How to Systematically Expand Your Comfort Zone: My Scandalous Australian Story and the Great Life Secret it Unveiled

Today, I’m going to share with you a story I’ve never written about anywhere.

comfort zone

For the last 2 years, I haven’t had the guts to do it…

Even writing about it today still feels outside my comfort zone.

It’s probably going to surprise you, shock you and make you smile, too.

Whatever you reaction is, your perception of me is definitely going to change after you’ve read this…

But it’s a part of my life story and it has shaped the man I am today, so whatever happens, I’m cool with it.

This story made me bolder, more confident, and helped me overcome my shyness in a big way (yes, I used to be shy, especially around new people).

It’s a big reason why public speaking doesn’t scare me, why I’m comfortable in social settings, and why approaching beautiful women is a lot easier than it used to be.

This story will also teach you a powerful lesson.

You’ll discover an unconventional way to build enormous courage, grow your comfort zone way beyond its current size, and become the type of person who can handle any situation, no matter how weird or crazy it is.

All right, here we go…

Living the Australian Dream… Almost

Let us begin this story in February 2011.

I was living in Perth, doing my MBA at the University of Western Australia.

My life was awesome on many levels… School was going well, the weather was fantastic, the beach was magnificent and the Aussies were as friendly as ever.


There was only one thing cramping my style: my job.

I was working as an administrative assistant for a local company, and while I made decent money, it just wasn’t that much fun.

Lots of paperwork, Excel spreadsheets and other admin stuff. Not my cup of tea.

One day, I decided I’d had enough.

I was 24 years old, in perfect health, living in one of the most beautiful cities in the world…

What the hell was I doing wasting my precious time doing boring work?

My intention for my 17 months in Australia was to live life to the fullest, experience as much as possible, and really put myself “out there”.

My job just didn’t fit with this grand plan.

I made up my mind quickly and decided to quit the job.

I still needed to make some money though… so over the next few days, I declared to myself and the Universe that I was going to find a new, better job.

This new job was going to fit 3 criteria:

1)   Good money
2)   Not a lot of hours
3)   A lot of fun

Nothing unreasonable, right? :)

I had no idea how this was going to happen, but I knew it’d work out somehow… as it always does.

The Strange Phone Call that Changed Everything

About 2 weeks later, my phone rang.

I looked down, and it was my buddy James.

The conversation went something like this:

Phil: “Hello?

James: “G’day mate!

Phil: “What’s up James? How are you?

James: “Ah mate, things are just great. I got a new job and I’m loving it.

Phil: “Oh that’s awesome, good for you! What’s the new gig?

James: “Well, you know how in Australia when a woman gets married, her friends throw her a party… it’s called a Hen’s Night.

Phil: “Yeah sure.

James: “Well, for my job, I essentially go to Hen’s Nights, serve drinks and food, and make sure the girls are having a good time.

Phil: “Man, that does sound great!

James: “Yes is it… Well I should tell you, there’s one more thing… When I go, I have to be in my boxers and wear a bow tie. But that’s no big deal.. It pays great money, it’s just a few hours a week and it’s a ton of fun.

Phil: “Woah.

***Time out***

Now, you gotta put yourself in my shoes for a second. The Universe had just delivered my job request, except not at all in a way I had envisioned.

At this point, I knew I was at a mini-crossroads in my life.

I had two options:

1) I could tell James I was happy for him and change subjects…

2) I could figure out how to get involved with this crazy job…

***Back to the story***

Phil: “Dude, that sounds awesome. [Takes a deep breath] Hmmmm…. Do you know if they’re looking for more guys? I think I’d like to give this a shot.

James: “Yeah mate, I’ll put you in touch with my boss. I think you’d be great for this.

Phil: “All right… Let’s do it.

I hung up, smiled, and burst out laughing.

Oh man… I had a feeling things were about to get real interesting.

Over the next few days, I got in touch with the boss, sent him a few pictures of myself, and he hired me.

Game on.

Merely a few days later, I received this text from my new boss:

G’day Phil! Get ready, you start work this Saturday. Here’s the address, show up at 3pm and wear some nice board shorts. It’s a pool party. Good luck.

I stared at the text, and realized that this was actually happening…

My First Day on the Job

When I woke up that Saturday morning, the first thought that came through my mind was: “Oh shit, I have to go to my new job this afternoon.”

My mind started spinning and I got super nervous.

And it was still 6 hours away…

I tried to go through my day normally, but I couldn’t stop thinking about it.

Like I said, by nature I’m pretty shy when it comes to meeting new people so this was WAY outside my comfort zone.

Eventually, it was time to go…

I got in my car and drove off, trying to stay cool and composed.

I got there, parked the car, and met up with the other waiter in front of the house.

Luckily, for our first time, we were paired off with someone else, so I didn’t have to do this all alone.

I could hear the music blasting in the back of the house and the girls laughing.

While this might sound awesome, it only made me more nervous in that moment.

I told my new colleague: “Hey man… I gotta be honest, I’m really nervous about this. Do you think we’re gonna be all right?”

He laughed and told me, “Mate, don’t worry. You’re all good. Just smile, have a good time and it’ll all work out.

That made me feel better… a little bit.

We started walking toward the back of the house, and I knew there was no turning back.

My Debut as a Topless Waiter

As soon as we walked through the pool gate, I had a vision of paradise.

25 attractive girls in and around a pool, wearing bikinis and having a blast.

Clearly, they had already had a few drinks… and they were really excited to see us. They all started screaming and giggling.

One of them ran over, welcomed us, and put a policeman hat on each of our heads.

This was definitely going to be an interesting afternoon. 

We asked what we should do and she told us these sweet words:

Make sure the girls have a drink in their hand, and a smile on their face.”

Mission accepted!

Over the next 2 hours, I served drinks to the girls, played games with them and took a few dips in the pool.

Eventually, they told me…

Phil, we have a big favor to ask you. We’d love to do body shots off you, is that ok?”

I thought about it for a very short second, and agreed. :)


After a few hours of wild times and semi-decadence, I got back in my car and drove home… with a giant smile on my face.

I knew I had just found my job for the rest of my Australian journey.

9 Months of Adventures, Sexiness and Comfort Zone Challenges

After this successful first event, I became a regular and now had a “gig” every Saturday night.

Even though things had gone very well the first time, I was still super nervous every time I headed to a new party.

It was the ultimate uncertainty scenario: I never knew in advance who the girls were, and how they were going to be.

They could be young or old, classy or crazy, fun or just weird…

I never knew what I was getting into. I walked in the door while 20 women stared at me and made excited noises.

Each night, strange/funny situations would invariably arise and I would just have to roll with it.

One of the funniest thing about all this is that I was living a very unlikely triple-life:

MBA student during the day, personal development blogger at night and topless waiter on the weekend. As you can imagine, there was rarely a boring week.


For the record, I was not a stripper, I never got naked (I promised it to my Mom when I told her about my new job…), and I always kept it relatively classy. :)

I have tons of funny stories about what went down during those nights, and if we ever meet I’ll be happy to entertain you with a few.

But funny stuff aside, I learned a very powerful lesson during that period of my life, and I want to share it with you.

The Fastest Path to Expanding Your Comfort Zone

You’ve heard it before: the more we get outside our comfort zone, the more it grows, and the more courageous we become.

But here’s the problem: we are hardwired to avoid getting outside our comfort zone. Our survival instinct makes it extremely hard to voluntarily do things that are uncomfortable.

So how do we navigate around that? Here’s one solution:  we have to structure our life in such a way that we consistently do something uncomfortable EVERY WEEK.

We have to schedule it. Make it non-negotiable.

For 9 months, every Saturday, I was nervous as heck on my way to the party. But I couldn’t back down. And as a result, every week my comfort zone grew a little bit.

Nowadays, I do it in a different way. I go salsa/bachata dancing at least twice a week, and even though it’s fun, it’s really challenging for me (that’s a whole other story, for another day).


To make sure I don’t get soft and decide not to go, I have to pay my friend Mariah $20 if I ever miss a class… 


So how can YOU systematically increase your comfort zone?

Here are a few recommendations:

1)   Sign up for improv classes
2)   Sign up for salsa lessons
3)   Go volunteering in a soup kitchen
4)   If you’re in school, raise your hand at least once in EVERY class
5)   Sign up for martial arts classes
6)   Join a debate team
7)   Become a topless waiter :)

The 2 important things to remember are:

1)   It has to be every single week, not just when you feel like it.
2)   There has to be a consequence for missing. I recommend giving $20 to one of your friends or charity. You can use Stikk to track it.


While I’ve now retired from topless waitering, I’m still committed to stepping outside my comfort zone every week.

I know without the shadow of a doubt that being able to overcome my fears is a pre-requisite to living my dreams, so I’ve made peace with it.

And I’ve learned something pretty neat… The best, most exhilarating, most memorable times of our life… always happen right on the other side of our fears.

So let me ask you… How are you going to systematically increase your comfort zone? Let me know the comments section below.

Choose Greatness (and Sexiness),


Please share this post because that’s how more people can learn to play outside their comfort zone. 

"PS. Ever feel overwhelmed when trying to reach your goals? Watch my TEDx talk to learn how to stop slowly killing yourself while accomplishing more."
Posted on : 22, Jul 2013


  • Hahahaha. I’m glad you decided to post this… Talk about pushing your comfort zone ;)

    Fear is like going on a roller coaster. The ride up can be very anxious and scary even if you aren’t used to it, but when you start going down it can be the most fun ride of your life.

    It seems like that’s exactly what happened when you took on the job of being a shirtless waiter.

    Frickin’ Awesome.

    I also recommend StickK. It’s helped me stay accountable every week with my writing and business goals, and in one case, I actually lost $10 to a friend because I didn’t meet my goal. I won’t let that happen again because it’s WAY worse to lose money that can be reinvested in my business.

    If whoever is reading this is having trouble with their goals, you HAVE to give StickK a try.

    Choose Sexiness,


    • Love the roller coaster analogy! So true…

      Really proud of you for stepping outside YOUR comfort zone and moving to Boulder next week… Get ready, we’ll have some crazy things in store for you.

  • Hahaha. I read the title as “… and the great SECRET LIFE it unveiled,” and thought that maybe you were going to reveal what woman who hold parties with topless waiters talk about behind closed doors. Now that would be scandalous … :P

    Looking back, I’ve done a lot of this kind of stuff in my life, but I’ve been mostly just sticking to my comfort zone since I got back from Costa Rica. I do feel that it has helped me regroup, but it’s time to really start putting myself out there again!

    Thanks for the continued inspiration, Phil!

    • LOL! Dude it is a SECRET LIFE out there… Women are so different where there’s no men (or only 1) around.. It was really fun/fascinating to see.

      What’s the first thing on your agenda to get outside your comfort zone? WIth your move to Burlington, you’ve got a whole variety of options in front of you…

      • Pickup beach volleyball. Tonight. I’m going alone and I don’t know anyone there. Also, I’m not that great at beach volleyball.

        And then I’m going again on Wednesday.

        Time to start rocking it :)

      • It’s on like donkey kong.

  • Phil I have so much to learn from you and the articles you write. You always do the thing I want to do, giving it your all. Thanks for the funny and helpful story keep up the good work!

  • Definitely a great post Phil! What a perfect experience to share that incorporates smashing your comfort zone and embracing change. Keep it up!

    • Yeah man, definitely a 9-month period I’ll never forget! :) What do you want to start doing to systematically step outside your comfort zone Adam?

  • Not what I expected :)

    • Haha, it was pretty hard to see it coming :)

  • This is such an awesome post! Thanks for putting yourself out there – I guess in more ways than one! I think it’s great that you now have those stories and it definitely adds to your character. And I agree that you HAVE TO schedule getting uncomfortable into your world, and create some accountability to get it done.

    I loved reading this post and appreciate you sharing a somewhat private journey with us. I am definitely looking forward to hearing more of the details!


  • Thanks for this! And, as always, in just a right moment. The owners of a raw food restaurant where I work decided to leave me to manage everything as they are going to the sea side to work for a month. So talking about responsibility… way out of my comfort zone, but I’ll do my best and hope it all goes well :)
    Cheers dude! ;)

  • Hi Phil, hehe, I was at the hens night you did in the wheatbelt on that farm where we did the pub crawl in the bus to other towns.Do you remember we got to Nungarin and the pub was shut(about 10pm) so we stood out on the footpath and yelled up to the window til the guy came down and opened it up for us :-) You and I chatted for some time after back at the house about the law of attraction and and our power to create whatever we want. I really enjoyed that talk, even though the other girls prob just thought I was chatting up the hot dude :-) Im in the photo you have posted, the blond next to the ‘hen’ and you. Great job getting way out of your comfort zone.I am atm as well, on the other side of the world in Europe while my family is back in Aus. Travelling alone is a great way of getting back to yourself. Cheers. BTW you were a great topless waiter, and you didnt look nervous at all!

  • I’ve been following for a year and a bit – and just wanted to tell you I enjoy your blog – and this post :)

    I completely love the comfort zone – fast track – boost sort of situation. I had never experienced it until last year when I was in istanbul and bought a bus ticket for Iraq – and got myself on that bus – 30 hours later I was alone in Iraq. When I returned to Turkey – and then on to India – you cant even imagine the ridiculous confidence I had – talk about out of a comfort zone. Iraq!
    :) Thats my little story. I hope I get to hear your other ones about your Aussie job some day :)

  • Great post Phil.I am surprised indeed but much respect to you man how you turned your experience into a lesson.Oh and i took your advice and signed up for Krav Maga Classes :D :)

  • Best. Post. Ever.

  • HAHAHA YES! So happy you posted this. I was randomly talking to my mate today about this very job you had, trying to explain what you did – I can just point him to this post now.

    There is no having (crazy) fun if you stick to the comfort zone. With that said tomorrow I’m 4WDing to Zambia for a self drive safari… With nothing booked and improper paperwork for exporting a car from Malawi. TIA, but YOLO. Lets see what happens

    PS you owe me a Bowtie!

  • A great message wrapped up in a fun story. I’m thinking about the ways to expand my comfort zone.

    I think your exotic Australian job is exactly the kind of adventure one has to have when he is young, in good physical shape, and full of energy. And it’s also a great way to build self-confidence.

    P.S. You can now give expert pick-up advice, “as a retired topless waiter.” ;)))))

  • Oh my gosh Phil, this was HILARIOUS and I am so glad you wrote it. I was laughing out loud. Thanks for stepping out of your comfort zone so we can step out of ours.

  • I was expecting a serious post but this got me laughing healthily. Brave of you to reveal :) I will have to make it to Aussieland one day!

  • Haha… cool post man. I thought this would be something along the lines of your parents being extra terrestrials or something wacky like that..

    Great job.

  • Wol…Really interresante and fun history

    And motivated me to do something I want to do some time, acting classes

    I will sign this week

    Thanks for sharing and keep inspiring us

  • I absolutely loved this!! I have been following your site for awhile – love the positive vibes (that’s what it’s all about) – but this story–Loveddd ittt!! I had a friend who did this in Australia for awhile too…Man, the perks of being a man in this instance. So happy for you that you took the plunge and opened up your world. Life is for living, and it sounds like you’re living it to the fullest. How long ago was this?

  • Oooooooooo phillllll…..hahaha……………

  • Can I know more examples of doing something uncomfortable every week which is easy and can be done at home??

  • First I would just like to say thanks for your posts they are always very motivational. Its funny you mention getting out of your comfort zone because I’ve actually been thinking the same thing to myself recently. A friend and I have been going out to Downtown Orlando and talking to women who we otherwise would have never had the guts to talk to and its tough at first but it builds up your confidence greatly if you keep at it. I have been looking for other ways to get myself out there and I never actually thought of taking Salsa lessons! I think its a great idea as well as a good workout. I may also have to consider the topless waiting haha

  • PHIL !

    This was a priceless story and gave me my 1st laugh out loud moment today, nice!

    I emailed you early last week to hopefully hook up a Skype call soon in regards to chatting about life after Speaker School. Currently in the middle of reading Give and Take which you recommended, thanks bud!

    Want to schedule a call sometime in early August? If you’re open, email me directly. Look forward to hearing from you.

  • I was literally just beginning the design of a “Wanderlust Schedule” for myself. That rush you get from sheer uncertainty will never go away and the overall feeling of “that wasn’t so bad” calm is extremely empowering. I relate it to teetering around a cold pool. That goes for diving into that book, talking to that girl/guy, quitting that job or whatever “red pill” moment you harness with a good ol fashioned F!CK IT!

    Truly the genesis of growth and not adding to the list of Jason Bourne skills and activities you plan to do on that mystical “one day”. I’m jumping into salsa and Pimsleur Spanish myself. Awesome Morning Yoga video by the way.

  • This reminds me of something I read once: “life begins outside of your comfort zone”

    It’s interesting and funny to see how you took that quote to the next level :)

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  • Hey Phil, one of your coolest posts by far.
    I will leave Germany in 3 weeks to travel Australia for a year.
    I was never longer away from home than 2 weeks right now.
    Some friends are doing the same, but i decided to travel alone just to totally crush my comfort zone. With every day that passes I get more nervous, but I hope all that will pay out in the end.

  • I want that bowtie back bud :P

    great post – about time this came out haha

  • Thanks for every other great post. The place else could
    anybody get that type of information in such a perfect means
    of writing? I have a presentation subsequent week, and I’m at the search for such information.

  • I really had fun reading this blog. I am challenged my self by going to the gym, It gave me new strength and comfort. =)

  • Wow, good job of stepping out of your comfort zone, seems really fun but I think i won’t be able to pull off what you just did (I have body issues and all that).

    I forced myself for a one-year membership in a gym as a way to push myself out and… well, it didn’t turn out great. I don’t do weights cause i don’t like people looking at me as I lift so I just attend the group classes there like Streetdance, Zumba, etc. Sadly I didn’t make any friends and going to the gym is kind of starting like a chore actually. There are days when I don’t feel like going because I have no one to talk to.

    So I thought to myself, “There goes my comfort zone.”

    I don’t go out much these days (for a 21-year old) but i’m sure someday I’ll be ready to go out again and try. Points for effort, right? ^_^

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  • It’s an amazing piece of writing in support of all the web users; they will get benefit from it
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  • Hey Phil,

    I am a great fan of you website. Your story sounds pretty cool and it sounds like you had the ‘Dream-job’ at that time ;)
    I have a blog similar to yours and recently published a post dealing with the importance of taking action (a topic I find related to ‘expanding your comfort zone’):

    I would appreciate if you could give me some feedback on it!

    Anyway, keep up the impressive work!!

So, what do you think?