I never turn down a good cup of coffee—especially when it’s paired with a conversation about careers.

Over the years, I’ve had countless colleagues ask if they could “pick my brain” over coffee. Most are standing at an important crossroads. Some are pursuing another executive position, while others are considering a much bigger leap: starting their own business.

I’ve been there.

After spending nearly two decades in executive leadership roles with Little Caesars, Clark Retail Enterprises, and Jimmy John’s, I launched Gray Cat Enterprises in 2004. Leaving the corporate world was one of the biggest decisions of my career. It involved risk, uncertainty, and more than a little anxiety.

More than twenty years later, I can confidently say it was the right decision.

I’ve had the opportunity to work with companies across multiple industries, lead transformational projects, mentor business owners, speak across North America, and build a lifestyle with far greater flexibility than I ever imagined.

People often ask, “How did you make the transition?”

The answer surprises them.

I didn’t wing it.

I planned it.

Start with a Business Plan

One of the first things I did was develop a comprehensive business plan for Gray Cat Enterprises.

Ironically, the foundation came from a simple interview. My then-wife, a journalism major, asked me questions about what I enjoyed doing most throughout my career. As we talked, clear themes emerged. Those conversations became the building blocks of my business.

From there, I identified the core service lines, defined target markets, estimated revenue opportunities, and created action plans for each area.

Entrepreneurs often skip this step because they assume business plans are only for banks or investors.

They’re not.

A business plan provides clarity—and clarity drives better decisions.

Know Yourself

Success begins with understanding your strengths, weaknesses, and motivations.

By the end of my corporate career, I had become more administrator than creator. My calendar was filled with meetings, approvals, and oversight responsibilities.

I missed building things.

I wanted to roll up my sleeves again, solve problems, develop strategies, write content, and work directly with clients.

Entrepreneurship gave me that opportunity.

The best businesses are built around work you genuinely enjoy doing.

Define Success Before You Begin

Many entrepreneurs chase revenue without first defining what success actually looks like.

For me, success included financial goals, certainly—but it also included lifestyle goals.

I wanted flexibility.

I wanted meaningful work.

I wanted to choose the projects I accepted.

That vision became my compass whenever difficult decisions arose. There were certainly challenges along the way, but having a clearly defined destination made it easier to stay the course.

Create Action Plans

Dreams don’t build businesses.

Execution does.

Early on, I identified four primary business pillars:

• Strategic planning
• Project management
• Interim executive leadership
• Public speaking

Each area had its own action plan that included:

• Defining the market opportunity
• Developing business development strategies
• Creating thought leadership content
• Building service offerings
• Establishing financial goals and performance metrics

Breaking the business into manageable pieces made the overall challenge far less intimidating.

Become Known for Something

One of the biggest mistakes new entrepreneurs make is trying to serve everyone.

I chose to concentrate heavily on industries where I already had credibility—particularly convenience retail and foodservice.

That meant consistently investing in visibility by:

• Writing industry articles and blogs
• Speaking at conferences and association meetings
• Serving on industry advisory boards
• Managing high-impact consulting projects
• Building relationships throughout the industry

Over time, those activities reinforced one another and established Gray Cat Enterprises as a trusted resource.

Expertise is valuable.

Visible expertise is even more valuable.

Think Long Term

Entrepreneurship isn’t built overnight.

It requires patience, discipline, resilience, and a willingness to continually learn and adapt. Your original plan will evolve—and it should—but having a roadmap dramatically improves your odds of reaching your destination.

Looking back, starting Gray Cat Enterprises remains one of the best professional decisions I’ve ever made. Not because it was easy, but because it allowed me to build a business around my passions, strengths, and values.

If you’re standing at that same crossroads today, my advice is simple:

Develop a plan.

Know yourself.

Focus on your strengths.

Commit to consistent execution.

And don’t be afraid to take the leap.

Who knows? Maybe twenty years from now, you’ll be sitting across the table from someone over a cup of coffee, sharing your own entrepreneurial journey.

Thanks for the coffee.

Want more ideas?  For more information on Gray Cat Learning Series, visit: https://www.graycatenterprises.com/gray-cat-learning-series