Why Planning Must Begin Now

When people go through the criminal justice system, they often tell themselves that they will get serious later. They may want to wait until they:

• get through sentencing.
• get designated.
• settle into prison.
• know the environment.
• feel release getting closer.

That kind of thinking is inconsistent with being the CEO of your life.

Many people postpone planning because they believe the right time has not yet come. They tell themselves that they need more certainty, more stability, or more emotional strength before they begin.

In reality, the opposite is usually true. Uncertainty is a reason to plan. A person should expect obstacles, resistance, and struggle, and he should plan to overcome them with a sense of urgency.

If a person waits until release gets close before he starts preparing for success, he has already waited too long. Ted Gray, a leader from whom I’ve learned, likes to say, “If you wait for the opportunity to present itself, it’s too late to plan.”

Begin planning now.

I learned that lesson while in solitary confinement during my first year inside. As I wrote in the previous chapter, I read the Bible to carry me through the days, weeks, and months. In the Parable of the Talents, I found an idea that changed the way I thought about responsibility. The lesson I drew from that story was simple:

• Every person receives gifts, and every person has a responsibility to develop them.
• If we squander what we have, consequences follow.
• If we develop what we have, more opportunities may open.

That lesson forced me to confront reality. I had lost my liberty because of decisions I made. The responsibility for rebuilding would also be mine.

From that point forward, I began to understand something that still guides me today. If I did not create a plan for how I would use the years ahead, the years ahead would simply happen to me. Time would pass. I would react to whatever came at me. I might survive the sentence, but survival alone would not prepare me for success.

That is why I encourage people to start planning now. Live with a sense of urgency, and work to get things done.

Waiting Carries a Cost

One of the most damaging habits a person can develop during a crisis is procrastination. He tells himself that planning can wait until the environment becomes more stable, until emotions settle down, or until more information becomes available.

The problem with that thinking is that a person who delays planning does not avoid living through the days. He still wakes up. He still moves through routines. He still deals with frustration, uncertainty, and the passage of time. But without a plan, his effort lacks structure. Actions may carry him through the day, yet those actions do not add much value to strengthening prospects for success in the future.

That pattern disrupts progress. And a person going through any stage of the criminal justice system cannot afford to wait. He should use the stage he is in to work toward best outcomes, putting himself in a position for more opportunities. Stages will change, but the person should always sow seeds today for the success he wants in the months, years, and decades ahead.

The person falls behind and misses opportunities if he makes statements about preparing such as:

• I will start after sentencing.
• I will start after designation.
• I will start after I settle in.
• I will start when I get closer to release.

With that pattern of thinking, ten years can pass without meaningful progress. Uncertainty is one of the main reasons a person should plan. We all have the same 24 hours in a day, but we do not all put forth the same strategic effort. As a result, we do not all get the same results. Early plans make all the difference.

A Plan Is Rarely Perfect

Some people believe a plan is only useful when every variable is known. They want certainty before they begin. Real life does not work that way.

I did not know where authorities would send me after the judge sentenced me to serve 45-years. I did not know what policy changes might come. I did not know which books would influence me most, which mentors would enter my life, or how long it would take before my work would begin opening opportunities. If I had waited until every detail became clear, I never would have started. Begin the plan with questions such as:

• What will follow from the predicament I’m in?
• What am I trying to become?
• What does success look like at this stage?
• What daily habits would move me toward that future?
• What weaknesses should I address now?
• What skills, records, and support systems should I begin building?

When a person starts asking those questions, he is no longer waiting passively. He is preparing.

Planning Gives Structure to Time

One of the hardest parts of confinement is the way time can lose shape. Days repeat. Weeks blend together. A person can keep telling himself that he will begin doing something meaningful later, but later keeps moving.

Planning changes that.

A plan gives shape to time. It helps a person divide the future into stages and define priorities within each stage. It reduces the emotional burden of trying to solve everything at once. It gives a person a way to move, even if the overall journey still feels overwhelming.

When I began serving my term, I could not fully comprehend what a 45-year sentence meant. The number was too large. The future felt too distant. Through reading and reflection, I learned to stop thinking only about what I wanted in the moment and to start thinking about the people I hoped to influence in the future.

• What would they expect from me?
• What kind of work would earn their respect?
• What kind of record would show that I had used my time well?

Questions like those helped me build a plan.

I decided that I would use every day of my sentence to work in three directions. I would educate myself. I would contribute to society in meaningful ways. And I would build a support network. That framework gave shape to the next week, the next month, and the next season of life. It guided the books I read, the skills I worked to develop, the writing I produced, and the relationships I tried to build.

A plan made the sentence feel less like one giant wall and more like a series of stages through which I would have to move deliberately. That principle applies whether a person is:

• facing sentencing,
• preparing to surrender,
• adjusting to prison,
• or preparing for release.

The stage changes. The responsibility to prepare does not.

Planning Turns Hope into Strategy

Hope by itself is not enough. Prayer by itself is not enough. A person must plan, and then he must work to execute the plan, regardless of external forces or conditions. Many people hope things will improve. They hope a judge will show mercy. They hope prison will go smoothly. They hope opportunities will appear later. They hope life will somehow come together after release.

Hope has value, but without a plan it does not lead to results. Planning turns hope into strategy. Strategy can lead to tactics, the development of resources, and better results. A person with a plan begins asking different questions:

• What am I doing right now that supports the life I say I want?
• What record am I building?
• What routines should become non-negotiable?
• What educational, vocational, or personal gaps should I start addressing?
• What should others be able to see if they review my effort months from now?

Once a person accepts responsibility for governing his own life, planning becomes the natural next step. To live as the CEO of your life requires you to think differently. It also requires you to plan differently.

Planning Is an Act of Self-Respect

When a person creates a plan, he is essentially living as if he recognizes the responsibility of organizing thoughts and actions. He understands that today’s conduct today leads to tomorrow’s outcomes, and an opportunity cost comes with every decision.

People may feel ashamed, discouraged, or overwhelmed if they come into the criminal justice system. A conviction, a prison term, or even fear of what lies ahead can temporarily paralyze a person’s confidence. He may dwell on the prospect of punishment, loss, and damage that cannot be repaired. Planning interrupts that erosion of self-confidence, because a planner starts to recognize:

• I am responsible.
• I must work to build a better future.
• I should become a good steward of time, resources, and truth.
• I must build.

A Plan Should Evolve

Plans give a person a working structure to think, act, measure, and adapt when situations change, and they will.

During the years I served, I had to revise my plans repeatedly. Some opportunities closed through no fault of my own. Others opened. Working toward some goals took longer than I expected. Other developments accelerated because one disciplined decision led to another. Those changes proved the value of planning. Even when things do not go our way, our plans should show how we are adjusting, advancing, and evolving.

At first, the plan may be simple:

• survive the immediate crisis,
• build emotional discipline,
• begin reading,
• begin writing,
• begin documenting progress.

Later, the plan may become more ambitious:

• pursue stronger educational goals,
• improve release readiness,
• build a support network that turns into a coalition of support,
• strengthen the quality of writing and memorialize the journey,
• prepare for work and contribution after release.

Planning is a living discipline, not a one-time exercise. Circumstances will change, and when they do, the plan should adjust.

What a Serious Plan Should Include

A plan does not need to be complicated to be useful. It does need to be intentional. My own plan had three simple parts:

1. I would work to earn academic credentials.
2. I would work to contribute to society in meaningful, measurable ways.
3. I would work to build a support network, a coalition of support.

By focusing on those three objectives, I believed I could strengthen my prospects for success. A serious plan should force a person to think about the results he wants and assess whether the decisions he is making will advance his prospects for success.

What does success look like at each stage?

Success while awaiting sentencing may look different from success in a high-security prison, a camp, a halfway house, or supervised release. A person serving a short sentence should not plan in exactly the same way as someone serving a decade or more. The plan should fit the stage.

What are my immediate priorities?

A person may need to focus on emotional discipline, educational structure, physical health, writing habits, relationship repair, or release preparation. Priorities bring order.

What habits must become consistent?

Without repeated habits, a plan remains a wish. Habits turn direction into pattern.

What record am I building?

The plan should not live only in the mind. It should begin showing up in biographies, journals, book reports, release plans, and other written records that show effort over time.

What obstacles should I anticipate?

A serious plan expects resistance. It does not assume smooth conditions. It anticipates delays, frustration, fatigue, distractions, and setbacks.

How will I measure progress?

A person should know what evidence will show that the plan is becoming real. Otherwise, good intentions can create the illusion of progress without producing much substance.

Questions like these transform planning from vague aspiration into visible preparation.

Planning and Writing

In the context of this book, planning and writing belong together. A person may have a vision in his mind, but until he writes it down, that vision often remains loose. Writing forces choices. It forces clarity. It exposes weak thinking, vague intentions, and contradictions between goals and habits.

That is one reason I place so much emphasis on documentation.

A release plan is one example. A journal is another. A biography can also reflect planning because it shows how a person understands his past, his present responsibilities, and the future he is trying to build. Over time, the written record turns planning into something others can evaluate and something the writer can refine.

Planning should begin now. It’s never too early, and never too late to start the plan. By seasoning the plan over time, a person builds a body of evidence that will become useful in self advocacy. The chapters that follow will offer more insight into using a profile to publish the plan. For now, the key point is simple: planning allows a person to say what he is going to build, opening opportunities for others to assess the plan’s effectiveness.

Plans build trust.

As an example, think of building a house. You have a better chance of getting the result you want if you provide a builder with blueprints than if you simply tell him what you want. A plan should work like a blueprint that guides you toward the life you want on the other side of this journey.

Another reason to begin early is that opportunities often appear before a person feels fully ready.

• A class may open.
• A mentor may appear.
• A program may become available.
• A supportive stakeholder may take interest.
• A family member may be ready to help.
• A chance to strengthen the record may arrive unexpectedly.
• A law or policy may change.

The person who has been planning is better positioned to respond. The person who has only been reacting often misses the opening. Planning does not guarantee opportunity, but it improves readiness.

That principle shaped the decisions I made in prison and after release. The relationships I built, the work I produced, and the opportunities I later received all depended on preparation that began long before those opportunities became visible. Even today, our nonprofit has received financial donations from thousands of people because they want to support our mission. It’s a mission that began with a plan. That plan allows us to give resources away at no charge to people in prison. So long as they are working to execute their plans, we will keep working to build support for the mission.

Start Building Your Plan Today

Some readers may think, I do not know enough yet to make a serious plan.

Start anyway.

Do not wait for the perfect plan. Start with the one you can build today. It may be incomplete. It may change many times. It may begin with only a few commitments:

• I will read regularly.
• I will write regularly.
• I will define success for this stage.
• I will keep a record of my progress.
• I will begin preparing for release long before release arrives.

That is enough to begin. The key is not perfection. The key is direction.

Self-Directed Questions

1. What would a serious plan look like for me at the stage I am in right now?
2. In what ways have I been postponing planning because I am waiting for more clarity or better conditions?
3. What priorities should define this stage of my life?
4. What habits would help turn my plan into something real?
5. What obstacles should I anticipate rather than ignore?
6. What written record would show that I am preparing deliberately instead of drifting?
7. What can I begin planning this week that would make the next stage of my life stronger?

Planning is one of the first visible signs of a person’s commitment to prepare for success. It requires discipline and courage to begin.