Can you relate to any of the following?

• You find it hard to start conversations, especially with people you don’t know
  
  
• You struggle to hold a conversation — specifically, to go from small talk to deeper conversation (you often think to yourself, “What should I say or ask??”, and worse still, your mind draws blanks!) 
  
  
• You end up avoiding social situations and even certain people because of your social anxiety
  
  
• You feel lonely because you aren’t having fulfilling  relationships (while others are seemingly having a good time without you)
  
  
• You feel envious when you come across people who just seem to “get it” in social situations  — they have loads of friends, they know just what to say or ask — and you think: “I can never be like them”

If so, this is the site for you. 

Why I Created Deeper Conversations  

Ian here, the founder of Deeper Conversations 🙂 Here’s why I decided to create this site…

1. While I love books and courses on communication in general, I’ve found the vast majority of them to be… mediocre.

Specifically, they share cliched, generic advice. For example, “to be interesting, be interested” or “don’t interrupt when others are talking” .

Some experts even teach you to be manipulative! But that’s not even the biggest problem…

Most communication books ignore the impact of social anxiety.

For some people, saying hi is enough to trigger a wave of fear and anxiety, let alone having a full-fledged conversation.

(When you’re overwhelmed by anxiety, you are much less able to utilize your social skills. And that’s completely normal!) 

2. I created this site for myself as much as it’s for you. 

For the longest time, I wasn’t a social butterfly. Wasn’t a “people person”. Wasn’t a “natural”. 

In fact…

I was bullied for nearly ten years, which led to me having social anxiety at a young age.

Because of all the bullying, I thought that I was just unlikable and unlovable.

And so whenever I talked with people, I was constantly haunted by my sweaty palms, shaky voice, and pounding heart. 

There were days when my anxiety kept me isolated in my university residence room, and convinced me that no one wanted to be my friend. (Let alone date me.) 

On one particular day — a cold winter morning —  I looked at myself in the mirror and said “Fuck it.” 

I was fed up living like this.

Always living in fear. Always craving for human connection… that I never had. 

I was desperate for change.

So I came up with a plan to overcome my social anxiety.

Many plans, in fact…

• I interviewed top achievers in 20+ countries (as part of a book  I co-authored) 
• I started a street journalism project and talked with 700+ strangers on the street 
• I cold messaged and emailed successful leaders, landing an internship at a national Canadian nonprofit among multiple career opportunities 

(I pretty much went all-out, as you can tell!) 

Over the last ten years — across three continents — I’ve had conversations with over 10,000 people, and I’ve been featured by top media outlets like CBC, Inc. Magazine, and TEDx.

Most importantly, I now have a wealth of meaningful relationships with family and friends. I’m not nearly as socially anxious as I used to be.

Having freed myself from the prisons of anxiety and loneliness, I’m on a mission to share everything I found that works in the art of communication & relationships. 

I hope this site is helpful to you as it would have been for my younger self. 

Review Board 

As I pride myself on creating high-quality content, I make sure that I only share ideas proven by experience and research. 

And that’s why I’ve enlisted the help of multiple psychology professionals! You can learn more about them below: 

Iffah Suraya Jasni, M.Couns.

Yue Yun Aw Yong, B.Sc(Psych)

What People Say About Me 

“The quality of your answers are directly related to the quality of your questions. And after 5 years and many deep collaborations, I lost count how many times Ian has helped me find the right questions for my problems. He is one of the very few people I know who genuinely listens to you, truly caring about what you are sharing. And this is a skill that I’ve learned from him that has made a huge impact in my copywriting journey.”

— Gianni Cara, Marketing Manager at The Home Service Expert (partnering with 9-figure entrepreneur, Tommy Mello)

“Throughout our conversations on online marketing, business and even life, he was able to hear me deeply and point out things that had eluded me for a long time, and that proved profoundly beneficial in my own entrepreneurial journey.”

— Drima Starlight (Amir Ahmad Nasr), founder of Assertive & Co. (clients include Mindvalley founder and other successful CEOs, leaders, creatives) 

“It’s hard to put a finger on why, but my conversations with Ian have made me a better conversationalist (and I don’t mean being good at making small talk). There’s a thoughtfulness to the way he communicates that will make it easy to focus on saying what you want to get across, and refining how you want to be understood, rather than worrying about how he perceives you. When I’m chatting with him, I have room to catch the mistakes I make as a conversation partner and correct them. Maybe I’ve gone on for too long without asking reciprocal questions. Or maybe I’ve been asking too many questions without offering something in return. Small things like that that you can’t really change if you’re just conversing with family and close friends – people who are used to your communication habits – but you can if you’re chatting with someone who’s objective, intentional, and empathetic in the way he approaches the conversation.”

— Caroline Wong, Head of Operations and Customer Success at ZilLearn

“In my experience organizing events with billionaire entrepreneurs, university presidents, congressmen, senators, philanthropists, and educators, Ian stands out… 1) His listening without judgment, helping me to completely open up – which I found it hard to do with most other people. 2) His knack to address my underlying thoughts and emotions, which gave me huge clarity in business.”

— Michael Simmons, serial social entrepreneur recognized by White House, Ernst & Young Entrepreneur Of The Year, Inc. 30 under 30, Businessweek 25 under 25, Bank Of America

“[Ian] has a knack of getting to the root of the challenge and listening without judgment, so that you shift your perspective and walk away with insights that seem obvious in retrospect. You’re carrying the answers around; Ian helps you see them.”

— Sheena Lindahl, founder of Meta Consulting (acknowledged by President Obama for her work as a young leader in America) 

“Every day we spend 70-80% of our waking hours in some form of communication, but is our communication effective and relatable? During my many 1:1 conversations with Ian about life, design, and business, he listens attentively, emphasizes, asks the right questions to reframe my mindset so I can see the problems from another perspective, and how he can add value. You’ll walk away learning so much from Ian!”

— Chip Dong Lim, Senior Product Designer at Grab

“Thank you for the genuine, thoughtful questions”

— Ian Beacraft, Fractional CMO at Coastal Spritz, former group director at Epsilon