220 - Stop Playing It Safe - Start with Small Steps

Introduction

What’s the best way to challenge ourselves and improve? Many people seek comfort by staying in familiar territory, but real growth comes from pushing beyond what we already know. A powerful lesson Jill from the North Woods learned as a child—through the game of chess—proves just that.

Her father, a skilled chess player, never let her win. Instead, he taught her that the only way to get better was to play against opponents who were stronger than she was. This lesson extended far beyond the chessboard and into every aspect of life. Whether it’s in work, hobbies, or personal development, improvement comes from surrounding ourselves with people who challenge us to be better.

So, how can we apply this principle to our own lives? Let’s explore how learning from those ahead of us can lead to transformation in skills, mindset, and personal success.

The Power of Playing Against Stronger Opponents

When Jill first started playing chess, she constantly lost to her father. Instead of making it easy for her, he encouraged her to play against people who were better than she was. Eventually, after years of persistence, she won her first game—knowing it was a genuine victory, not something given to her.

The takeaway? Whether in chess, business, fitness, or creativity, you won’t improve if you only engage at your current skill level. Growth comes when we struggle, adapt, and learn from those with greater expertise.

This applies to:

Work & Career: Seek mentors or colleagues who push you to think differently.
Fitness & Health: Work out with people who are slightly stronger or faster.
Creativity & Skills: Study experts and analyze their techniques to elevate your own abilities.

If you’re not being challenged, you’re not growing.

Finding the Right Level of Challenge

One key to learning effectively is finding the right balance of difficulty. If you play against someone far above your level—like a chess grandmaster—you might get discouraged. But if your opponent is only slightly better than you, you can learn and improve step by step.

This same principle applies to every aspect of self-improvement:

Writing & Communication: Improve by studying well-written articles, books, or using tools like Grammarly and AI-assisted editing.
Public Speaking: Watch experienced speakers to pick up techniques, rather than comparing yourself to the best in the world immediately.
Career Development: Work on projects that challenge your current skills but are still achievable with effort.

By steadily increasing the level of difficulty, you prevent burnout while ensuring progress.

The Role of AI in Learning and Growth

Jill also touches on an important modern lesson: using AI to support learning. While she doesn’t use AI to write her podcast or create her content, she does use it to refine her ideas, improve writing, and generate summaries.

AI, like a skilled chess opponent, can help us analyze and rethink our approach. However, the key is to use it as a learning tool, not a shortcut to avoid developing skills altogether.

If you’re using AI or technology to assist in a skill you want to improve, ask yourself:

Am I actively learning from what it produces?
Am I using it to refine my own work, rather than replace it?
Am I still making an effort to challenge myself in this area?

Used wisely, AI can be like a coach—helping us improve without taking away the effort required for growth.

The Importance of Learning from Others

Jill describes how she had “secret mentors”—colleagues she admired for their skills. Instead of formally asking for mentorship, she simply observed their habits, communication styles, and decision-making processes.

This approach works well for self-improvement:

Identify people who excel in areas you want to grow.
Observe and take notes on what makes them effective.
Slowly apply their techniques to your own work and life.

By watching and learning, you can adopt the strengths of others while still developing your unique approach.

Overcoming Discomfort to Achieve Growth

Growth is often uncomfortable. Whether it’s stepping into a new leadership role, starting a fitness journey, or learning a new creative skill, the initial stages can feel awkward and frustrating.

But discomfort is a sign of progress.

If you feel awkward on video, keep practicing.
If writing is difficult, keep doing it.
If speaking in front of others makes you nervous, keep stepping into those situations.

Every challenge builds resilience. If something feels tough today, it will feel easier in the future—only if you continue practicing.

Applying What You Learn

Learning from others is only valuable if you apply what you observe. It’s not enough to watch TED Talks, read books, or listen to inspiring people. Growth happens when you act on what you learn.

Action Steps to Start Today:

Identify an area you want to improve in. (Career, fitness, communication, creativity, etc.)
Find someone who is ahead of you in that area. This could be a mentor, coach, coworker, or even an AI tool.
Observe and take notes on what they do differently. What strategies or habits make them successful?
Try applying one of their techniques to your own work or routine.
Reflect on your progress and adjust. Learning is a process—keep refining your approach.

Final Thoughts: The Growth Mindset

Jill’s story about learning chess from her father is a perfect metaphor for personal and professional growth. Improvement doesn’t come from staying comfortable—it comes from playing against stronger opponents, embracing discomfort, and consistently learning from those ahead of us.

So, the challenge for you is this:
👉 Put yourself in a situation where you are the least skilled person in the room.
👉 Learn from those ahead of you.
👉 Apply what you observe and track your progress.

That’s how you level up in chess, in life, and in everything you do.