EP20 - Where Do I Begin?

In this podcast episode, Jason discusses the best ways to approach succession planning. He focuses on tackling succession with intention and covers common obstacles that stand in the way of owners achieving their vision for a successful ownership transition. 

Transcript

Introduction: Where Do I Begin?

Jason Miller:
Welcome everyone to the Journey to an ESOP and Beyond podcast, where our goal is to make information surrounding Employee Stock Ownership Plans understandable and accessible. I’m your host, Jason Miller, and this is my very first solo episode.
As I prepared for this episode, I found myself asking the same question many business owners ask when thinking about succession: Where do I even begin? There’s so much to talk about—culture, taxes, retirement outcomes, legacy—and it’s easy to feel overwhelmed before you ever take the first step.
This podcast isn’t about me—it’s about you. Many of you are facing that same starting point in your succession journey, and today’s episode is designed to help. I want to walk through three common issues business owners face and offer specific actions you can take to begin accelerating your succession plan on your own terms.
Information Overload and Analysis Paralysis
One of the biggest challenges in getting started is the sheer volume of information available. I keep a whiteboard above my desk where I jot down ideas and quotes during client calls or while reading. One phrase that’s been sitting there for months is:

A wealth of information creates a poverty of attention.

When it comes to succession planning or ESOPs, there is no shortage of information. Podcasts, conferences, Google searches, and advisors all offer valuable insight—but consuming too much at once can actually slow you down. The more you learn, the more confusing things can feel, and the easier it is to fall into analysis paralysis.

The goal isn’t to know everything. It’s to focus on what matters most to you and your business.

The Illusion of Choice in Exit Planning

Another major challenge business owners face is what I call the illusion of choice. Private equity firms call regularly. Competitors hint at acquisitions. Joint venture partners explore opportunities. Investment bankers promise options.

On paper, it can feel like you have a deck of cards full of possibilities. But do you really?

There may be many names and offers, but most exit paths fall into a limited number of categories. The abundance of perceived options often creates paralysis rather than clarity.

Defining the Game You Want to Play

At the core of every successful transition is vision. It takes a visionary to build a thriving business, and that same skill set applies to ownership transition.

Distill your ideal ownership transition into clear qualities that define success for you. Avoid jargon. Focus on what matters—timing, financial outcomes, people, and legacy. Write it down wherever you can: a whiteboard, a notepad, even a napkin.

When you define your goals, you’re deciding which game you want to play with the deck of cards in front of you.

Sorting Options Into Manageable Paths

Once your goals are clear, the next step is to simplify your options. Instead of focusing on every possible card, sort them into suits. Exit options tend to fall into a few main categories: private equity, competitors, management or family transitions, and ESOPs.

Within each category, you decide what matters most. The number of true options is far smaller than it initially appears, and this clarity removes much of the fear and overwhelm.

Taking Action and Building Momentum

You get to choose the rules of the game. You decide who sits at the table. Don’t invite players who want to play a different game than you do.

Clarity of purpose is what carries you into the next phase of both your business and your personal life. Many owners worry about making the wrong decision, but progress comes from action—not perfection.

One phrase that’s stayed on my whiteboard comes from a personal fitness journey:

Six months from now, you’ll either have six months of progress or six months of excuses.

The same applies to succession planning. Small, consistent actions—one call, one meeting, one step—add up to meaningful clarity and momentum.

Good Exit Planning Is Good Business Planning

Transitioning ownership on your terms is critical. No one wants terms dictated to them, whether in health, life, or business. Succession planning doesn’t require an immediate exit—it requires intention.

Good exit planning is simply good business planning. When done early and thoughtfully, it strengthens your company today while preparing you for the future.

Final Takeaways

• You don’t need to have everything figured out to get started
• Too much information can stall progress
• Most exit options fall into a few clear categories
• Defining your vision brings clarity and confidence
• Small actions create momentum over time
• Exit planning strengthens both your business and your future

Resources & Next Steps

• Explore ESOP education and resources at journeytoanesop.com
• Reach out with questions or future episode ideas
• Follow along for upcoming solo episodes and expert interviews