How To Go From Small Talk To Deep Relationships

I love those beautiful nights under the stars, engulfed in conversations about life, purpose and love. When time stands still and the only thing that exists is the connection between you and the other person.

Those are the connections that I live for.

I think everyone has that deeply beautiful side to them, just waiting for someone to reach out and connect to it. Sometimes I just want to walk up to a person and ask them about their dreams, the things they are afraid of and the disappointments that have forged their character.

I want to know every detail about them, the good, the bad, and the ugly. I love that imperfectly perfect image that you discover as you chip away the walls that we build so high.

But you can’t connect to someone on that level right away. You need to start somewhere and build rapport, and there is only one way to do that.

Small Talk

Anyone that knows me well enough knows that I hate small talk. I don’t like all the fluff that surrounds it.

“Wow, the weather is really terrible today, right?”
“How about X sports team, they’ve really been doing badly, right?”

Maybe it’s just me but I don’t really care about that kind of thing, and two people talking about things that don’t interest them, excite them, or reveal any of their beauty makes for a pretty mundane experience.

small talk (1)

But, since small talk is never going to go away and is necessary for building a relationship, I’ve decided that I will make it my goal to have the best small talk experiences and transition to real conversations as quickly as possible.

Once you build rapport you can start to relate to a person and explore who they really are. That is where real relationships are forged. That is where you find the people that you can call crying at 2am, the people you can rely on during the good and the bad.

So this is my guide to getting through the small talk as quickly and gracefully as possible, allowing real conversations to flow and real relationships to be cultivated.


I was going through the motions with a customer when he stopped me.

“What’s your name?”
“Oh, It’s Steven.”

And from that point on he used my name in every other sentence. The conversation was amazing and I felt like I had known him my whole life by the end of it. There was a certain warmth to the whole exchange that made it feel that much more real.

Everyone knows that when you meet someone the first thing you should do is introduce yourself, the part where most people fail to capitalize is that they are just going through the motions. Most people don’t even remember the names of those that they engage in small talk with.

When you introduce yourself make sure that you remember the persons name and use it throughout your conversation. People love hearing their name and it creates a sense of familiarity that is essential in transitioning from mundane small talk to anything bigger.

Another thing to keep in mind is that after the introduction people usually never hear your name again, so it’s easy for them to forget it. If you can, mention your own name more than once throughout the conversation so they have a chance to convert it to their long term memory.

You can do this two main ways:

  • Address yourself by name. For example, “So I thought to myself, ‘Steven, you have got to get better sleep.'”
  • Use your name in dialog. For example, “So my friend said to me, ‘Steven, you have got to get better sleep.'”

If you remember their name while helping them to remember yours, you will have a much better chance of leaving a lasting impression and deepening the connection.

Ask Questions

The second way to ensure that you build a real connection and avoid being stagnant in small talk is to ask questions.

We love our names, and we also love talking about ourselves. It’s understandable, we know ourselves better than any other subject so it comes naturally. When we ask someone about themselves it makes them feel important and interesting.

A real interest in other people is the best gift that you can give them. Too many people only care about themselves and it ruins a lot of potentially beautiful relationships.

Whether it’s deeply revealing questions or just your basic small talk questions, you should always keep in mind the 5 W’s. (And the one H)

Who, what, where, when, why, and how.

Whenever someone makes a statement you can build the conversation off of it by asking a question that gets them to reveal more details about their statement.

If someone mentions that they went to a certain university you now have the ‘where’ and ‘what’ but you can still ask them why they chose that university, how they got along there, or when they started.

When you keep those 6 questions in mind you can always slip one in to continue the conversation and reveal a little bit more about the person.

Another thing to keep in mind is that you should avoid questions that have one or two word answers. If you get a short answer, ask a follow up question and continue exploring the details.

Offer Compliments

You might be noticing a trend by now. Having productive small talk that actually leads to a real relationship is all in making the conversation about the other person.

We say their name to create familiarity and make them feel important. We ask them questions to make the conversation flow better, since we are all experts in the subject of ourselves. And we should also offer them compliments.

There is nothing more powerful than a real compliment and there is something to be noticed in everyone.

My general guideline for compliments is that I try to avoid anything generic. It is always better to give a compliment that you actually believe. Also, I usually like to break my compliment into two statements, first I introduce the compliment and then I detail it.

“You are honestly such a positive person. It’s so nice to see someone with such a genuine smile on their face.”

A real compliment can go a long way in cultivating a connection with someone.

The saying goes, “If you don’t have something nice to say, don’t say anything at all.” But I have always preferred my own version, “If you have something nice to say, you have to say it.”

Mirror Them

People feel more comfortable when they are talking to someone who reflects their mannerisms, tone, talking speed, and general energy levels.

It helps to cultivate that feeling of familiarity and give the impression that you are both on the same page.

While you should follow your partners lead to make them feel comfortable, don’t copy everything they do down to the T.

If they are calm and relaxed, and you are chock full of energy, there won’t be any cohesion in your conversation.

Match their general vibe and the conversation will be smoother and overall more enjoyable.

Hopefully with these tips you will be well on your way to having small talk that actually leads to something instead of being a stagnant dead end.

I still dream of the day that I can walk up to someone and immediately have those amazing discussions about life, love, fear, ambition, and all the other things that make my heart beat a little faster.

But until then, let’s take our small talk from being a chore, to being a door to something beautiful. Because we all have that beauty inside of us, we just have to get comfortable enough to let it out.

Thank you for being a part of this beautiful conversation, I love you all.

The Reason YOU Are Unfulfilled At Work AND Home

Not many people are happy with their jobs.

The jobs I’ve worked in the past usually make it on the “Top ten worst jobs” lists.

I’ve worked filling stock at a discount grocery store, bussing tables at restaurants, and the holy grail of all terrible jobs: Door to door and telemarketing sales.

Even though this seems like a recipe for a depressing life, I’ve always enjoyed my work and derived great meaning from it.

Most people work jobs that don’t fulfill them, then at home they laze around until the next shift—which isn’t very fulfilling either.

So why are we leading lives that have left us so unfulfilled?

We’ve Completely Separated Work And Play.

We’re not having any fun at work, and we’re not seeking any challenge at home.

One thing I’ve learned throughout my study of happiness is that finding meaning or purpose in your daily activities is an absolutely necessary ingredient for a long lasting sense of fulfillment.

If you don’t derive meaning from your work, and your free time is devoid of any effort or challenge, then you may be on your way to a crisis.

Finding Meaning At Crappy Jobs.

I’ve always enjoyed myself at work because I didn’t see my job as meaningless. I tried to somehow fit my work into the bigger picture or gain whatever meaning I could from those menial tasks.

When I was doing door to door I worked with a lot of miserable people. They only saw the negatives.

“It’s so hot out and we’ve been walking for hours!”
“There is too much pressure, if I don’t get commission my cheques are so small!”
“We have to work every Saturday and I never go out anymore!”

Don’t get me wrong, those points are valid. The job sucked sometimes.

But I chose to focus on something different. I would focus on my interactions with the people I was talking to. Every time someone opened a door I saw it as an opportunity to share a connection with someone new.

We joked, we laughed, we complimented each other, we even ended up talking about life over tea.

You would seriously be surprised how many people invited me into their homes and shared a real connection with me once I stopped focusing on the negatives, and started to find the meaning in my work.

Crafting Your Job To Cultivate Fulfillment.

Dr. Amy Wrzesniewski has done a lot of research into figuring out how people derive meaning from their work. She found that you can become happier with your job whether you are a CEO, a sales rep, or even a janitor at a hospital through what she calls “job crafting.”

In one study she observed a group of hospital cleaners who found their jobs boring and meaningless, and another that found their work to be engaging and fulfilling.

The second group would ‘craft’ their job in creative ways. They would engage more with nurses, patients and doctors, taking it upon themselves to uplift the mood of the people around them.

In general, the second group crafted a perception of their job that saw themselves as an indispensable cog in a well oiled machine. They weren’t just cleaning garbage, they were helping their hospitals run smoothly and contributing to a cause that saved lives.

In this mindset, these hospital janitors could find more fulfillment in their jobs than some of the doctors who might just be looking for a paycheque.

But finding fulfillment at work is only one half of the problem. We have to find fulfillment at home as well.

All Play And No Work Makes Jack An Unfulfilled Boy.

After a long day at work it is understandable that we want to relax, but it is possible to relax too much.

When we separate work from play, avoiding all effort and challenge in our free time, we are robbing ourselves of a fulfilling personal life.

In the book “Happier” by Tal Ben Shahar, Ph.D. he examines many interesting studies that look into the relationship between challenge, happiness and fulfillment.

One study in particular run by Donald Hebb jumped out at me.

In 1930 six hundred students between the ages of six and fifteen were told that they no longer needed to do any school work. If they misbehaved, their punishment was more recess. If they behaved, their reward was more schoolwork.

Hebb quickly discovered that “In these circumstances, all of the pupils discovered within a day or two that, within limits, they preferred work to no work (and incidentally learned more arithmetic and so forth than in previous years).”

Even children—who are notoriously opposed to work and love to play—realize very quickly that they would not enjoy a life devoid of challenge.

Without challenge we don’t grow, without growth we feel stuck.

Challenging Yourself At Home.

If you’re job isn’t providing you with the growth and challenge that you need for long term happiness, you have to find it at home.

That is why I learned drums, why I study self development and write these articles.

The good thing about challenging yourself in your free time is that you get to do everything on your terms.

You can pick something that you truly enjoy, even if it is just playing video games. Just be sure that you are challenging yourself, learning, and gaining some sense of meaning and fulfillment from your activities.

Breaking down the barrier between work and play is the key to fulfillment. When you are at work, have fun with with it, share connections and find meaning. When you are at home don’t just relax all the time, challenge yourself and learn something new.

It’s a challenge in itself to break down this deep rooted barrier, but if we can accomplish this, we can lead truly fulfilling lives at work and at home.

fulfillHow do you view your job to gain fulfillment?
How do you challenge yourself in your free time?
Discuss in the comments!


Here is a secret.

I don’t know where my life is going.

I have goals, hopes and plans, but there is no way to know whether any of them will work out.

There are a million situations that could arise at any moment and change the entire course of my future.

Even if nothing life changing happens externally, in six months I could be a different person with different goals.
You never know.

You might think this is a negative way to view life, but I find it to be freeing.

When you are looking too far forward into the future the uncertainty can seem daunting.

But every marathon is finished step by step, every wall is built brick by brick and every life is lived day by day.

If you live your life trying to get as much out of each individual day as possible, you can rest assured that you have done all you can to achieve a life that makes you proud.

You have to design your days to design your life.

Here are three things you can do to ensure that you get the most value out of today.

days count

Do something that moves you forward.

This is anything that improves you physically, emotionally, spiritually or intellectually.

It is important to try and improve yourself at least marginally every day.

Read a book, go for a walk, meditate or hit the gym. Whatever you have to do to feel like you are a slightly more balanced and stable person than you were yesterday.

When you get into the habit of doing something that moves you forward every day, you will never be stagnant.

You will feel like a completely brand new person every six months.

Do something you haven’t done before.

Without novelty in our lives the days seem to blend together in a mix of early morning coffee spills and beaten up alarm clocks.

It’s hard to notice when your life has been going on autopilot. You look back in shock as you realize that you haven’t done anything new in months.
Where did the time go?

Novelty is the spice of life. Go to a film festival, check out a farmers market. Do something you’ve never done before, go somewhere you’ve never been before.

Add some colour to your life to prevent it from becoming a symphony of greys and blacks.

Do something selfless.

There is no better way to have a meaningful day than to devote some of your time to something other than yourself.

There are more than seven billion people on this planet but we often only think of life from our own perspective.

Devoting some of your time to others can help you see life in a new light.

Spend some time volunteering, reach out to a friend you haven’t seen in a while or show some love to your pet.

Any time spent on someone else, is time well spent.

You may not know what will happen in the future, but decide what happens today.

If you consciously try to get value out of every day, you will have a valuable life.

A life with meaning is a life well lived, but your whole life doesn’t happen at once.

It’s built brick by brick, step by step, day by day.

As always, I’ll see you next Sunday.