Game Mastering Shamelessly: The Shameless Challenge Revisited

Shame is a crippling thing. We worry so much about people’s judgement that we stop letting our true selves flow naturally; we tie our true selves down to avoid confronting others, and when the things within us inevitably break loose, such is the force of their escape that people nearby instinctively shield themselves.

It makes the practice of marketing – the practice of finding people whom you can help with the willingness and budget to pay you for it – trickier than it needs to be.

I want to do something about my own shame of being a geek, a game master. So, I’m returning to a challenge I first attempted back in 2015.

Care to join me?

What do Shameless Maya and Gary Vaynerchuk Have In Common?

A couple of years ago, whilst searching for tips on creating videos for YouTube, I came across a social media personality called Shameless Maya. In her YouTube page, she had a playlist for something called “The Shameless Challenge:” An effort to get over her own blocks to being herself in public and on social media. As far as I could see, the experiment was a success: When I compared her videos from before and after the challenge, I discovered a lady who’d discovered the brassy side of her personality and how to deliver it to her audience.

I took a whirl at the challenge, but got burned out on it fairly quickly. Something in me was still resisting. What was it for? What in hell did I have to offer?

Doubt. It’s a short word for a complex challenge.

Fast forward to a couple of days ago. I’ve discovered my overarching theme of being a game master – a host, referee and story-driver of tabletop roleplaying games – and am in the midst of preparing Season 5 of The Paid to Play Podcast for go. After coming across a video by Gary Vaynerchuk, the king of new media marketing, in my Facebook feed somewhere, I head over to the guy’s YouTube page and find a Q&A video where a guest asks him about his “document vs. create” strategy:

I’m reminded of Shameless Maya’s Shameless Challenge. All of a sudden, I’m thinking about all the RPG stuff I’ve been doing lately, from rules summaries to actually GMing for friends again.

And I think, maybe it’s time to try some documenting. Could I revisit the Shameless Challenge?

Well, let’s go over the goals and objectives from 2015 in light of my resources in February 2017 and see what I come up with.

The Goal and Objectives of the Shameless Challenge

Goal: Same as last year (and Maya’s original goal) – following through on accepting that I’m awesome and presenting myself accordingly.

To be as me as I can possibly be on social media.

To push outside my comfort zone and my fear of judgment in particular without trying to damage myself or anyone else.

Objective: Get me into the habit of sharing stuff on social media and responding to feedback.

Maya’s specific objectives (with option to review based on progress) were:

  • 10 tweets and 3 Instagram photos per day.
  • 4 blog posts per week.
  • 1 YouTube video every 2 weeks, with the aim of eventually going weekly.

(These aren’t fixed; Maya made sure to review on a regular basis and adjust what she was doing based on the results she got.)


Maya’s original challenge was to blitz social media, blogging and video for a year. For now, I think I’ll challenge myself for four full weeks – Monday, February 6th to Sunday, March 5th – with a review every week and an end-of-month review to see how I feel about continuing.

Producing Content

Let me take a look at the challenge’s requirements:

Thirteen Daily Updates on Social Media

Since 2015 I’ve got to know Instagram and am still in the early stages of friendship with Snapchat. While I have my @PaidPlayPodcast account automated via Social Jukebox, I’m not counting that toward my quota as it’s not so much focused on me-as-gamemaster. Still, I’m cooking along well n Twitter and I’ve created some lists based around the RPG hobby which will give me plenty of content to retweet – and there’s the 30 Days of RPGs social media questionnaire that Hyper RPG put out!

One thing I want to avoid is keeping a precise count. Some may see it as a requirement for change but I want to avoid driving myself up the wall – and this project is about finding my own pace on new media as much as anything else.

Weekly Web Log Posts

Maya aimed to produce four new web log posts a week. This will be a tough challenge as I tend to write long form posts (such as this) – but on the other hand, this could help me keep my blogging focused. I still have a nice list of post ideas about RPGs and related toipics in my Evernote files; I think the trick is going to be fleshing them out when I can (lunch breaks, etc.).

Fortnightly YouTube Videos

This one’s going to be interesting. I bought a Logitech web cam with some birthday money the year before last, so I’ve got the necessary kit. Again, I think the focus is going to be on keeping it short, although the good bit is, I only need to output two in the first month.

Fighting Shame and Doubt

As I wrote above, doubt is a short word for a complex problem. My main worry is is what others will think of my embracing the smart phone as a marketing tool.

I think a lot of doubt comes from shame, from that fear that others will think of you, how they’ll judge. In response, I’ll give you another Gary Vaynerchuk video:


I’m sick of living like I ought to be in fear of my own existence, of the world around me, of being one of “those people”. I already am. To borrow the words of another creator whom I’ve looked up to over the years, I want to find the future thrilling. It’s here. We’re in it. The tools are already everywhere. Let’s stop letting shame throw our curiosity out of balance.

And finally, to once again quote Uncle Keven, the Hollywood Career Coach:

“Less think, more do!”

Let’s all flow!

I’d love it if you could join me on this challenge. You can find the links to my social media presences at the bottom of every page, and here’s my Snapcode: