The Tragic Question That Has Ended So Many Dreams

Jay Gross
4 min readJun 29, 2021
Image by Arek Socha from Pixabay

It happened to me just this morning.

In fact, it happens to me on many occasions.

Whenever I’m about to step outside my comfort zone and do something new — something to grow — one of the first questions to pop in my head is usually the one that derails me.

I go from giddy about my new endeavor — maybe even a new path in life — to fearful. To doubtful. To giving up…usually before I’ve even started.

I just wish I would have known that it was this question that was the source of so much fear and doubt.

Let’s talk a little about this question and how to avoid it.

And the ONLY question that matters to drive you forward.

The Tragic Question That Has Ended So Many Dreams

Sad woman sitting on open dock by sea
Image by Sasin Tipchai from Pixabay

Have you figured out what the question is?

It’s killed more than a few of my dreams before they even got started.

It strikes fear in the heart of even the strongest-willed person.

It has the ability to crush your aspirations and dreams — literally.

The question is:

HOW?

Have you ever had a spectacular idea of a way to change your life for the better?

Maybe starting a side-hustle, or a new business, or a career change — but no matter what, it’s a big change that you think will make your life better, happier, more meaningful.

And you’re filled with hope and excitement. You lay in bed excited about the possibilities. You wake up excited for the day.

You’re radiant.

But you’re branching out, you’re outside your comfort zone, and you really don’t know exactly what you’re doing.

And you start thinking to yourself:

“But HOW will I do this?”

Because you’re not sure how to do it, exactly. You’ve never started a business before, or you don’t know that you’ll be able to juggle starting a side-hustle right now.

You begin to get scared. Self-doubt creeps in.

And you decide you’ll do it once you take a class, read a book, practice.

Or you decide you should wait until the timing is better.

The problem? None of that will ever come.

Maybe you’ll read a book, or finish the class you want, but then you’ll find something else you don’t know, so you’ll take another class.

And you’ll keep putting it off until you’re completely ready or the timing is just right.

I can tell you from experience that time will NEVER come.

And if it does, it’ll be too late.

HOW is an aspiration crusher and a dream killer.

It’ll fill you with self-doubt and fear—all of that radiance and moxie you had only days before, gone.

As is that smile on your face as you subconsciously realize that you won’t be doing that thing you just wanted so badly.

And so you go about your life just like every other day, week, and month.

You just get by, never changing a thing.

The memory of the dream you had fading with each passing day.

Ask Yourself This Life-Changing Question Every Morning Instead

Image by Avi Chomotovski from Pixabay

But what if there were a question to ask yourself every day instead?

A question that would get you that radiance and moxie back, and that would keep it around.

A question that would push you every day, even though you don’t know exactly what you’re doing — heck, maybe you have ZERO clue what you’re doing and how you’re going to do it — but this question will help you push past those boundaries.

And this question will help bring the HOW into focus.

The question is:

WHY?

Why do you want to pursue this? Why do you want to follow this dream?

And if you have a great answer for that, you can do anything.

Because WHY you do something is much more important than the HOW.

If your WHY is strong enough, then the part that scares you most and crushes most people’s hopes and dreams — the HOW — will come.

So make sure your WHY is strong enough. Make sure you want to do this no matter what, and the rest will come to you.

WHY will make you take action ***.

And action will lead to confidence.

To get on the right track, ask yourself the same question every morning:

WHY are you doing this?

Ask yourself at night too, or whenever you get stuck. Or whenever self-doubt creeps in. Or whenever HOW gets to you.

Because remember: If you have a passionate enough WHY the HOW will come.

If you’re up for it, post what you’re doing now (or thinking about doing) that’s outside your comfort zone.

And if you’re open to sharing, post your WHY. I’d love to know more.

Hi, I’m Jay Gross, a mango-obsessed entrepreneur and mindset coach. A writer and creator focused on personal growth and business. Helping others to live their best life one day at a time. Find me at www.lifenextlevel.com or email me at jay@lifenextlevel.com.

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Jay Gross

Jay Gross is a writer, podcast host, lives to travel, with an unhealthy mango obsession. Focused on personal growth. Find him at www.lifenextlevel.com.