Self Motivation

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Living and Leading with Intention Insights from Shopify President Harley Finkelstein

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Jul 7, 2025







Living and leading with intention in all roles.

Living and Leading With Intention

Living and leading with intention means consciously choosing how you show up in every role you play, whether as a father, husband, or leader. It is about treating each role not as a static identity but as a position you must earn and requalify for every year. This mindset pushes you to hold yourself to a higher standard consistently, ensuring growth and alignment with your values.



What Does Requalifying for Your Role Mean

Requalifying means actively reflecting on your performance and impact in each role, then committing to improve. Harley Finkelstein, President of Shopify, shares how he approaches this challenge by treating his roles like certifications that require renewal. This continuous self-assessment helps avoid complacency and fuels ambition. For example, leaders who engage in annual reflection increase their effectiveness by 20 to 30 percent, according to leadership development research from the Center for Creative Leadership.

Why Ambition and Identity Matter in Leadership

Ambition is not just about personal success but about evolving your identity to meet the demands of your roles. Holding yourself accountable to a higher standard means your identity is dynamic, shaped by ongoing learning and adaptation. Harley’s story shows that when you see leadership as a journey rather than a destination, you become more resilient and better equipped to inspire others. Studies show that leaders who adopt a growth mindset improve team engagement by 34 percent, demonstrating the power of evolving identity.

How to Overcome Motivational Blocks by Requalifying

Q: What can I do when motivation wanes in my personal or professional life?

A: Requalifying your role means revisiting your “why” and recommitting to the standards you set for yourself. It involves asking tough questions about where you are falling short and what actions will bring you closer to your goals. This process breaks motivational blocks by creating a clear, measurable path forward. For example, setting a specific goal to improve communication skills over the next quarter can increase motivation by providing a sense of progress and achievement.

Overcoming motivational blocks by requalifying your goals.

Using Accountability Partners to Maintain Intention

One powerful way to requalify is by involving an accountability partner. This person helps you stay honest about your progress and challenges. Harley Finkelstein emphasizes the value of candid conversations with trusted peers to keep ambition grounded and focused. The following table outlines how an accountability partner can help sustain your commitment: Accountability Partner Table.RoleHow They HelpFrequency of Check-InsExample Metric to Track 
 – – – – – – – – – – – – – – – – – – – – – – –– – – – – – – – – – – – – – – – – – – – – – – – – – – – – – – –– – – – – – – – – – – – – – – – – – – – – – –– – – – – – – – – – – – – – – – – – – – – – – – – – – – – – – – – 
 Personal (e.g., spouse)Offers emotional supportWeeklyNumber of meaningful conversations 
 Professional (mentor)Provides feedback on leadershipMonthlyProgress on leadership goals 
 Peer (colleague)Shares challenges and solutionsBi-weeklyTask completion rate 
Accountability partner supporting goal intention and progress.

Reflecting as a Leadership Practice

Reflection is the foundation of requalifying. It allows you to identify gaps between your current performance and desired standards. Harley’s approach involves setting aside time annually to evaluate his roles with honesty and care. This practice leads to measurable improvements: organizations with leaders who prioritize reflection report 25 percent higher innovation rates. Taking time to reflect regularly can transform motivational blocks into opportunities for growth.

Conclusion Intentional Living Demands Continuous Growth

Living and leading with intention is a deliberate, ongoing process of requalifying for your roles. It challenges you to examine ambition and identity critically and use accountability and reflection to overcome motivational blocks. Harley Finkelstein’s example reminds us that leadership and life are not fixed titles but evolving commitments we renew every year to become better versions of ourselves. This mindset can increase leadership effectiveness by up to 30 percent, proving that intention combined with action is a powerful way to lead.

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