Welcome to Rethink 40. Here, we explore the reflections, challenges, and opportunities that come with turning 40 (and beyond)—navigating careers, family, and life’s changing priorities. Whether you're looking for clarity, growth, or just a little inspiration, you’re in the right place. 

 

About Me

 

Hi, I’m a married father of 2, and like many of you, I find myself at a crossroads. As I approach 40, I’m navigating one of the most challenging yet pivotal stages of my life. For the past few years, I've been living with my wife, two boys, and mother-in-law, after pressing pause on our dreams of owning a home. The housing market just didn’t and stil doesn't make sense, and instead of forcing the issue, we chose to wait—though the decision hasn’t been easy and we are tested daily with news of new homes hitting the market.

 

At the same time, I’ve found myself questioning my career path and myself as a man. As someone who’s spent years working in sales-centric jobs, I often wonder if this is what I want to spend the rest of my life doing. The pressure to get it right—to make sure the next step is the right one—is something I wrestle with every day. Will I feel immense regret on my deathbed, wishing I had spent my days doing something I enjoyed? The fear of making the wrong decision, combined with the self-doubt that comes with turning 40 and feeling like I have accomplished nothing, has been a constant companion. And yet, here I am, rethinking, reflecting, and searching for clarity.

 

Rethink 40 is my space to process these struggles, but it’s more than that. I knwo that there has to be others out there that feel this way. It’s my hope that this blog becomes a community where we can support one another as we face the complexities of midlife. Here, we’ll explore the big questions—about career, purpose, family, and everything in between. My goal isn’t just to share my story, but to help you find inspiration, clarity, and maybe even some answers along the way.

 

So whether you're feeling lost, uncertain, or just curious about what this next chapter holds, you’re not alone. Together, we can rethink, reflect, and redefine what life at 40—and beyond—can be.

 

Let’s figure this out, one step at a time.

 

Living Out of Alignment: How Chasing Money Over Meaning Led Me to Regret and Resentment

 

For much of my life, I thought I was doing everything right—climbing the career ladder, chasing higher paychecks, and focusing on financial stability. I believed that achieving these goals was the path to success and happiness. But somewhere along the way, I realized I was living out of alignment with my true self, prioritizing money over meaning. Instead of feeling fulfilled, I found myself grappling with deep regret and growing resentment. In this post, I want to share my journey of how chasing financial success at the cost of my own values led me to rethink everything.

 

How the Pursuit of Money Can Create Internal Misalignment

For years, I convinced myself that accumulating wealth and reaching financial milestones would ultimately bring me satisfaction. I pursued job opportunities that promised better pay and bigger bonuses, even when they didn't align with what I truly wanted in life. I thought that once I reached a certain level of financial success, everything else would fall into place. But it didn’t.

 

The more I focused on making money, the more I lost sight of what really mattered to me—creativity, family, and the freedom to live authentically. My decisions became dictated by external factors: how much I was earning, what kind of house I could afford, and whether I was keeping up with others’ expectations of success. But in doing so, I disconnected from my own values, and the result was a profound sense of emptiness.

 

Chasing money can create a false sense of alignment. You may look successful on the outside, but inside, you feel discontent and adrift. The truth is, living out of alignment with your true self can have lasting effects on your mental and emotional well-being. When every choice is based on financial gain rather than personal fulfillment, it’s easy to lose sight of who you really are and what you truly want.

 

The Regret of Prioritizing Money Over Meaning

The regret didn’t hit all at once—it built slowly over time. Every promotion I took that didn’t resonate with my core values, every opportunity I accepted solely for the money, compounded into a sense of resentment. I started to feel trapped, as if I were living someone else’s life, chasing goals that weren’t mine to begin with.

 

I began to resent the jobs that demanded more time and energy than I wanted to give, the hours that kept me away from my family, and the lack of fulfillment in my day-to-day work. More than anything, I resented myself for falling into this trap, for convincing myself that I was doing the “right” thing by focusing on material success. It wasn’t until I hit a breaking point that I realized I needed to step back and reevaluate everything.

 

How to Know When You’re Living Out of Alignment

So, how can you tell if you’re living out of alignment? It often manifests as a feeling of disconnection and dissatisfaction. You might find yourself constantly questioning your choices or feeling as though something is missing. Here are a few signs to look for:

Persistent Discontent: Despite outward success, you feel a persistent sense of unhappiness or emptiness.

 

Conflicting Priorities: You often make decisions based on what others expect or what looks good on paper, rather than what resonates with you personally.

 

Loss of Passion: You no longer feel excited or passionate about your work or daily activities.

 

Emotional Exhaustion: You feel drained, burned out, or resentful, even when you’re achieving your financial or career goals.

If you’re experiencing any of these symptoms, it might be a sign that you’re out of alignment with your true self. The good news is, recognizing this is the first step towards change.

 

The Turning Point: Choosing Meaning Over Money

Once I realized that chasing money wasn’t bringing me happiness, I knew I had to make a change. I had to redefine my idea of success—not in terms of income or material wealth, but in terms of what genuinely brought me joy and fulfillment. This shift required me to reconnect with my core values and decide what I wanted my life to look like, beyond the numbers in my bank account.

 

I started by asking myself some hard questions:

  • What do I really want from life?
  • What makes me feel fulfilled and happy?
  • What am I willing to sacrifice to align with my values?

 

The answers to these questions helped me create a new vision of success, one that prioritized meaning over money. It wasn’t an easy transition—letting go of deeply ingrained beliefs about financial stability and worth took time. But as I began making choices that were in alignment with my true self, I felt a weight lifting. The resentment I felt towards my career started to fade, replaced by a sense of possibility and hope.

 

The Benefits of Living in Alignment with Your Values

Living in alignment with your true self has profound benefits. You’re no longer at war with your own decisions, and you start to feel more content and at peace. When you prioritize your values, you create a life that feels authentic and meaningful. You no longer have to compromise your happiness for external success because you’re building a life that reflects who you truly are.

 

Some of the benefits of living in alignment include:

 

Increased Fulfillment: You feel more satisfied and fulfilled because your actions are in harmony with your values.

 

Reduced Resentment: You no longer harbor resentment towards others or yourself because you’re not sacrificing your well-being for external validation.

 

Greater Clarity: You have a clearer sense of purpose and direction, making it easier to make decisions that support your long-term happiness.

 

Final Thoughts: Redefining Success for a Happier, More Meaningful Life

The journey to aligning your life with your true self is not without its challenges, but it’s worth every step. Chasing money and material success might bring temporary satisfaction, but it can’t fill the void left by living out of alignment with your core values. The real reward comes from living authentically—choosing paths that resonate deeply with who you are and what you truly want.

 

If you’re struggling with regret or resentment because you’ve been chasing the wrong kind of success, know that it’s never too late to start over. Take the time to get honest with yourself, define your own version of success, and have the courage to build a life that aligns with it. Because at the end of the day, the only person who can decide what success means to you—is you.

Ready to take the first step toward alignment? Start by identifying your core values and redefine your path to success today.