Don’t Ask Why, Ask Why The Fuck Not

Launch, iterate later. Perfection is procrastination in disguise. You’re never going to be ready enough.

Written by Amy Chan · 4 min read >
Don't Ask Why, Ask Why The Fuck Not - Heart Hackers Club - why not - Several People Are Typing

“It’s nearly impossible for a Canadian to get a visa to the US.” 

“You can’t be C-level exec so fast, learn some humility Amy.”

“Most businesses fail after 2 years. Are you sure you want to leave your job?”

“Why do you want to write a book? You know you won’t make any money from writing a book right?”

This was the advice that was given to me by various friends and family throughout the years. With good intentions mixed with unconscious projection, they wanted to protect me… from my dreams.

I remember each one of these conversations clearly and the feeling of motivation I felt after, saying to myself:

“Just wait, one day I’ll show you.”

And I did.

I got a visa—five visas to be exact.

I climbed the corporate ladder to become Chief Marketing Officer of a national brand in my early 30s.

I’m now in year two of my business and going strong.

And I’m writing a book—and getting paid for it.

I don’t say these things to brag. I say these things because I want you to know that what might at first seem impossible, is possible—and it starts with a mindset.

In a sea of reasons why you can’t do something, I urge you to change the question from why to,


I know how hard it is to pursue your dreams, let alone share them. Whether that dream is to start a side hustle, launch a business, get the corner office, or become a stand-up comedian—we all have dreams that we have ignored and silenced because we let doubt overshadow possibility.

The internal skepticism is enough of a battle, and the additional judgment of others can make taking a risk feel debilitating.

There is always going to be a dreary statistic, rationalizations of why your current state is “good enough,” and a handful of people who think you’re crazy.

But for every example of someone who tried and failed, there’s also an example of someone who tried and succeeded. I’m not promising you’ll succeed in the traditional sense of the word, but I can say from my own experience that the journey is worth it.

The joy of being an entrepreneur is not just about the peaks, it’s about the climb.

Shifting your mindset to start focusing on possibility and expansion is a muscle you can build. You get better as you practice. Not everything is going to stick, but you commit to getting back up each time you stumble. You keep creating as a way of being. You keep planting seeds. You focus on your side hustle, passion, or dream until you reach that fork in the road.

Here’s some practical advice on how you can take that first step:

  • Get in the habit of asking yourself WHY NOT each time you automatically say no to something. Start peeling back the excuses and rationalizations of why you really can’t. Decades of wiring have likely caused you to default to saying no on autopilot. You’ll need to make a concerted effort to override this programming.
  • Start saying yes to things. When something positive comes out of it, reflect on that. The positive feedback loop of trying new behavior is what helps you rewire old thought patterns.
  • Meditate and get yourself into a calm relaxed state, so that you shift from beta brainwaves (alert consciousness) to theta brainwaves (creative, insightful, subconscious). Start to imagine your dream life as if it’s happening in the present. What are you doing? Who’s around you? What do you see, smell, hear? How do you feel? Relish in the feeling. Afterwards, write down what came up and most importantly how you felt. This is a good starting point of creating your vision. Know how you want to feel, start from there.
  • Reflect on what you love doing. Do more of it. What are you excited about? Curious about? What question do you feel you have an answer to? What problem can you be a part of solving?
  • Be intentional about honing your craft. Do not think about how you’re going to monetize yet. I never imagined that doodling to release my teenage angst would turn into a side business. Doodlempire, here I come.
  • Start planting seeds. I cold-contact EVERY DAY. My mindset is that out of every 100 times I’m ignored or rejected, I’ll get one yes. That’s how I started my writing career over a decade ago. I pitched over 100 publications to get my first article published. One newspaper, the 24 Hours Vancouver, said yes. I wrote for them for seven years. Reframe your relationship with rejection – it’s just a necessary part of the process.
  • Figure out your niche.  Mentally prepare yourself that it takes 5-10 years to own a market segment. If you work on being a thought leader in one area, eventually, you’ll get really fucking good at it, and then people will come to you.
  • Dare to put yourself out there – start a free blog, make short videos on YouTube, interview people smarter than you… whatever your medium, just get it out there. Don’t worry about who’s going to read it, see it, or buy it. Your only objective in the beginning is to start creating content around the area you’re building expertise on.
  • Launch, iterate later. Perfection is procrastination in disguise. You’re never going to be ready enough. You also cannot foresee all the pivots that will happen later down the road, so trying to plan it all out now is futile.
  • Commit to a date. The moment you have that idea, that spark – commit to the next step. Buy the ticket, book the space – do something that energetically commits you to actioning the next step. This holds you accountable. There’s a small window period where the courage to get out of your comfort zone exists, and once it expires, your left brain will flood you with every rationalization why you’re not ready and why you can’t.

Dare to dream bigger

Don’t think about how you’ll get to the end goal as your brain will overwhelm you with fear and magnify all the reasons why you can’t. Your brain is designed to keep you safe and comfortable. You need to exert extra energy and override this in order to create expansion because it won’t feel natural – at first.

Just take the first step. That’s it. Once you finish that first one, then focus on the one after that. One small step after another and you’ll get closer to your goal. Eventually the steps add up. There’s compound effect. You’re tricking your brain with smaller, achievable steps and creating a positive feedback loop that eventually creates momentum.

Go get it. ⚡️

Photo by Vince Fleming

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