The One Question That Can Shape Your Next Decade
How to honor your past, clarify your values, and take the first step toward a future you’ll be proud of.
Every so often, someone asks a question that stops you in your tracks.
A friend reached out to me recently. I’m in my late thirties and he just turned twenty-five, so I wished him a happy belated birthday, and we started talking about life. He asked,
“Standing between my past and my future, what question will help me live the next chapter with clarity, purpose, and vitality?”
I told him I was honored to be included in this thought-provoking rittime, and I also needed some time to think about this. He wasn't looking for general information or advice; he wanted a question that would allow his own guidance. I took a few days to think and journal on this and I wont lie I allowed life to get in the way. But eventually, between my life’s fires that needed to be put out and making a living, I did have a well-thought-out yet simple one-question answer for Raheem. As I tried to narrow down my question, I found myself asking a few questions that I've been asking myself annually since my early twenties.
As I thought about it, I saw a few layers in what he was really asking. There’s an identity check-in; who have I been up to now, and which parts of that person still feel essential or ready to be let go? And there’s the vision for becoming; what qualities, values, or contributions are calling me forward into the next stage of life? The answer I gave him is
“What do I most want my 35-year-old self to thank me for starting now?”
It’s forward-looking, but it also pulls you back to the present, asking for clarity about what really matters. A few reflections you should explore when answering this question, and more questions that hopefully lead to better answers.
Clarify Your Core Drivers
You have to dig a little deeper if you want an answer that’s worth anything. Ask yourself,
“Which values light you up so much that you would defend them even if no one was watching?”
Then borrow from the Japanese idea of Kaizen and condense it into one question. Winston
“Where do curiosity, service, and creativity?”
Your values need to be rock solid, because the world will test them. It will try to pull you into debates with yourself, or tempt you to trade them for quick wins or self-serving comforts.
Examine Your Relationship With Risk
I have written about courage in the past. It has been well studied, and many more qualified writers have written about it than I have. Winston Churchill famously said, “Courage is rightly esteemed the first of human qualities because it is the quality which guarantees all others.”
So you have to ask yourself, “Which small acts of courage will stretch you without being overwhelming?” Committing small acts of courage helps you build your courage muscles. A form of exposure therapy, every time you flex this “muscle,” it gets stronger and faster.
“Courage is rightly esteemed the first of human qualities because it is the quality which guarantees all others.” - Winston Churchill
Invest in “Compounding” Areas
There are everyday actions that, when repeated, create a massive return on investment. A few that most people will understand and are well-known. Physical training, mobility training, a healthy diet, and mindset work may seem simple, but over time they compound in ways that go far beyond their original purpose. A morning workout does more than build strength; it trains discipline and sharpens focus for the entire day. Choosing whole foods and resisting the ultra-processed foods so many love doesn’t just support your body. It clears your mind, fuels long-term vitality, and offers another opportunity to train discipline. Mindfulness and inner work aren't only about positive thinking; it’s the daily ritual of resilience, clarity, and even a form of courage.
These practices look small in the moment, yet their ripple effects touch every area of your life. How you show up in relationships, how you pursue goals, and how you handle adversity. Keep stacking these small, intentional habits; they will pay you back for decades. A few more compounding areas in life are relationships that foster growth, and skills that make you both employable and alive with interests. Anecdotally, I am a naturally curious person. I chose sales because I am curious about my clients' lives, their needs, and what drives them. Coupled with my love of overcoming challenges and my masochistic mindsets, sales is a perfect avenue to be employable and have fun while doing it. The skills necessary to be an effective and ethical salesman are worth learning. Communication skills, emotional regulation, negotiations, and a love of constant learning and overcoming challenges are wide-reaching skills that spill into every aspect of my life.
Every so often, someone asks a question that stops you in your tracks.
Raheem asked, “Standing between my past and my future, what question will help me live the next chapter with clarity, purpose, and vitality?”
Integrate Past Lessons
You're almost at the end of this. Now, we have to reconcile our past.
What patterns or stories from your first 25 years deserve to be honored and kept?
Maybe it’s the resilience you built through challenge, the kindness someone once showed you that still shapes how you treat others, or the grit that helped you stay the course when things were hard.
Which ones need to be retired so you can travel lighter?
Perhaps there are habits born from survival that no longer serve the life you want to create. Maybe there are labels, regrets, or scripts about who you “must” be that weigh you down more than they guide you.
Reconciliation isn’t about erasing the past or pretending painful parts never happened. It’s about deciding, with intention, which elements of your story belong in the next chapter and which deserve gratitude for what they taught you before you set them down.
When you do this work, you give your future self a clean foundation: a place where lessons become fuel, not anchors.
My Closing Thoughts
If you are standing on the edge of a new chapter, pause long enough to ask yourself,
“What do I want my future self to thank me for starting today?”
Let the question steep, give it room to stir your imagination and tug at the darkened corners inside you. Your answer doesn’t need to be grand or fully formed. Sometimes a single habit you've been meaning to build, a conversation youve avoided, a boundary you need to honor, or a creative spark waiting to be nurtured. The key is to start, however small the first move may seem. Even the tiniest deliberate step plants a speed whose roots will grow deeper than you can see now. I tend to do this annually at the closing of the year. Over the months and years, that one choice can echo through every part of your life, shaping who you will become and how you experience the world.