Journal Entry 


Picture of Michael Santos

Michael Santos

What obstacles block prospects for success?

This morning I spoke with Harold, a man who recently finished serving a lengthy sentence in prison. Before his incarceration, Harold had a successful career. He founded a healthcare company that grew to employ hundreds of people. With several locations, the company generated eight-figure revenues. 

After more than 25 years of success, a bad decision led to a government investigation and a criminal conviction. Harold acknowledges his mistake, but he does not complain. While he served his sentence, Harold devoted his time to preparing for the challenges ahead. 

SWOT Analysis:

As we recommend in our course, Preparing for Success after Prison, Harold assessed his strengths, weaknesses, opportunities, and threats. He had extensive experience in business, which would serve him well as a strength, but he had the liability of a felony conviction. He perceived opportunities in building a consulting business to help people navigate crises. His probation officer would not allow him to interact with other people who had felony backgrounds. Harold perceived that as a threat to the business he wanted to build. 

As a man in his 60s, Harold understood the challenges he would face in the job market. Throughout his career, the businesses he built employed more than 1,000 people. Harold offered jobs to people who promised to grow with the company when hiring. His company had to invest time and capital to integrate a new employee, and he didn’t want to hire people who would quickly move on. Job market realities presented challenges for people older than 50, and a criminal background exacerbated those problems.

In response, Harold launched his business. He anticipated that people like his probation officer would present obstacles. Harold did not expect to receive resistance from members of his family.

When Harold laid out his plan, his son told him:

  • Let’s be honest about your business prospects. What have you done over the past six years besides running your business into the ground and serving a prison sentence?

That question gave Harold a reality check. He did not consider all the obstacles he would face. Suddenly, he felt that he faced resistance from all sides. He needed a jolt of confidence. A quote from Thomas Edison could help:

“I have not failed 10,000 times. I have not failed once. I have succeeded in proving that those 10,000 ways will not work.”

Thomas Edison

Overcoming a crisis requires a powerful mindset. It also requires perseverance and preparation. While going through prison, we must anticipate all our challenges. And we need a plan to break through those challenges. The sooner we begin our preparations, the harder we work on them, the more we bolster our confidence. We’ve got to modify the famous lyrics of Frank Sinatra: “If I can make in New York, I can make it anywhere.”

Grow stronger with preparation. “If I can make it after imprisonment, I can make it anywhere.”

The strategy that leaders taught me:

  1. Define success as the best possible outcome,
  2. Build a plan.
  3. Prioritize the steps you must take in anticipation of obstacles.
  4. Create more tools, tactics, and resources to accelerate the plan.
  5. Measure progress with clear accountability metrics.
  6. Adjust the plan as necessary to accommodate changing circumstances,
  7. Execute the plan every day.

Those strategies lead to you being the CEO of your life. Use them daily and prepare for success.

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