I’m really excited about closing escrow on a house that I purchased several years ago. Carole and I have loved living in that home, but we’ve decided it’s time to move on to the next opportunity. Living in prison conditioned me to set long-term plans and to assess them day by day, month by month, and year by year.
Those who have an interest can see how I do that with the fitness logs, or the finance logs, which anyone can see by clicking the buttons above or below:
That strategy of planning and assessing helped me through prison, and I’m confident it will guide me to the next phase of life. These journals reflect the work I do to plan and measure progress. The entire website we’re building at www.PrisonProfessors.org is an example. It should show how I put into practice the lessons I learned from a mentor, Marshall Goldsmith.
I first encountered Marshall Goldsmith’s work around 2008, when I was confined at the Taft Federal Prison Camp. He built his career coaching high-level executives. The basic premise I got from his book follows:
- If we want to move from one level of success to the next, we must accept the challenge of learning new skills or developing new resources.
- The strategies that get us to one level open opportunities, but to reach the next level, we must create or seize new opportunities—and learn new skills along the way.
I took that message to heart. When I became friends with business leaders such as Lee Nobmann, or Greg Reyes, or Bill McGlashan, or CZ, I heard how they used those same strategies. Such strategies led to their becoming billionaires.
Carole and I have always followed that path of setting incremental goals that would put us into a position for new opportunities. From the time she came into my life, we’ve set five-year plans. We started our life together in a prison visiting room when I was in my 16th year of confinement. To power through the remaining 10 years of my sentence, I showed her the strategy I had relied on from the start. We had to set five-year goals. By working intentionally toward those goals, we believed new opportunities would open for us.
Those who want to learn more about the journey can read it in Earning Freedom: Conquering a 45-Year Prison Term.
When I read Marshall Goldsmith’s book, I was in the final five years of my term and already laying the groundwork for a post-release career. The choices I made early in my journey positioned me to make faster progress later on. Thanks to the skills I developed inside, I was able to earn an income, start a savings account, and work toward my goal of accumulating enough resources to support myself for an entire year if necessary. Meanwhile, Carole was working toward becoming a registered nurse. We were on our path.
After my release, I took a deliberate approach to building assets, eventually creating a portfolio worth more than $1 million. As the markets improved, our assets appreciated as well. Although I cannot predict the future, I stay aware of market conditions, spotting trends and opportunities while deciding how to deploy or shift resources.
In the fourth quarter of 2024, Carole and I decided it was time to launch our next five-year plan. I made a video describing our thought process once we put the plan into action.
By selling our personal residence, we could capture more than $1 million in equity. We aim to reinvest those assets into vehicles we believe will appreciate more quickly than real estate. If we’re successful, we’ll reach a higher level of financial success—and we’ll be able to pursue other goals that allow us to make a greater impact on the world.
We expect to close escrow on our house by mid-month. At that point, we’ll redeploy our resources into the asset classes we believe hold strong potential for growth—specifically, companies advancing artificial intelligence and cryptocurrency, particularly Bitcoin.
As I’ve written through the site, I’m not a financial advisor. I encourage people to invest in themselves first, then learn how to create plans that will lead to new opportunities that align with how they define success. That is the pathway to living as the CEO of your life.
We should always make plans that keep us moving in the direction of our goals. By journaling, we stay focused, hold ourselves accountable, and continue building momentum toward each milestone.
Self-Directed Question:
What steps can you take today to ensure that your decisions align with the five-year plan you’ve set?
