I’ve been speaking at digital conferences since 2001, and I’ve spoken at everything from social media cons to usability cons to Linux cons to sociology cons, so I have a really good feel for what makes a Digital con good or bad.

I just attended the LessConf in Atlanta; one of my favorite cons to date. Limited to 225 participants, LessConf breaks rules. Leaders Allan and Steve really get it and get what their crowd is into. Every day was a surprise, from having speakers talk about how they failed with their startups to afternoon ice cream trucks to giving onstage wedgies to audience members (yes, you read that right).

A few weeks prior, I attended a large digital conference in Manhattan—let’s call them “MoreConf”—that had Fortune 500 CMOs speaking—and clearly an enormous amount of money behind it. Yet had it not been for outstanding presenters, the bigger conference would have been an epic fail.

What made the smaller conference so awesome and the well-funded one so full of suck? Plenty, it turns out.

I could cite several more examples, but I’d prefer to leave you with some words from LessConf promoter, Allan Branch. I asked Allan what he thought made LessConf different from other cons.

“We wanted to make the conference we’d want to attend. It’s more like a party than a conference in some ways. If you take away two or three things from the speakers, that’s great. But if you leave with 30 new friends, that’s what it’s all about.”

Chris Brogan’s recent post on flying tips got me thinking on my own experiences as a frequent traveler. It may seem glamorous to the outsider to fly around the country speaking to CMOs and CEOs about social media—and it can be—but you are only seeing part of the story—the fun part.

The traveling itself can be grueling. Even the best hotels have a bad room, flights frequently get canceled or delayed leading to more unwanted, overnight stays than I care to remember.

“What? Stating an extra night in San Francisco? Poor baby!” It’s not like I got a free vacation day. Staying an unexpected evening means one more night in unwashed clothes. I travel as light as possible to get through lines quicker, and that means no extra clothing (although I do bring extra boxers and socks).

Hotel cleaning services rarely align with flight schedules, so you either travel dirty on the return flight, or get your clothes cleaned and possibly miss a flight.

My biggest pet peeve are hotel ironing boards. Invariably, a shirt will need a quick press before speaking to a crowd, but most hotels buy ironing boards that look like they were used to pen in goats. If they aren’t filthy, they’re so wrinkly, I often feel the need to iron the board itself lest I add permanent wrinkles to my shirts.

How about you? Ironing boards got your goat, or does something else about travel bug you?

Dear Foursquare,

I’ve been seeing someone else. I know. I know. We had such a good run together. But it’s just not working out anymore. You’re just… how do I say this politely? Unstable. I want to go places and you take forever to get ready. Your locations load like black strap molasses and frequently they’re just plain wrong.

You even forget where I am. How rude is that? I fly to New York and you think I’m still in Detroit. What kind of relationship is that? I ask so little of you and you just can’t deliver on your meager promises.

So I”ve found someone new. We’ve glanced at each other for years but it was always from afar. Yes, I know, stop your crying. It’s just that Gowalla takes care of me. Even has better icons and more to do. And Gowalla knows where I am and rewards me. I’ve given you over 1,000 checkins chances. It’s time to let go.