How to Conquer Shyness

Be bold.

If you want to become successful as an entrepreneur, photographer, or anything in life, you cannot be shy.

Are there any upsides to being shy?

Are there any benefits to being shy? I don’t think so.

Generally the shy individual is afraid to interact with other people; generally the fear of interacting with strangers.

Shyness comes from a fear of the foreign and the unknown person. Obviously if you’re a child it is good to be fearful of strangers who offer you candy from a white (unmarked) van. But as an adult, I don’t really see any potential upside to being shy.

Why are we shy as adults?

Perhaps we were teased a lot as children, and this we became risk-averse with interacting with other people.

Perhaps we are fearful of being made fun of by others.

Perhaps we lack the social skills of better interacting and engaging with strangers (this is a skill which can be cultivated).

Is shyness something that needs to be overcome or conquered?

It depends on your personal goals in life.

For example, if you desire to find a romantic partner, obviously you cannot be shy. You must be bold, confident, and audacious if you desire to find the ideal partner for you.

If you want to start your own business or be self employed, you cannot be shy. A shy individual will not be able to charge people money for their products or services.

If you want to make better street photographs, obviously being shy is a crutch. The only way to make better street photographs is to to be bolder.

It seems that most scenarios in life, being shy is a downside.

How to become less shy

The good thing is that overcoming shyness is a skill you can cultivate. Some tips:

  1. Practice making small talk with all strangers you encounter in your everyday life. Chat up your barista, security guard, waiter or waitress, airline attendant, or any service worker. Experiment by asking for their life story, or what their passions or dreams in life are.
  2. Perhaps sign-up for some acting, or stand-up comedy lessons: This seems to be one of the ultimate way to conquer shyness.
  3. Ask for strangers for permission to make a portrait of them (street photography portraits). The point isn’t to make a great portrait of them, the point is to simply have the guts to ask for permission, and not to be affected by their response (whether they accept or reject you).
  4. Chat up a stranger at a coffee shop or bar. Interact with strangers you’re genuinely interested in, and ask them a lot of questions about themselves, while also revealing your own personality.
  5. Treat it like a practice: The more you interact with strangers, the better. Joke and laugh with them, like they were a close friend.
  6. Compliment them: Tell them what you find interesting or fascinating in them. Be genuine. Don’t bullshit, and also don’t censor yourself.
  7. Don’t hesitate: The more you hesitate before you interact with a stranger, the more likely you are to get cold feet. This happens to me all the time. The rule I have is this: When I feel nervous, then I truly must interact with that person.

Benefits to not being shy

By not being shy, you open up the doors of possibility and opportunity.

Some personal benefits I’ve gained by not being shy:

  1. Practical: Not being shy to ask for directions or help is FASTER and often more efficient than checking your phone. When I’m lost in a new city, I always ask a local for directions (even though I could check Google Maps).
  2. Strangers are often nicer than you think: When a stranger helps me, it reawakens my faith in humanity! It reminds me that most people are kind, generous, open, and helpful! It is a good way to battle pessimism against human nature (modern media has scared us into thinking that most humans are scary and bad people, whereas in reality most people are super friendly).
  3. Making new friends and connections: I’ve made a lot of great friends, simply by being friendly to strangers. My friend Walter was a barista at a coffee shop I liked, and we have become great friends over the years, simply because I want shy in opening up conversation with him!
  4. New business opportunities: By not being shy, I’ve been able to make new business connections and have new business opportunities. Better to to be bold and ask, and get rejected and ignored (than to never attempt to take the risk)
  5. Better photographs: By not being shy when shooting street photography (with or without permission), I’ve made stronger photographs that I’m more proud of!

When in doubt, don’t be shy.

Better to risk it and get made fun of, insulted, rejected, or ignored than not to have the courage to attempt in the first place!