By Dave Smith, The Ultimate Retirement Coach
Let’s be honest: most of us spend a good part of our lives chasing what we’ve been taught to want—money, recognition, status, security. And for a while, it can feel like we’re on the right track. Promotions, pay raises, the house, the car, the resume that impresses strangers.
But then one day, something feels… off.
You start to realize that even though you’ve been checking all the boxes, you’re not as fulfilled as you expected. You’ve gained the world, maybe—but something’s missing.
That something is often what truly matters to you.
So today, I want to offer 5 powerful questions that can help you reconnect with what’s real—and redefine success on your terms.
- Am I living true to myself—or to others’ expectations?
It’s easy to live a life that looks good on paper but feels empty inside. You follow the rules, meet the expectations, achieve what you’re “supposed” to—and still feel a quiet disconnect.
Ask yourself: Are the choices I’m making a reflection of who I truly am, or who I think I’m supposed to be?
- What truly matters to me now?
For a long time, money and status might have driven you. And there’s nothing wrong with achievement—but it shouldn’t come at the cost of your peace, relationships, or purpose.
What do you value now? Is it time, health, creativity, freedom, connection?
Getting clear on this can change everything.
- How do I define success—for me?
If you’re constantly chasing a version of success that never feels satisfying, it’s time to ask whether it was ever yours to begin with.
Real success might mean being present with your kids. Or having the freedom to travel. Or finally starting that side project that lights you up.
Whatever it is—make sure you’re not just climbing someone else’s ladder.
- What am I avoiding—and why?
We avoid the things that scare us the most: change, vulnerability, honesty. But these are often the exact areas where growth lives.
Ask yourself: What truth have I been avoiding because it might require me to change?
You don’t have to fix everything overnight—but naming what you’ve been dodging is the first step toward real freedom.
- If I died tomorrow, what would I regret not doing?
This one stings—but it’s powerful.
Would you regret not spending more time with loved ones? Not creating something meaningful? Not living more boldly, more honestly, more you?
Don’t wait for a wake-up call. Start now. Align your life with what you value—not what impresses others.
Final Thoughts
There’s nothing wrong with wanting success. But make sure it’s your definition of success.
Don’t trade years of your life chasing money or status only to find yourself empty at the top. Get clear. Get honest. And make space for what really matters.
These five questions are a place to start. Journal about them. Reflect on them. Use them as a compass—not just for where you’re going, but for who you’re becoming. Use the “Perfect Day Worksheet” for reflection of what matters most.
To a life that feels as good as it looks,
Dave Smith