How to get out of your Comfort Zone- Email & Coffee Challenges

If you’re not completely satisfied with where you currently are in a particular area of your life (work, health, relationships, etc), chances are that your willingness to NOT reach out of your comfort zone enough has played a direct role in where you’re currently at.

Whether you’re naturally an extrovert or naturally an introvert, we all place invisible limitations on ourselves that keep us in our comfort zone (our own version of it).

Not all of these constraints are bad (some of them are good), but the ones that are bad severely hinder us from reaching our full potential.

As human beings, we are all “creatures of habit” to some extent……..

When you were 9 years old, you probably:

  • sat in the same seat on the bus everyday
  • ate lunch at the same table at school.
  • talked the same people (your friends)

When you were 19 years old, you probably:

  • drove/walked to class the exact same route every single day
  • drink the same cheap brand of beer/liquor you were accustomed too week after week

Today you still follow many of the same habits in your everyday life, but you also carry with you many bad habits that involve imagined fear, uncertainty, and risk.

Maybe you fear making a sales or business call at work……..

Maybe you fear saying hello to the pedestrian you walk past on the sidewalk everyday……

Maybe you fear ordering something new at a restaurant (even though you’ve order the same 1st dish you tried there the past 27 times in a row)…..

Overtime though as we get older……………too many people unknowingly constrict their comfort zones to the extent that it prohibits us.

My intention with this post is to leave you with 3 challenge activities to help you get out of your comfort zone further than you currently do. Even if you’re already super outgoing, I still strongly recommend them.

You may be surprised on certain ways you still hold yourself back, without even noticing it.

Note: It’s not necessary to perform all 3. You can if you’d like, but I would suggest trying 1-2.

1. The Sidewalk Smile

The Sidewalk Smile

Don’t let the odd name for you. This entry-level challenge may be easier for some than it is for others, but it will be sure to make you a more likable person nonetheless.

Challenge: for the next three days, every single time you walk by someone, I want you to make eye contact & smile at them.

This could be as you are:

  • walking down the aisle at the grocery store
  • making your commute to work
  • taking your dog/cat for a walk (okay….maybe not your cat)

***If it so happens that you live in a densely populated city such as New York City, San Francisco, and so on, you can limit your count a little. Making eye contact and smiling at 135 people one by one in a 2 minute time span in Manhattan train station would be a little creepy.

Make sure you remember to blink too (equally important).

This challenge may feel uncomfortable at the beginning, but get past that & you’ll be fine………it’s for 3 days!

Whether you know this already or not, it is good to hear it repeated:

Human beings use body language mirroring. We subconsciously copy facial expressions of others. In social groups, this can be even more evident (laughing at parties, etc).

As Dr. Adrian Furnham eludes to in a piece here on Psychology Today, “people respond to, and evaluate, those who smile differently and more positively than to those who do not.”

While everyone else is busy with their face buried in their smart phone, you’ll be busy brightening other people’s days while simultaneously enhancing your social skills.

By you smiling at a stranger, you’ll trigger positive emotions in them as well as yourself.

It’s a win-win!!!

2. The Email Elevator

The Email Elevator

Ever felt a little nervous at first when you were communicating with a high profile individual? (celebrity, sports star, successful business person, etc)

We all have at one time or another……..whether it has happened yesterday or 20 years ago, it happens to the best of us.

Last time I can remember that happening to me a little bit was during the 2012-2013 NHL Lockout when I trained with the Buffalo Sabres.

At the first skate, each guy introduced themselves as they came into the locker room one at a time by first name:

Them: “Hi, I’m _______.”

Me: “Hi, I’m __Ryan__.”

(in my head, I’m thinking…..I’ve watched you play hockey on TV since middle school, I know your name man).

The point of this challenge is not only to reach high profile people…………but to confirm that they are indeed reachable with the proper approach.

An amazing luxury the world wide web provides us with today is that a vast amount of people who used to be unreachable (just 10-15 years ago) are now accessible to some degree to outsiders…….via email, social media platforms, a website, and so on.

Of course if you go about your outreach in a lazy/unprofessional manner, you won’t get far at all.

We’re not here to do that…………we are here to do it the right way!

Challenge: The challenge is to get in contact with 3 influential people online via email/messaging in the next 30 days.

In order for a person to count, you just need a response back from them.

It’s up to you to set the bar as high or as low as you please (getting in touch with a state Senator will often be much harder than say a local musician or author).

Here’s some examples (feel free to use them in your outreach):

  • favorite author– they are usually accessible via their website or you can interact via their social media pages. If you email them, keep it short & sweet (they are busy people too). If you go the social media route, leave some comments first to build up some rapport.
  • musician/band– most musicians are much more accessible than you think. The more interaction they have with fans, the better their brand. Put some thought into your outreach & you’ll increase your odds.
  • a hard to reach person who’s very well known & respected your industry/field
  • sports star/athlete– most are usually very accessible via social media (Twitter & Facebook- just figure out which platform works for each)
  • business leader– start building a relationship with a business person you look up to by reaching out to them. Show gratitude & respect their time (more times than not, you can get a response if you craft a solid intro)
  • Anybody you admire or who you find interesting

When I was writing a blog piece this February, titled 14 Experts Key Advice on Starting Your Own Online Business, I needed to figure out a way to get in contact with various highly influential business people (ranging from CEO’s, multi-millionaires, authors/speakers) to get personal quotes from them in a span of 2 weeks.

I used the following email script below to reach out to many of them (each varied a little bit):

My response rate back was 70% (which is astronomically high- email open rates are at an all time low today).

The email script I used is just an example to give you for reference…….but feel free to use parts of it in your outreach.

Your email will look different since you’ll be trying to ask different questions than I was for my piece.

If you’re unsure what to say, ask your favorite author/athlete/mentor a question you’re curious on. Another idea is to mention something you have in common with them, followed by a question…………

Not only will it be cool to communicate with these people, but you’ll be surprised with how much you also learn on communication skills along the way.

Since you’re already this far into reading this challenge, I urge you to give it a try.

If you don’t at least attempt it, you’re selling yourself short………only good can come from it 🙂

With having 30 days time to hear back from 3 of them, I’d first jot down a list of 10-20 people you have interest in even talking to first this week. Then browse the web (google) to determine the best means of getting into contact with them.

Then reach out to 5-10 within a few days of your research……….all this only takes a few hours total!!

If you don’t hear back from anyone after a week, tweak your strategy/pitch a little & measure your 2nd approach results.

Note: please email me with your results if you do hear back (I’d love to hear about it). If you’re having trouble hearing back & getting responses, email me your strategy & I can give you some solid pointers.

3. The Coffee Challenge

The Coffee Challenge

The Coffee Challenge is a favorite amongst the startup & entrepreneur communities, but you may not have heard of it before. Noah Kagan (an awesome internet entrepreneur who’s CEO of AppSumo & also created the “status update” when working for Facebook) popularized this challenge a few years back.

The challenge is easy & straight forward.

Challenge: Walk into your local coffee shop & ask for 10% off your coffee (then wait for their reaction).

Depending on the establishment you’re in & how flexible the employee is able to be, you may or may not get a discount on your coffee.

Whether you do or not doesn’t really matter……..the point of this challenge is to better get over fear.

Even though this challenge seems silly, we all shy away from certain types of confrontations like this at times & can all benefit from this exercise.

Why do some people keep paying annual price increases for cable/internet bills year after year? You know you can call them up & haggle them out of it……it costs them more money to acquire a new customer than it does to keep your rate where it currently sits.

Why do some people leave car dealerships without bargaining them down on the sale price? You know you have more leverage as the buyer than they do & you can walk out to choose a different dealership.

These are just two examples, but there are countless others…….

By doing challenges that push us out of our comfort zones, such as The Coffee Challenge, we realize that it’s not too hard to “just ask.”

Just ask for 10% off your coffee.

Just ask yourself why you don’t smile more often at people as they pass you during the day.

Just ask someone you admire to talk to you via email/messaging & you’ll realize that it’s possible to reach them.

As I eluded to earlier in the post, most of the limitations we face are ones that we unknowingly impose upon ourselves.

So go out there………and get out of your comfort zone.

With the 3 challenges that I’ve shared………….my hope is that you’ll now go ahead & take action in attempting 1-2 of them (maybe even all 3 if you’re feeling ambitious). I’ve done all three & have certainly learned a ton from each one.

Share this with someone 🙂


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