How a sailboat can help you make better decisions
How a sailboat can help you make better decisions A simple yet effective exercise I’ve come to rely on over the years is the sailboat. The sailboat is an alignment exercise that helps teams quickly get on the same page. Over time, I’ve been amazed at how powerful this exercise is in bringing divergent thinkers into alignment and agreement. The Sailboat Exercise The general premise is simple: picture a sailboat on the water with a person in the boat and a large sail. Ahead of the boat is a bright sun—or sometimes an island—which represents the destination we’re heading toward. Behind the boat, squiggly lines represent the wind, giving us forward momentum. Below the surface, an anchor drags across the seabed, slowing the boat down. Just ahead of the anchor is a massive rock—the big watch-out, the looming threat that could capsize the boat if not addressed. Normally, this is all drawn on a board so that everyone can see the metaphor in action and immediately grasp the concept. Now here’s where the real magic happens: the sailboat exercise revolves around four key questions. 1. What is the bright horizon we’re working towards? This question sets the destination—the high aspirations, objectives, and goals that drive the team. It opens up conversations about motivation, vision, and alignment. Often, as people share their bright horizons, it sparks moments of realization: “Oh yeah, me too! I want that outcome as well.” Some facilitators steer the group toward specific goals, especially for project-based discussions. But for general team alignment, I like to leave it open, allowing personal and professional motivations to surface. 2. What is the wind in our sails? Momentum matters. Here, we highlight what’s already working in our favor—the wins, strengths, and positive forces pushing us forward. This part of the exercise is uplifting. Even when a team feels stuck, I challenge them to identify small victories. “You’re all here for this session—that’s already momentum. What else?” More often than not, once they start looking for wins, they find plenty. 3. What are the anchors slowing us down? This is where we get real about the struggles—both internal and external—that are slowing us down. By this point, trust has been built, and people start sharing candidly. Lack of resources, burnout, internal misalignment—whatever the blockers, calling them out brings relief and fosters camaraderie. The team realizes they’re not alone in their frustrations 4. What are the big rocks we need to watch out for? These are the looming threats that haven’t hit yet but could derail us if we’re not careful. Restructures, budget cuts, external shifts—this is where leaders get an invaluable window into what their team is worried about. It’s also a chance for leaders to be transparent and share their own concerns. By the end of this conversation, the team has clarity on where everyone stands. Enjoying the insights? Get this and more straight to your inbox Subscribe to our Newsletter Fresh ideas and tips to fuel your growth Email Confirmation By ticking this box you agree with sharing your details with Esarzee, Subscribe Applying the Sailboat to Business and Life Beyond team alignment, the sailboat framework is a powerful tool for business strategy, storytelling, and personal development. Sailboat as a Business Strategy Tool Think of the sailboat as a dynamic alternative to a SWOT analysis: Bright horizon = Your business’s vision, long-term goals, and desired impact. Wind in sails = Competitive advantages, successful initiatives, customer wins, or internal strengths. Anchors = Operational inefficiencies, bottlenecks, internal struggles that need attention. Big rocks = Industry shifts, regulatory risks, or market threats that could impact your trajectory. For example, let’s say your company aims to reduce carbon emissions by 100% by 2030 (bright horizon). You’ve already achieved a 20% reduction and are making steady progress (wind in sails). However, supply chain challenges and slow policy changes are making it difficult to accelerate progress (anchors). Meanwhile, unpredictable government regulations or shifts in public sentiment could disrupt your plans (big rocks). Mapping this out makes it easier to prioritize next steps and communicate with clarity. Sailboat as a Storytelling Framework Great stories follow the sailboat structure. Take any compelling brand story: Bright horizon = The ultimate goal or promise your brand offers Wind in sails = Customer testimonials, proof points, and case studies. Anchors = The challenges that justify why your product or service is needed. Big rocks = The risks of not acting—what happens if the audience ignores the problem? Let’s say you’re marketing a fitness app: Bright horizon = Helping people build lasting, healthy habits Wind in sails = Users who have transformed their health using your app Anchors = Common struggles—lack of motivation, confusion about where to start Big rocks = The long-term risks of inactivity (health issues, rising medical costs). By structuring messaging this way, you create a compelling narrative that resonates with your audience. Sailboat as a Personal Development Tool The sailboat exercise is just as effective for self-reflection and goal-setting. Here’s how you can apply it to your own growth: Bright horizon = Your personal goals—career aspirations, health targets, lifestyle changes. Wind in sails = Your past successes, skills, and habits that support your progress Anchors = Limiting beliefs, bad habits, or external obstacles slowing you down. Big rocks = Unseen fears, doubts, or external risks that could derail your journey. For instance, if you’re working towards launching your own business, your bright horizon might be financial independence and creative freedom. Your wind in sails could include relevant skills, supportive mentors, or past entrepreneurial experience. Your anchors might be self-doubt, procrastination, or lack of funding. And your big rocks could be economic downturns, market saturation, or unexpected personal setbacks. By laying it out visually, you gain clarity and can start addressing what’s holding you back. And that’s just scratching the surface of how this exercise can be applied. Hopefully, you see why I’m such a big fan of it. Until next time—keep moving forward. Serge XX How a sailboat
How might we move you forward today
How might we move you forward today? Hey There, Thanks for stopping by. I’m glad you’re here. This section of the site is designed to be a space for insight, reflection, and action—so I encourage you to check back often. If you find value in what we share, that means we’re doing our job right. Running a creative agency like Esarzee has always been a vision of mine, but if I’m honest, I didn’t leap into this—I was pushed. After spending nearly 11 years at a FTSE 100 company, circumstances forced me to decide: stay in the comfort zone or create something that truly aligns with my purpose. I chose the latter. I wanted to build a business that harnesses my skills, passion, and drive to create meaningful impact. Esarzee is built for decision makers—the ones who shape change. Over the years, I’ve seen first-hand how great leadership isn’t about power or prestige; it’s about prioritizing impact over optics. The best decision makers are those who put their people first, who focus on transformation rather than ticking boxes. I’ve also had the privilege of speaking with leaders who carry immense responsibility. Leadership is more than a title; it’s a calling. That’s why Esarzee exists—to support decision makers in both the big and small ways that make a lasting difference. As a facilitator, I help leaders align their teams, define strategy, and create better ways of working. The right questions open doors to solutions that once seemed impossible. Facilitation isn’t just effective—it’s engaging, dynamic, and a far cry from the typical uninspiring corporate meeting (if you’ve been in one, you know exactly what I mean). As a filmmaker, I help decision makers communicate their vision. Whether it’s internal messaging or external storytelling, how we say things is just as important as what we say—and even more crucial is why we’re saying it in the first place. I collaborate with leaders to craft content that resonates, inspires, and drives action. While I’m not a designer, I work with experts who bring brands to life. I’ve led design projects for branding, websites, and training content—helping businesses strengthen their identity and engage their audiences. I find purpose in knowing that the work we create equips leaders with the tools they need to build better teams and better businesses. How might we move you forward today? One of the core questions that drives Esarzee is: How might we move you forward today? It took me over a year to craft this phrase, and now it guides everything we do. Progress matters. Stagnation leads to frustration, stress, and inaction. Our role is to disrupt that cycle and create momentum. Some challenge the word ‘might’ in our slogan, seeing it as uncertainty. I see it as possibility. How reflects our problem-solving mindset. Might represents the open-ended nature of innovation—there’s never just one way to solve a challenge. And we reinforces the collaborative nature of our work, because real change happens when we build together. You’ll see How might we woven throughout our site—it’s the mindset that fuels everything we do. “So, what exactly do you do?” I get this question a lot. For a long time, my answer felt scattered. I’ve said yes to projects that stretched me, built new capabilities, and introduced services I hadn’t originally planned. That’s how design became part of our offering—someone had a need, and while I didn’t have the expertise myself, I found the right people who did. By solving that challenge, I learned and expanded Esarzee’s capabilities. Eventually, I realized my niche isn’t in a specific industry or service—it’s in who we serve. Our ideal clients are decision makers who need a trusted partner to help them execute their vision. Whether they’re solo founders or leading large teams, their need is the same: reliable, strategic, and creative support that helps them move forward. So, my answer to that question now? I work with decision makers to achieve their highest objectives. Whether through facilitation, content, or design, those are just tools—the real focus is the outcome. The goal defines the method, not the other way around. Thanks again for stopping by. If you have a challenge or objective we can help with, reach out. Let’s move forward—together. Serge See Below other insights How a sailboat can help you make better decisions How might we move you forward today Back to insights
