When he was 19, Chris Wilson asked himself, “What’s my end game?” He had hit rock bottom. In prison serving a life sentence, he knew he was a good person and was determined to write a different ending to his story. As he started to reimagine what his life could look like in the future, a plan began to emerge. 

Now a successful social entrepreneur and artist, Chris has dedicated his life to helping others. He is the owner and founder of several business ventures, including multi-service social enterprise Barclay Investment Corporation, high-end furniture restoration and design company House of DaVinci, and art enterprise CuttleFish. He wrote The Master Plan: My Journey from Life in Prison to a Life of Purpose to share his story and help others build their own master plans. 

In this conversation, Chris shares lessons he’s learned about resilience, his principles for success against the odds, and tips for crafting your own master plan to make the most of the new year. 

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Principles for success against the odds

As Chris clarified his end game and began working on his master plan to get there, several principles for success emerged. These ways of thinking stay with him in everything he does—especially when faced with hardship—and he teaches others to use these principles too. 

• Resilience — After contracting Covid in early 2020, Chris’ health and his businesses suffered. He drew on his time in isolation in prison to see opportunity in hardship and focused on his love of art to start a new venture, an art and social justice enterprise called CuttleFish. 
• Positive Delusion — “The positive delusion is about believing in yourself and surrounding yourself with people who also believe in you and your potential,” Chris says about the belief he maintained during his years in prison: that he would one day be free and become the person he wanted to be. 
• Brainstorming — Chris started connecting the dots between where he was and where he wanted to be by asking himself questions like ‘What are the things I need to do to get there? What do I need to stop doing? Who has done it before me that I can emulate? Who do I know that can help me?’ Start with a bunch of ideas before narrowing in on your next steps. 
• Lifelong Learning — A voracious reader, Chris seeks new information even if he’s not sure how it will benefit him yet. In prison, he taught himself several languages, and later that skill helped him secure a job. 
• Personal Health — Chris is a firm believer that your health is your number one investment. If you’re not in a good place, how can you help someone else? He balances work with time for exercise and passion projects and works with a therapist regularly. 
• Relationship Maintenance — Chris values his personal and professional connections and expects relationships to go both ways. Look for ways you can benefit each other. Be genuine, show care and respect to your network, and surround yourself with positive people. 
• Demanding Your Worth — Whether you launch a business or start a new job, he advises everyone he works with to value their own time, do their research to understand the market they serve, and clearly articulate their value in business relationships. “Always demand your worth in all aspects of your life.”

Making your master plan real

Even if your journey has looked different from Chris’, there’s much to glean from his special mix of resilience, dreaming, and preparation. A master plan is about adding structure to your life, Chris says of the tool he crafted to go from life sentence to serial entrepreneur. Many people have aspirations or hate their current jobs, but haven’t thought about what exactly they could do to achieve their goals. “Once you create this master plan and start to execute it, it changes your life,” he says. To make your master plan real, start with these steps. 

It’s hard to take the first step when you don’t know where you’re going. Clarify your end game by asking yourself questions about your ideal future: 

• What would it look like if I were wildly successful 10 years from now? 
• What do I want to be remembered for?
• What kinds of experiences do I want to have? 
• Who do I want to help? 

Go beyond work to include your personal life and be as specific as possible to imagine what you’re doing and how it feels. “That end game, as you work towards it, it's actually fun,” Chris says. “It's beautiful.” 

2. Plan your time. 

Having a master plan doesn’t mean 100 percent of your time should be dedicated to work. Ensure balance by setting aside time for your personal and professional goals. Be intentional about this time. How can you make more time to do the things you love? What can you cut out? 

3. Build a personal board of advisors. 

Chris’ secret to building a network of advisors is simple—don’t tell them about it. Most people you’d want on your personal board of advisors are already busy and hesitant to make more commitments. Instead of asking them to mentor you, identify people with expertise in areas you want to learn about and take them out for coffee or lunch once a month. Be bold, Chris says, and make sure the relationship is mutually beneficial by helping them in any way you can. His two pieces of advice for connecting with mentors are to find the right introduction from someone who can vouch for you, and to demonstrate your commitment through hard work. “Everyone wants to support someone who’s working hard,” he says.

Evolve your plan and bring others along

As you work toward making your master plan real, know that it’s meant to evolve over time. “There’s many different ways to get to your end game,” Chris says. Keep an open mind and be ready to pivot when you see an opportunity. As long as your end game is something positive that would make you happy and allow you to be impactful, the way you get there isn’t as important. For Chris, art was a later addition to his master plan. As he fell in love with art and started to understand its power as a tool for social change, he shifted his master plan to make more space for it. Write down your plan, but review it, tinker with it, ask people to critique it, tear it apart, and put it back together.  

Throughout this process, Chris advises what he calls “leaving breadcrumbs.” “A master plan is more effective and feels better when you incorporate other people,” he says. If you care about a particular issue, as you move forward in achieving your master plan, think about how you can help other people without expecting anything in return.

So what’s next? Once your master plan is sketched out, share it with someone you trust and give them the power to hold you accountable. No matter how far away your end game feels, take inspiration from Chris: your dreams are possible if you put in the work. 

Follow Chris Wilson on Instagram at @chriswilsonbaltimore and read his book, The Master Plan, for continued inspiration. Go to The Marshall Project to see how you can support criminal justice reform, and learn more about education programs for corrections facilities with American Prison Data Systems, two organizations Chris works closely with.

Learn how to articulate and activate your purpose and bring more meaning to your every day in our online course, Power of Purpose.