Keith Orlean is currently serving time at the Satellite Camp at FCI Otisville in Upstate New York. He is a member of our White Collar Support Group that meets online on Zoom on Monday evenings. We will celebrate our 250th weekly meeting on Monday, March 29, 2021, 7 pm ET, 4 pm PT; all Fellow Travelers are invited.


On May 3rd 2018 at 6:00am the first steps in the reinvention of myself began with a visit from 7 FBI agents who placed me under arrest, charging me with conspiracy to commit securities, mail and wire fraud.  This is certainly not the way I had planned my life but sometimes plans get upended by unexpected events.  Over the next 32 months I went through the kind of life changing experience that can only occur when the stakes are so high and your choices are limited.  This was the wake up call I needed to finally look at the kind of person I had become.

Over the last 30+ years I have spent most of my days with a singular focus of making a significant income that would afford me a certain lifestyle and “things” that would show my peers that I had “made it”.  These things included, a big house, luxury cars, expensive dinners, jewelry and vacations all for the purpose of soothing my own ego.

More often than I would like to admit I had failed at earning the big money I had hoped for and would take tremendous financial risks to maintain the vision that I wanted to project. Outward appearances became an obsession and taking risks to protect the facade was an addiction. For some reason having a great wife and kids, a beautiful home and a stable business just wasn’t enough. I needed more.  This false sense of self drove me to make decisions that were risky and would finally land me in a federal prison camp which is where I reside at this time. My journey through the criminal justice system has been long and painful but it also provided me with the greatest opportunity to change the direction of my life.

Navigating the Criminal Justice Process

I’ve never been very good at accepting advice but after my arrest my plate was so full trying to keep from falling apart it became clear that I needed help. My emotional survival depended on taking one day at a time, avoid obsessing over past mistakes, and not thinking too far into the future. Within a month of getting arrested I started seeing a therapist to deal with my anxiety and to explore events in my life that had driven behaviors that led to my arrest. I knew that I had taken chances my whole adult life and had become quite adept at finding my way out of trouble. Unfortunately I had finally met my match. No matter what you feel about your guilt or innocense the chances of beating the government are slim. Prosecutors have unlimited resources at their disposal which leads to an unfathomable 97% success rate. Had my first attorneys advised me of my chances of winning at trial I would have tried to negotiate a more favorable plea early in my case. Of course hind sight is 20/20 and it did not help me to move forward in my life if I didn’t let go. My purpose of even mentioning is to help others who are struggling and need advice from those who have already been through the system.

The Long Road Back

As I had mentioned earlier, from the day of my arrest till reporting to prison took 32 months which is interesting because that was the length of my sentence.  When I think about the earliest days of this journey all I could see was darkness, loneliness, shame and fear. The emotional ups and downs made each day difficult to get through. At my weekly therapy sessions I began to explore the life events that paved a path that was extremely difficult to navigate. I had lost my dad when I was 15 and my mom for her own reasons was not around much to help me through this life changing moment.  There are other events as well that contributed to my problems but the details of these are not important.  What is important is that I finally was willing to see patterns of behavior that were destined to end badly.  During my many years in business I had borrowed significant sums of money without regard to whether I could pay the money back.  On top of that my arrest was due to financial issues which only added to what should have been obvious which is I have a problem with managing money. My therapist recommended that I join a 12 step program called Debtors Anonymous to deal with financial risk taking issues that I had encountered my whole adult life. This became an additional vehicle to gain awareness for my problems and have a group of people and a proven program that helped me make the changes that were necessary.

White Collar Support Group

In spite of all the self exploration and support I was getting I still felt alone and scared as year one of my journey was coming to a close.  I still hadn’t decided if I was going to trial or whether to negotiate a plea.  My lawyers seemed more interested in bleeding me dry and I felt conflicted about what to do.  I was making progress in therapy and with my 12 step program but there wasn’t anyone who I could speak with that was going through a similar situation or had already been through the process. I needed to see if there was a support group that focused on white collar crime.  A simple Google Search led me to Jeff Grant and his Prisonist organization that focused specifically on helping white collar offenders like myself navigate the criminal justice system and gain support from others.  This was a key turning point in getting through the final stages of my case and gaining valuable insight about what to expect as each step unfolded.  Jeff invited me to my first meeting a few days after we spoke and I immediately felt through my own sharing and the sharing of other members that I was no longer alone and could gain strength from hearing what others went through.  My fears lessened and I now had a place to go and people to speak with that could help whenever I had questions.  With each week of attendance at the meetings I became more comfortable and felt part of a community of people that freely share their thoughts, feelings, fears and triumphs.  I attended meetings every week for almost two years with my last meeting being three days before I reported.  I went to prison with the confidence that I would be fine and that this chapter in my life would eventually end with so much promise for the future.  When I come home I intend on getting right back into my weekly attendance with the hope that I can do for others what Jeff Grant and his organization did for me.

The Future

My experience over the last 32 months has taught me so much about myself and has allowed me to regain hope.  I still have to finish my sentence which due to the First Step Act has been reduced by 1/3rd.  I do have a number of personal issues that need to be addressed when I arrive home but I feel that regardless of how things turn out I will be well prepared to tackle the future.