Breaking Free From Your Internal Prison Guard
Why that voice telling you to play it safe might be your biggest enemy
That voice in your head has a lot to answer for.
You know the one. It's that internal warden that patrols the boundaries of your comfort zone, ever-vigilant for any signs of risky ambition. It masquerades as wisdom, whispering about being "realistic" and "sensible." But more often than not, it's fear wearing a prison guard's uniform.
When Protection Becomes Prison
I learned about my internal prison guard early. Looking at my high school report card, you'd see a string of A's marching proudly across the page... until you hit the lonely D in Craft Design and Technology. This wasn't because the subject was impossibly complex. It was because I couldn't rely on my usual strengths of memory and logic. Instead of memorization and pattern recognition, we had to create something useful from scratch.
And rather than risk trying my best and still falling short, I chose not to try. I distracted myself and others, protecting my ego while sacrificing any chance of growth. That certificate still sits in my office folder today – a constant reminder of how early we learn to avoid situations where we might try our best and still fall short.
Your prison guard might show up differently than mine did. Maybe it's the novel you've been "meaning to write." Perhaps it's the career change you've been dreaming about but never "found the right time" for. Or it could be that business idea you've convinced yourself is "unrealistic."
The fascinating thing about these self-imposed limitations is that they operate on a spectrum. Sometimes, they genuinely keep us alive (like preventing us from trying to leap across crocodile-filled ravines). But far more often, they needlessly hold us back from achievable growth opportunities that could transform our lives.
The Adult Ego Maze
As adults, this pattern becomes deliciously complex. We're not just fighting against time constraints or diminishing brain plasticity – we're battling decades of carefully constructed self-image. Every time we step into something new, we're also dragging along every previous version of ourselves, complete with their expectations, fears, and carefully crafted defense mechanisms.
I've been facing this head-on recently in my journey toward competitive chess. At 500 ELO, I regularly face the humbling experience of being outplayed by eight-year-olds. My goal of reaching tournament level (1100 ELO) feels both ambitious and achievable, but only if I'm willing to check my ego at the door every single day. Each loss is a choice between protecting my self-image and improving.
The fascinating thing about the adult ego is how sophisticated it becomes in its self-protection. We don't just avoid challenges – we intellectualize our avoidance. We transform our fears into seemingly rational arguments. "I need to wait until the kids are older." "The market isn't right." "I should focus on my existing career." "Better to be realistic than chase pipe dreams."
These aren't just excuses – they're elaborate defense systems built by our internal prison guard over years of carefully avoiding discomfort. They sound wise. Responsible. Mature, even. And that's what makes them so dangerous.
Think about the last time you wanted to try something new. Maybe you caught yourself watching someone do something amazing on YouTube and thought, "I wish I could do that." What happened next? Did you immediately start listing all the reasons why you couldn't? Did you remind yourself of your age, responsibilities, and limitations? That's your prison guard at work, using decades of experience to keep you safely in your lane.
This is where most of us get stuck in our own pursuits. We're more afraid of trying our best and failing than not trying at all. It's a peculiarly adult form of self-sabotage – we've gotten so good at protecting ourselves that we've forgotten how to grow. We've mastered the art of staying comfortable while convincing ourselves we're being wise.
And here's the real kicker: the more successful you've been, the harder this becomes. Success builds layers of identity that feel too precious to risk. "I'm the person who's good at X" becomes a cage that keeps you from trying Y. We end up trapped not by our failures but by our previous successes.
Finding Freedom in Community
Here's where things get interesting: I've discovered that the key to breaking free often lies outside ourselves. When I joined a competitive 8-ball pool league last year, I was one of the worst players by far. But instead of letting my ego keep me safely on the sidelines, I embraced being the beginner. Each defeat became a question: "What are the other players doing that I'm not?"
The same pattern emerged when I stepped into entrepreneurship. Walking into rooms full of established CEOs and business owners while openly acknowledging my newness felt terrifying. But that vulnerability invited others to share their wisdom and support.
I recently watched a fascinating demonstration of the community's power on Beast Games that left me questioning everything I thought I knew about human nature. Picture this: 500 contestants divided into four teams, each led by someone they'd only known for a few days. These leaders were brought to a platform with buttons in front of them, and here came the twist - a monetary prize that would keep climbing as long as no one pressed their button. The catch? Press the button, and you'll win the money, but your entire team will be eliminated.
We'd already seen in this game that people would take between $20,000 and $100,000 to bow out when they were playing as individuals. So you'd expect someone to crack, right? The prize kept climbing - $100,000... $200,000... $500,000. The tension was palpable. You could see the leaders wrestling with temptation while their teams watched from below, calling out their names and reminding them of their shared journey.
Then came the moment of truth - the prize hit one million dollars. Mr. Beast, the host, let it sit there, tempting them. He even gave them ten seconds after the timer ran out, goading them to take the life-changing money. Yet not one of those leaders pressed their button. None of them betrayed the trust of people they'd only known for 2 days. Incredible television.
This wasn't just about moral fortitude or the power of peer pressure. It was a stunning demonstration of how quickly we can transcend our limitations when connected to something larger than our ego protection. These strangers had formed bonds strong enough to resist life-changing money in just a few days.
Breaking Out Together
The truth I've learned through all this? Growth isn't about avoiding failure – it's about being willing to fail better, surrounded by people who understand the journey. Your internal prison guard thrives in isolation, but its power fades in good company.
Think about that dream you've been putting off. The one your prison guard has convinced you is "unrealistic" or "not sensible." What if believing you must figure it out alone is the only genuinely unrealistic thing?
The path forward isn't about grand gestures or perfectly planned escapes. It's about small acts of defiance against your internal limitations. It's about finding others on similar journeys who can help you see your prison guard's tactics for what they are. Most importantly, it's about permitting yourself to be temporarily bad at something new in service of becoming who you might be.
Your prison guard's biggest lie isn't that you can't do something; you have to do it alone.
Tell us what you thought of today's email.
* Good?
* Ok?
* Bad?
Hit reply and let us know why.
This is so true. I love failures. They have been my major source of growth since I started 3 years ago.