#DYFConf2015 Retrospective: My Personal Journey From Introvert to Public Speaker

September 20, 2015

I’m flying back to Chicago from Norfolk as I write this, and I wanted to reflect on my experience and share that with you. I was in Virginia because I was invited to speak at the Double Your Freelancing Conference. It’s easily been one of the top 3 most amazing moments of this year for me. There’s a lot of reasons for that.

It was a phenomenal conference and experience. Loads of actionable advice from brilliant and exceptional business people. Including me. Does that sound conceited? Yes, of course it should, but I’m proud. As a human being I like that validation. “Validation from speaking gig” should be on Maslow’s Hierarchy of Needs. I’m surprised it’s not. You know what, let’s just say it is, because it felt great.

I was lucky enough to be a speaker at the event. People I know, respect, and look up to told me I did great. It was a personal watershed moment for me because this year has been hard, it’s had its personal and professional ups and downs. It’s hard enough as a person, let alone a business owner, to know how you’re doing. There’s no teacher or boss for entrepreneurs to say, “Great job, little buddy! We’re putting a gold star in your permanent record.”

When asked to speak by Brennan, I didn’t even think before saying, “yes!” After all, I got to check something off of my bucket list. It was actually a recent addition to my bucket list too. Last April I went to MicroConf. Kai Davis and I were sitting in the front row, listening to Brian Casel speak, and we both realized that Brian was not a super human on a pedestal giving a state of the union address, he was A Real Person performing a dramatic reading of a blog post. That’s not a slight against Brian at all, quite the opposite, it was a testament to the quality of his work. And when I realized that, I was inspired to do the same.

Things clicked: we all have things we do in our everyday lives that seem simple and obvious to us, so we assume they’re obvious to everybody else. Of course this isn’t true at all, we’re sabotaging ourselves. We all have something we can teach others: skills, habits, mindsets, and experiences. But instead of trying to teach those things to others, we’re too busy telling ourselves we’re nobodies so we don’t.

As Brian talked about his experiences that I’m sure seemed simple and obvious to him, he had the attention of hundreds of people. That’s when Kai turned to me and said, “Life goal: next year we speak at a conference.” Done, yes, sure, of course, why not?

Why not? Because public speaking is fucking terrifying, that’s why not. That’s the self-sabotaging part of my brain talking. I assume that’s the same part that plays highlight reels of embarrassing memories to me as I try to fall asleep, and erases my memory of when my fiance’s birthday is directly before it happens.

I also know that pushing myself out of my comfort zone is how to grow as a person. If you’re not regularly doing things that make you uncomfortable, you’re not really living. So I jumped at the chance to speak at DYFConf.

I’m glad I did too. Attending the conference as a speaker is entirely different from being an attendee. You’re a rockstar when you speak. But unlike a rockstar, you’re admired because you’re helping your peers and your community.

I’m a recovering introvert. With social anxiety. I know you don’t believe me because most people don’t. Hell, Amy Hoy didn’t believe me and she’s a pro at this. Here’s how bad I was: I used to get stressed out by the idea of calling up a restaurant to place an order. That seems crazy to me now. To go from that to giving a forty minute presentation followed by a Q&A is quite the personal achievement for me, so excuse me if I sounded a little cocky earlier.

Plus as fellow recovered introvert and speaker Nathan Barry pointed out, being a speaker is the ultimate networking hack. As a speaker, you know that everyone in attendance has paid you with their time and attention. They know your name, and what you’re about. People will come up to you say hello, pick your brain, and congratulate you. It’s a free pass to talk to anyone else there as well. The tension and awkwardness inherent to social interaction is entirely dissolved.

Some individual personal moments that I’m sharing here so I can remember them:

• On our first night, Brennan and his wife Deborah took the speakers to a dinner at their favorite date night restaurant. Aside from being a fun and quirky restaurant, it was very nice that they were able to include the lot of us in their personal lives in that way. It made me feel welcome, and it made the dinner feel special. Plus “smoochie bear ham” is fucking delicious.
• Meeting folks I had great online relationships with in real life, and discovering that their meatspace selves are even more fantastic than real life. The formidable Jonathan Stark, the charming Mojca Mars, and many many others.
• Reconnecting with people I dearly love like Kai Davis and Jeremy Green.
• Making more new connections than I can count, and making new friends among them.
• Doing live website teardowns with Kai. It was fun, spontaneous, and gave me a chance to speak a second time and discover I wasn’t the slightest bit nervous then.
• Discovering we’re all a bunch of huggers. I’m a hugger, and getting hugs from folks like Brennan and Amy Hoy was nifty.
• Having at least half a dozen people tell me some variation of how I’ve helped or inspired them. I’m humbled, thank you.
• And one of the most personally important to me: Seeing my fiancé, Julie, absolutely thrive. She’s new to this, it’s been less than a year since she quit her job to pursue Just Tell Julie as a full-time gig, and she absolutely killed at that conference. Her presentation was surprisingly funny even for me, and I could not be more proud of her. Everything clicked for her, she made new friends, found new opportunities, and came back inspired, confident, and happy. I’m sure it’s brought us closer together. You can read her recap here: blog.justtelljulie.com — she’s a better writer than I am anyway.

I know I’m not alone in this either. Here’s what silver fox speaker Jonathan Stark had to say about it:

I second Kurt re: DYFConf… It was amazing. I’ve been to 100+ conferences in the last 10 years but DYFConf was singular. I’m 100% sure that in 2025, I’ll look back on DYFConf 2015 as a milestone moment in my life.

I know a year from now, I’ll look back on DYFConf as a turning point in my life. I’m literally misty-eyed writing this. There’s nothing stopping you from having the same experiences. Pick two conferences to go to in the next 12 months. And yes, they’re pricey compared to your local networking events, but the ROI is massive. At the same time, if you’re not already, start writing publicly. It’s a great habit. Once you’ve been to a conference, figure out what you can teach people. If you’re not sure, ask your immediate network what you’re great at.

If I can do it, you can do it.