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

Lucky Break 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!


The Lucky Break Calendar – January 2018

Hip hip hooray! It’s official; we survived 2017 and have landed firmly in January of the new year. I hope you recovered nicely from that big holiday push, because if you’re looking to grow your wholesale business, then there is no rest for the weary, my friend. Your big outreach period begins this month!


The Lucky Break team is setting sail this month, huddling together around crystal clear Carribean waters as we plan what’s happening in 2018. We have some big ideas in mind, and I can’t for you to hear all about them. Wish you were crusin’ with us? Although I’d love to bring you along, tune into my Instagram Stories (I’m @lelabarker!) for the next best thing. I’ll be sharing our trip all week.


Whatever you’re up to this month, know the entire team is cheering you on! Let’s kick 2018 off in style!




A Look Back at Lucky Break’s 2017



Is anyone else relieved that 2017 is behind us?


I aaaaaaaammmmmm! The year seemed ripe with division, disaster, and scandal.  I spent many a morning in 2017 asking myself what in the world was going on. But I’ve held tight to my belief that times of immense transition give rise to new opportunities, rebirths, and movements. I begin 2018 full of hope and prayer for a year that’s a wee bit less exciting (who’s with me?). I find reflection to be cathartic and I as took inventory of the year that was, I was reminded of how very much there was to celebrate.


Here’s a look back at 2017 through the lens of Lucky Break…


Wholesale Matchmaker

  • The Lucky Break team has now welcomed more than 450 Wholesale Matchmaker members – a monthly service that includes a wisdom-infused crash course in wholesale, twice monthly Q+A strategy calls with me, a matchmaking service that connects makers and product designers with independent shops around the U.S., and a robust CRM software system to help members manage their buyer outreach.


  • We’ carefully research each store that we match our members with, meticulously building profiles for every shop. In 2017, we added more than  1,300 new store profiles to our portfolio.  Our members can also request specific stores that they find out in the wild and we’re happy to research those shops and provide more information.  Those requests resulted in another 1,148 store profiles built. It takes an average of 90-120 minutes to build each profile… let’s do some math shall we?

         2,448 new shop profiles in 2017

         x An average of 105 minutes each

         = 257,040 minutes of store research on behalf of our members.

         That’s 4,284 hours of research or 107 weeks of full-time work in research for Wholesale Matchmaker members in 2017!


  • Because the Wholesale Matchmaker community is dedicated to empowering people around the globe who are building their dreams, my team proudly reserves 15-20% of the sales from the independent-study workshops we offer to our members, earmarking it to support various philanthropic programs. In total, Lucky Break donated more than $4,250 in 2017 – including funding the dreams of 40 American entrepreneurs through Kiva. Many of those recipients came directly from the Wholesale Matchmaker community, and they were able to access up to $10,000 in business loans at zero interest and without posting any collateral.  We’re proud ot have played a role in those successes!


  • I spent more than 55 hours of consulting time with members of the Wholesale Matchmaker community, building wholesale strategy and navigating retailer relationships via our twice-monthly Member Q+A calls. Every moment was carefully recorded and transcribed, so our members can listen to the playbacks or read the call logs, even if they couldn’t join us live.


  • I retired my flagship LBU “how to wholesale” course – and then rebuilt the curriculum into a new top-tier, 12-month education option within Wholesale Matchmaker. 163 WMM members joined one of 2 groups of the LBU Cohort and we’ve spent 2018 diving deep into wholesale strategy while connecting one-on-one within private Facebook communities and monthly group calls.


Lucky Break's Look Back at 2017


Brick House Branding

  • I graduated 3 semesters of Brick House Branding this year, sending 87 students out into the wild to put their new branding prowess into use!


  • I went “behind the scenes” to profile the “before and after” stories of seven BHB graduates. You can check them out right here!


  • BHB hosted students from 26 states plus Washington, DC. We also rolled out the red carpet for participants from Canada, the United Kingdom, Barbados, and Malaysia.  There was a delicious amount of diversity in product categories this year, too, including: apparel, apothecary, men’s products, candles, toys, children’s and parenting products, gourmet food, jewelry, stationery + gift, home + garden, and pet products.


  • I spent a significant chunk of hours in 2017 rebuilding the curriculum for 2018 for the new year and evolving it into a new class format that includes private one-on-one sessions with me throughout the semester. While enrollment is full for the first semester owe’re18, we’re looking forward to throwing open the doors for the spring semester on January 30. Mark your calendar if you’d like to join us… enrollment will be very limited!



  • Price-O-Matic, my product pricing software, was reimagined from top-to-bottom and relaunched in April of this year as a cloud-based service. No need for Excel to crunch those numbers – ever! POM is now universally compatible, cloud-based, and accessible from anywhere on the planet. And every single user (there are THOUSANDS of you!) received a free upgrade to the new version.


  • The new version can crunch calculates and articulate prices in 5 separate currencies: U.S., Canadian, and Australian Dollars as well as British Pounds and Euros. International users can now add GST + VAT, too.


  • I put my development team through the ringer with a 52-page scope, which we then followed up with 96 total pages of revisions gleaned from multiple rounds of testing. The result is a thing of beauty that features all kinds of new functionality and helpful tools, including:
    • The Reverse Pricing Tool, which helps you pivot to a value-based pricing mindset, and then use that mindset to create a product development budget.
    • The Revenue Projection Calculator, which enables you to see the revenue paths you’ll need to carve out to in order to make the kind of money you desire each month.
    • A new feature on the Pricing Strategy page which helps you understand how various promotions affect your ultimate profitability
    • Plus, there’s a whole suite of printer-friendly reports that show a profitability snapshot for each product, a cost analysis for each product, and a listing of inventory items for each product. Hooray!
    • Price-O-Matic is now instantly delivered (it’s ready within 60 seconds after purchase!) and a fancy new help desk system ensures that we can service tech issues quicker and more efficiently.
    • And as for looks? The software is 36 times prettier and 94 times easier to use. Yes, I counted!


Speaking + Events

  • I returned to my favorite conference ever – Craftcation – in Ventura, California for a second year. I was honored to speak with attendees about brand development and value-based pricing. Team Lucky Break even took first place in the Wanderings competition, which is a self-guided art walk/traveling party tour held in various hotel rooms by and for conference attendees. My teammate Shannon and I transformed our hotel room into the “Get Lucky Lounge,” complete with a photo booth, a wishbone keychain craft, and bowls of Lucky Charms cereal and organic milk.


  • I’m thrilled to say that my crew and I will be at Craftcation 2018 for the third consecutive year, where we’ll be hosting yet another Wanderings room and I’ll be hosting a few workshops on product pricing for makers. And pssst…I’m also the closing keynote speaker. I’d love to have a cocktail with you while I’m there! Registration is now open and I encourage you to snag a ticket now if you know you’d like to go – they’re known to sell out quickly…


  • My entire team and I made another appearance at the HSCG conference in Las Vegas, where we jumped off a building together (no really – there’s video evidence!) and I spoke to 600+ attendees about brand development. I’m honored to return to speak at HSCG for the 8th time as I keynote at the 2018 Annual Conference in May in my hometown of Atlanta. I’m also speaking at the first HSCG Canada conference in June of 2018 in Toronto. I’d love to see you there!


  • I was honored to be a guest on three fun podcasts this year:
    • I spoke with Jeffrey Shaw on the Creative Warrior podcast about creating a compelling brand, from the purpose of creating strong brand architecture to the top mistakes to avoid in brand development.
    • On the Your Handmade Business podcast, I dished about one of my biggest failures (and how I overcame it) with Isaac Watson of Academy of Handmade.
    • I chatted with the oh-so-lovely Delilah and Nicole on the Dear Handmade Life podcast about creating a business that has staying power, from defining what success means to you to creating systems that help you work more efficiently.
  • If you’re looking for a 2018 speaker or podcast guest, do give me a shout… I’m all ears!


Lucky Break's Look Back at 2017



  • My teammate Shannon painstakingly went through every single blog post on the Lucky Break website (359 and counting!) and updated all of the graphics and images to match the new aesthetic branding we launched a year or two ago. The effort took a few weeks, but it helped breath life into some long-buried gems from the blog. I’m forever in her debt for taking the helm of that project.


  • Want to catch up on the top 3 most-read blog posts of 2017? Feast your eyes…

A Better Way to Manage Black Friday/Cyber Monday Promotions

Prioritizing Where to Invest in Brand Development: Behind the Scenes with Hettie Joan

Road Trip Recap: Craftcation in Cali + HSCG in Las Vegas


On a personal note, I…

  • Sold my house in Columbia, South Carolina.


  • Fulfilled a lifelong dream of relocating my family to Atlanta after my husband made a major job change.


  • Said goodbye to older daughter as I sent her off to her second year as an entrepreneurship major at Butler University (she scored a 3.73 GPA this semester!)


  • Survived my younger daughter’s 16th year of life. Teenagers keep it mighty interesting, don’t they?


Looking ahead to 2018

  • The Lucky Break team is hopping on a ship and pulling up anchor the second week of January. We’ll spend 8 days sailing around the Caribbean, making grand plans for the year ahead.  Between meetings and mindmelding, there will be plenty of cocktails, a catamaran or two, turtle-spotting, and horseback riding through the rainforest.  Want to follow along? I’ll be sharing the journey via my Instagram!


  • The new year always bring new travel opportunities, and I’m excited to have my team accompany me to speak at several conferences across the country. Because we all work remotely in different states, the magic really happens when we all gather together in one place, and maker conferences are our favorite place to convene to both speak + nosh with clients old and new!


  • 2018 will also see the release of my pricing book and a pricing class, both of which delve into the psychology of pricing for makers. Hint: Pricing is so much more than your cost of creation…


  • I’ll be rebuilding my wholesale curriculum from top to bottom, a project I take on every 18 months or so ensure that everything is deliciously up-to-date. I’m a little obsessive about making sure my curriculum is current and top-notch, and it’s time to delve into wholesale materials once again!


I’m raising a toast to every maker and product designer that I was lucky enough to cross paths with in 2017. Thank you for allowing Lucky Break to be a part of your entrepeneurial journey.  Here’s to more sleep, more success, more fulfillment, and more peace in 2018!


If you spend some time reflecting on your 2017, then I’d love to hear a few of your revelations on the triumphs and the struggles.  Leave a comment below and I promise to write ya back!


Could you be the next Lucky Break teammate?


We’re hiring!  The Little Team That Could is searching for a new teammate to join our spunky crew of passionate peeps with a deep + abiding love for entrepreneurs.


This is a remote position open to those in the eastern half of the United States, averaging 30-40 hours per week. You’ll be working from the comfort of your living room, communicating daily via email, Slack, and phone with other members of the Lucky Break team.





• Getting to know Lucky Break classes + services like the back of your hand.

• Supporting Lucky Break clients via email + phone. They’ll need you to help them navigate offerings to determine what will serve them best.

• You’ll also field more traditional customer service queries: locating + updating customer accounts, handling billing questions, scheduling private strategy sessions, etc.

• Managing my work schedule: booking clients, meetings, interviews, etc.

• Proofing line sheets, curriculum slides, blog posts, and handouts.

• Conducting detailed internet research for new projects.

• Helping match our Wholesale Matchmaker members with “good fit” stores that might be interested in carrying their work.



• Live in the Eastern or Central time zones of the U.S.

• Have access to your own phone line, computer, internet connection, and printer.

• Be willing to travel domestically 2-3 times per year for up to 5 days at a time for team retreats + company events.

• Have an eye for detail, a killer work ethic, a patient spirit, extraordinary communication, ninja-like organization skills, and a heart for people.

• Be a motivated self-starter capable of managing a robust workload while working independently.

• Enjoy being part of a small team of highly motivated women who have a deliciously low threshold for B.S.

• Be flexible. You’ll need to continually prioritize projects + learn new skill sets.

• Be capable of striking a healthy balance between professional + personable. We pride ourselves on delivering knock-your-socks-off customer service.

• Possess better-than-average writing + editing skills.

• Be ridiculously trustworthy. You’ll be signing both no-compete + non-disclosure agreements.

• Know how to have a good time. We work hard, but we play hard, too!

*** Some experience as a maker or product designer is strongly preferred. Our community has unique challenges and strengths that are easiest to relate to if you’ve traveled this path yourself! ***



Oh sugar, we can’t wait to connect with you! Please dispatch an email to hello@luckybreakconsulting.com with the subject line: NEW TEAMMATE. Include your resume with salary history. Additionally, please answer the following questions…

• How did you discover Lucky Break?

• What are you most excited about with this opportunity?

• What facet of this opportunity gives you the greatest pause?

• Which of your past employment opportunities brought you the most joy + why?

• Have you ever owned your own business?

• What did six-year-old-you want to be when you grew up?


Applications are open through December 15, 2017. We’re looking for a start date in the third week of January. Please, no phone calls. We’ll be in touch if it feels like a good fit for us, too!


The Lucky Break Calendar – November 2017


It’s here! It’s here! November has started, and that means we’re officially into the beginning of the retail holiday season. All of that hard work you’ve been doing to prepare is about to pay off. I know many of you are in the final stages of finalizing your Black Friday / Cyber Monday offerings, and, well, you know me. I’m never one to shy away from sharing my thoughts on discount promotions.Just. Don’t. Do. Them.


Need a few ideas on what you can do to still attract those clients like bees to honey? I’m sharing my ideas here, and I hope they’ll prove useful to you.


Whatever you’re working on this month, know that I’m cheering you on! And that the entire Lucky Break team is forever thankful for you.