7 Lessons I Learned About Confidence From One Awkward Hello

Here are seven confidence lessons from one painfully awkward hello and how to stop overthinking every introduction.

It was supposed to be simple. Walk up, say hi, sound normal. Instead, it became a slow-motion car crash of nerves, silence, and small talk that didn’t go anywhere.

But that one awkward introduction turned into one of the best confidence lessons I’ve ever had. Here are the seven takeaways that stuck.

1. Say hi before you talk yourself out of it

“I was asking everybody I was with, should I go up and say hi? Should I not?”

Overthinking kills more opportunities than rejection ever will. You’ll never feel ready, so stop waiting to.

Confidence doesn’t start when you walk over. It starts when you decide to. That single moment, the decision to move instead of think, is the hardest part.

If you’ve ever psyched yourself out before a conversation, you’ll get it. Read more in How to Talk to Girls Without Overthinking It.

2. Have one line in your back pocket

“If I had a little bit more of a fallback or something really prepared, maybe that would have helped me.”

You don’t need a script. You just need a start.

A simple opener like “I’ve been meaning to say hi” or “I wanted to meet you” works better than anything forced. Preparation isn’t fake. It’s how you sound natural when your nerves hit.

That’s the secret: confidence isn’t charisma. It’s clarity.

3. Awkward is proof you tried

“I really am happy I did that because I now learned that I have a lot to improve on in terms of introducing myself.”

No one learns from the moments they avoid. You get better by doing the thing badly and realizing it didn’t kill you.

If it was awkward, that means you showed up. And that’s progress.

4. People remember energy, not words

You can stumble through a conversation and still make a good impression if your energy’s right.

“I just kept picking up the ball and dropping it again and again.”

No one remembers your exact words. They remember how it felt. Were you open? Present? Genuine?

That’s what confidence looks like in real life. Not perfect delivery, just real energy.

If this idea hits home, check out What to Do When You Feel Behind in Your 20s for more on staying grounded when things don’t go your way.

5. Always have a next move

“I wanted to at least say I’d love to stay in touch or get your contact, but I just didn’t.”

Confidence isn’t just saying hi. It’s what you do next.

Don’t end a conversation without a way to follow up. Even a simple “It was great meeting you, I’d love to stay in touch” changes how the moment lands.

You don’t need a business card or big ask. You just need direction.

6. Recover fast and move on

You’re going to mess up sometimes. That’s the point.

“Confidence isn’t built in your wins. It’s built in the recoveries.”

The key is to bounce fast. Laugh it off, learn something, and keep moving. Every bad interaction builds the muscle for a better one.

If you need a mindset reset, read How to Build Confidence from Scratch.

7. The only bad hello is the one you never try

“It’s never better to stay wondering. I’d always rather at least try and then build from there.”

You’ll regret inaction way more than imperfection.

That’s the real takeaway. Confidence is choosing awkward over invisible. Trying over wondering. Speaking up over staying quiet.

The next time you’re standing across the room, just go for it. Worst case, it’s a story. Best case, it’s a connection.

Final Thought

Confidence isn’t something you have. It’s something you build by acting before you’re ready.

Every awkward introduction is practice. Every small risk is a rep. Every “hi” you say anyway is proof you’re becoming the guy you want to be.

And that’s what it’s all about.

Want to hear the full story?
Listen to The Art of the Introduction on Spotify or Apple Podcasts.
Then check out:
👉 Feature Article: The Art of the Introduction
👉 Practical Q&A: How to Introduce Yourself Without Overthinking It
👉 Episode Landing Page