Your First Convention and You: Is the ‘Con Life’ right for you?

2019 was a year of firsts for me. My first time DMing for charity, my first time making bratwurst from scratch, my first year working freelance full-time, and my first time going to a convention. What did I learn from the experience, what insight can I offer to you kind people? Let’s unpack exactly what to expect as learned from my 2019 travels.

The Convention Goalpost

This isn’t a bright note to start out on, but it is the most true thing I can say to you: When you begin talking about your “first convention,” if it is not literally “the biggest Gencon in recorded history” you will have people tell you that whatever convention you are at/going to is not a big deal.

It comes from a good place, I believe: trying to convince you that there is no reason to be concerned, confused, or anxious because it could be much worse. But, as we all know, those comments come across more belittling or elitist than anything else. Things could always be bigger, badder, worse, etc. So before you talk about it being your first convention, consider if you have the spoons to deal with hearing about how small it is compared to ______, which often goes hand in hand with how much more EXPENSIVE ______ is. You will hear it a lot, and I urge you to not be disheartened. Do what you can when you can and don’t feel obligated to bite off more than you can chew.

Having said that, there are a lot of amazing things to talk about and more pertinent warnings to discuss.

The Overview:

D&D Live

D&D Live 2019: The Descent was, as people love to describe, something of a “Dungeons and Dragons summer camp.” The convention center was small, sectioned off for only 300-400 people in total. Despite its size, there was a lot of time spent on presenting the theme of the upcoming Descent Into Avernus adventure book coming out later in the year.

The first day was actually pretty weird. General attendees were kept in a large outside courtyard crisscrossed with canopies, huddled around a few picnic tables. Pasty nerds in the California sun with little to do but mingle was /just/ as awkward as it sounds. However, there were tons of announcements telling us about the adventure to come and swag bags full of interesting goodies. The adventure was actually announced on Amazon and other reporting websites HOURS before we, who bought tickets to hear the announcement first-hand, were told what it was. It was a little disappointing, but not unheard of. I’d report on the announcements inside the auditorium, but they were all broadcast, so…

Day 2 was the highlight of things, for me. Most of the big named personalities of the D&D community arrived for games or announcement panels such as Matthew Mercer, Travis McElroy, Deborah Ann Woll, Joe Manganiello, Matthew Lillard, and many many more. The whole time our favorite podcasters were brought into small booths inside an off-shoot area near the select few vendors to record podcasts relating to The Descent. I hate they didn’t get better accommodations for their craft, but it was still awesome to see them at work, many in cosplay for their parts. The mornings started out with the entire auditorium made into a play area for the Epic that went along with Descent Into Avernus. The epic itself was pretty story-light, as it is supposed to be, by design, but having people in-costume (dressed as devils, ogres, kenku, etc) wandering around the play area was absolutely incredible. I even had James Introcaso, dressed as a Kenku, wander up to my table and ask if anyone had magic items for trade. I handed over a Blue Dragon Fang that I had since Season 1, Session 1 (over 5 years ago) for an immortal demonic goat. So that was a thing!

Day 3 was a wind-down and much more close and personable. Many big personalities did signings and people like Kate Welch and the unbelievably awe inspiring Christopher Perkins mingled with fans and content creators all day. Games were ran inside the auditorium and toward the end of the day, the bar opened for alcoholic drinks and merrymaking while a concert was held on the stage inside the auditorium. Everyone left from day 3 wishing D&D Live was just 1 day longer – but alas.

Overall, the selling point of D&D Live is the experience. There’s nothing happening there that you cannot see on Twitch or read about online, but seeing it first-hand and shaking hands with people you’ve previously only dreamed of meeting is amazing. Mingling with friends you knew from across the country (or the world) and watching performers who relish the chance to send people on small adventures cannot compare to any videos or photos. Talking with the entertainers, out of character, was just as amazing as hearing their bombastic performances; they practically exploded with kindness and enthusiasm for the event and their parts in it. I handed out 10 sets of dice to performers that matched their outfits and was so amazed when every single one of them looked abjectly touched. Many were starting their own D&D games or were turned onto it by the event itself, and I couldn’t have felt happier to contribute even a small piece to them.

Meeting someone I’ve idolized for nearly a decade and having them know me, by name and correspondence, made me a blubbering mess for a few minutes on Day 2, but talking shop with some of the people instrumental in the development of D&D over the past several years really made D&D Live the perfect introduction into the world of Conventions. And, I’m told, VERY FEW people got sick!

Pax Unplugged

A completely different monster from D&D Live, Pax feels much more like the book fairs we all loved in middle school dialed up by 30,000%. The atmosphere of Pax is so completely different as to boggle the mind as a second convention. The convention center where Pax:U is held is, to put it mildly, a f*c#$ing g%*@!mn nightmare designed by devils in hell. But once you realize how to navigate it, it has a plethora of things to offer. I am told Pax:U in 2019 was 3x bigger with 40% more people than 2018 – meaning 2020 could have been huge at a better date (I fear very few people will manage to make it during the THANKSGIVING TRAVEL SEASON when costs are highest and year-end crunches are at their worst).

One can sign up to play games, walk through hundreds of booths and stalls filled to bursting with TTRPG goodies of all kinds. Many panels were on offer, some with INCREDIBLY long queues, all hours of the convention day. The center itself is central in Philadelphia, meaning a lot of places are within walking distance, if you can manage the traffic and cold. Unlike D&D Live, and despite my best efforts, the convention center is not a great place to mingle with peers outside of the gaming table (which, no joke, I never found. I never found the Game Hall in 3 days of looking.). Passing hellos while frantically looking for the right path to reach your next destination means a lot of short conversations and photos with very little substance. My biggest and most memorable moments were /outside/ of the convention center: having lunch with Celeste Conowitch, Joe Dye, Ted Sikora, and Renee Rhodes. And having an amazing breakfast and coffee meet-up with my DMs Guild peers as-thrown by Lysa Penrose. I’ll never forget the Geekly Inc meet-up at Destination Dogs with the incredible cast of Greetings Adventurers and Dear Internet as well as the owners of DieHardDice. Or even a humble dim sum dinner among new and old friends from the community, listening to their passion for projects finished and coming soon.

Overall: Pax Unplugged feels like a marketable networking experience and goods fair. Chatting with the proprietors of my favorite companies and seeing my peers and friends get the attention and recognition they deserve was surreal and worth the trip. If you are going into Pax Unplugged without traveling buddies or roommates, I fear it may be quite taxing and incredibly expensive. Your mileage may vary compared to those of us who eat, drink, and breathe tabletop RPGs and the community that surrounds them.

How to Travel

No one in their right mind would call me a travel expert. I’ve only been to about 30 out of 50 states, many due to a 5-day road trip in which I saw 1% of several states. I’m in my 30s and my first time on a plane was 2018. BUT, I may have some tips for you that saved me quite a bit of cash.


I highly recommend you grab the app “Hopper” (not sponsored, though I wish). I planned my trip to Los Angeles for D&D Live on my own – hunting various websites and looking for cheap deals. The general admission ticket was $300 (quite pricey) and proved a barrier to entry I could not overcome on my own. It was with the help of my peers and the incredible community that I managed to afford my trip, and I will never forget that kindness. The flight from Las Vegas to L.A. was a modest $85 round-trip, but I only managed to snag a price so low by waiting 4 hours before my flight, 5 hours after landing before check-in at my hotel, and 8 hours after check-out before my return flight. 17 hours of waiting to save about $30 will not be the best bet for most people. AND I brought no carry-on luggage, only what I could fit in my travel bag.

$0.02 in Airfare… pretty cheap.

Fast forward to December and Pax: Unplugged. Using Hopper, which live-updates the cheapest flights to whatever destination you’re going to, I managed to get a flight to Philadelphia for $15 each way… $30 round-trip flight to Philadelphia, over 2,000 miles away. My head nearly exploded. I paid forward my good luck by buying a carry-on bag for $37 each way, bringing my total flight cost to $102.62. So, uh… yeah – that was the best I could have ever hoped for (hopped for, hyuck) really.

Hotel vs Air B&B

This is a nearly impossible comparison, but I will break it down for you as simply as I can: If you have more than 4 people pooling money with you, get an Air B&B. The extra space, additional sleeping areas, and more lax rules for number of guests means you’ll have a much easier time LIVING. I pooled together with 5 other people (6 total) to get an Air B&B for our 5-day stay in Philly for Pax Unplugged and grand total it came out to around $130 each. For the area and how close we were (about 6 blocks) to the convention center, it was VERY cheap, and the apartment we rented was pretty nice with tons of towels, soap, washer, dryer, cookware – all the stuff you’d expect in a furnished apartment.

If you have 4 or fewer people staying together, get a hotel. A hotel costs more up-front. Sharing a hotel room with Ted and Renee cost $210 for a 3-day stay. BUT, look to get a hotel with a free breakfast. Breakfast in L.A. can cost anywhere from $6 to $30 if you can see the Hollywood sign. Having the sheets changed every day and fresh towels brought in means you’ll have no issues should sleeping arrangements need to change or roommates cycle out for your stay. Hotels also have attendants that can see to your problems immediately, while an Air B&B makes you deal with it, mostly. On top of it, you can not only haggle rates with a Hotel more easily, but there are far fewer hidden fees (an Air B&B in LA charged some of my friends a $200 cleaning fee because they had an extra person sleep there one night. Yikes.)

In addition, a hotel will, generally, have much better accommodations for people with mobility issues, such as elevators, ramps, handrails in the bathrooms, and other conveniences that people may find absolutely necessary. Know you roommates’ needs!

Gett’n Around

Taxis are overseen by whatever malicious force shrouds our universe in misery. I have spoken. They’ll be RIGHT THERE! You can touch them with your FINGERTIPS – but on average they can cost $10-$15 more than a Lyft or Uber, especially if you ride share. If you’ve got the money to burn or you’ve got exactly 2 other people with you – nab a taxi. Otherwise, just use a ride share to get away from the airport. No airport in the United States of America is designed to be easily accessible on foot, so don’t bother. You can take one of the shuttles that run 24/7 FROM the airport to literally anywhere other THAN the airport and Uber/Lyft from there if you’re really strapped for cash, it’ll be cheaper even if you add 5-10 miles to your journey by going to the wrong direction. An Uber from the Las Vegas airport cost me $35. And Uber from 2 miles east of the Las Vegas airport cost me $12.

Luckily for me, both D&D Live and Pax:U were close to where I was sleeping and I spent most of my time on foot. LA was nice weather (with sunglasses and an umbrella) and I only sweat a whole lot instead of a disgusting amount. Philly was freezing and people wanted to run you over, BUT – round-trip only cost me about 40 minutes of my day. Well worth the savings, if you can manage it. Get those steps in.

Absolute Necessities, In My Opinion

You hear stories all the time about conventions, many are exaggerated or twisted to seem unreasonable or downright hostile, but here are a few things I found ubiquitous to both D&D Live and Pax:Unplugged:

  • A travel buddy. Someone going to/from the event at the same time as you that you can rely on at least a little, in the city. In my case, Adelaide ( ) helped drag me out to have fun at Pax and Ted ( ) and Renee ( ) did marvels to keep me from feeling overwhelmed at D&D Live.
  • Good shoes. Listen, I know this is a tired suggestion at best. But I averaged 20,000 steps every day of D&D Live and almost 30,000 steps every day of Pax: Unplugged (one of which was carrying my luggage with me). A blister on day 1 can make an overwhelming situation feel like torture. If you can walk and plan to do so during the convention, please bring good, broken in, tried and true comfortable shoes.
  • Find ways to relax between big moments. It can feel like you need to go-go-go or miss out on something, but these events are SO BIG that you’ll never see everything. Even at D&D Live, which is tiny, there were announcements in one place, games in another, and friends asking me to go and do. There is no way to be everywhere at once, so don’t try. Give yourself time to recuperate if you’re feeling burned out. Better that than lashing out or hurting someone unintentionally.
  • Do you hug?” Ask it. Every time. Even if you hugged them before. People at Pax chittered happily when I would ask if they hugged before going in for one. It’s less about if they hug at all and more about having the option of saying no and relief of being asked. People may be sick, people may have forgotten their deodorant, people may be obscenely nervous about a panel or bad interaction they just had, they could be sweaty, you could be sweaty, the ghost that haunts their hair may want your teeth – you never know why someone may feel relieved to have the option to say no to being hugged (or touched in any way).
  • Get your bearings. Pick a point at the convention and relate it to everywhere you go. I got lost every day of Pax:U, but on the 3rd day, I finally anchored myself to “Crab God Theater” and worked out how to get everywhere from there. It was a life saver.
  • Ask for the selfie, ask permission before posting candid photos. This is pretty obvious, y’all. Don’t assume people are up for it. Assume everyone is just as tired or run-down as you are (or more) and ask. Ask, ask, ask. It’s a self esteem buster to have a photo taken and posted in which you think you look like hot trash (even if others say you look fine).

A Word on Anxiety

We’re all human. With being human comes some pretty harsh baggage. For me, it’s social anxiety. My anxiety comes in the form of believing I’ll represent myself as something I’m not and any attempt to fix it will only make matters worse. Lots of people heighten that anxiety. A professional setting worsens it even more. There’s a paralysis that comes from it that makes me over-analyze every word and facial expression to the point I become this awkward meat golem that trundles around so lost in my own head that people think they should avoid me; on the inside I’m begging the noise to stop.

I will fully admit that D&D Live had me completely destroyed every morning when I arrived. From the time I could /see/ the line, I started feeling like I should shatter my knee just to avoid going any further. The one thing that made me keep taking those steps was the idea that someone there might want to see me. That I could try, even if I failed, to brighten someone’s day.

Currently, I take no medication for my anxiety (though I know a should) so it was particularly challenging trying to keep an approachable air about me while struggling not to just climb into the sewer to get away from everyone.

You. Are not. Alone. Most of the people there with you suffer from something: anxiety, depression, physical aliments, stutters, body dysmorphic disorder, even just social ignorance or ineptitude. Several times I, the gargantuan mess that I am, took someone by the shoulder, told them they are okay, and made an introduction with a celebrity or Tabletop Personality that they desperately wanted to meet but were afraid to talk to – not because I was somehow better equipped than they are, but because I KNOW what that feels like and in that moment I was more okay than they were. It’s okay to need someone, it’s okay to not be okay, and everyone of importance, anyone worth your consideration, will know that. Be up-front and honest with people: “I’m feeling overwhelmed.” You’ll be surprised how many people will be there for you, myself included.

Final Thoughts: some good, some bad

There are going to be some issues you deal with at any convention. Not only from my experience, but from countless stories I’ve been told by my peers. Going into these conventions, you have to weigh the good and the bad for yourself or be driven crazy by it. The last thing you want to do is head out to one of these things, spend your hard-won money, and come away feeling regret.

For me, the negatives of these con experiences were:

D&D Live

  • The venue is uncomfortable. Standing in line under the harsh California sun is a nightmare born from hell for a pasty ghost like me. Myself and several others struggled HARD to deal with the sun and the lack of comfortable space at D&D Live itself. There’s only so much you can do with outdoor picnic tables trying to service 300 people. Day 3 of D&D Live I didn’t sit for nearly 9 straight hours, luckily I am able to do so, but many are not.
  • Day 1 was actually a little boring. Again, there is very little to do other than buy pricey (“gourmet”) food from the food trucks and sit around at the picnic tables, so the majority of the day was spent inside the auditorium watching product announcements and interviews. You very much have to make your own fun on that first day before general attendants get access to the vendors.

Pax: Unplugged

  • The convention center is gargantuan and confusing. You will get lost. People said over and over “I have to learn this convention center again every year.” One way in, infinite ways out, if you take a wrong escalator you may find yourself having to walk all the way around the building, through security, in the middle of December. It’s a big burden that could be alleviated by some $0.10 signs.
  • Despite the diverse and interesting topics, Pax:Unplugged had the same few panelists appearing on SEVERAL panels. I’m not crying ‘favoritism,’ but it was quite jarring hearing the same few voices over and over at panels on all three days of the convention. With hundreds of submissions from thousands of TTRPG personalities, it would have been so easy to populate the panels with a huge variety of content creators and designers. Alas.
  • Unplugged is held at the worst time of year. It’s just a fact. Travel prices are higher, Hotel and Air B&B prices are higher, the weather sucks, people are stressed, and the vendors have to deal with Gencon, Black Friday, Pax: Unplugged, and Chrismas all in just a few short months. There is a high likelihood, nay guarantee, that someone you’re over-the-moon to see and talk to is having one of the worst days of their entire year – its what winter does to people.

But past the complaints, past the financial strain, past the looming fear and awkwardness… These conventions are about the people. The community that comes together to share a very specific love, the friends you never realized meant so much to you, the moments you share amid the noise and chaos you will look back on and smile at. I, personally, feel like opening myself up and attending these conventions has been a huge positive influence on my life, despite anything negative that I could say or experienced in the moment.

If you have any specific questions, thoughts, comments, concerns, or fears – reach out to me. I’d love to chat and help you find a way to make your first Convention experience a damn good one.

Until next time.

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