Chris Strouthopoulos is the founder of Ascent Empowerment, which helps adventurous men beat professional burnout.
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The questions you ask yourself determine your focus. They point your thoughts like a flashlight in a dark room, illuminating whatever you aim them at and leaving everything else in shadow.
Here’s the problem: Most of us ask the wrong questions. Or, just as damaging, we ask the right questions in the wrong order.
Think about the last big dream that grabbed you. Doesn’t matter if it was professional or personal: I’d love to start my own practice. I want to give a TEDx talk. I’m going to write that book.
That flash of inspiration always arrives wrapped in a generalized vision of possibility. And then, almost instantly, and for reasons well beyond this article, our brain jumps straight to “how.” We get strategic: I need a training plan. A course. The right consultant.
If you’ve walked this road before, you know what happens next. Analysis paralysis sets in. You start evaluating every plan and every guru, terrified of picking wrong and wasting precious time.
That’s where so many dreams go to die.
The Correct Order To Ask Your Questions
Here’s the fix: Reorder the questions. What. Why. How. In that order, every time.
1. What
What comes first, but it doesn’t need to be precise. Follow the intuitive pull toward your dream, and let that be enough for now. Steps two and three will do the fine-tuning.
Nailing it down too early just wastes time because your vision’s granular details will evolve throughout the journey anyway. So, let go, and trust the process.
2. Why
Why comes second, and it’s the part that matters most. Simon Sinek built a career on this idea, and for good reason: Your why is rocket fuel. The more you load into the tank, the farther and faster you’ll go.
Consider hysterical strength, the well-documented phenomenon of ordinary people displaying extraordinary strength in life-or-death scenarios, like lifting cars off loved ones trapped underneath. Or Archimedes, who famously said that given a lever long enough and a place to stand, he could move the world. Your “why” is that lever. Your “how” is simply the fulcrum you rest it on.
3. How
How comes last. Has to come last. It’s also, ironically, the easiest part. Want to start that business? There are shelves of books and rosters of coaches and consultants who specialize in exactly what you’re after. Pick one and go.
In my experience, most people don’t fail because they chose the wrong plan; they fail because they quit before results arrived. The failure is not the “how”; it is the “why” that proves unable to sustain you.
Real-World Proof
I know this because I lived it. One of my biggest adventure goals was climbing El Capitan, the legendary 3,200-foot wall in Yosemite that Alex Honnold famously free-soloed. I value my life, so I planned to use a rope. Still, scaling El Cap is a massive and terrifying endeavor.
My “what” had been set since high school, reading stories from John Long and the other Stonemasters. (For more about this legendary group, check out the documentary Valley Uprising.) The “why” that finally moved me arrived 20 years later, in the form of my first child on the way. I knew the training and focus required wouldn’t be there once a baby entered the house. I’d always assumed the obstacle was “how”—that I needed to become a better climber. But it turned out the real obstacle was that my “why” hadn’t carried enough urgency, until suddenly it did.
Once the “why” was big enough, the “how” became pure execution. Climb four times a week. Lift weights. Sign up for a big-wall workshop. Build a progressive series of climbs to get ready. That was it.
I pulled it off, and I’ve been grinning ever since. Ascending a free-hanging rope off the Harding Headwall with 3,100 feet of air beneath me, watching the sunrise light up Half Dome after a 22-hour push through the night, is a moment of transcendent euphoria I’ll carry to my grave.
I’ve watched the same pattern rescue clients, too. Dr. J is a double board-certified dermatologist, brilliant in his field, who hated the 15-minute consults and profit-driven grind of practicing medicine for someone else. For years he told himself, “One day I’ll open my own clinic,” and his mind went straight to how. A tsunami of decisions—location, staffing, logo, paint color—overwhelmed his perfectionist brain and shut him down.
We didn’t start with “how.” We got him deeply, emotionally connected to his “why,” until he could picture it in his mind’s eye. A year later, his clinic is open and profitable.
I saw the same thing recently in a coaching mastermind I’m part of, when someone floated the dream of giving a TEDx talk. I’d given one for Georgia Tech that’s since landed in the top 1% by viewership, so I offered to share what I’d learned. Seven accomplished coaches messaged me that same day. Every single one felt stuck and asked for tactical advice on “how.”
I just smiled and asked about their “why.”
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