How to Apply Strategic Thinking to Overcome Obstacles
Strategic thinking is the backbone of transformational growth, turning challenges into stepping stones. Having spent 26 years in prison, I’ve learned firsthand how a strategic mindset can reshape even the most adverse circumstances into opportunities for long-term success. This article will explore strategic thinking’s role in overcoming obstacles, offering actionable steps that align with proven frameworks and real-life examples. It’s not based on theory, but what I learned while growing through multiple decades in prison, and what I’ve applied to my life.
Why Strategic Thinking Matters
Obstacles often test us, whether they involve financial crises, health challenges, or personal struggles. Strategic thinking equips you to address these challenges by breaking them down, anticipating risks, and finding adaptable solutions—all while staying focused on long-term goals. Leaders like Viktor Frankl, Marcus Aurelius, and even entrepreneurs like Elon Musk have demonstrated the importance of strategic thinking in navigating hardship.
I’ve written about the influences those leaders had on my adjustment.
I still remember one of the most pivotal moments early in my prison sentence. Confronted with a 45-year term, I had to ask myself hard questions about how I could transform my life under extreme constraints. I was still locked in solitary when I started thinking about the bad decisions I had made that led me to prison, and how I could make better decisions going forward.
There wouldn’t be any shortcuts. I had to build a personal-development system of deliberate actions that could eventually lead to a better outcome. The same approach works for anyone facing seemingly insurmountable challenges.
Step 1: Define the Problem Clearly
As I wrote in the course I created, The Straight-A Guide, many people fail to overcome obstacles because they misdiagnose the issue at hand. Defining the problem with clarity is the first step toward resolution.
Why it’s important:
Addressing surface-level symptoms wastes time and energy. To craft an effective solution, you need to identify the root cause.
Example:
Consider a struggling business with falling sales. Rather than blaming market conditions, a strategic leader would investigate deeper issues—product-market fit, customer satisfaction, or marketing effectiveness—to uncover the real problem.
Action:
- Write down the obstacle you’re facing and list its symptoms.
- Ask “why” repeatedly to dig deeper into the issue until you identify its core.
When I was in solitary confinement, I had to think about how I could use the resources I had—and the best resource was time to learn how to think differently. I shifted my focus to finding purpose, I could begin building a meaningful plan to transform my sentence into an opportunity for learning. Anyone can do the same.
Step 2: Anticipate Challenges and Risks
Every solution carries potential risks and trade-offs. Strategic thinkers anticipate challenges ahead of time and create contingency plans. They don’t wait for others to resolve their problems. They live in the world as it exists, and they make decisions accordingly.
Why it’s important:
Foresight helps you avoid unnecessary setbacks and equips you to adapt seamlessly during periods of uncertainty.
Example:
Think of how space exploration companies like SpaceX anticipate risks (mechanical failure, weather, financial constraints) and build comprehensive contingency plans. This foresight enables them to move forward despite immense complexity.
Action:
- Brainstorm potential risks or obstacles that could arise from the steps you’re considering.
- Create contingency plans for each risk.
When I planned my post-prison career, I anticipated rejection due to my criminal record. In fact, as I’ve written many times before, I considered myself to be unemployable. I built a diversified plan to prepare educational credentials, writing skills, and a robust professional network—all of which minimized the impact of rejection. Those skills, I hoped, would lead to income opportunities and a better life.
Step 3: Develop Multiple Solutions
Instead of relying on one rigid plan, strategic thinking encourages you to explore creative problem-solving by brainstorming diverse paths to success.
Why it’s important:
Flexibility allows you to pivot when circumstances inevitably change.
Example:
During economic downturns, businesses that find ways to pivot—adopting cost-effective models, launching new products, or entering new markets—tend to thrive while others collapse.
Action:
- Use brainstorming techniques to generate at least three different solutions to the problem.
- Evaluate their feasibility and potential risks.
For me, this meant preparing to contribute in multiple ways post-release. I didn’t just plan for one specific job. Instead, I explored opportunities in writing, professional speaking, and teaching, increasing my chances of landing on a sustainable path. As I built resources, I began investing in appreciating assets (or at least assets that I believed would appreciate.)
Step 4: Prioritize and Take Action
Strategic thinking also requires execution. Without well-defined priorities and swift action, even a brilliant plan falters.
Why it’s important:
Prioritization ensures maximum efficiency by focusing resources on the actions most likely to produce meaningful results.
Example:
Tools like the Eisenhower Matrix help leaders determine which tasks are urgent and important, enabling them to focus on what truly moves the needle.
The Eisenhower Matrix, also known as the Urgent-Important Matrix, is a time management tool that helps individuals and teams ensure efficiency and clarity in prioritizing tasks. This approach originated from former U.S. President Dwight D. Eisenhower, who was renowned for his ability to make clear decisions under intense pressure. He once stated, “What is important is seldom urgent, and what is urgent is seldom important,” which became the foundation for this matrix.
The Eisenhower Matrix divides tasks into four quadrants, based on whether they are urgent or important—or neither. Quadrant one includes tasks that are both urgent and important, requiring immediate attention. Quadrant two focuses on tasks that are important but not urgent, which often encompass long-term planning and personal growth. Quadrant three involves tasks that are urgent but not important, helping individuals recognize distractions. Lastly, quadrant four contains tasks that are neither urgent nor important, suggesting they should be minimized or eliminated entirely.
Based on what I learned about quadrants, I created lessons that are a part of our course, Preparing for Success after Prison.
I first encountered this framework while seeking ways to improve my productivity during a particularly overwhelming period. A mentor introduced me to the matrix, and its simplicity helped. I liked the statement about Quadrant three tasks—urgent but not truly important—and neglecting Quadrant two activities that aligned with my deeper goals. This experience highlighted the power of intentional prioritization and reshaped the way I approach work and decision-making.
Action:
- List out all potential actions and rank them by impact and urgency.
- Start small but focus intensely on the steps that will deliver the greatest results first.
For example, while I was earning degrees in prison, I prioritized daily education and writing over less productive activities. Those consistent micro-actions culminated in opening long-term opportunities.
Step 5: Learn, Adapt, and Improve
Strategic thinkers know that no plan works exactly as envisioned. Measuring progress, analyzing outcomes, and adapting based on real-time data are critical components of enduring success.
Why it’s important:
Continuous iteration allows you to stay flexible and improve outcomes, even in the face of unexpected challenges.
Example:
Thomas Edison’s development of the light bulb was a testament to perseverance and iteration. Testing thousands of filaments, he treated every failure as valuable data that brought him closer to success.
Action:
- Set specific milestones and measurable goals.
- Conduct regular reviews of your strategy to refine and improve your approach.
When Bitcoin’s price volatility wiped out some of my early profits in 2024, I treated my losses as data. I adjusted by diversifying my financial strategy to preserve gains while continuing to grow assets. When the asset class had a significant drop in February of 2025, my wife and I decided to make changes so that we could add more to our portfolio. In times of fear, acquire.
Real-World Application
I often refer to strategic thinking as “living like the CEO of your own life.” Whether you’re rebuilding after adversity, tackling ambitious financial goals, or navigating a career pivot, these five steps work universally. By following this method, I not only survived 26 years in prison but emerged with a career, financial independence, and an unshakable sense of purpose.
Self-Reflection Challenge
Ask yourself:
- What significant obstacle are you currently facing?
- How can you define the root cause more clearly?
- Have you identified potential risks, and do you have a Plan B?
- Which actions can help you achieve meaningful progress right now?
Start drafting your roadmap today. Transform your challenges into opportunities—step by step.
The power of strategic thinking lies in its ability to shift your focus from immediate frustrations to long-term impact. Remember, the more intentional and disciplined your approach, the more resilient and successful you will become.
