.

That’s the start conversations that actually matter.

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Looking back, I can see how talking to people has led to my best and most exciting work.

Random discussions about startups. Feedback on what’s working with my writing and what isn’t. Questions from someone I’d just met that reframed a problem I’d been stuck on.

They opened doors I couldn’t have found on my own.

That’s what reaching out does.

Every message you don’t send is a conversation that never happens, a connection that never forms, and an idea that stays locked inside your own head with nowhere to go.

So, I’m making a commitment to reach out to one person every week.

It can be anyone. Someone I admire. Someone whose work makes me think differently or someone I think I could help. The goal is simply to reach out, say what I have to say, and ask anyway.

There’s a good chance some might read my message and wonder who I am. Some will ignore me, while others will say no.

That’s okay.

Because the alternative of staying silent and isolated will cost more than any rejection ever could.

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If you’re reading this, I want to hear from you. Do the same patterns play out on your end? Do you have ideas and questions you’re sitting with but are too afraid to share?

This week, I’m opening a subscriber-only chat. So if you’ve ever wanted to share something, ask something, or say hello, that’s the place.

Or if that feels like too much, just reply to this email. Trust me, all it takes is thirty seconds. Tell me what you’re working on and how/if I can help.

The door is open. It always has been.

Talk soon,

Pranav

P.S. I’ve been working on a project I can’t wait to share with you all next week. If you’d like a sneak peek before it goes live, just let me know.

P.P.S. Special shoutout to Carly Valancy for inspiring this piece and catalysing for the shift in perspective

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