220 - Stop Playing It Safe
In this episode of Start with Small Steps, Jill from the North Woods shares a powerful lesson learned from playing chess with her father: the best way to improve is to challenge yourself against stronger opponents. This principle extends beyond the chessboard and applies to personal growth, career development, fitness, and creative pursuits. Jill explores how surrounding yourself with skilled people, finding the right level of challenge, and embracing discomfort can lead to transformation. She also discusses the role of AI as a learning tool and the importance of applying what you observe from others.
The Power of Playing Against Stronger Opponents
Jill’s father never let her win at chess, and this tough love approach taught her to embrace challenges rather than seek easy victories. Whether in work, hobbies, or personal goals, true growth comes from learning from those who are ahead of us.
The Right Level of Challenge for Improvement
Growth requires finding the right balance—not too easy, not too difficult. Jill explains how to assess what level of challenge will push you forward without overwhelming you, whether it's in writing, public speaking, or fitness.
Using AI as a Learning Tool (Not a Replacement)
Jill shares how she uses AI to refine her writing rather than replace it. She discusses the importance of maintaining personal effort while leveraging AI for insights and efficiency.
Learning from "Secret Mentors"
Sometimes, the best mentors aren’t the ones we formally ask for help, but those we quietly observe. Jill explains how watching skilled colleagues and analyzing their methods has helped her improve in various areas of life.
The Importance of Embracing Discomfort
If something feels uncomfortable—whether it’s public speaking, learning a new skill, or pushing past fitness limits—it’s often a sign of growth. Jill encourages listeners to lean into discomfort as a necessary step toward mastery.
Applying What You Learn
It’s not enough to listen, read, or watch others—you must put what you learn into action. Jill provides practical steps for tracking progress and continuously improving through observation, reflection, and practice.
Takeaways
✅ Challenge yourself by learning from those ahead of you. Staying in your comfort zone won’t lead to growth. Seek out opportunities to be around people who push you to be better.
✅ Find the right level of difficulty. Growth happens in stages—too easy, and you won’t progress; too hard, and you may give up. Identify challenges that stretch but don’t break you.
✅ Leverage AI and technology as tools for improvement. AI can help refine your skills, but real learning comes from effort and practice.
✅ Observe and learn from successful people. Whether it’s a mentor, coworker, or expert in your field, analyze their techniques and apply them to your own journey.
✅ Embrace discomfort as a sign of progress. If something feels difficult, that means you're learning. Stay persistent and celebrate small wins along the way.
✅ Take action. Don’t just consume information—apply it. Growth only happens when you put knowledge into practice.
Challenge for You
This week, put yourself in a situation where you are the least experienced person in the room. Whether in a meeting, a class, or a fitness session, find someone who is better than you and learn from them. Write down what you observe, practice what you learn, and reflect on your progress.
https://startwithsmallsteps.com/220-stop-playing-it-safe/
Jill’s Links
https://abetterlifeinsmallsteps.com
https://affiliate.notion.so/NorthwoodsJillday
https://affiliate.notion.so/NorthwoodsAI
https://www.youtube.com/@startwithstartwithsmallstepscast
https://www.buymeacoffee.com/startwithsmallsteps
Email the podcast at jill@startwithsmallsteps.com