Learning to Let Go of Playing it Safe: Why I Regret Not Listening to My Sons About Bitcoin

For years, I’ve been the voice of reason in my household. As a single mom, I always prioritized stability and security, especially when my two boys, Oliver and Robert, were younger and relied on me. Keeping the lights on, ensuring food was on the table, and making sure there was enough saved for rainy days were my top priorities. But now, at 48, I’ve found myself at a crossroads, grappling with a growing regret that I didn’t take more risks—particularly when it came to investing in digital currency, like Bitcoin.

 

 

The Missed Opportunity

 

It’s no secret that Bitcoin and other digital currencies have been on an upward trajectory. In recent weeks, the headlines are ablaze with stories of record highs. There’s a sense of “I told you so” in the air, and I can’t help but think back to the times my sons tried to nudge me in that direction.

 

Oliver and Robert have always been curious, adventurous, and technologically savvy. They understood Bitcoin before I even grasped what it was, and over the years, they urged me to consider investing. I remember them telling me stories about people who were seeing incredible returns, explaining how the technology behind Bitcoin was more than just a passing trend. They were excited, adamant, and convinced that I was missing out on a golden opportunity. But each time, I hesitated.

 

Why I Played it Safe

 

Looking back, I can trace my reluctance to the years I spent as the sole provider. Being a single parent means you don’t just think about the next month—you think about the next five, ten, twenty years. Every decision feels like it carries twice the weight because, if something goes wrong, there’s no safety net.

 

I’ve always been cautious with money, keeping it in safe investments that might not provide massive returns, but I could sleep at night knowing that it was secure. Digital currency felt volatile, unpredictable, and frankly, risky. At the time, the thought of investing in something as nebulous as Bitcoin seemed reckless when I had two boys to support. I thought I was doing the right thing by playing it safe, and perhaps I was—then.

 

But times have changed, and so have my circumstances. My boys are grown, financially independent, and living their own lives. They no longer need me to be that constant safety net. And in the stillness of my own life, I’ve come to realize that maybe it’s time I stop playing it safe—for my own sake.

 

Seeing the Rise from the Sidelines

 

The hardest part about regret is watching the very thing you were warned about come to fruition. Over the past few weeks, I’ve seen the rise in digital currencies—Bitcoin, Ethereum, and countless others—all reaching all-time highs. Friends, colleagues, and acquaintances are talking about their profits, and social media is buzzing with stories of life-changing investments. It’s hard not to feel a knot of regret settle in my stomach when I realize that, had I listened to my sons, I might be in a very different financial position today.

 

More than the missed opportunity for financial gain, what really stings is the realization that I wasn’t as open to risk and change as I thought I was. I let fear drive my decision-making, and as a result, I missed out on more than just potential profit—I missed out on a chance to grow and challenge myself.

 

A Sign to Take More Risks

 

This regret isn’t just about money; it’s about a mindset. I’m taking this as a sign that it’s time to let go of old habits and embrace a new approach to life—one that allows for more uncertainty, adventure, and, yes, risk. My children are no longer dependent on me, my house is quieter, and I have fewer obligations tethering me to “what’s safe.”

 

When you’re in your forties, it’s easy to think that you should have it all figured out. But what I’m learning is that this time of life can be about rediscovery, about giving myself permission to step outside of my comfort zone. And I realize now that taking more risks isn’t about being reckless; it’s about making choices that align with who I am now, not who I was when my boys were little.

 

Learning from My Sons

 

As parents, we often think we have to be the teachers—the ones with the wisdom and answers. But my sons have taught me that wisdom doesn’t only come from experience; it also comes from staying open to the world and being willing to embrace new ideas. In their early twenties, Oliver and Robert have been willing to take risks that I couldn’t fathom. They didn’t have the burden of decades of financial responsibility weighing them down, and they saw opportunity where I saw danger.

 

Now, I’m learning to view the world through their eyes, to understand that not every risk is a threat. Some risks are opportunities to learn, to grow, and to challenge the status quo. And some mistakes are worth making because they lead to growth. My sons’ enthusiasm for the digital world didn’t come from recklessness; it came from seeing the potential in technology and the future.

 

Rewriting the Narrative

 

I can’t go back in time and change my decisions, and honestly, I wouldn’t want to. Those choices were right for who I was and the circumstances I was in at the time. But I can choose how I move forward. I can rewrite my narrative from one of playing it safe to one of curiosity and courage.

 

So, what’s next? I’m not planning to throw all my savings into Bitcoin, but I am planning to start small, to educate myself, and to make informed decisions that align with the new phase of my life. It’s not about the thrill of quick money; it’s about giving myself the chance to explore, to learn, and to feel more fulfilled as I grow older.

 

Letting Go of the Fear of the Unknown

 

I used to think that security meant knowing exactly what my future would look like—retirement plans, steady savings, and the comfort of predictability. But life doesn’t come with guarantees, and the more I try to control every outcome, the more I realize that true fulfillment comes from letting go of the need to be in control.

 

Investing, whether it’s in Bitcoin, a new hobby, or an unexpected life choice, is about having the courage to embrace the unknown. There will always be risks, but I’m learning that some risks are worth taking, not for the potential financial gain, but for the joy of knowing that I tried.

 

Finding Fulfillment Beyond Money

 

At the end of the day, what I want isn’t more money—though that would be nice—it’s a sense of fulfillment. I want to be able to look back on my life and know that I wasn’t afraid to try new things, that I allowed myself to grow, even when it felt uncomfortable.

 

Maybe Bitcoin will continue to climb, or maybe it won’t. But that’s not really the point. The real lesson I’m taking from all of this is that I don’t want to be the person who looks back with regret, wondering what might have been if I had taken a chance. I want to be the person who lived fully, who was willing to make mistakes and learn from them, and who embraced the adventure of life, even when it felt risky.

 

In Solidarity and Strength

 

So, here I am, feeling a little wiser and a little more open to taking risks. The regret I feel over not listening to my sons is real, but it’s not the end of the story. It’s just the beginning of a new chapter—one where I’m willing to embrace change and step out of my comfort zone.

 

I’m not going to be defined by what I didn’t do, but by what I choose to do next. And as I continue this journey of self-discovery and personal growth, I hope my story inspires others—especially women my age—to take their own steps toward a more fulfilling and adventurous life.

 

In solidarity and strength,

Evelyn

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