I almost bailed on my first networking event due to anxiety. Instead, I stayed, met a New York Times reporter, and completely bombed my pitch to her. Here's the story of what went wrong and why I'd do it all again.

What You'll Learn:

• How to overcome social anxiety at networking events when you don't know anyone

• Why being "bold" beats being comfortable every time

• My biggest networking mistakes and what I learned from them

• Practical tips for starting conversations at professional events

• How to handle rejection and awkward moments with confidence

Key Takeaways:

✓ Strategies for managing imposter syndrome in professional settings

✓ The power of asking for feedback after difficult conversations

✓ Why taking opportunities matters more than the outcome

✓ How to network authentically without seeming desperate

Whether you're facing your first networking event, dealing with social anxiety, or just trying to be bolder in your career, this episode breaks down exactly how to push through discomfort and grow from every interaction – even the cringeworthy ones.

Perfect for: First-time networkers, anxious introverts, anyone who's ever stood alone at a professional event wondering what the hell they're supposed to do, young professionals ready to take uncomfortable chances on themselves.

Real talk: This isn't about becoming a networking master overnight. It's about showing up scared, making mistakes, and learning that the worst-case scenario (total embarrassment) is actually survivable – and valuable.

Bonus: Behind-the-scenes from my sweaty interview with Phoebe Gates and why I almost asked to pause mid-conversation to towel off.

Stepping Into the Room: Why Being Bold Beats Being Comfortable

Last week I got invited to my first industry event through Guyset - which is outrageous to say out loud. What started as excitement quickly turned into anxiety and almost backing out. Here's what I learned about stepping outside your comfort zone and why being bold is always worth it.

The Invitation That Changed Everything

When I got the email three weeks before the event, I was like "What? That's crazy. That's cool. Sure, I'll go to an event. I'll go to anything basically - you can invite me to the opening of an envelope."

But then life got in the way and I totally forgot about it for two weeks. When I got the reminder email the day before, I started coming up with excuses for why I couldn't go even though I was completely free.

The anxiety hit hard. I started getting really anxious about why they even wanted me there in the first place, who I was supposed to talk to, what I was supposed to do. I was trying to think of reasons to back out and downplay the excitement to make not going hurt less.

The Power to Make Things Good or Bad

Here's something I realized: we have the power to make something exciting even if it's not, and we also have the power to make something unexciting if we don't want to be interested in it. We have that choice at any given time.

I was excited at first, then talked myself down and started downplaying it to make the hurt of not going easier. All because of nerves - the nerves of going to an event alone where I don't know anybody.

Walking Around the Block to Delay the Inevitable

Even when I got off the subway, I could see the restaurant where they were holding the event. It was a one-minute walk from the subway. But I turned the other way and walked all the way around the block just to make more time before I had to go in.

When I finally went in, there was a photographer at the front. I took three pictures giving thumbs up to the camera with people watching, thinking "what the fuck am I doing?"

But then I took a deep breath and decided: if I'm going to be here, I might as well make the most of it.

Finding Your Stations: The Food Table Strategy

Once I got past the initial host introduction, I felt like I was just standing there while everybody else knew each other. I felt like Wally on a different planet.

My first move: I went to the girl pouring water. I asked for a cup of water, chugged it, and she said "wow, you must be thirsty." So I struck up a conversation and even asked if I could help pour glasses.

Then I found my home ground: the food table. This became a crucial strategy because once you're there, you have common ground with other people. You can start conversations about the food or whatever - you're not just walking up to random people.

Having stations you can go to - whether it's the water station, food table, or anywhere with a natural conversation starter - gives you a foundation for meeting people.

The New York Times Disaster (And Why I'm Proud Of It)

At one point, I was standing alone again (there were probably four different times I felt like a lost dog). I saw a table with two to three women and thought "fuck it, I have nothing to lose."

I sat down and introduced myself. One was an influencer, one was the influencer's friend, and the third was a New York Times reporter.

When she mentioned she writes stories, I blurted out: "I would love to pitch you a story."

Immediately, she was taken aback. The other girl said "that's bold." I instantly felt panic - "Is that bold? I'm sorry, I don't have to. I just thought since you're a reporter who writes stories, that would be interesting conversation."

The Pitch That Went Horribly Wrong

She said if I had a pitch, it must be good since I was being so bold. Problem: I hadn't prepared anything to talk to a reporter about.

I pitched my last episode with Phoebe Gates, going on about why it was a great angle for the New York Times. I could tell from her face the entire time: her expression read "no." The people listening looked like "who is this kid and why is he talking?"

You know that feeling when people are about to talk about you as soon as you leave? That's exactly how I felt.

The Best Thing I Said All Night

She didn't really respond to my pitch, so I asked: "What do you think? Do you have any feedback for me?"

This was probably the best thing I said in the entire interaction. Asking for feedback is something I do a lot in work and I've gotten better at in conversations.

Her feedback was direct: My pitch didn't make sense, and when she asked me to pitch my podcast, that was more interesting. The other woman said my pitch was too much "me, me, me."

I left that conversation feeling like I should leave the entire event.

The Split-Second Decision

But in that moment, I realized an opportunity had presented itself. It was like seeing something beautiful and not taking out your phone to capture it - you wish you had that picture to remember the moment.

I had a split-second decision: Either pitch this thing to her or leave and think about what could have been.

She didn't pick up the story. The New York Times isn't going to write about me. But in the off chance they did, or maybe at some point in the future, maybe I set a small brick in that road. Maybe I did something to be memorable, whether in a good way or bad way.

If I had just said "cool, nice to meet you, bye," they would have thought "okay, just another person at the party." But I made an impression.

Why I'm Proud of the "Failure"

I'm proud of myself for several reasons:

1. I Decided to Go Despite the Anxiety

There were so many things holding me back - the imposter syndrome, not knowing anybody, feeling uncomfortable. But most likely if I had known I could bring a plus one, I would have, and then I wouldn't have had this uncomfortable experience where you grow the most.

2. I Shot My Shot

I would rather be anxious about how it went than thinking about how it could have gone if I never tried. I did feel anxious after the event about what I said and what I could have said better. But ultimately, I was happy I took a chance on myself instead of staying in my comfort zone.

3. I Learned Without Intention

I went into conversations without the intention of getting anything out of it. I thought this would create better connections than going for networking first. After having genuine conversations and getting to know people, then they became interested in what I do.

The Door That's Starting to Open

As Phoebe Gates said in our last episode: "It doesn't matter how you get into the room. It matters how you act once you're in the room."

I'm proud of myself for not giving up the chance to be in the room. You never know what could come from it - I met people, made connections, and might have someone from The Atlantic come on the podcast.

This felt like a crack in the door. It was the first thing I've ever been invited to, the first opportunity to network and introduce myself to people who hadn't met me before. That was really fucking scary.

The whole day leading up to it, I wanted to shut that door back up because I've always been outside of it and it's more comfortable there. But I decided to step in and start having conversations.

Being Bold About What You Want

The woman told me I was bold. And being bold isn't a bad thing, no matter who tells you it is.

Being bold about what you want is what it's all about. Being bold about the things you want for yourself in life is never a bad thing.

Being bold is what got me:

• My first job

• My second job

• Into that room at the event

• The interview with Phoebe Gates (I responded to her DM asking if she wanted to come on the podcast)

There are also a million stories where I shot my shot and it didn't lead to anything. But there are times like last week where it does, and you just never know what can happen when you're bold with what you want.

The Lesson: Take the Opportunities

Whether it's in work, life, relationships, or anything in your 20s - there are going to be doors or cracks in doors where you can finally see a little light coming through. When that light shines through, it's so much easier to say "nah, I'm just gonna close that door back up. It's better that way. I'm more comfortable with it closed."

But when it's starting to open, that's uncomfortable. Having to step into that room is really uncomfortable because it's an area you don't know, a place you've never been before.

What I Learned About Myself

Putting ourselves in uncomfortable situations teaches us that we actually have resilience we didn't think we had. I learned I do have confidence I didn't think I had.

All those thoughts and feelings - that people are looking at you thinking "why is that guy not talking to anybody, he's such a loser, why is he here" - weren't real. None of that happened.

I left saying "I'm never going to another event like that again." But that's not true. If another opportunity like that presented itself, I would take it again and again.

The Bottom Line

There's no happy ending where I got the story written or landed some big opportunity. The happy ending is that I learned about myself, took a chance, and was bold.

Being bold is what got me the interview with Phoebe - she reached out after I posted a video, and I responded asking if she wanted to talk about her new company on the podcast. That was a total shot in the dark, but she said yes.

The worst that can come from being bold is they say no or don't respond. The best is they say yes and it happens.

So be bold with the opportunities presented to you. Be bold with yourself. You just never know what can happen.

Want to hear more about stepping outside your comfort zone and taking chances? Follow @theguyset on social media and subscribe to the Guyset Toolkit newsletter on Substack for weekly insights on navigating your 20s.

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