Ep 3: Intentional Confidence - Bart Greenberger

Sep 3

In this episode of The Holritz Business Design Podcast, Bart Greenberger shares insights on how to build confidence, set effective goals, and live intentionally by appreciating each day. We explore the importance of understanding who you are now, the power of small wins, and how to leverage systems and processes for success.

Summary

When you’re always looking for ways to improve, it can be difficult to appreciate where you are. There’s another goal to reach, another process to fix, and another version of yourself you’d like to become.

In this episode, I talk with business coach Bart Greenberger, author of I’m a Descendant of the Middle Finger: My Journey to Finding Confidence, about approaching that growth more intentionally. We explore defining success for yourself, turning goals into manageable actions, and creating space for the people and experiences that make life meaningful. Bart also challenges me to think more carefully about the connection between understanding who I am today and deciding what I want to change.

Key Takeaways

1. Define success before you start pursuing it

When Bart begins working with a business owner, he asks what that person most wants to accomplish. He uses a playful question: if he could wave a magic wand and change one specific thing about the business, what would it be?

His point is that the owner’s priorities need to shape the work. A coach may see several opportunities, but the person running the business needs to understand and care about the direction they’re taking.

Bart describes happiness as his own measure of success. I connect that to the freedom to spend time with important people and have experiences outside work. Money has a role, but it isn’t the only consideration. Give yourself a definition of success that reflects what you actually want your business and life to look like.

2. Turn a distant goal into smaller actions you can complete

Bart uses examples from golf and bowling to explain the value of a nearer target. A large annual goal can feel abstract; a smaller milestone gives you something more immediate to work toward.

He distinguishes an end goal from the repeatable actions that support it. He also encourages clear deadlines and regular review, so a goal stays connected to the decisions you make during the week.

I compare that approach to cleaning a garage. As one enormous task, it can feel overwhelming. Breaking it into individual steps makes it easier to begin and notice progress. Bart shares his own experience of struggling to install garage shelves, then feeling more confident about the rest of the project once that first challenge was handled.

Small wins give you concrete progress to build on. They also help you see where a process needs adjustment before you repeat it on a larger scale.

3. Give your priorities a place on your calendar

Goals need time allocated to the work behind them. Bart encourages business owners to “plan to plan”: set aside time to think about the week before getting absorbed in emails, calls, and requests.

His examples include a quiet planning block on Monday morning and scheduled time to follow up with potential customers. I bring up email as a common source of distraction, particularly when irrelevant messages make important ones harder to find.

The opportunity is to make deliberate choices about attention. Look at the work that moves your priorities forward, then give it space alongside the responsibilities of keeping the business running. Being busy all day doesn’t necessarily mean you spent that day on what mattered most.

4. Understand your starting point while choosing what to change

Bart describes confidence in terms of understanding and accepting who you are right now. I push back on the acceptance part because, as someone who spends a lot of energy on self-improvement, it can feel like settling.

He brings the conversation back to understanding. You can recognize the choices and circumstances that brought you here while still deciding to make a change. The past gives you context; the actions available now give you a place to begin.

Bart also shares that he reviews his goals and removes ones that no longer matter. Framing his world-record certificate stayed on his list until he recognized it wasn’t important enough to keep prioritizing. That example offers a useful question: are you avoiding something you value, or carrying a goal you no longer want?

5. Make room to appreciate the days you’re living

Bart’s interest in counting days becomes one of the most meaningful parts of our conversation. For my birthday, he translated my age into sunrises and opportunities to tell someone I love them. I found that reminder especially moving because time and relationships matter so much to me.

He shares how his family celebrated his father’s 30,000th day alive and how he keeps a written list of meaningful experiences to revisit. Those habits help him pause and appreciate life between the bigger milestones.

His end-of-day question is simple: did you win the day? You get to decide what that means. It might include progress in business, a meaningful conversation, or making time for something you enjoy. Leave room for those experiences in the life you’re working to build.

Put It Into Practice

Choose one idea from the conversation and put it into action this week:

- Write your own definition of success. Include what matters personally as well as professionally and financially.

- Choose a near-term milestone. Break one larger goal into a smaller result, a deadline, and the actions that support it.

- Schedule a planning block. Decide when you’ll review your priorities and put the necessary work on your calendar.

- Add a little accountability. Ask someone you trust to check in about a goal you’ve chosen, as Bart describes doing with people close to him.

- Recognize a meaningful moment. At the end of the day, note something you appreciated or a small step you completed.

Bart and I both enjoy learning from books and podcasts. The challenge we discuss is turning a useful idea into something we actually practice. Start small enough that you can follow through, then review what you learn.