When I was in high school, I got in a lot of trouble. As a result, I often wondered if anybody would ever give me a chance at life. Because I ended up receiving multiple chances despite my screw ups, I've learned to be more thankful and not take things for granted. I also developed an affinity for people who also had a rough time growing up, but found a way to make things work.
The following is a guest post from Bill, a man who spent 10 years in prison before getting on the path to financial freedom. Hopefully his post will give you the motivation to stick with things when times are tough and not lose faith that everything will turn out OK in the end.
I walked into my jail cell. I heard the door close behind me. I had just been sentenced to ten years in prison. It was my first time ever in trouble and I was in shock. I didn’t know what to think.
The emotions came in horrible waves. I felt an overwhelming sense of relief at first. The night before, my attorney had braced me with the reality that the negotiations with the district attorney had not gone well, and that the state was going to be recommending 20 years of incarceration.
In court that day, the judged looked down at me in handcuffs and I heard him read his sentence in shock: “The state sentences you to ten years in prison. Due to sentencing guidelines, you will have no chance at early release or parole. Good luck to you.”
That night the harsh reality of being sentenced to 10 years in prison settled in my mind like slow mental torture. How was I going to survive it? How could I hold onto my sanity with such a horrible future ahead of me?
I reflected how I found myself in this position. I had first used drugs when I was 14, smoked a joint, and liked it. For years, drugs and parties provided an escape from my otherwise normal life, and drugs provided me a fantasy of happiness I thought was real. But that illusion was shattered after a friend left my college apartment one night after partying, overdosed, and died in his sleep.
The next morning, I was arrested and charged with “reckless homicide by delivery of a controlled substance.” I had provided some of the drugs that contributed to his death that night, and that’s all the state had to prove to convict me of the charge.
I had gotten high hundreds, or thousands of times, but I never meant to harm anyone. It was a terrible accident. Everyone involved in the tragedy lost. I learned that when you play with fire, you don’t get to decide how badly you get burned.
Life as I knew it was over. No one was going to fight for a comeback for me. My life was now a mission to prove that I was a better human being than the one they threw away for a decade.
The Awakening: Step 1
The morning following my sentencing hearing, I was driven to prison in a van filled with 5-10 other inmates I’d never seen or met. We rolled across the highway in blaze orange jumpsuits, and chains wrapped around our wrists, ankles, and waists. When we arrived at the prison intake dock, we were given a badge displaying our prison inmate number. That badge would be my identity in prison for the next decade. To the people who knew me in the free world, I basically fell off the face of the earth.
After intake, we were directed into a large holding-pen area with 20-30 other male inmates consisting of all races, ages, and backgrounds. Being men, we naturally sized up each other’s strengths, weaknesses, and intelligence. If this was a prison movie, a fight probably would have broken out. But in real life, every man just stood stone-faced in shock, silently evaluating what their life had become.
We walked out of the intake area in single-file line carrying our new life’s belongings: a bed sheet, blanket, and criminal case folder. The halls felt as big as airport concourses as we moved deeper into the 2,000 man prison. Cell blocks were stacked multiple-tiers high. Hundreds of other inmates passed in blurs around me.
A guard led me to my prison cell. I walked in and looked up. On the wall, above my bed, I saw this photocopy taped to the wall. (The previous inmate must have hung it, because prison systems aren’t into the motivational quote business.)
At the time, it was impossible to grasp how I could hold my life together in this nightmare, but it gave me my first sense of hope that giving up just wasn’t an option for me. (I kept the photocopy and currently have it framed in my home-office).
Prison time felt like I was slowly suffocating to death at first, but then the days, weeks, and months began to pass in a bearable routine. I once read that it takes human beings two years to adjust to traumatic events, such as a bad divorce, physical paralyzation, or in my case, a prison sentence.
Humans need two years to forget the daily details that made them the people they used to be and two years to adjust to the new a new details they feel normal.
This is what adjusting to prison life was like for me. It took me two years to forget the normal dreams I had as a young adult (graduate college, get a corporate job, and start a family) and create a new dream to chase in my prison cell.
My new dream had nothing to do with money or a career. I simply wanted to get the hell out of that prison world one day, and I wanted to be mentally, physically, and spiritually stronger that I’d ever been on the day I’d get out.
I also had to adjust to a new society inside the prison walls. I once was transported to a new prison to begin a treatment program. I walked into an outdoor courtyard and sat at a picnic table. People were watching me. I felt tension in the air. But I didn’t know why.
After a few minutes, a man approached the table I was at. He didn’t smile, and I prepared for anything. My blood pressure rose. I tried not to show any fear.
“What's up?” I asked the man who confronted me.
He silently judged me and evaluated my intentions. He pointed at a different area of picnic tables, and aggressively asked. “Are you sure you’re in the right place?”
I looked around. The men sitting at the other picnic tables were white. The men around me were not white. I suddenly realized why I felt so much tension. He was questioning why I had crossed the invisible racial lines dividing the courtyard. Was I trying to make a statement? Start a fight? Or cause a scene?
I just wanted to sit down, but nothing was ever easy in prison.
I eventually learned that prison is like a choose-your-own-adventure story. If you wanted prison to be a mean and racist world like you saw depicted in movies, you could choose to create that reality. Or, you could choose to lay low and avoid the drama constantly surrounding you.
Life is the same way: You can create it to be whatever you want it to be with the choices you make.
My Timeline: 10 Years Of Prison
My prison life became a daily routine of reading books, writing journals, and working out. During a visit to the prison library, I remember randomly checking-out a Tony Robbins book titled, “Awaken The Giant Within.” One sentence in that book changed my perspective on time and achievement forever.
The wisdom in the sentence exploded in my brain as I read it: “Most people overestimate what they can accomplish in a year–and underestimate what they can achieve in a decade.”
As far as resources go, I realized I didn’t have a lot in prison. Prison is a world devoid of a real economy. The prison economy consists of using stamps, candy bars, and sodas as currency to trade for services like extra food in the cafeteria or for artwork to send to your loved ones.
Prison is not a good place to build wealth, businesses, or learn to practice financial literacy. But I did have ten years of time, access to a library full of new ideas, and a ton of imagination to help me prepare for my second chance at freedom.
I remember going through a stage that was very important to my new personal growth. It was almost like a healthy rebellion where I abandoned the dreams I used to have (a corporate job, and a normal life in my 20’s), so I could I embrace the new opportunities I had in prison.
I had an opportunity to create my own self-education, and for the first time, choose the path I wanted to live and the person I wanted to become. I had the time to plan ahead and build a bridge to where I wanted to go. I even wrote a novel for young-adults based on my experience.
The Doors Of Opportunities
Looking back on it, the best decision I made was not pigeon-holing myself into a career or focusing on one purpose-of-life to pursue. I decided to keep every option open.
I envisioned my new path to be a “Professional Opportunity Seeker.” This means I would pursue any opportunity as long as it led me to a life I wanted to live.
This way of thinking helped take the stress of trying to make the perfect decision, or choose the perfect path. I simply had to identify the best opportunities life was offering to me, and then turn those raw opportunities into exciting experiences for myself.
An opportunity could come in many shapes and forms: A job, a mentor, a business idea, etc. I would just have to be able to spot the correct opportunities, and do something special with them.
“If you can learn to see life as a never-ending hallway of opportunities, you’ll never run out of interesting places to travel to.” A friend once told me, “But…” He continued, “You don’t have to enter every doorway you find open. You are free to enter the opportunities you want to open, and close the doorways you want to walk past.”
This insight cemented my vision of how I’d handle life when I got out. My plan was to find as many opportunities as I could, and then selectively choose the best ones to enter. Conversely, if a bad opportunity presented itself — like the chance to use drugs again — I had the choice to close that door and look for a better opportunity that would lead to a better outcome.
The rest of my time in prison was full of equally enlightening and terrifying moments.
One of my best memories from prison was walking out into the prison yard early in the morning. The sun would rise slowly above the fences, and sunlight would flash on the razor-wire coils all around me like light beams through a crystal.
I became a long-distance runner in prison, and those early-summer mornings were especially beautiful as I ran around the prison yard track. I'd dream about my future, and I felt like anything was possible the day they'd finally let me be free again.
I also remember a few sleepless nights because I was afraid I had gotten too close to a psychopath. During most of my prison time, I felt starved for intellectual conversation, and I remember a few times where I was fascinated with a man's seemingly brilliant exterior, only to learn that there were crazy monsters on the inside.
I often forgot that I was in prison with murderers, rapists, and gangsters because that world was the only world I knew and it felt normal after awhile.
Luckily, in ten years, I never did get into a physical altercation. But there were a few times that I thought I was going to get my ass kicked for being in the wrong place, wrong time, while interacting with the wrong person. But I was always able to escape those moments and make it to a better day.
After a decade of time finally passed, on August 20th, 2012, my release date finally arrived. I have no idea how I slept my last night in prison, but I remember how I felt when I woke up. It was total nervousness and elation at the same time. I had made it. Today was my day to start over. It was now time to put my plan into action and start my mission to reclaim my path in the free world.
Finally Getting My Shot At Freedom
“Most people overestimate what they can accomplish in a year–and underestimate what they can achieve in a decade.”
This sentence was still very alive in my brain. I realized I didn’t have to accomplish all my dreams overnight. I started with small goals: like graduate college, get a $10 an hour job, and eventually move out of my parents basement where I first lived. Then once I accomplished those goals, I could set bigger goals.
I wasn’t going to judge myself by what I could accomplish in one year. I only imagined what I could accomplish in 10 years if I worked every day at my dreams. I committed to the mentality that excuses, anger, and blame were worthless. Positive action was the only thing that could make my life better.
A person can only make a finite number of positive actions in one day. But they can make millions of positive actions in a decade. When you add millions of positive actions up over a decade, I believed a person can create a life for themselves beyond their wildest dreams.
My first steps and positive actions looked like this: I got a job stacking magazines for $10 an hour, and graduated college at the same time. I saved my first $1,000 living in my parents basement. My main goal was to have enough money to buy my freedom.
My Steps To Self-Employment
The next two years passed in a blur of networking, saving money, and exploring as many opportunities that I could find. For example, I went to a job interview with a business-owner of a corporate apparel and promotional products business. He immediately saw natural sales skills in me that I didn’t even know I had.
He made me this offer: I’ll teach you how to start your own business and work from home, as long as you start by selling my products. I immediately saw this as a huge door of opportunity where I could have control over my work week, and at the very least I wanted to explore this opportunity.
Success Is A Numbers Game
My next step was to learn how to sell in a business to business environment. I made a goal of introducing myself, and my business, to ten new potential clients a day, and then follow up with 10 old contacts every afternoon.
I didn’t have any super-human influencer skills, or any sales education. I just had to be on the positive side of the numbers game, like gaining a client. And not let the negative numbers get me down, like being told no thank you by a potential client.
I chose to be fearless if people were going to judge me by my past. If someone was going to look down their nose at me, rather than being discouraged by their opinion, I'd just erase their opinion from my brain, and go onto the next person and see if they could help me. My job was not to get demoralized by negative people. Instead, my job was to find positive people who wanted to give me a chance.
I sold $10,000 worth of product in the first six months. But $10,000 in revenue wasn’t enough to make a living. I almost gave up and started looking for another opportunity.
But that Sunday at church, I heard a message about how so many people with a dream are on the verge of a breakthrough when they give up. Those words hit me, and so I gave it another month.
I’m glad I did because in the next 6 months I sold $180,000 in revenue, and I could finally start saving significant amounts of money — thousands at a time — rather than $100 or $200 at a time at my $10 an hour job.
Dreams Becoming Reality And Building Wealth
Four years passed since I left prison and I realized I had built a $100,000+ net-worth. I got married in that time. We bought a modest house with 20% down and a mortgage based on only one of our incomes, so we could save and invest the second income.
Eventually we bought a second house as an investment property and we learned how to rent it out. Becoming rich was never our goal. Freedom, and the desire to help other people, was always our goal.
It’s been seven years since I was released from prison. I now have a portfolio of real-estate, stocks, and cash, that is quickly rising above $350,000. My next goal is to become a half-millionaire, and then a full-millionaire after that.
Even though society threw me away for a decade, I came back because I believed I was an important human being. We all are. Everyone can help others from the suffering they’ve endured, and I wanted to play my role in this story called life.
Happiness is not a dollar amount for me. Happiness is having the time, drive, and character to make a positive impact on people’s lives. That is now the ultimate dream I am trying to achieve. Making a positive impact makes me feel like the wealthiest person alive no matter how much money I have.
Readers, ever experience prison or a difficult hardship for a long time? How did you survive? And how did you make the best of your second chance?
Bill, Wealth Well Done
46 thoughts on “Don’t Ever Give Up: Surviving 10 Years Of Prison”
Great story Bill! It really hit home with me. I am not sure what my future holds for me. I thank God for your success brother! Thanks for sharing your story with us. The world needs to hear about these types of stories more ofter to give Ex-Convicts an opportunity to demonstrate what their potential is and allow them to have a gainful life and career opportunity. Like you said, about 95% of these people made a bad decision and are overall good people. Thanks again!
Keep kicking butt Bill!!
Wow!! Losing ten years from your life and coming back from it hard is no mean feat. Not only is that 10 years of work and relationship building, but the small things that are often addressed on this site would be affected too. That’s 10 years of no 401k additions. 10 years of no savings. 10 years no employer valued experience. What’s more, since I’m guessing you would have to check the “felon” box on job applications, getting a job would be brutally hard.
I think it is beyond impressive to not only come back from that with a stable job and healthy relationships, but to go far and beyond with a happy marriage and raking in the money. The amount of self-belief required for that is truly impressive.
Congratulations, sir – this was without a doubt the most inspiring story I have read this entire year. Good luck on your future work!!!
Thanks for sharing your story. It’s easy for me to sometimes take things for granted and lose perspective in the pursuit of success on all fronts. In my work to consistently grow as a man, husband, and father, underestimating what can be accomplished in a decade and looking back at what I have done over the last decade is an excellent thing to reflect on.
Congratulations to you and your wife on the life you have built, and what you have overcome. Cheers!
I used to sell and do drugs as a kid. I got in a lot of trouble when I was young, arrested a few times and almost always on probation. My final straw was when I was put on house arrest for 6 months with an ankle bracelet at 20 yrs old. I had a very similar experience to Bill during those 6 months and decided to get my life in order. I graduated college by 25 and got a job at a fortune 100 company. I worked hard every day and have been able to climb the corporate ladder quite quickly and make quite a few investments. I am now 38 years old and am an executive at my company with a net worth of $1.6M. My stretch retirement goal is 45 yrs old, but I definitely will not work a day over 50. I say all this not to brag but to try to inspire others to do the same. Your life can be whatever you want it to be. You just need to push everyday in a direction towards those long term goals. Outline a path to get there and go after it!
I really enjoyed reading your story, Bill. I respect your grit to make the best of a terrible prison sentence and accepting personal responsibility for the 10 year sentence. I am glad that you turned your life into a wonderful next chapter with a lovely wife. All the best to you.
Thank you for sharing, I will always remember this.
“When you play with fire, you don’t get to decide how badly you get burned.” That’s a powerful message.
I heard my mother say that line years after I got in trouble, and I thought, “Wow. She’s exactly right. You have the freedom to decide your choices. You don’t always get to decide your outcomes.”
Great story about never giving up. Most successful people have experienced some tough times along the way but somehow find a way to persevere. Congrats to Bill! I’m going to share this article with friends and family. It is truly a motivating success story.
Thanks Frank!!! My only goal is that is gives someone else the courage, confidence, and energy to run through their own brick wall of self-doubt and struggle in their life. Thanks for helping my dream come true.
Inspirational and motivating!
Although I never did drugs, I get chills thinking about how I have been in the almost-did-enough-to-screw-up scenarios in my life. When you play with fire, you don’t choose how much you get burnt.
Thanks much for sharing.
You have learned a lot, grown a lot and have shared your hope with others. I know you’re genuine and that sets you apart from others. Keep encouraging others and make some time to visit us!!! I am so proud of you and I think highly of you and your lovely wife. Renee
For anyone reading Renee’s comment above, the coolest part about Renee is that I originally met her when I was an inmate in prison. She was a church volunteer who used to volunteer her time to help inmates who had less than 2 years in prison get ready for their release dates. Renee and I became close friends there, and we are still close friends 10 years later. Not all inmates transform their lives like me, but some do. She gave me hope and confidence that I could make awesome friends like her and do something incredible with my life when I got out. Never underestimate the power you have to give someone else hope when they are struggling. :)
What is the title of your book? I want to send it to my brother who is currently in jail. He is facing 2-4 years for drug related charges. His life spiraled out of control in about 2 months due to becoming a drug addict and being an undiagnosed bipolar didn’t help either. He is in the blame others stage right now.
This is my full story of crime, arrest, and incarceration: https://purposepages.com/2428-2/going-to-prison-purpose-of-life/
You should print this out and send it to him. The first step to make a success out of your adversity is to abandon the blame game. The second step is to look at yourself in the mirror, take accountability for your actions, decide who you want to be, and then go on a mission to get the life you want to live. The only way to your success is to do it yourself, because no one is going to do it for you.
When I read your article, it makes me touch in my heart. That why I believe that every second has a chance to change yourself into better person. Same as Robert Downey, Jr. does.
Kudo’s to you.
Great post! A truly inspiring story. Nice work.
Thank you for sharing your story. I am so sorry you had to go through this and I admire your strength and determination to make it through your difficult times. When I read your comment about psychopaths in prison, it reminded me of the reason why I am pursuing financial independence. I was pursued by one for most of my life. Since you saw inside the minds of some of them, you know what this means. I love reading success stories like yours. Thanks again for sharing, and best of luck to you in your life.
I do know what you mean. Inside the mind of a psychopath is a very scary, unstable, and dangerous place, and I am very sorry you had to experience that. Those are the moments I never want to re-live, and I am glad it sounds like you were also able to escape them for good.
That being said, I do want to note that most men in prison are not psychopaths. 95% of men inside prison walls usually did something stupid while they were intoxicated or high on drugs and got caught for it. They were remorseful and kind while they were sober doing their time in prison, dreaming of a better life. But 5% were just bad people I did my best to avoid being around. I just wanted to mention that so I didn’t unintentionally label all men in prison as true psychopaths. Most men were your brothers, uncles, fathers, and grandsons who had made a mistake and were paying the consequence by doing the time.
I love your story. Your NEVER giving up and CAN DO attitude Made you who you are today. Life is difficult and brighter days are ahead no matter how hard life is. People who are able to get through the dark days are the Heroes! I will visit your website as well. Thank you so much for sharing!
Yesterday’s post: How to pick a preschool!
Today’s Post: How to serve Ten years in Prison!
hahaha; Man the pendulum sung fast on that one!
Awesome story though. Really a good read.
Life comes at ya quick sometimes, doesn’t it!!! Lol.
Thanks for sharing your experience. I remember your story from the ChoseFi Podcast and did not realize you had a blog as well.
I can totally see how one incident can totally alter the trajectory of life. It is great that you came out the other end and were able to rebuild.
Well done, sir!
Well done, indeed.
Inspiring story Bill! So glad to hear about how you turned things around and are making a name for yourself running a business helping others. Do you still run sell promotional products and do you serve Texas? I’d like to get a quote about placing an order.
Hey Ross! I didn’t even think about linking to my promotional products sales business as I was so focused on telling the story. But yes, I’m always looking for cool new clients to work with. I currently sell around $300K+ a year to large (household-name corporations nationwide) and small (local businesses.) If there’s an opportunity to work with you, send me a message in my contact form and I’ll respond right away: https://www.wealthwelldone.com/contact-us/
Here’s a few compliments from clients who have purchased well over $100K of product with me to let you know I care about the promises I make:
“Thanks Bill! I really appreciate all the attention to our orders! You make it super easy to do business with your company!”
“You are really proving yourself here…thank you! It is really nice to have things ordered fast, and then delivered! Please pass my note on! They deserve to know you are taking care of your customers.”
Thanks for giving ordinary folk a chance. I have been following you since 2012-2013.
Bill, yours is such a motivational message, I’m pleased to see you getting the opportunity to share it on Sam’s site. No matter what your situation, your attitude dictates your direction. Yours is an attitude which sets an example for all of us. I’m proud to know you and proud of what you’ve accomplished.
Wow! Thanks to Bill for sharing your inspiring story. Thanks to you, Sam, for sharing Bill’s story on Financial Samurai.
Thanks for sharing your inspiring story! Wow. I’m sure many people would have given up long ago if they were faced with the same challenges you had to overcome. What an incredible come back story. I’m so glad to hear you’ve found a renewed purpose, happiness and have become financially independent. Congratulations!
Thanks for sharing. Inspiring and best wishes to your continued success. Never give up!
Thank you! Giving up is always a personal choice. Unexpected things happen in life, but never let failing be your fault!
That is an uplifting story Bill. The only difference between your story and mine is I didn’t get caught during my drug years. Congratulations on your successes!!
P.S. cool name
I wish I would have never gotten caught, and had the chance to grow out of it like many normal kids, but a tragedy happened and I did get caught. The only choice that made sense at that point was to try and make the best out of the grimey situation I was in. As I try to say on every podcast I’m on: “I’m not proud of the decisions I once made, or the person I once was, but I am super proud of how I responded when my life went sideways and I had to fight to turn it all around. We should all be proud of when we respond positively to a negative situation, no matter how we got into that situation.
Captivating story. Best thing I’ve read in a long time. The same book turned me around in 1996, “Awaken the Giant Within”, so I can relate. I was addicted to pain killers and alcohol at the time I read it. After reading that book, I became laser focused on life in all areas, including wealth building (and still haven’t stopped). I also agree with your statement about the two years to return to normalcy after a traumatic event. I lost my wife to breast cancer in 2013 at age 41. It took about two years for things to feel normal again. I am sharing this this article on my blog and my social media outlets. It’s a great read that I think many can relate to it in some way. I feel uplifted having read it – inspirational. Thanks for sharing your story.
Thanks for sharing your story. I admire your self-courage in selling those products and services and basically starting 10 years later. And congrats all your success thus far! Your mental strength will enable you to achieve your goals!
Congratulation Bill – you came a long way!
There is one excerpt that caught my attention:
“Most people overestimate what they can accomplish in a year–and underestimate what they can achieve in a decade.”
I would change this phrase to match with reality:
Most people UNDERESTIMATE what they can accomplish in a year
And OVERESTIMATE the comfort and safety of life in a decade for doing absolutely NOTHING different starting today!
This is why most people do not take any action.
THis is pretty dang true too!!!! You can accomplish A TON in a year if you start today, and you can also WASTE a ton of time in a decade if you wait for a time to start that sounds easier. Great point I definitely support and approve!
I was on a panel with Bill at FinCon this year. He is infectious with his positivity and energy. Amazing comeback.
I lost my 20s to online poker and other online addictions.
I was able to turn it around by replacing the addictive behaviors with constructive ones: CrossFit, skiing, caring for a dog, reading, podcast, and – like Bill – long distance running.
With a different mindset I was able to eventual the opportunity doors more intelligently and was able to build wealth and have a family.
But I easily could have gone another way. It’s good to realize no one is coming to save you and that you have to make change for yourself.
Thanks Drew!!! I wanted to link your story too, because like you said, when you find yourself in a hole, you have to learn how to save yourself. You’ve done a great job at showing how to do this yourself: https://themoneymix.com/overcome-a-gambling-addiction/
Fantastic! Really inspirational. It’s almost as though prison became, ironically, a huge opportunity for you; absent the normal expectations and obligations of young adulthood, you had the freedom to make choices about what kind of *person* you wanted to become, and do focused work on your attitude and approach to life. I suspect not many people forge such a path in prison.
Thank you so much for sharing your story. Wow!
Inspiring! Thanks very much for sharing.
Echo on the 2-yr part, eerily spot on.
You did it, Bill! Thanks for sharing this story. What a way to be recreated into someone new. I’m so glad you didn’t get destroyed by prison but made the choice to improve yourself.
Thanks for sharing your experience. A lot of people would not have come out of a decade of prison as well as you did and it was due to the choices you made and your ability to seize any opportunity that was given to you.
It is interesting what you mention about taking 2 years to adapt to anything. It was pretty much a little over 2 years when I finally picked myself up from my awful divorce and started living again (did not date for 2 years and essentially was wallowing at home on the coach during that time).
This warms my heart. Your life story reminds me of the sentence I wrote in the article, “So many people give up right when they’re on the verge of a breakthrough. You need to stick with it!” If you would have given up 1 year and 6 months into your challenging time, you would have been so close to your break through of feeling normal again. You got to stick with it. Even the worst times can pass, if you give yourself enough time to heal and get back up again. God bless and keep rocking on!