Small business planning retreat

Time for a Mid-Year Checkup: My Business Planning Retreat with A Trusted Friend

After jumping back into the day-to-day at Pinstripe after a few years of taking a back seat, I realized I needed to spend some time re-evaluating my goals and ambitions for the agency with a fresh perspective. For many entrepreneurs, a business planning retreat with trusted friends can be a game-changer. This was certainly the case for me and my best friend Julie, a supremely talented mosaic artist with a burgeoning online audience. We both started our businesses in 1998 and have continuously shared our successes and challenges over the last 25 years. Last January, we decided to hold a planning retreat at a charming Airbnb in Naples over MLK weekend, and the experience was incredibly beneficial. Six months later, I can confidently say that not only was it good for my soul to hang out with my bestie, but it was good for me professionally as I get back up to speed.

Here’s why you should consider organizing a similar retreat.

Neutral Location and Limited Distractions

Besides the convenience of finding a midway point so we could make the most of our weekend, it was important that we stay in a neutral location so neither of us would be distracted by “life.” Our Airbnb was tucked back into a little secluded, wooded area with beautiful natural light and deer that visited us each morning, but still close enough for Uber Eats to deliver!

Objective Perspective and Honest Feedback

One key benefit of holding a planning retreat with friends is the ability to receive honest and constructive feedback in a safe environment without judgment. Julie and I are well-acquainted with each other’s businesses but not so involved that we lose objectivity. This allows us to provide impartial advice and ask the right questions, such as “How do you approach this issue?” or “What potential challenges do you foresee here?” Having an independent ear and fresh eyes to review each other’s plans and goals was immensely helpful.


Tailored Collaboration and Mutual Support

Whether you already have a business or are planning to start one, a retreat helps you clear your mind and get in the zone. We recommend inviting friends who are at similar stages in their business journeys—be it dreaming, starting up, growing, maintaining, or succession planning. This ensures that you can tackle similar problems and share relevant experiences. Keeping the group small allows everyone to have a voice and fosters a deeper level of collaboration. For me and Julie, a duo was perfect.


Structured Agenda with Pre-Retreat Homework

A well-structured agenda is essential for a productive retreat. Here’s how we organized ours:

Goals and Objectives: We came prepared to review our personal and professional goals, challenging each other to make them measurable and to ensure we were pushing ourselves. For instance, mine included:

      • A number of new clients each quarter
      • Completing a business course I had been putting off for years
      • Optimizing our website to generate more leads with deadlines for tasks
      • Completing our 25th anniversary marketing plan 
      • Bookkeeping goals (my least favorite part of the business) each month to not fall behind
      • Learning more about AI by subscribing to newsletters, finding courses and other resources
      • Read six fiction books by the end of the year
      • Find six new dinner recipes by the end of the year
      • Purge and organize my closet rack by rack, drawer by drawer with deadlines

Tactics: We examined our tactics one-by-one by goal and sought feedback at each subject. This step involved posing questions like, “If you were in my position, how would you handle this?” My sample tactics:

      • Connecting with former clients and prospects with details about the best way to accomplish this
      • Being a guest on three podcasts with a plan to pitch opportunities
      • Speaking at three industry events with a plan to pitch opportunities
      • Auditing the website for improvements and updating SEO by the end of Q1
      • Find audiobooks to make it easier to “read” my six books
      • Start following home cooks on Instagram to discover new options and see who I like
      • Start by pulling all clothes that no longer fit or need repair to donate or toss

Discussion Items: We prepared specific topics and questions to discuss and solicit opinions, aiming to gather a variety of perspectives. We also selected items from our goal and tactic discussion that resonated with both of us.

Next Steps: We outlined actionable steps to implement everything post-retreat. We created our calendars, identified milestones, and set a schedule for us to regroup and connect on our goals.


Incorporating Educational Elements

To enhance our retreat, we added an educational component. On our way to Naples—Julie from Miami and me from St. Petersburg—we listened to selected podcasts (see the episodes in the resources below). This helped us to build anticipation and get into the right mindset even before arriving.

Additionally, we each brought several options for courses, primarily digital marketing, to watch together, pausing frequently to talk about how to incorporate the ideas into our businesses. We cast the videos from my laptop to the television in the living room and watched the lessons most appropriate for both of our businesses.


Continuous Learning and Resource Sharing

During meals, we exchanged key learnings, takeaways, and additional resources such as books, articles, podcasts, videos, courses, software, memberships, conferences, associations, and educational social profiles. This sharing of resources ensured that we both left the retreat with a wealth of new information and tools to implement in our businesses.

I was (and still am) on a mission to find the best way for me to stay organized and motivated in this remote work environment. I even bought the requisite planner and several iPhone apps with little to no success. It’s all been abandoned and I’m trying new options all the time. Julie has always been the most organized person in the room, so I definitely take her advice to heart.

To break things up and find additional inspiration, we picked cards from Gabby Bernstein’s The Universe Has Your Back deck. While it may be a little “woo woo” for some, we enjoyed the colorful designs and motivation from the cards.


Follow-Up and Accountability

To help continue the benefits of the retreat and to hold each other accountable for our goals, Julie and I schedule follow-up calls, video conferences, and we watch additional videos and courses together, further solidifying our learnings. We recently did Mel Robbin’s free Make It Happen trainings as a kick-off to our mid-year reset. These check-ins allow us to revisit our commitments, stay inspired, and reinforce the strategies we discussed.

A business planning retreat with trusted friends can provide invaluable benefits—offering fresh perspectives, tailored collaboration, and structured, actionable plans. By incorporating educational elements and committing to follow-up, you can ensure that the progress made during the retreat extends well beyond the time spent together. For me and Julie, our retreat in Naples was not just a getaway but a strategic move that significantly impacted our businesses for the better. In fact, we plan to do this every year! If you want to elevate your business planning process, consider organizing a retreat with friends you trust—you won’t regret it.



Watch Julie’s recap of our weekend in January from her perspective, including a look at our cute Airbnb. If you or someone you know is interested in learning how to make mosaic art, please subscribe to her channel!


On-the-road Podcasts

Here are the podcasts we listened to on our way to and from Naples:

And the course for our mid-year reset:

Goals & Objectives

This is the format we used to prepare for the weekend so we could start our discussions immediately, using this as an agenda:

  • Outline at least three business goals and objectives for your business in 2024. It could be financial, audience growth, milestones, customer/client achievements, etc.
  • Outline at least three personal goals and objectives in 2024.
  • For each goal, outline at least three tactics necessary to achieve it.
    1. How will you measure it?
    2. What is the deadline? Are there interim milestones to measure and adjust?
    3. Will you need help? Training? Resources?


We scheduled time for training appropriate for both of our businesses to learn some new skills together:

  • Watch course materials (we selected digital marketing courses)
  • Discuss which ideas can be incorporated into our businesses. How do they fit into your goals and objectives?
  • Create a list of content topics for our websites, newsletters, social media, speaking engagements, podcast episodes, etc.
  • Review tools, resources, tips and tricks that may help one another. For instance, we discussed ChatGPT, Canva, project planning tools, social media management, business organization and optimization methods.

We would love to hear about your business planning retreat with your bestie!