Learning Outside the Lines: How to Test Your 2027 Goals
When leaders and founders hit a wall with their business growth, they often try to find solutions within the same ecosystem they have always operated in. But sometimes, finding the right path forward requires stepping outside the lines. If you are swimming in the same ocean, you will keep finding the same answers.
This month, as we returned from the summer break, I hosted our Elevate Gather joint workshop at an art studio instead of a standard conference room. I partnered with San Carlos Art Circles founder and creative artist Tiffany Potter Karow. We brought together a table full of high-achieving women, tech professionals, and entrepreneurs to take a step back and look at 2027 planning through a completely different lens. While my usual coaching centers heavily on business systems and action plans, this time we tested those plans using watercolor and mixed media.
Yearly planning is a long process. It is incredibly easy to get lost chasing macro goals and end up biting off more than you can chew. If you want to ensure your plans for the next four quarters are realistic and executable, here is how you can test them before committing your resources.
1. Map the Milestones, Not Just the Metrics
Before you worry about KPIs, break your overarching goal into simple, actionable milestones for the next four quarters. Ask yourself where you are today in Q4 2026, and what major milestone must happen in Q1 2027 to press the gas pedal. Focus on what success feels like at each step rather than just the numbers.
2. Identify Your Emotional Theme
In our workshop, we used AI as a diagnostic tool. Participants input their quarterly goals into their AI chatbot to generate a "word of the year" and identify potential emotional blind spots. Identifying a core theme like momentum, alignment, or amplification helps focus your attention on what actually matters to you, cutting through the noise of daily operations.
3. Test the Emotional Reality of the Work
A vision on paper is clear, but execution is emotional. We had participants paint over their generated word using handmade colors and symbols to visualize the plan. While one might expect this to cause anxiety, the opposite happened. Translating goals into a visual medium brought hidden feelings to the surface and left participants feeling energized and motivated. The objective is to see if your plan makes you feel aligned or overwhelmed.
Small wins and careful calibration often yield better results than chasing grand, disconnected targets. If you are a leader or founder mapping out your next move, remember that you don't have to navigate it alone. An outside perspective helps you get out of the daily weeds and build what comes next.
Bring This Experience to Your Team
If you are a corporate leader or founder looking to bring this level of clarity to your organization, I design custom workshops and executive offsites for teams. Standard team building often falls flat because it lacks actionable business integration. By stepping outside the usual corporate environment, we can structure a session that helps your leadership group realign on their 2027 vision, uncover operational blind spots, and foster genuine cross-functional collaboration.
View my availability and book an exploratory call to discuss bringing an Elevate workshop to your company.
For individual professionals, our next public Elevate Gather workshop will be announced soon. Stay tuned for details on how we will continue to tackle executive growth from fresh perspectives.