Hello from the Caribbean! A Recap of our 2018 Annual Strategic Retreat

Lucky Break Strategic Retreat

 

Turquoise waters. Mimosas for breakfast each and every morning. Dessert served on white china multiple times per day. Crisp linens turned down each evening just before bed. Postcard-worthy sunsets.

 

It’s safe to say that there are worse ways to tuck yourself away and do some business planning. Right? RIGHT. The Lucky Break team has a tradition of gathering together once per year for our Annual Strategic Planning Retreat. In years past, we’ve huddled in NYC, Asheville, and Savannah (you can see my reports from those retreats here and here). But I decided to kick things up a notch or three this year and take the retreat to the seas.

 

 

Earlier this month, Shannon, Melissa, and I boarded a Royal Caribbean ship and set sail for a 7-night cruise through the Eastern Caribbean. Yes, there was horseback riding through a 2,200-acre Puerto Rican ranch. Yes, there was catamaran sailing. Yes, there was sea-turtle-spotting, acrobatic shows, jaw-dropping sunsets, and plenty of poolside sunbathing. It was divine in so many ways. It also involved a fair amount of seasickness, which was far less divine. It’s all about balance, right (no pun intended)?

 

 

This year, we decided it was just too damn cold to stay stateside. And we’ve been digging extra deep in our workloads lately, too, so some teal Caribbean waters felt like just the ticket. And the Caribbean did not disappoint. Exhibit A…

 

 

We stayed in a swanky Royal Sky Loft Suite, which meant that we had two (!) bathrooms, a generously-sized balcony, a dining area, a bigger living room than I’ve ever seen on a cruise ship, and a lovely loft bedroom. Melissa and Shannon crashed there, and I slept where I always do: on the balcony. The room stewards always think I’m slightly mad to sleep outside, but have you ever seen the nighttime sky from the middle of the ocean? So. Many. Bright. Stars. And the wind swirls around me as the waves lap against the boat and I promise you: it’s the best sleep ever.

 

 

Some of our favorite moments:

  • Melissa had recently commented that she had never had a corn dog (HOW? How is that even possible?). I scoured that boat for corn dogs to no avail. I finally asked our room steward where a girl could get a corn dog and the answer was: Not on this ship. But a few evenings later, the chef paraded out a plate of the most decadent corn dogs, especially for Melissa!

 

 

  • My birthday is in January. and I typically take a very Buddhist view of the occasion. It’s a quiet affair by choice: no cake, no balloons, no parties. I prefer to spend the day in quiet reflection. I sleep in a bit, eat something delicious, get in some extra meditation time, and think about what I want for myself in the year to come. Our room steward noticed that my birthday was coming up soon and surprised us by decorating the room with signs, mobiles, and crepe paper pom-poms suspended from the ceiling. The chef and wait staff presented me with song and cake at dinner. It was much more “high key” than I generally prefer, but it was so incredibly sweet that it made me cry.

 

  • Mimosas that magically appear when you sit down to breakfast. And wine glasses that never go bare at dinner.

 

 

  • Melissa was one of just three (out of 6,000 people!) selected for additional screening by Immigration and Customs Enforcement. That sounded intimidating at first blush, but it simply meant that we were able to skip the dreadfully long passport lines and go directly to an enforcement agent who informed us that “This is all b.s.!” and sped us right through.

 

Inbetween the ice cream cones and sunbathing and swanky dinners, we accomplished a surprising amount of work. At each retreat, we pull sales data and financial reports. We launch surveys for each of our key programs before each retreat and review the insights those surveys reveal. We review the report from the previous year’s retreat and reflect on what we did (and didn’t accomplish). We pull back and look at the bigger picture of what we’re doing, reconnect with our core values, analyze team responsibilities and technology to look for fresh efficiencies. We perform competitor analyses, so we can keep a finger on the pulse of the landscape. We explore new collaborators and colleagues, too.

 

And the very last thing we do is plot every product launch, speaking engagement, and enrollment period on a giant desk calendar that we’ve deconstructed and taped to the wall. Color-coded post-its are arranged and rearranged until we have a solid roadmap for the year ahead.

 

 

So what decisions did we make this year? I can’t dish on all the good stuff just yet, but here are a few sneak peeks:

 

  • My book on the psychology of smart pricing will be published this year! Look for it this summer. This is a subject that I’m hyper-passionate about… how do you go from a pricing system that’s based on your costs to a pricing system that’s based on your brand? I’ve been collecting examples for the past few years and I have some interesting strategies up my sleeve.

 

  • We’re playing with the idea of introducing a whole new product category to Lucky Break’s offering. It would be a big departure from what we do now (*insert big tease here*). I have an appointment with my IP attorney in the next few weeks to get the green light, but I’m so excited about the possibilities!

 

 

  • I finally moved over from Snapchat to Instagram Stories. I know, I know… you’ve probably been there for a year already. What can I say? I’m late to the game. But I’m having a ridiculously good time with it. I’d love to have you follow along!

 

  • We’ll soon launch Instagram Story takeovers featuring some of our favorite clients. I’m so eager for them to pull back the curtain and give you a peek inside the day-to-day mechanics of running their empires.

 

 

  • At the end of 2017, we hired a part-time Technical Product Manager (Hi, Helen!) and that opens up a world of possibilities with regard to new product development in the software space. We’re still deciding which direction we want to take that, but the possibilities have us positively giddy.

 

  • We also just hired a new full-time teammate (Hi, Angie!) who was onboarding while we circled the Caribbean. She’s whip-smart, decidedly lovely, and she has a few skill sets that we’re exploring how to put to work, too.

 

 

All in all, not a bad way to spend a week. We have some big things on tap for 2018 and I hope you’ll keep an eye on Lucky Break as we roll out new things. Even better: hop on my mailing list and you’ll never miss a thing (Bonus: I’ll deliver free business wisdom to your inbox every few weeks). Will we take the retreat to the seas again next year? Who knows, but I certainly wouldn’t mind it!

 

2 comments

  1. Wow! What an amazing adventure you all had! From the pictures, it looks a lot like a space that would calm you and get everyone’s creative juices flowing and thinking positive. Your post-it note adorned calendars make me wish I worked for Team Lela Barker! That kind of organization is what I live for!

  2. That’s definitely the way to do a retreat! I’m excited to see what this year unveils from Lucky Break (and me). And thrilled that Angie’s on board! Having finished BHB with her, I know you have a winning addition to your great team. Happy New Year and Birthday!

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