THE PAST: A TEACHER, NOT A JAILER
Let’s be honest, letting go of the past isn’t that easy. I say this because it’s something I personally wrestle with. There are times I find myself replaying old mistakes, missed opportunities, and moments I wish I could change. It’s frustrating because deep down, I know that holding onto the past only keeps me stuck. And yet, I do it anyway. Maybe you do too.
We often hear the adage, “Those who cannot learn from history are doomed to repeat it.” While this holds some truth, it’s also important to recognize that fixating on the past, whether its victories or failures, can hinder our ability to dream boldly and build the future we desire. We tend to cling to past experiences, successes, and failures, allowing them to dictate our present and limit our aspirations.
There’s something oddly comforting about the past, even when it wasn’t great. At least it’s familiar. The future, however, is uncertain. What if I fail again? What if things don’t work out? What if I dream bigger than my current success and fail, losing even what little I’ve worked so hard for? Isn’t it safer to just stay where I am and protect what I already have? These fears are valid. In fact, it’s often because of these fears that we retreat to the past, mistaking its familiarity for safety. When we’ve experienced successes or failure, it’s tempting to stay where things feel predictable, even if it means staying stuck. But what if we allowed the past to teach us instead of trapping us? What if we viewed it not as our jailer, but as our guide, equipping us with lessons for the journey ahead, rather than chaining us to what’s already behind?
You are not alone!
It’s important to realize that struggling to move beyond our past is a common experience. As Dr. Daniel Kahneman explains in his book, Thinking, Fast and Slow (2011), people often fall into cognitive traps involving regret and loss aversion, where the pain of past failures disproportionately influences current decisions. This psychological tendency can cause hesitation in pursuing new opportunities. Similarly, psychologists Neal Roese and Kathleen Vohs explore the powerful role of regret in human behavior in their article Hindsight Bias (2005), highlighting how regret over past actions frequently impacts present-day choices and can hold people back from risk-taking. Brené Brown’s book The Gifts of Imperfection (2010) addresses how fear of failure and shame about the past can prevent people from living wholeheartedly, emphasizing the importance of embracing vulnerability to move forward.
These insights show how universal this experience is. Many people, at some point, find themselves stuck in the loop of regret and fear. Perhaps you recognize yourself in one of these situations:
- A student who allowed fear to prevent them from applying for a scholarship or to their dream school, perhaps due to self-doubt or previous rejection.
- A professional who has given up on career advancement after a series of unsuccessful job applications.
- A young entrepreneur who has experienced multiple business failures may vow to never venture into entrepreneurship again.
- A married person entangled in past relationship mistakes, unable to fully embrace their current partnership.
- A single person who has closed off emotionally after heartbreak, convinced that love isn’t worth the risk.
These examples illustrate how diverse our experiences are, yet how universal the feeling is of being stuck by the past. But what if we flipped the script? What if instead of letting the past define us, we allowed it to equip us?
Trading Fear for Future Peace
Not long ago, I listened to an episode of The Mel Robbins Podcast titled “3 Questions That Determine Who You Really Are.” In it, Mel shared how Jeff Bezos asked himself a life-defining question before starting Amazon: “When I’m 80, will I regret not taking this risk?” That question struck a chord. It made me pause and reflect: What decisions am I postponing out of fear? What dreams am I shrinking because the risk feels too big or the outcome too uncertain?
Then in June 2025, I read “Lean In” by Sheryl Sandberg, where she asks, “What would you do if you weren’t afraid?” Again, I felt confronted. Two powerful voices, asking two life-altering questions, I definitely didn’t have answers for.
What would you do if fear wasn’t in the way? What risk would you take now so you don’t carry regret later?
The truth is, I haven’t fully stepped into the answers. I’m not there yet. I haven’t figured it all out. I haven’t suddenly become fearless. I’m still reflecting, still battling the urge to stay where it feels safe. I’m still navigating doubts and the tendency to play it safe. The future can be scary! I won’t pretend otherwise. There will be moments when the past tries to pull us back, whispering that it’s safer to stay where we are. But in those moments, I hope we quickly remember that, the past is not our jailer, it is supposed to be our teacher! We should use it as fuel to dream bigger, to take chances, and to live fully.
One thing is clear: I no longer want fear or even past success, to limit the future I can create. Maybe you’re just like me, still a little scared, still unsure, but ready to try. If so, let’s do this together. Let’s dream again. Let’s take risks (well they say calculated risks. Whatever that is, let’s figure it out). Let’s ask ourselves the hard but freeing questions. Let’s step into the future with courage. Let’s make choices that our future selves (hopefully at 80) will thank us for. And let’s dream – so big, bold and fearless such that we leave no room for regrets.
The central theme for this article was written based on the words of Thomas Jefferson: I Like the Dreams of The Future Better Than the History of the Past.
By Portia Anani
