Full Tank: 5 Things I Learned at #CaboPress

You know those items on your goal list that you just can’t seem to achieve?

Big confession: even this goal-getter has those insurmountable items that get stuck in goal purgatory.

The biggest one that keeps getting pushed to next week, then next month, has been: Getting support for myself.

Those of you with a service business are probably nodding your heads right now. As people whose livelihood comes from supporting others, we’re often intrinsically motivated to make an impact. Yes, it’s incredibly fulfilling, but that spirit of service alone can’t sustain us. We’re continuously pouring out, but not that great at filling our own cups.

I’ve been acutely missing a mix of high-level business insight, moral support, entrepreneurial empathy, and space to relax, rejuvenate, and dream.

Enter: CaboPress.

Chris Lema’s annual conference brings together founders and rising stars in the WordPress world, including those of us who are WordPress-adjacent. I met Chris nearly a decade ago through his fantastic blog, got to know him via Twitter, and even booked consulting calls with him over the years. This past year he was pivotal in building Pregame on Demand. Now, I’m lucky to count him as a mentor and a friend.

So when he invited me to host a talk on PR at this year’s retreat – in Cabo – in a poolat a five-star resortsurrounded by like-minded people, it was an absolute Hell Yes.

And CaboPress exceeded my highest expectations.

After that week of education, motivation, and connection, my tank is full. So I’m here to share the overflow with you with these top five takeaways:

This is what it looks like to be a speaker at CaboPress.

Now is the Time to Create Ridiculously Unconventional Events.

There is much hand-wringing about the present and future of events: organizations that previously relied on live, in-person events as a major part of their revenue, product offering, or growth strategy, are too attached to the old school event model.

The impulse to try to restore what events used to look like is misguided. Now is the time to get ridiculous and creative with your events.

To be relevant in post-pandemic life, event producers must reimagine their format and get to the heart of what people really need right now.

The structure of CaboPress was both Covid-safe and conducive to real learning and transformation. Breakout sessions in a pool meant that we couldn’t be on our phones, keeping everyone’s attention on the topic. Loosely structured, small group meals gave us the opportunity for deep connection, building a foundation for relationships that will reach far beyond the week.

The Bigger You Want to Go, The Bigger Investment You Need to Make in Yourself.

It’s true: if you want to level up, you need to level up your environment.

It was a gift – to myself, to my business, and to my clients – to meet and have extended conversations with people who are ahead of me in business. Connecting with them in a relaxed environment meant that our conversations could be longer and that we both approached the dialogue with genuine openness and helpfulness.

The World Will Not End If You’re Unreachable.

We all say that it’s important to take time away from our screens, but how many of us are actually doing it?

Again, the pool sessions were brilliant because the only distraction was sunscreen application. The smartest attendees cleared their calendars for the week, ensuring that they had extra time to connect and forge new relationships, not to mention relax. We work hard. We deserve time that’s actually unplugged.

You Can Build Productive Teams Remotely and Make Meaningful Friendships Virtually

This may seem obvious to those in the WordPress world and the tech sector at large, but for the rest of us who may be nervous about continuing to work remotely remote office, the successful businesses and years-long friendships at CaboPress prove that remote work, works.

Of course, it takes a different kind of effort and deliberate design, but it’s definitely possible. Again, don’t get so caught up in the old model that you fail to see the opportunities ahead.

The Us-pert is the New Expert

Yes, I just made up that term.

Once you get to a certain level in business, all your peers have incredible treasures to share. So it no longer makes much sense to have a lecture structure for professional development in which one expert gives their perspective. A well-facilitated group conversation is the best way to leverage the power of the group to distill best practices for real life.

Facilitated peer groups is also how we do it here at Pregame; it works and it has the added benefits of building strong relationships and expanding networks.

Hangin’ with my buddy Chris Lema at CaboPress.

Do you have to campaign for a CaboPress invite in order to get these benefits? Absolutely not (although I’d love to see you there next year!). Here’s how to get some of the action without waiting until next year’s event:

  • Grab a few peers and have a topic-driven conversation in an unconventional space, like a on a hike or at a park. Put your phones in airplane mode.
  • Take a mini-retreat and make sure at least half the day is designed for play.
  • Organize a meal with a few of your favorite founders For best results, mix up the types of businesses, i.e. products and services.
  • Organize a pregame or afterparty to connect with a few select people from the next event you plan to attend.
  • Check out Chris Lema’s blog and follow him on Twitter.

Interested? Here’s more info on CaboPress!