Case Study: Planning Support

Two Paths. No Clear Direction.

A business owner was running a successful videography company and was known for his work in that space.

At the same time, he felt pulled toward something new. He wanted to step into personal and life coaching, but wasn’t sure how to make that shift without disrupting what he had already built.

Stay where things are working, or move toward something new and uncertain?

He didn’t need more ideas.
He needed clarity.

What did the future actually look like?
How could both businesses coexist, at least for a period of time?
And what would it take financially and operationally to make that transition real?

The Engagement

Jess was brought in to lead a strategic planning process, helping the founder move from uncertainty to a clear, structured plan for the next stage of growth.

The work started with defining the foundation. Together, they documented core values, a mission statement, and a vision that reflected where the founder wanted to go, not just where he had been.

From there, Jess built out a 1, 2, and 3-year plan that accounted for both businesses. The plan created a clear path to continue running the videography company while gradually building and transitioning into the coaching business over time.

Financial clarity was a key part of the process. Revenue, expenses, salary, and net profit targets were mapped out so decisions could be grounded in real numbers, not just ideas or assumptions.

Jess then broke the vision down into execution. A detailed 12-month roadmap was created, organized into quarterly phases. Each quarter outlined key initiatives across marketing, finance, operations, product and service development, and sales, along with the specific milestones required to move each initiative forward.

Everything was captured in a structured Google Sheet, giving the founder a clear, centralized place to see the full picture and track progress over time.

The plan was delivered on a live call, where Jess walked through each piece, integrated feedback in real time, and ensured the plan felt both realistic and aligned. From there, the founder had the option to continue with ongoing support or take the plan and run with it independently.

The Outcome

The founder moved from feeling stuck between two paths to having a clear plan for both.

He now had:

• Defined values, vision, and direction
• A realistic financial model to guide decisions
• A phased plan to grow one business while transitioning into another
• Clear quarterly priorities and next steps

The uncertainty didn’t come from a lack of ambition... it came from not having a plan to hold it all together!