I’ve been to prison multiple times; with no regrets.

Here’s what I learned from those trips.

In my mid-twenties, I was looking to make a career change, so I quit my software marketing job, to join a telecommunications company. Brand new to the industry, the job involved a steep learning curve. Little did I know, it would also lead to multiple trips to jail.

My entire youth, I was taught the virtues of a decent, meaningful life, away from any activity that could lead to prison. But here I was in my mid-twenties, working for a company that paid me to go to jail. What luck!

This privately held, mid-sized company provided telephone services to city and state correctional facilities nationwide. Like all government contracts, the business to procure prison phone system contracts involved a lengthy bidding process.

The bidding process starts with a mandatory onsite pre-bid conference at the correctional facility. As the Lead Technical Writer, my job entailed attending pre-bid meetings, at the prison.

How did I land this coveted job?

Anyone could tell that a petite Asian-Indian like me was a misfit for this hostile job environment. The jail trips required long hours of driving to non-scenic locations in the remote outskirts of the city.

The pre-bid meetings were held in the correctional facility conference rooms followed by a detailed tour of the inside of the prison to inspect their inmate phone systems. Definitely not a glamorous job.

Every company bidding for this multi-million-dollar, 5 to 10-year contract, had to physically inspect the layout of the phones inside the prison facilities.

Prison pay-phones are generally located inside the inmate cell units. As part of the inspection, we had to pick up the instrument and listen to the voice prompts that inmates hear when they place a prepaid or collect call. Inmates could only make outbound calls and not receive incoming ones, for obvious reasons.

Back to the story of how I landed this ‘dream job’.

While working at the software company, I was completing a graduate certificate technical writing program at a local California State University. A friend I met there, ended up finding a job as a proposal manager at this telecommunication company. She remembered I was looking for a career change and offered the opportunity to work alongside her. Without much thought, I accepted.

While signing the offer letter I had no clue that the job involved day trips inside the correctional facilities to meet the facility officers, understand the phone system set up, and test the phones inside the prison cells!

Obviously, this wasn’t a brag-worthy job to share with my folks back in India. “You found a new job where?” Fortunately, they took it in their stride. The fact was that I had traveled halfway across the globe, to study in America, and then ended up working for a company that paid me to go to jail. An impressive career path.

My first trip to jail

As a newbie in the company, my first trip to a correctional facility was like being baptized by fire. The Lancaster Correctional Facility pre-bid meeting was coming up and my department manager (the friend) decided it was the perfect opportunity to send me there along with the Sales Lead.

A day before, the salesperson politely informed me of the strict dress code. Fully clothed, top to bottom, no skirts, or high heels that make a clickity sound. Basically, dress drab, with no skin showing and no high heels. Since we were expected to be inside the inmate cells, the Sheriff did not want us to call for any undue attention from the inmates.

Was I nervous? Heck, yes.

The drive to the facility was uneventful, my sales lead did not share much of what I should expect inside the jail. I tried to remain calm.

Upon arrival, we were greeted by two burly six-foot-something Sheriffs that were eager to show us around. Proudly walking us through every inch of the facility, like excited homeowners showing off their new abode.

Inside the inmate cell, my colleague asked me to pick up the phone and listen to the phone prompts. Do what? The germophobic in me was visibly repulsed. He took the cue, picked up the phone, and held it to my ear as I heard the different calling options. Then we visited a few more areas and mentally noted the phone locations and signages.

Besides the phone inspection, there was another incident that stood out. On the way out of the cell, an inmate yelled at us saying, “The phone call charges are too high, please do something about it.”

It was a genuine request. Yes, inmate phone services are pricey. A standard collect call from the jail can cost anywhere from $2.50 to $4.00 to connect and then $1 to $2 per minute depending on the contracted rate. Most inmate families end up paying a ransom to stay in touch with their loved ones inside the jail.

Another memorable trip to jail

After that first trip, the others became easier and less stressful. Some involved extensive tours inside the prison while others were just a conference room visit at the correctional facility.

It took me a few years to understand the nuances of the inmate phone service industry. I genuinely felt sorry for the exorbitant price inmates and their families paid, to stay connected.

Then came a new trip request. A sales lead from Sacramento requested that I join him for a pre-bid conference at the Imperial County Correctional Facility, near San Diego. I agreed. He was flying in while I was to drive down from Los Angeles.

When I mapped the trip (this was the pre-iPhone era, when we printed google maps) it showed a 3.5-hour drive covering, 202 miles. Easy-peasy, I love to drive. The conference was at 10 a.m. which meant I had to start at 6 a.m. to account for any traffic.

Halfway through the drive, along the deserted Imperial County highway, radio announcements mentioned an unexpected freak-storm heading towards Southern California with possible flash floods. Surely, within minutes, it was pouring heavily.

Thankfully, I reached the conference on time but when I stepped out of the car, my boots plunged straight into sludge. Covered in dirt, and drenched with the heavy downpour, I walked into the conference room looking like a wet cat. The salesperson was shocked, not so much with my soggy appearance but the fact that I drove through a freak-storm and still made it on time.

I had forever won his respect and admiration.

The trip back home was another wild experience. The journey that took 3.5 hours in the morning, became a 5.5-hour painful drive back through thunder and lightning in a raging storm. Not to forget the bumper-to-bumper traffic once I reached Los Angeles.

After a while, adventure trips to the prisons became second nature. We were always escorted by courteous Sheriffs and the inmates inside the facilities were mostly respectful and peaceful. Their life inside the fenced walls was not easy - they followed a strict work routine and a tight schedule. Sometimes we were offered a buffet lunch, proudly cooked up by the inmates. I would graciously excuse myself from these lunch invites.

As I moved up the corporate ladder, trips to prison became rare and were replaced with attending Tradeshows for correctional facility officers. When our company won any new jail contracts, our marketing department was tasked to create phone-use instructional videos for the inmates. Even after all these years, several correctional facilities may still be airing my voice-recorded prompts.

Finally, after 7 years of serving time at this company, I made another career change and decided to follow an entrepreneurial path. By now, I was also newly married, and my husband generously bailed me out of my prison life.