Building Confidence & Overcoming The Impostor Syndrome

“The exaggerated esteem in which my lifework is held makes me feel ill at ease. I feel compelled to think of myself as an involuntary swindler.”

Albert Einstein, Scientist

Even the best of us are privy to the Impostor Syndrome.

It holds us back in all the obvious ways:

  • Prevents us from sharing great ideas.
  • From taking action and starting amazing projects.
  • From applying for jobs that we could excel.

But we need to recognize, when we’re holding ourselves back, we’re also short changing others:

  • Your negative feelings rub off on others
  • You don’t give as much value
  • You can’t be there for people who need you

Step 1: Recognize it

Obvious as it seems, you can’t begin to improve or fix something if you are not first aware of what it is/what is causing it.

It’s not just “I feel like I’m faking it”. Impostor Syndrome is also present if we start to think things like:

  • “I’m not good enough”
  • “I must not/can’t afford to fail”
  • “I was just lucky”
  • “It wasn’t a big deal”
  • “I don’t think I can do it”
  • “I want to make sure I’m an expert before I get started”
  • “I want it to be perfect before I release it”
  • “What will others think of me if they find out…”

Step 2: Shift our mindset


Everyone makes mistakes, and even if you don’t make mistakes, there are still external factors that may prevent you from achieving the definition of success you’ve defined.

Failure only happens when you give up.

Or if you don’t learn anything.

Otherwise, pivot, detour. Your destination is still the same, you’re just changing your approach.

Review your definition of success, you may have unrealistic expectations?

Don’t let the pressure of failure prevent you from enjoying the journey to success.

Call To Action: Document failures and what causes them (You’re often not the cause).


Yes, luck matters, but it’s only a small part of the equation.

Imagine a graph of success. Luck determines where you start.

But you CAN control the slope of the graph.

Luck can give you the opportunity, but you can still botch it

  • e.g. you meet the ideal investor for your business, but have no idea how to speak investment lingo and come across too strong. (same works for romantic relationships).

You can “create luck” too, and by playing an active role, you are a key factor in your success.

  • Build your skills — so you can take full advantage of opportunities when they come your way.
  • Build your awareness — so you can recognize opportunities better and act on them.
  • Understand your values & discover your purpose, dedication matters — you’ll eventually succeed if you keep trying (as long as you’re not doing the same thing expecting different results — that’s just the definition of insanity).
  • Build your network — create more favourable conditions for “luck” to happen

Learn to make the most of every opportunity — good or bad.

Call To Action: Take a chance

“You miss 100% of the shots you don’t take.”

Wayne Gretzky, NHL Player

Success is no big deal

It kinda is!

Call To Action: Celebrate the moments instead of rushing to the next peak.

Small things like these matter and help build resiliency.


“Perfection is the enemy of progress”

Winston Churchill, Prime Minister of UK, 1940–1945

Strive for progress, not perfection. Instead, aim for “Good Enough”.

This doesn’t mean that you should be satisfied with sub-standard work.

Check out this great blog post from HubSpot on When “Good Enough” is Good Enough.

TLDR? It’s good enough when

  • It’s creating value
  • It’s solving the problem/addressing the need/conveys the intended message
  • It’s on-brand (business/personal).
  • Quality is consistent/above your previous work
  • It has been approved by other qualified peers.

Call To Action: Be comfortable with an imperfect release, you can always improve upon it.


Yes, people will judge. So? Who cares?

The only person who really matters is — do you care?

Don’t overthink things and allow it to hold you back.

As an introvert, I’ve always worried that my silence would make people think that I’m stupid/a pushover/uninteresting. This created a negative spiral which would make me uncomfortable + hold me back from interacting with people. I’ve come to realize that it’s OK to be silent and still make friends. By being comfortable in my own silence, I make others around me comfortable by not pushing too hard to be who I’m not.

Why is the Impostor Syndrome so pervasive? Pluralistic Ignorance

The Emperor’s New Clothes is a perfect story of Pluralistic Ignorance in manifestation.

In a nutshell:

  • We all doubt ourselves (privately)
  • But because people don’t often voice their doubts or share stories of failure and detailed accounts of how they found success.
  • We feel that everyone else has got their shit together.
  • So we believe we’re alone in it.

Another common manifestation of this is when a presenter asks “Any questions?”

  • Everyone is unsure
  • But no one speaks up
  • Because they feel that everyone else must all get it if they’re not speaking up too
  • They conclude that they are the only one that’s unsure
  • And chose to remain silent rather than expose themselves as ignorant.

4C Framework for Reflection

On making Commitments

My 3 main takeaways:

  • Burn your bridges behind you:
  • Most point of no-return experiences are usually triggered by some form of financial investment.
  • Identity needs to be in alignment with your goals
  • If your goals are up there, but your identity is down here, you’re acting in conflict with how you see yourself.
  • E.g. If you identify as being obese, then everything you do feels like something that is against you.
  • If you identify as being fit, your behaviour will naturally shift to being that of a fit persons
  • 100% is easier than 98% — having that 2% doubt creates that room for wrestling with yourself.

“Once I make a decision, I never thought about it again”

Michael Jordan, NBA Player

Other Activities that may help you

  1. Talk about it
  • Get out of your own head.
  1. Focus on value creation
  • Instead of worrying about “Do people think that I did a good job?” (you can never please everyone).
  1. Practice reflection
  • Reflect on your achievements, own your accomplishments, collect positive experiences.
  1. Embrace uncertainty
  • It’s ok to not have all the answers, acknowledge that you’ll seek them out.
  • Say and share what you can instead.
  1. What about authenticity? I feel fake.
  • There is no such thing as a one-true-self.
  • We are different around different people.
  • You feel authentic when the HOW aligns with your values.
  • Salespeople who don’t believe in their products are inauthentic, those that do are passionate.




Startup go-to-market and sales specialist, father, avid packrafter

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Chang Chin Hing

Chang Chin Hing

Startup go-to-market and sales specialist, father, avid packrafter

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