Measure What Matters

If you believe in the power of setting goals, tracking progress, and staying disciplined, then John Doerr's Measure What Matters is a book you’ll want to read. You may also want to refer back to it periodically, as I do. The book offers a a blueprint for accomplishment in any area of life. By showcasing the Objective and Key Results (OKR) framework, Doerr demonstrates how this method transformed organizations like Google, the Gates Foundation, and even global movements like Bono’s efforts to fight poverty. 

This book teaches a lesson I lived every day throughout my 26 years in prison: measurable goals, broken into incremental steps, are the key to overcoming adversity and building a better future.  The lessons inside coincide with all that we teach in the Straight-A Guide.

Why I Read This Book 

John Doerr has always been an inspiration to me. While in prison, I used books as tools to shape a vision for my future. I immersed myself in literature about technology, leadership, and venture capitalists who drove innovation in companies like Google, Amazon, and Cisco. Doerr always stood out—not just as an investor but as someone who provided a framework for turning ambitious goals into measurable achievements. 

When I came across Measure What Matters, I was eager to connect the lessons in the book with my own experiences. The OKR system fascinated me because it mirrored the frameworks I built during my incarceration to stay focused and productive, even under seemingly impossible circumstances. 

What I Learned from Measure What Matters 

The essence of Doerr’s book lies in the OKR system, which is broken down into two parts:

• Objective: A clear, ambitious, and inspirational goal.
• Key Results: Specific, measurable milestones that define progress toward the objective. 

For example, an objective could be “Build a thriving community for justice-impacted individuals.” Key results might include:

1. Organizing and building the platform: Prison Professors Talent. 
2. Enrolling 10,000 participants, or super users, who memorialize the steps they're taking to prepare for success upon release. 
3. Raising $2 million in annual funding to support the mission and to ensure people in prison do not have to wait for government programs to prepare for success. 

This framework resonated deeply with me. Goals without accountability and structure are dreams. What makes OKRs effective is their measurability. By tracking specific metrics and holding individuals accountable, success becomes inevitable—as long as you stay disciplined. 

Here are some standout lessons I took from the book:

Start with Clarity 

Whether building a business, a personal transformation plan, or a new project, success demands a crystal-clear vision. Like the objective in the OKR framework, your purpose needs to inspire you to push through barriers. 

While in prison, my objective was simple but powerful: “Develop myself every day to emerge successfully.” My “key results” revolved around earning college degrees, completing courses, and writing books. Each task built momentum toward my ultimate goal of thriving after release. 

Iterate and Adapt 

Doerr emphasizes that OKRs aren’t static. They’re meant to be reviewed, revised, and refined as circumstances change. This adaptive approach mirrors life. When my first goals didn’t pan out in prison, I regrouped. If a college degree wasn’t immediately available, I pivoted to studying biographies of entrepreneurs and leaders. 

Failing Forward 

One memorable takeaway in Measure What Matters is how OKRs encourage risk-taking. Leaders like Larry Page of Google embraced the idea that ambitious goals often mean falling short—but even in failure, you grow. This mindset helped me through mistakes during my incarceration. I learned to view setbacks as lessons, not endpoints. 

Leaders Must Align and Inspire 

Whether you’re running a company, a nonprofit, or leading your family through adversity, alignment matters. Doerr highlights how OKRs don’t work in isolation. They should connect across teams and communicate a shared mission. While building Prison Professors, I applied this principle by aligning my vision with contributors, volunteers, and supporters. When everyone understands the mission and feels invested in the results, teamwork thrives. 

How Reading Measure What Matters Contributes to My Success 

Reading Measure What Matters confirmed the importance of staying strategic and disciplined in achieving goals. OKRs now influence the way I run every aspect of my work with Prison Professors. Here’s how I’ve applied these principles to my daily routines:

Building a Community with a Cause 

Through Prison Professors, my objective is to empower justice-impacted individuals to overcome adversity. Key results shape my approach:

• Creating clear, actionable content to inspire resilience and growth. 
• Expanding our reach through live events, partnerships, and digital resources. 
• Tracking engagement metrics to measure the impact of our work. 

Breaking Big Goals into Steps 

Goals like scaling Prison Professors can feel overwhelming. But with the OKR approach, I break huge projects into manageable milestones. For instance, growing our educational programs might include:

• Interviewing experts for 10 new podcast episodes. 
• Publishing two books on financial literacy for people in prison. 
• Developing a mentorship series with 1,000 enrollment spots. 

Tracking progress not only keeps me focused but also motivates others involved in the mission. 

Accountability as a Daily Habit 

Doerr’s emphasis on accountability has reinforced my belief that self-discipline isn’t optional. Simple habits like tracking my daily progress and creating weekly check-ins allow me to stay on course. Whether it’s responding to emails, conducting workshops, or budgeting for new projects, accountability turns intentions into results. 

Takeaways You Can Act on Today 

1. Define Your Objective Today 

What do you want to accomplish that could change your life within the next year? Write it down. Make sure it pushes you outside your comfort zone. 

2. Identify 3 Key Results 

Determine how you’ll measure your progress. For each key result, assign clear, quantifiable targets. 

3. Commit to Check-Ins 

Set aside time each week to review your progress. Celebrate wins and recalibrate as needed.  

4. Fail Forward 

Don’t aim for perfection. Pursue goals so ambitious that minor failures teach you more than small wins. 

5. Create Alignment 

If you’re working as part of a team, make sure everyone agrees on the mission and how to measure success. Shared goals matter. 

Closing Reflections 

Measure What Matters offers an excellent guide for anyone determined to create meaningful, measurable change in their life. It taught me to measure incremental progress, adapt to new challenges, and stay accountable to my bigger purpose. 

If you’re facing adversity, whether it’s a personal setback, loss, or the challenges of rebuilding after incarceration, Doerr’s OKR system can help clarify your path forward. Success requires discipline, planning, and the courage to take small steps every day. This book provides the framework to make those steps count. 

Map out your OKRs, and take action today. If I could use the power of structure and discipline to transform my life from prison to purpose, you can too. Start measuring what matters, and you’ll be amazed at where that focus can take you.

Self-Directed Question:

• What is one meaningful goal you can set today that aligns with your long-term vision?

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