At 10:02 this morning, I received the following message from an anonymous person:
“What do you have for someone after 20 years of incarceration who’s in recovery and wants to start a business??”
The question struck me as odd, even though I’ve heard similar questions countless times. People who’ve gone through my courses should know how to devise a strategy to work toward overcoming adversity. Anytime a person faces struggle, the person should introspect:
- How do I rebuild?
- How do I create something of value?
- How do I start over?
Real power comes from how we approach those questions.
From the question I received, I can’t even tell what the person wants–other than to know what someone else can do for him. The truth, as I’ve lived it, is that people must work to change their own life so that others will view them as a better candidate for success. It’s understood that the person wants:
- A Fresh Start – Rebuilding after 20 years of incarceration isn’t easy, but it’s possible. The fact that this person is in recovery suggests they’re already making strides in self-improvement. But the person should also have a solid story showing what he did to prepare while he served the 20 years.
- Independence Through Business – Rather than seeking traditional employment, this person wants to create a business. But he didn’t offer any details, nor did he mention what qualifies him to run a business.
- Guidance – By reaching out, the person is seeking direction on how to turn his wish into reality. I wouldn’t call his statement about wanting to start a business a goal, because goals are much more specific.
When evaluating whether a man is likely to achieve his goal, I ask a few key questions:
- In what ways has he invested in himself?
- Success requires relentless learning and adaptation.
- Does the person have a plan?
- An idea isn’t enough—execution matters.
- Will he commit to consistent action?
- Business requires persistence, resilience, and patience.
- Is he resourceful?
- He should build tools, tactics, and resources that will accelerate the plan.
- Can he build relationships, seek guidance, and find ways around obstacles?
- He is reaching out to me, anonymously, without providing any context as to why he is asking me.
The truth is, anyone can start a business. But very few will do what it takes to build a successful business. I’m not trying to discourage anyone—just being honest. Success is never about what we want. It’s about what we’re willing to do to get there.
If this person were sitting across from me, I wouldn’t offer a magic formula or a list of quick steps. Instead, I’d offer a framework for action, built on the same principles that guided me through 26 years in prison and helped me build businesses after release. I’d encourage him to answer these five critical questions:
1. What Problem Will Your Business Solve?
Every business exists to solve a problem. What value will you create for customers? If you can’t answer that clearly, success will be difficult.
2. What Skills Do You Need to Develop?
No one is born knowing how to run a business. I spent years reading books, studying successful leaders, and developing my skills in writing, communication, and finance. What skills will you need, and how will you acquire them?
3. What Resources Are Available to You?
Lack of capital or experience isn’t an excuse—it’s a challenge to overcome. Who can mentor you? What free resources can you leverage? What steps can you take with what you already have?
4. What Systems Will You Create?
To succeed, we’ve got to work smarter. What daily habits, accountability tools, and structured plans will ensure that you keep moving forward?
5. Are You Prepared to Keep Going, Even When It’s Hard?
Building anything meaningful takes time. Most people give up too soon. How will you keep going when you face setbacks?
The Reality of Business After Prison
I don’t sugarcoat the truth—starting a business after 20 years of incarceration won’t be easy. Going through 20 years in prison doesn’t necessarily mean a person has resilience. To be resilient, we must show how we’ve developed our strategic action plans. The biggest mistake people make is waiting for the system to change us. We have to work hard to change our life, and we cannot expect anyone to change it for us.
To the person who sent this message, and to anyone else asking, “How do I start?”—my answer is:
- Invest in yourself first – Read books, develop skills, learn from those who have built businesses before you.
- Start small – Don’t focus on launching a perfect business overnight. Start with one step, one product, one service.
- Create systems – Success isn’t about motivation; it’s about discipline and habits.
- Commit to the long game – If you’re serious about building something great, expect it to take years—not months.
We all need a plan, action, and perseverance.
Self-Directed Learning Question:
- If you had to create a plan today to build a business or reach a major goal, what steps would you take in the next 30 days? What challenges might arise, and how will you overcome them?