Scott H Young

I have to say I’ve been dissatisfied with the current self-help information on communication. Much of the material I have read focuses on how to become a more empathetic listener, problem solver or better transfer information. Very little focus is put on what is probably the most common form of communication, the conversation.

Learning empathetic listening skills and effective communication of your ideas is great for when you need to understand and relate, especially in high intensity situations. Unfortunately, most of the time you talk with others it isn’t to find solutions to a mutual problem or to gain a deep understanding but simply to relate or entertain.

People don’t judge you so much for who you are as they judge you for how you communicate yourself. And most of this marketing is done through conversation. If your conversation skills are poor you will appear boring, humorless and unlikable. Conversational masters make friends easily and others genuinely enjoy spending time with them.

Seeing as your social life depends on you being a great conversationalist, what can you do to improve your own skills and become the person everyone wants to be around?

Conversation Isn’t About Content

Here is the first rule of conversation: It isn’t about content. A lot of people falsely assume that conversation is more what you are talking about. This is wrong. Conversation is a lot more about how you communicate than what.

I’ve had fantastic conversations with people that were about something completely trivial and unimportant. My first impressions about people were often based on similar discussions. People don’t have most conversations to get information but simply to interact with other human beings. It is about entertainment and subtly proving you are a person worth being around.

There is an old quote I like, “Who you are screams so loudly I can’t hear what you are saying.” This is a great example of what I am talking about. Conversations aren’t so much about the content about your speech but really what that speech says about you. Are you interesting? Funny? Important? Likable?

I come from a family of conversationalists so I know the difference between sharing a great talk with someone and struggling to keep on a boring interaction. When I talk with someone who shares this skill we can talk about anything and make it interesting and great. With other people they can have great material but still come off wooden and dull.

People Don’t Care About You

Unless of course, you are interesting. One of the worst mistakes someone can make when having a conversation is the belief that people have any real interest in the events of your life unless they make great conversation. Ever have dinner with your spouse or friend and ask, “How was your day?” That sentence alone indicates you are struggling for material.

People don’t want to find out about you from what you explicitly say. Telling everyone you are a banker who likes to golf and take long walks on the beach doesn’t say much about you. But if you have a conversation about how you eat crackers and you make them laugh you will speak volumes about your personality.

I think this is often a big problem when people first meet in a more formal context like at a wedding, party or for a date. They ask questions like, “What do you do for a living?” or, “Where did you grow up?” or my personal favorite, “What do you do for fun?” Although these questions can trigger interesting conversations the actual information gleaned from them doesn’t make a noticeable impression.

The Three Skills of Conversation

In my opinion there are three major skills that come with being a master conversationalist. Skill in these three areas makes the difference between someone who can leave a great impression, magnetize people and form friends. By now I hope you realize that these skills rarely have much to do with what you say as opposed to your personality and who you are.

Be Funny and Interesting

The first part about being great at conversations is to simply be both funny and interesting. If you are humorless and dry people will quickly forget you and likely form a neutral to negative impression about you. Without interest you appear very mono-dimensional and boring. If you lack one category you can make up by including more of the other, but a lack of both will kill conversations.

Humor is an incredibly complex skill that can’t be learned overnight. It takes a lot of practice until you can figure out the natural timing and flow of a joke. Once this rhythm sets in, it will become part of your personality. Practice makes perfect.

If you aren’t naturally funny the best way to start is to simply start asking yourself, “What is funny about this?” Generally the reason most people aren’t funny is simply that they think of something funny but fail to effectively verbalize. Keep trying and eventually the timing will set in.

If you have trouble thinking of funny things to say, read some jokes and try to work them into your conversations. Using scripted humor isn’t as good as genuine humor but it can be good training material until you get your funny bone.

Interest comes from having an interesting life. You can be interesting by telling stories (which I’ll mention later) or by simply being quick to bring up an interesting fact. Interest is similar to humor whenever people discover something they didn’t expect.

A favorite piece I do when conversation gets dull is to ask this question: If I fold a piece of regular paper in half fifty times, how thick would it be? By asking this question and getting answers (most are usually within the range of six inches to a few feet) you can astound people with the actual answer. A piece of paper folded on itself fifty times will be approximately the distance between the earth and the sun in thickness. (.1(mm) * 2^50)

Why is being funny and interesting important? Shouldn’t people like you for who you really are? The answer is because people rely far more on conversation than a resume to determine who you are deep down. I recently heard a statement which I thought to be incredibly true: “You tell one joke and it was a funny joke, you tell ten and you are a funny person.” People will judge you based on conversation skills so get over it and start practicing.

Tell Stories

The second skill in being a great conversationalist is to know how to tell a great story. Being funny an interesting is great but when you can only pull off one liners you won’t create the intensity of interest you want. People relate all things through metaphor and story and becoming a great storyteller is critical to creating a connection.

So how do you tell a great story? Being a great storyteller is incredibly complicated so if you end up getting “uh-huh’s” from people after boring them into the ground with your mediocre tale, it is going to take a lot of work. But the basics of good stories is fairly simple and by practicing them you can hone the finer details of your conversational craft.

Rule One: Know Where You are Going

A story is told simply to provide context for one or a sequence of interesting points. Don’t tell a story just to tell it. You need to have an interesting point to make it worthwhile. If your story has a couple of interesting points, better, but it needs to have at least one. When someone asks you how your day was, you’d better respond with something more than the summary of your itinerary.

Rule Two: End With a Bang

Your most interesting point should be the last thing you say in your story. Saying an interesting point followed by a bunch of boring ones reduces the impact of your story. So if the main point of your story was that you met Tom Hanks in the produce aisle of your grocery store, don’t keep talking about what type of lettuce you eventually settled upon.

Rule Three: Keep it Short or Keep it Interesting

If your story only has one really interesting point, keep it short. People will stop paying attention if you spend fifteen minutes to provide only one interesting point. If your story needs to be longer, pace it out with humor or interesting points to keep the attention sustained up until your final point.

Rule Four: Keep it Personal

People prefer stories about people they know. Try to only use stories that somehow involve you. Just because a friend has an excellent story doesn’t mean it is worth retelling to people who never met her. Conversational stories are interesting because they form a window into your life from an intriguing context. Even fantastic stories that are unrelated to you or the person you’re talking to will appear noticeably dryer. This is a common mistake by people who don’t realize that I (or any other human being) don’t care about people I’ve never met before.

Rule Five: Don’t Grasp for Stories

In an effort to get a conversation going a lot of people start grasping for stories to tell. Questions like, “How was your weekend?” are a perfect example of story grasping. You should have enough material that questions like that are a last resort. These statements should be used out of kindness but you should always have a great story as back up if the person can’t think of one.

Rule Six: Practice Your Stories

A story can be told more than once. I have many stories, anecdotes and humorous topics from which I know people react favorably to. Whenever the conversation needs it I simply use one that I haven’t used with this group of people before. The more you tell a story the better you get the natural timing and emphasis. Just don’t reuse the same story with the same people.

Watch the Tempo

The third skill to understand when mastering conversations is to understand the natural tempo and rhythm. Each communication you have will have a natural flow of ideas at a certain relative speed. This also relates to how fast the switch-offs between speakers are and the amount of pauses.

If people are having a very fast conversation, don’t break out a slow building fifteen minute story with just a few points of interest or they will be dying to interrupt you the entire time. Don’t bother speaking if you can’t capture attention, and people aren’t paying attention when they have their own story to tell.

If you don’t have an incredibly valuable story for a fast conversation it is probably best to stick with interesting or funny quips instead. Slower paced conversations, however, can make use of a long story which can then provide fuel to speed up the tempo.

Conversational rhythm is of critical importance when you are trying to enter a conversation, particularly with strangers. Starting out with a long story isn’t nearly as effective as offering a quip. Once you integrate yourself into a conversation you can start offering longer stories to fill the space.

Often people don’t go and meet people because they aren’t sure what to say. The key is simply to throw a small comment. Small quips are like asking for an invitation and if they get a response you can easily work your way into even the most high energy conversations. When your humor and interest skills become worked into the deepest levels of your personality you can enter just about any conversation smoothly.

Communication is largely about conversation and when you begin to understand this you will improve your relationships. Ultimately it breaks down to improving your ability to use humor, interest and tell captivating stories. Watching the tempo is critical so you can smoothly insert your conversational skills and join any conversation you want. Have fun conversing!

“The best way to get a better answer is to start asking a better question.”
-Tony Robbins

One of the biggest challenges you will ever face in your life is to look above all the minor distractions of today and envision the bigger picture. Unfortunately most people are so caught up in the minutia of daily life that they neglect to ask the right questions. I hear a lot of questions from people wanting life to be easier or for more success.

In my opinion asking for ease or success is asking the wrong question. I think these questions are based off the idea that the most satisfying life is the one with the least troubles and the most results. I disagree. I would say the best life is the one that is the most interesting. As you approach your own end the ease of your life or sustaining results won’t matter nearly so much as how you lived the process.

Here are nine steps for taking a dull or mediocre existence and creating a life that is actually worth living. A life that is interesting.

Step One: Meet More People

One of the best ways to make your life more interesting is simply to have a larger social reference group. Each connection you make with another human being is like a small opening into their world. If that connection is valuable then many of the interesting events, ideas and growth they experience can be shared with yourself.

Some people who are poor at meeting new people justify this outlook with an elitist attitude. Other people are inferior (ignorant, unkind, shallow, mean) in some way so as to justify not meeting them. Unfortunately this attitude corrupts every relationship you form and you become stranded on a social island.

I disagree with the psychological hypothesis that says our tendency towards meeting new people and forming relationships is fixed and unchangeable. I am incredibly outgoing today but this wasn’t always the case. I can remember times just a few years before where I had trouble sustaining more than a few friends, now I know hundreds of people and have strong ties with a few dozen. Socializing is a skill that may come from birth but can certainly be learned through practice.

Step Two: Take Up New Hobbies

Remember that activity you always wanted to try but never had time for. Do it now. Life won’t wait for your schedule to clear up so you need to take the initiative. I’m not saying you need to abandon all your duties, but you need to actively invest some of your time in trying new things.

Don’t stick to one hobby for too long either. Most hobbies are non-essential skills so achieving a mastery level of them generally doesn’t yield much more benefits than proficiency. If you love your hobby stick with it, but it is important to keep trying new things to keep your life interesting.

Not sure where to start? My personal advice for a ‘hobby’ everyone could benefit from is to go stop by your local Toastmasters club. Communication is the key to life (and meetings are fun too). Besides if you enjoy it you might just complete steps one and two at the same time. You can find a club in your area here.

Step Three: Be Spontaneous

I must say that my ability to be spontaneous was incredibly low until just recently. I was a big fan of having a fixed schedule and sticking to it. Only later did I realize that by sticking to a rigid schedule I missed as many opportunities as I capitalized on by using it. Spontaneity isn’t a hard skill to learn, it is combining flexibility with discipline that is difficult.

Successful flexibility comes from having a very strong inner sense of discipline. This is the ability to act upon opportunities knowing the costs associated. Without this inner discipline it is too easy to waste time pursuing opportunities when demands are placed on you.

Ironically the key to practicing this discipline has to start with a fairly rigid approach to productivity. From this point slowly act on more and more spontaneous opportunities all while adhering to the things you need to do. Eventually you should be able to recognize the costs associated with taking up an opportunity or not without requiring extreme rigidity.

Step Four: Tackle Fears

The ultimate enemy of an interesting life is fear. Boredom is just another symptom of fear because you are limiting yourself within a box of ‘safe’ activities. When you build up your courage to taking down fears your life suddenly becomes a lot more interesting, challenging and most of all satisfying.

I’ve written fairly extensively about overcoming fears already, so if you would like to so you can check it out here.

Step Five: Do Things You Won’t Like

This may seem like a very bizarre step, but it is essential to creating an interesting life. Every once in awhile you need to step outside your zone of preferred activities and test the waters of activities you dislike. You might be displeased or you might just discover something you now enjoy. Many of the things I now love I once though I would hate.

Have no rhythm? Take some dancing lessons. Not an athlete? Join a community sports team. Everything you make in the kitchen starts on fire? Try some cooking lessons (and pick up an extra fire extinguisher).

Step Six: Add Some Spice

What’s the spice of life? Variety of course! If there is one thing you can do to create a more interesting life it is to add more variety. Humans are habitual creatures and readily settle into patterns of behavior good or bad. You need to mix up your life by breaking out of these patterns and doing something completely different.

This may seem like a complete turn around from someone who wrote an entire series on forming habits. I trust you it isn’t. The amount of habits you consciously choose to install will be less than 1% of all the habits you use every day. Most of these habits are neutral or worse and could use a good shaking to add some variety.

So take a different route to work next morning, try a different breakfast or listen to a radio station you have never heard before. And that’s just before you get to the job. There are endless ways to add tiny bits of variety and while it might seem trivial, it is essential to make each day worthwhile and memorable.

A friend of mine introduced me to an interesting challenge to add more variety. Next time you go to the grocery store, head over to the imported foods aisle and pick out one item you have never had before. Last week I had plantain chips and guava juice. Today I have grass jelly juice cooling in my fridge.

Step Seven: Orient Purpose Outside Yourself

You want to know what it is the best way to feel awful and miserable all the time? Keep thinking about all your problems. Maybe it is time to stop worrying about that garbage and instead focus on helping other people solve their problems? Not only does this make others appreciate you more and strengthens relationships, but it makes your life more interesting as well.

Many people wrongly assume that helping others is something you do purely out of altruism. This is incorrect, you help people because helping others helps yourself. Why do you think your body is hardwired to feel good after being charitable? Because being charitable helps you as well. It’s win-win!

Solving others problems doesn’t usually bear the negative weight that tackling your own does so it is a great way to add interest to your life without the burden of more and more challenges. Even if it is as simple as trying to make people laugh or feel good. When you orient the purpose of every interaction outside yourself you get to experience an interesting life.

Step Eight: Abandon Dead-End’s

Pursuing goals is a great way to fill your life with more passion and interest, but there comes a time when your goals no longer inspire or hold the same fire they once did. Abandon any pursuit that no longer holds the value it did when you started. There is no honor in finishing something that has lost meaning. The person who said, “Always finish what you start.” must of had a very boring life.

I’ve made the mistake of giving up on goals because I felt they were too hard. This was a bad mistake, but I usually take up a new challenge when I grow restless. Unfortunately a bigger mistake is to keep pursuing a goal that has lost value. I’ve done this and wasted solid months and years pursuing things that when I finally arrived at them resulted only in emptiness. Abandon a dead-end and keep every moment interesting.

Step Nine: Never Settle

When most people tell you not to settle they mean don’t give up until you have exactly what you want. Although this is an important lesson I’m using the term settle in a different way. When I say don’t settle I mean don’t lock your life into a set of behaviors and experiences. Your life should always be growing, expanding and fresh.

Now I know what you’re thinking, sure this is fine advice coming from a young man with no commitments but I have a spouse, children and mortgage payments. Of course we all have varying responsibilities which we need to uphold, but what you are really offering is just an excuse. You can grow and expand in any setting no matter the restrictions, so long as you have conscious power.

Being in a situation with more responsibilities simply means you need to be more creative in keeping life fresh. Nobody will care that you wasted your life because you had to. If there isn’t a way, make one. Don’t excuse yourself out of a great life.

Of course these nine steps are just the start. What would you recommend to make life more interesting? I’d love to hear your responses.

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