Waking Up in a World You No Longer Recognize
In Washington Irving’s classic 1819 tale, Dutch colonist Rip Van Winkle, too lazy to care for his own property, wanders into the mountains to escape his fussy wife, drinks a mysterious liquor, and falls asleep for twenty years. When he finally wakes up, his world has completely changed. The American Revolution has passed, his wife and friends have died, and he is suddenly an old man who is now a citizen of a brand-new nation instead of a subject of King George III.
It’s a famous piece of folklore. But for hundreds of thousands of individuals reentering society after long prison sentences, the story of Rip Van Winkle isn’t fiction—it’s their daily reality.
The Paralysis of Institutionalization
Attempting to rebuild a life after years, or sometimes decades behind bars is an immense psychological hurdle. In a prison setting, personal autonomy virtually disappears. Every decision is controlled by someone else:
- When you wake up and when the lights turn off
- What and when you eat
- Where you walk
- When you take your medication
- When to stand for count
At the same time, long-term incarceration starves social connections. Visits from family are often infrequent, strictly monitored, and lacking real privacy. Individuals are isolated not only from loved ones, but from the natural progress of human culture.
Then comes release day. The sudden shift from total control to total autonomy is overwhelming on its own, but it is compounded by a world that moved on without them.
The Ultimate Barrier: The Tech Time Capsule
Imagine going to sleep in an era dominated by payphones, landlines, and physical paperwork, only to wake up to a world driven by touchscreens, app-based public transit, QR-code menus, and two-factor authentication.
Because correctional facilities heavily restrict access to modern technology due to security protocols, incarcerated people are effectively kept in a technological time capsule. When they step out, simple tasks like buying a bus ticket, ordering fast food on a kiosk, or applying for SNAP benefits or a job can feel like trying to understand a foreign language.
Bridging the Gap Through Mentorship
When we expect formerly incarcerated individuals to successfully reintegrate without teaching them how to navigate today’s changing world, we set them up to fail.
Reentry cannot just be about handing someone a bus ticket and a set of prison clothes. It must include counseling, mentorship, and accessible support systems. If we want people to successfully rebuild their lives, we have to give them the tools to live in the present, not the world they left behind.
This is why mentoring is so critical to navigating society upon release.
How You Can Step Up with TPOM
TPOM was recently awarded three mentoring grants across three state prisons. We are actively seeking volunteers to mentor men and women nearing release so they can prepare for life outside the gate. Additionally, our reentry program—which provides housing for both men and women—has residents who need guidance right now.
Here is how you can help:
- Give Your Time: Stand alongside someone facing the overwhelming task of starting over.
- Provide Practical Support: Help a mentee navigate simple, modern tasks that have changed radically since they were last free.
- Get Trained: TPOM provides regularly scheduled training and handles the entire mentor-mentee matching process to ensure you are fully equipped.
These men and women reentering society need our time, our patience, and our encouragement. Let’s step up to the challenge and allow God to use us to bless the life of someone else.
Ready to make a difference in someone’s fresh start? Reach out to TPOM today to sign up for our next mentor training session at https://www.tpom.org/events/ and your life will be as blessed as the life of your mentee.




