Surprising Questions That Help You Find Your Why

Did you know that about 80% of people have a tough time figuring out their purpose? Yep, you read that right—most of us are just winging it, hoping we’ll stumble upon that big “aha!” moment. If you’re feeling stuck or a little lost, that’s perfectly okay. In fact, it’s a sign that you’re human (and maybe a little adventurous).

But here’s the exciting part: finding your “why” isn’t about having it all figured out—it’s about getting curious and starting somewhere. It’s about asking yourself bold, sometimes uncomfortable questions that reveal what really makes your heart beat faster, what values truly guide you, and what you’re ready to roll up your sleeves for, even when it’s messy.

In this article, we’re diving into seven unexpected questions that might just help you connect with your deeper purpose. And yes, some of these questions might feel awkward or downright weird (hello, “favorite shit sandwich”). But that’s part of the process! By the end, you’ll have a clearer picture of what drives you, what lights you up, and how to pursue a life that feels authentic and aligned.

Embrace Your Favorite “Grind”

Let’s get real for a moment: every passion comes with its own grind. No matter what dream you’re chasing, there will be setbacks, sacrifices, and plenty of not-so-glamorous moments. The real question is: which grind are you willing to embrace?

Whether you want to launch a business, become an artist, or master a new skill, there will be days when you’re knee-deep in challenges and wondering, Why am I even doing this? But that’s exactly the point: which struggle makes you say, “Yep, this is worth it”?

This question is powerful because it helps reveal where your true passions lie—not in the fun, shiny parts, but in the battles you’re willing to fight and the resilience you’re ready to show. It’s not just about finding something you love; it’s about committing to the process, even when it’s tough.

Research shows that making consistent, purpose-driven decisions over time can lead to major achievements in your career. Take, for example, the author’s brother, who rose from big dreams to becoming a political party leader, judge, and even a state congressional candidate—all before 40. It didn’t happen overnight; it happened because he found a grind he was willing to stick with.

Many of us are still figuring this out well into our 40s or 50s, and that’s okay. It’s never too late to dive in, get a little messy, and start living with intention. The only question is: which grind are you willing to tackle?

What Did You Love as a Child?

Think back to when you were a kid. Remember those days when you could lose yourself in an activity for hours, purely for the joy of it? Whether it was drawing, playing make-believe, building things, or even daydreaming, those childhood passions were unfiltered and real. There was no need for applause, awards, or gold stars—just the thrill of doing what you loved.

But then, adulthood shows up with its responsibilities, routines, and the pressure to be “practical.” And somewhere along the way, we start to lose touch with those early loves.

Here’s the good news: rediscovering your purpose might just be about reconnecting with the things that once brought you joy. What were the hobbies that sparked your curiosity? Maybe you were the kid who devoured books, got lost in make-believe worlds, or loved to tinker with anything that had moving parts. Whatever it was, these childhood interests often hold clues to what truly lights you up.

By tapping back into these old passions, you can reignite that sense of play and rediscover what feels real for you. And when you do, you might just find a path toward more fulfilling personal and professional growth.

So, give yourself permission to revisit those early loves. It’s more than just a walk down memory lane—it’s a step toward finding your why and living a life that feels authentic and true to you.

What Activities Keep You Up All Night?

Have you ever been so wrapped up in something that you completely lose track of time? Maybe it’s coding, writing, painting, or even diving deep into a late-night conversation that sparks new ideas. In these magical moments, hours fly by, and it feels like the world fades away. This isn’t just random—it’s a sign of what truly fuels you.

These moments of deep focus, also known as “flow states,” aren’t just about the activities themselves; they reveal the deeper motivations behind them. It could be the thrill of solving a complex problem, the drive to improve a skill, or simply the joy of creating something meaningful. The key is to look beyond the task and recognize what makes it so captivating for you.

The activities that keep you up all night offer clues to the kind of work that will bring genuine fulfillment. When you’re in that state of flow, you’re tapping into an intrinsic drive—one that could potentially lead to a more aligned and purposeful life.

But while chasing passion is great, it’s important to keep self-care in mind. Pulling all-nighters regularly might seem productive, but lack of sleep can have serious consequences. Studies show that drowsiness can impair performance just like alcohol, leading to risks like accidents on the road. So, while caffeine may give you a temporary boost, balance is key.

Ultimately, the activities that captivate you are valuable signposts on your path to purpose. Just make sure you also give yourself the rest and recovery you need to keep pursuing them with full energy!

What Makes You Feel Vulnerable?

Let’s face it—vulnerability isn’t exactly a warm, fuzzy feeling. In fact, it often feels more like stepping onto a stage without knowing your lines. But here’s the secret: leaning into your vulnerabilities is where real growth happens. When we allow ourselves to be truly seen—flaws, quirks, awkward moments, and all—we unlock the potential for deeper self-awareness and authentic connection.

Research shows that sharing our vulnerabilities makes us more relatable and approachable. We all have those parts of ourselves that we’re hesitant to reveal, whether it’s a childhood fear, a quirky habit, or a long-held insecurity. But here’s the twist: the very things that make us feel exposed can actually become our strengths. When we embrace what makes us feel vulnerable, we find the courage to live more authentically.

Brené Brown, a renowned researcher on this topic, says it best: “Vulnerability is the birthplace of innovation, creativity, and change.” When you explore what makes you feel vulnerable, you start to see patterns that can lead to growth. Maybe it’s admitting you’ve always struggled with public speaking, or maybe it’s a hidden creative passion you’ve never shared. By acknowledging these feelings, you allow yourself the freedom to be imperfect—and that’s where the magic is.

So, what makes you feel vulnerable? Reflecting on this question isn’t about seeking discomfort; it’s about understanding the parts of you that need acceptance. When you can lean into your vulnerabilities instead of hiding from them, you move closer to a life that feels real, purposeful, and truly aligned with who you are.

By embracing our embarrassment and vulnerability, we pave the way for personal growth, creativity, and a more authentic life.

What are your happiest and saddest childhood memories?

Ah, childhood memories—where else can you find equal doses of pure joy and awkward moments? It’s funny how the same years that made you believe you could be a superhero also made you terrified of speaking up in class. But here’s the thing: your happiest and saddest childhood moments can tell you a lot about who you are today. They hold clues about your core values and hidden motivations.

Think back to the times when you were beaming with happiness—maybe it was winning a potato sack race, mastering a magic trick, or getting lost in a good book. Or, on the flip side, those days when you felt like the world was crumbling, like losing a beloved pet or trying to make friends in a new school (always a classic struggle). These memories, whether joyful or painful, aren’t just part of your past; they’re part of your playbook.

Research shows that those who struggle with depression often find it tough to reconnect with their positive childhood experiences, feeling less joy and more heaviness. But those who can embrace both the joy and the messiness of their past have a knack for using those moments as fuel for growth.

It’s like Brené Brown would say: “Vulnerability is the birthplace of innovation.” Or, in this case, the birthplace of rediscovering your truest passions. And you can almost hear Tony Robbins cheering you on in the background: “Turn your pain into power!” Meanwhile, Tim Ferriss might chime in with a question like, “What’s the one childhood passion you abandoned that you wish you could revisit?”

The ages of 10 to 15 are when many of our most vivid and formative memories take shape. So, as you sift through these moments, don’t forget to laugh a little at your old quirks. That time you tried to start a lemonade empire? Or convinced your siblings you had secret powers? Those were the seeds of something real.

So, what’s your earliest memory of pure joy? And what’s the one that still stings a little? Reflect on these with a sense of curiosity and compassion, and maybe a hint of humor. This isn’t just about nostalgia—it’s about finding the raw, unfiltered parts of yourself that have been guiding you all along. In the end, understanding your childhood memories is like finding a map to a life that feels more authentic and aligned—just with fewer awkward school pictures.

How Your “Why” Can Fuel Motivation and Focus

Let’s be real: pursuing your dreams isn’t all rainbows and motivational quotes. There will be roadblocks, bad days, and more than a few “What am I even doing?” moments. But that’s where your why comes in. Think of it as your personal GPS—it keeps you moving forward, even when life throws detours your way.

A strong, deeply-rooted why isn’t just some fluffy feel-good idea; it’s what fuels your motivation and focus. It’s the difference between sprinting toward your goals with excitement and hitting the snooze button on your alarm—again. Your why is connected to your core values and what really matters to you, making it a lot harder to quit when things get tough.

ALSO READ: 10 Ways to Motivate Yourself

Want to get a better sense of it? Try fast-forwarding to your 80th birthday: What’s the one defining sentence that sums up your life? No pressure, right? But seriously, thinking this way can help you uncover a why so compelling, it could keep you going through a marathon of setbacks, with or without coffee.

In recent years, there’s been a boom in people trying to find their why. It’s all over TED Talks, self-help books, and your aunt’s favorite inspirational Facebook post. Simon Sinek’s famous talk on this topic has been shared more times than cat videos—because it works. He makes it clear that having a purpose isn’t just about feeling good; it’s about creating a meaningful, fulfilled life.

And it’s not just individuals who benefit. Companies with a clear why tend to see better sales, higher customer satisfaction, and employees who actually want to show up to work. On the flip side, entrepreneurs without a strong sense of purpose are like marathoners running without water—it’s only a matter of time before they burn out.

So, what’s your why? By uncovering it, you tap into a powerhouse of motivation that fuels your focus and commitment. It’s what drives you forward, even when the journey gets bumpy. And trust me, it will. But with a compelling why, you’ll have what it takes to keep going—because a life lived with purpose is always worth the grind.

Crafting Your “Why” Statement

Defining your purpose statement, values-based goals, and personal mission is key to unlocking your intrinsic motivation. It sets you on a path of impactful living. As Simon Sinek notes, “People don’t buy what you do, they buy why you do it.” Exploring your core values, passions, and inspirations helps craft a compelling “why” statement. This statement will guide you in all your pursuits.

Many have created personal statements for resumes, social media, or college applications. Experts suggest using a single sentence to capture your purpose. Companies also use mission statements to outline their identity and goals. For instance, Apple aims to “challenge the status quo,” while Microsoft seeks to “empower every person and organization to achieve more.”

When crafting your “why” statement, consider the examples of Walt Disney and Malala Yousafzai. Disney wanted to “make people happy,” and Yousafzai focused on “education for every child.” Aim for 1-2 sentences to clearly outline your personal and professional purposes. The goal is to express your true values and goals without generic phrases.

Simon Sinek’s “Find Your Why” book suggests a “TO ____ SO THAT ____” structure for your statement. This framework makes your purpose statement clear and actionable. Remember, your “why” statement is a work in progress. It will evolve as you delve deeper into your motivations and aspirations for impactful living.

Putting Your “Why” into Action In Business

Aligning your business purpose with your personal “why” can transform your entrepreneurial journey. Often, we chase superficial goals like wealth and status. Yet, our true drive comes from deeper passions and values.

Using your “why” as a compass ensures your business decisions are driven by intrinsic motivation. This approach helps you stay focused, overcome challenges, and find deeper fulfillment in your work.

When your work serves a meaningful purpose, it transcends being just a job. It becomes a way to live out your true calling. As Simon Sinek (2017) noted, “People don’t buy what you do; they buy why you do it.”

To integrate your “why” into your business, consider these strategies:

1. Clearly define your “why” statement, using the formula: “To [your purpose] so that [your impact].”
2. Ensure that your business goals, products, and services align with your “why.”
3. Infuse your “why” into your brand messaging, marketing, and customer interactions.
4. Surround yourself with a team that shares your passion and “why,” fostering a culture of purpose-driven work.
5. Regularly review and refine your “why” statement to maintain clarity, discipline, and consistency.

By anchoring your entrepreneurial pursuits in your deeper “why,” you’ll achieve greater success and find profound fulfillment. Data shows that those with a clear “why” are more motivated, productive, and impactful.

So, embrace your “why” and let it guide your business journey. The rewards of passion-based, purpose-driven work are immeasurable.

Living with Purpose

Discovering your “why” is more than reaching specific goals or career peaks. It’s about embracing a life of authentic living and purposeful existence. Uncovering your deepest motivations and values can enhance self-awareness, emotional intelligence, and life satisfaction.

Aligning your daily actions and long-term dreams with your “why” leads to a more intentional, fulfilling life. It’s not about achieving perfection or having all the answers. It’s about the journey of self-discovery and growth.

Statistics show a rise in drug and alcohol abuse, depression, and suicide, along with increased antidepressant use. This points to a crisis of purpose and meaning. Yet, there’s hope. Companies like BACKROADS have shown the power of aligning business with a clear “why,” leading to significant growth and profitability.

Discovering your “why” means exploring your talents, skills, passions, and values. It’s about finding ways to add value and focus on endeavors that inspire you. This journey may take months or years, but daily writing and self-experimentation can help.

Your “why” statement is often hidden but waiting to be found through deep introspection. By tapping into this well of meaning, you can live a life that’s truly fulfilling and impactful, leaving a lasting legacy.

Conclusion

Discovering your personal “why” is crucial for a fulfilling life. It involves asking deep questions, facing discomfort, and reconnecting with your passions and values. This journey helps you find motivations that go beyond superficial goals or external praise. A clear “why” statement gives you the focus, resilience, and drive to overcome obstacles and make a real difference in your life and work.

Finding your “why” is a continuous journey of self-discovery. It leads to a life of authenticity, satisfaction, and contribution. As you explore this path, remember that your insights can change your life and inspire others to find their purpose too.

The journey may face challenges, but the benefits of a strong “why” are clear. Embrace these challenges, stay curious, and trust the process. Your true purpose is waiting to be found.