What a Business Retreat in Puerto Rico Taught Me (The Expected and the Unexpected)

Street art of Puerto Rican flag

Sometimes you need to get out of your office to get a fresh perspective.

I was reminded of that recently when I packed my bags for Puerto Rico to meet my business accountability group, the Creatives Roundtable. We talk virtually every week, but there’s something powerful about being together in the same place, away from our normal environments. In previous years, we’ve met up in Savannah and Playa del Carmen, and this year we landed in San Juan.

It was cold in Georgia, so I wasn’t just thrilled to see my community—I couldn’t wait to feel the 80-degree heat in San Juan. (It was glorious.) We learned and shared, ate delicious food, took an art walk, visited the beach and rain forest, slid down a waterfall, and even overcame some “surprises” together, which made the experience even more perspective-shifting.

The expected, and what we learned…

We had some pre-planned sessions. Here are the topics we covered:

  1. Making your own GPT in ChatGPT. I have the paid version of ChatGPT and use it for all kinds of things—marketing, coding, skincare, random stuff. But I had never made my own custom GPT. You can create one that’s tailored to your needs by giving it examples and instructions. We had a working session, and I actually used what I learned to add content to my WordPress maintenance page on my site. Very helpful!
  2. Hot seat sessions. We each brought something we wanted advice on. I was telling them about the SEO 101 for Creatives product I’m working on, and they suggested I add audio recordings so people can listen instead of just read. They suggested going into a closet or under a comforter to record, so I tried it on my iPhone. I recorded an intro, sent it to the group for feedback, and they gave their approval. Who knew “recording booths” were this readily available?
  3. How to have conversations on LinkedIn. This session was about expanding your reach and presence through meaningful engagement. I’m terrible at commenting; my social anxiety makes me hesitate because I think nobody cares. But the formula they shared was simple: Find a discussion that’s already going (where there are comments), add your comment, and then ask a question. This creates a way to carry on the conversation and gain visibility. 

The unexpected, and what we learned…

Logistically, there were some surprises:

  • The pictures of the Airbnb we stayed did not match the actual place. They had clearly been AI-enhanced. (While we are all finding AI quite useful for many tasks, I do not recommend it for this one!)
  • The house was right next to a highway. It was very loud, and people had trouble sleeping. But I discovered something about myself: apparently I can sleep through anything! I think my kids and dogs are to blame. I gladly switched rooms to the noisier side of the house.
  • The water in the shower was lukewarm, at best.
  • The pool was not the oasis that had been sold to us. We had imagined sitting around the pool having our sessions, but that wasn’t happening. So we made lemonade out of lemons! We found a cafe and some cool local places where we did our scheduled sessions. 

The retreat was worth it, many times over.

The trip was good for the soul. Being with a group of folks you like, who are also business owners—is invaluable. Even the surprises fostered a sense of unity and resilience—a mutual challenge to overcome. The unexpected is part of the deal when you leave your comfort zone!

Granted, I was really happy to come home to my hot water. (And I appreciated it even more!) 

About Jill Anderson

Hi, I’m Jill, a WordPress web designer/developer who partners with talented designers, copywriters, and agencies on their websites, and their client’s sites. I’m passionate about crafting beautiful and innovative WordPress websites focused on clear positioning and positive user experiences. Get my free report, Get Your Website Done: 12 Actionable Steps for Designers, and check out my Client Onboarding Toolkit, a simple 4-step digital course for converting prospects into a paying clients.

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One thought on “What a Business Retreat in Puerto Rico Taught Me (The Expected and the Unexpected)”

  1. SO GLAD you took some time for a retreat with some biz friends, Jill — sounds like it was a great reset and perspective-builder! Great images, that coffee looks heavenly!

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