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The Perfect Transition For Military Leavers

Where It All Started

Despite never serving, I have always had a deep affinity to people who serve in the military. 

This feeling started when my brother joined the Royal Marines when I was 17 and developed throughout my University years whilst living with two reservists -both of whom went on to join the forces proper.

Partly due to this multitude of connections and partly due to my healthy appetite for ‘socialising’ between the ages of 17 and 26, I was mixing with one group or another, seemingly on a weekly basis. 

As I have mentioned before,  if you really want to get to know someone, go to the pub with them. 

With this theory in mind, I got to know a whole host of Marine and Army personnel extremely well during my formative years.

If You're Going To Do A Job…

Aside from the robust banter and iron-clad trust that exists between military folk, their default setting of approaching EVERYTHING they do at 100%, is what I admire and relate to most.

Whether playing a game of ‘see who can spend the most time at the bar naked before being thrown out’ or deliberately skiing into each other, the games were a notch or two above what everyone else played…and I loved it!

As I have said many times, if you're going to do something, damn well do it properly.  Well, this is a sentiment wholeheartedly shared by all those who serve.

Why I Am I Writing This?

But this is not a Ramble extolling the virtues of those in uniform. 

That introduction was merely designed to provide some background as to my current business relationship with those in the armed forces and to illustrate the deep foundations that shaped it.

Let’s cut to the chase shall we?  I believe many military personnel are tailor made for a life as Untamed Entrepreneurs and the following words will explain why.


For those who haven’t read my last Ramble, it is probably wise to start off by defining the term ‘Untamed Entrepreneur’.

‘Untamed Entrepreneur’: Noun, often referred to as ‘UE’

“A person possessing an entrepreneurial mindset who engages in both life and work activities in an unconventional manner.  They are distinguishable by their gregarious nature, disregard for half measures and insatiable appetite for adventure, fun and challenge.”

Untamed Entrepreneurs prioritise the following in no particular order (excluding family):

  • Running their business
  • Outdoor activities
  • Extreme sports
  • Adventure/travel

Now we understand the fundamentals of what makes a UE unique, let’s look at why I believe military personnel are so well suited to this lifestyle.

To keep this analysis simple, I shall cover the two aspects that most clearly define the life of a UE: work and play.

Work Time - Why Do People In The Military Make Good Entrepreneurs?

It is a well-worn theory that military leavers make good entrepreneurs.  Indeed, a study at Syracuse University in the USA established that a staggering “49% of WWII veterans went on to own or operate their own businesses.”¹

Amongst other things, these theories typically cite hard work, problem-solving and resilience as key factors in a successful cross-over - and they are all correct.

To make a successful Untamed Entrepreneur however, a few additional ingredients need to be in the mix - most notably, a willingness to not only embrace the unknown but actively seek it. 

For the Untamed, unchartered territory is where the juices really start flowing.  The thrill of not knowing what’s around the corner or even how to get to the corner, is the business equivalent of kayaking off an unknown waterfall.

The moment the learning curve slows and the comfort zone expands, boredom sets in.  On to the next challenge.

This eagerness to potentially bite off more than one can chew and then chew like crazy, is one shared by many military folk. 

For soldiers and officers alike, the base level of excitement required to offset boredom is far higher than in most of us.   After all,  adrenaline rushes -whether through combat or competition- are one of the main reasons most of them signed up in the first place.

So what is a leaver to do once the the uniform is handed back and civvy street beckons?  What possible work exists that could even come close to the thrill served up by the armed forces?

In reality, aside from doing the same type of work in the private sector, I imagine nothing comes close and it is this step-down in pace that causes many leavers problems as they make the transition.  But it doesn't have to be so…

Keep Up The Pace

Enter stage left Untamed Entrepreneurialness…ness.  A perilous blend of unpredictability, risk, excitement and reward.

Entrepreneurship is a tough gig.  It’s a fast-paced, dog-eat-dog world where only the fittest survive.  Harsh lessons come thick and fast and there is no hiding place for the weak.

Sound familiar?  It should do.  It bares much resemblance to military life.

As I know it, military folk thrive in a ruthlessly competitive environment where the correlation between hard work and success is direct and progress is measurable…Don’t put the work in and suffer the consequences - simple.

Whilst the consequences of failure in the business world are far less extreme than in the military, a couple of poor decisions can still make or break ones entire livelihood.

Such a high risk/reward ratio is what provides military leavers the spark that is so devoid in other careers.

What Does An Untamed Business Look Like?

There are no set criteria governing the type of businesses a UE can create and it doesn’t have to be inherently dangerous -hell, my business is one on one mentoring…hardly bomb-disposal work!

What the business does have to do though, is be adaptable enough to allow the Untamed lifestyle to flourish and align exactly with the passions and interests of the founder.  This melding of work and play into a synchronized unit is a key component and helps distinguish an Untamed lifestyle from many others.

By defining what Untamed Entrepreneurs' businesses may be by their suitability to a lifestyle, rather than a specific industry or sector, the door is open to military leavers from a wide range of skill sets, interests and talents.

Play Time

So now we understand the entrepreneurial piece of the Untamed jigsaw, let’s look at the other aspect…play time!

This is where the fun really starts.  The jumping off point for the tamed.

Let’s cut to it…spending time outdoors, adventuring, taking part in extreme sports, travelling and putting ones body on the line in the name of entertainment are all things held dear by Untamed Entrepreneurs and military personnel alike.

Whether through extra-curricular or on-the-job activities, these aspects are tightly woven into both the military and UE lifestyle.

In the same way that real soldiers differ from those who call themselves Bravo Two Zero and run around mock battlefields wearing second hand cammo uniforms; Untamed Entrepreneurs take their love of the outdoors, sports and travel one step further than the average weekend warrior.

In a nutshell, one set of people love it, the other set live it.

It stands to reason therefore that upon exiting the forces, becoming an Untamed Entrepreneur would be the best way to maintain this high intensity curriculum and keep those juices flowing.

Have Your Cake and Eat It

And that’s ultimately what it comes down to - a smooth transition; a way of living that is both very similar to the military and completely different at the same time.

Filling the void left by a career as impactful, intense and unique as the military is no mean feat.

As a minimum, the replacement must provide adequate stimulation through healthy doses of competition, risk and the unknown in order to keep the boredom at bay.  Yet it must also be different enough to represent a fresh challenge and provide the individual the opportunity to add significant value by other means.

Thankfully the world of Untamed Entrepreneurship does just that.  It offers all the high octane thrills and spills of military life with added freedom for spontaneity should one desire. 

I can see no other more suitable lifestyle for the adventure-loving, purpose-driven military leaver to get their kicks!


If a life of extreme sports and entrepreneurship is right up your street and you want to learn the best places in the world to live such a lifestyle, then check out my latest e-book.  Download it here and take the first step to living like an Untamed Entrepreneur!




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Leverage Strengths

8 Mis-Perceived Weaknesses of an Untamed Entrepreneur and How They Should be Leveraged

Untamed Entrepreneurs - A Not Quite Oxford Dictionary Definition

‘Untamed Entrepreneur’ - Noun
a person possessing an entrepreneurial mindset who engages in both life and work activities in an unconventional manner. They are distinguishable by their gregarious nature, disregard for half measures (in any form) and insatiable appetite for adventure, fun and self-development.
“It’s easy to spot an Untamed Entrepreneur. They will first to the top of the mountain and first in the bar"
synonyms: N/A

Why I Am Writing This Ramble

Finding ones purpose, pursuing ones dreams, and living a life on ones own terms, are three of the narratives I champion with the most vigour.

Ever since my own self-analysis led me to major life-changing realisations -and the opportunity to achieve all three- I have been on a mission to help others do the same.

My default setting is to help anyone who asks for it -and many who don’t. My business mentor on the other hand, fights a constant battle to keep me focused on my niche.

In homage to him and his discipline I shall therefore focus this Ramble on said niche. My favourite audience. The people to whom I can most relate and thus provide the most effective help.

I am speaking of course about the Untamed Entrepreneurs of this world.

During the last 10 years of my life, I have lived two extremes. Five years ruining my body, liver and wallet in Whistler, followed by five years of career focus, fiscal responsibility and a diligent approach to health when living in Australia (I told you we don't do half measures).

Whilst ultimately, neither lifestyle was sustainable, one was true to my natural personality and one was not.

Whilst living in Whistler, whether I was ski instructing, plumbing or partying, I was surrounded by like-minded people and encouraged to be myself. Retreating within my shell would have served no purpose.

At the time I took it for granted but after five years in Perth working in a proper job and taking life more seriously, I soon realized I had been on a pretty good wicket back in BC.

Upon reflecting on my time in Perth, I have learned some pretty valuable lessons. It is these lessons I wish to share with you fellow Untamed Entrepreneurs.

In doing so I hope to shorten your route to finding your purpose, passions and a life on your own terms.

Re-Framing Weaknesses and The Importance of Self-Awareness

Perhaps the single biggest turning point in my path to self-discovery was when I realized I had spent years perceiving some of my biggest strengths, as weaknesses.

Whilst a lack of self awareness ultimately allows these types of misunderstandings to prevail: society, and the manner in which it consistently misconceives strengths and weaknesses must cop a lot of the blame.

In Australia -whilst I value every minute of my time spent with the company- I was ultimately working in the wrong industry, in the wrong role, serving the wrong people.

To make it more relatable and hopefully more useful I will quickly breakdown all three aspects and explain their misalignment.

Firstly, lets look at my role. I was managing a small business. This meant paying attention to small details and getting bogged down by day to day operations. Neither of which I enjoy.

Secondly, the industry -mining. A large, antiquated industry reluctant to embrace change and more concerned with risk mitigation than innovation. Not ideal stomping ground for the young and hungry looking to try new things.

Lastly, the people I served. When one works in an industry with the characteristics described above, two things can happen. You either stay true to your beliefs and spend everyday frustrated, or you give up, fit in and become part of the fabric.

Unsurprisingly, the majority of the old timers I dealt with were in the latter camp. They were tired, unmotivated and spent most of their time in meetings, finding ways to avoid risk and complicate the system in an attempt to justify their own existence.

It is not hard to see how my personality was at odds with my situation. I would spend meetings ‘playing the game’, pretending I cared about the latest iron ore price, rather than taking the piss out the hair of the old git I was talking to.

Occasionally I would misread the situation and go all in with a joke or two. They rarely went down well. It got even worse when beers were involved!

The Best Time Is Now

I tell you all this because I want to help those who find themselves in similar situations.

It took me five years to realise the problem was not with me, but my environment. I was convinced that this was all part of growing up and working in a proper job.

Gone were the carefree days of Whistler and turning up for work still shit faced to unblock someones drain. This is what working life looked like for adults.

My conscience was convinced this was the reality and my environment supported it.

Thank fully, I realized my situation and got myself out. The longer I had stayed in, the harder this change would have been - there is every chance I could have ended up like my embittered peers in the industry.

And now, I want to do the same for you.

The Most Commonly Misperceived Strengths

So, as someone with a larger-than-life personality and adventurous nature; what perceived weaknesses do you possess and how can they be turned into a strength?

Here is a list of what I believe to be the 8 biggest misunderstandings of an Untamed Entrepreneur.

The Most Commonly Misperceived Strengths of the Untamed

Perceived Weakness Actual Strength
Can’t focus on one task or project until completion Best at getting new projects up and running
Moves too quickly, others can’t keep up Has energy others can’t match
Speaks mind too much. Quick with opinions Always trusted to give honest answer. People know where they stand
Not serious enough at work, always attempting to entertain Best motivators. Great at engaging people and creating an enjoyable atmosphere
Talks too much Best communicators/salesmen/advocates
Lacks attention to detail. Often misses small things Great at seeing the bigger picture whilst not getting bogged down in details
Divides opinion. Either liked or loathed Doesn’t waste time and energy appealing to everyone. Friendships created are long lasting
Requires specific environment to thrive Can outperform all others in correct environment

Do any of those resonate with you?

How have you -and others around you- labelled these characteristics?

Have you ever re-framed them in this way before?

Don’t Change Yourself, Change Your Environment

The phrase ‘one mans trash is another mans treasure’ springs to mind. The notion that if your energetic personality is viewed as a weakness by those around you, it simply means you’re in the wrong crowd.

Rather than change who you are in order to fit in, change your surroundings. There’s a business or marketplace out there craving someone with your positive outlook, dynamism and ceaseless enthusiasm.

As I mentioned in my last Ramble, when you find this place, magic happens. This where you truly begin to add value and start having fun.

If my story, or the aspects listed in the table above bare a resemblance to your situation, I implore to re-frame what you may view as weaknesses.

I encourage you to view your role in society, and the business world, differently: to realise that every trait you possess can be reframed and used as leverage to add more value.

Look around, find the people and the markets that want what you have and continue to be yourself.

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road to wealth

The Grass is Actually Greener

Check Your Birth Certificate - You May Have a Problem

Are you under the age of 35 and love travelling? If so, you have likely faced an issue many older folk didn’t even know existed.

How many of you have embarked on long term travel, living it up in some of the worlds most exotic places for six plus months?

How many of you then became clinically fed up when you returned to the real world and went back to work? Back to the daily grind, the office cubicle and the bitter co-workers who couldn’t care less about your vagabonding adventures. Horrible huh?

A quick count please, of those of you who had the misfortune of going through this emotional ordeal, how many of you began planning your next trip 18 seconds after you got home? Furiously creating a daily budget and calculating how long it will take your annual leave balance to build back up…it makes for grim reading doesn’t it?

Then comes the chat with the boss. How long do you have to wait before you can ask them for another huge chunk of time off? A couple of weeks should be enough shouldn’t it? Yeah that seems fair. You’ll work extra hard in that time won’t you?

Shit, is it still only 10am on your first day back? Maybe you can just quit and ask your parents for a loan? Yes, that’s the best course. They’ll understand, they must have gone through something similar? Right?

Modern Times - Modern Problems

But Did They? Not likely. The truth is, back then only the most free spirited or wealthy undertook the kind of adventures we post 1980’ers consider our divine right.

Back then, when everything was brown and hair was enormous, seeing so much of the world was limited to wandering hippies in camper vans and James Bond. In the ‘real world’, it wasn’t feasible.

But why?

Lot’s of reasons. Firstly, job mobility was low. People spent entire lifetimes working for one or two companies. If you had a sizeable gap in your CV, your chances of re-entering the workforce at a decent level were slim.

Secondly, pre TripAdvisor and Google Maps, venturing into unknown lands was sodding hard work and required much bigger balls than now. Every bar, cafe, hotel and tour had not been reviewed 372 times by eager beavers keen to journal their every move.

Added to this, prices were higher, disposable income was lower, accommodation -especially in the developing world- was sparse, the English language wasn’t as widely spoken and there were few people you could ask for advice.

People’s reality was very different back then. I am generalizing of course (it’s easier that way and requires less research), but in the main, you were considered exotic if you spent 2 weeks in Spain.

Spain…Just Wasn't The Same

The silver lining in this brown, travel-less world? That’s easy. Not having to go through the torture of dipping your toe into the life of your dreams, only to return to grim reality when the money runs out.

Any oldies out there…you think you had it tough…? Two weeks in the Costa Del Sol, drinking San Miguel and eating deep fried calamari, was not the same.

It was too short a time to become engrossed in the lifestyle or to get a proper taste of what a life with endless sunshine and no work on Monday was like.

Six months however, is a different kettle of ball games. This is ample time to get used to a life of waking up with mountains on the horizon one day and clear blue waters of a tropical island the next.

For anyone who thinks returning to a 9-5 after two weeks in the Med was tough, imagine the slap in the face after 12 months of this reality escape?

But Seriously

Joking aside, the effect this exposure has on the younger generations is not to be ignored.

Never before have so many people witnessed what life on the other side of the fence is like. Never before have an entire generation had the option of wrestling between prioritizing a career and travelling the world; saving for a flat in the city vs saving for a 6 week yoga retreat in Nepal.

The choice is a tough one and it’s staring many a young traveller in the face.

Without much thought, I could name 5-10 friends who are going through this exact dilemma as I type (the surprise of course, being that I have 5-10 friends). I have seen first hand the dialogue they have with themselves and others.

What makes it harder to contend with, is that nearly all of them are degree qualified. The prospect of a good salary and comfortable living is a realistic one. But so too is working a mid-level job for just long enough to be able to afford the bucket list adventure.

The Untamed Entrepreneur To The Rescue

Fear not, everyone, I have a solution.

First we have to look at the cause. As is so often the case, the issue is caused by a lack of commitment.

I am very much an ‘all or nothing’ type person. One only has to look at the contrasting phases of my adult life (discussed so eloquently in the About Me page of this site), to see this.

The way I see it, if you’re going to do something, damn well do it properly. Half committing to two activities, undermines both.

Take riding the train through the mountains of Japan whilst trying to write a blog as a perfect example. By doing this, not only am I missing the beautiful scenery, but I am writing a shit blog. See my point?

Commit Fully Or Not At All

The same principle can be applied to living the life of your dreams exploring the wonders of the world vs fully focusing on your career and earning a good salary.

Try both and you will likely falter. You will spend half your time feeling guilty for wasting your education and the other half wishing you were wasting your education.

If you love travel that much and spend every waking hour wishing it was a permanent state, then make it happen. Find a way of turning your talents into income and work as you go.

Don’t think you have talents worthy of supporting a life on the road? Bollocks! You do, you just haven’t dug deep enough to find them yet.

Call To Action

I started this Ramble making an entirely different point but ended up getting sidetracked into a little rant. I’m glad I did.

It was supposed to be an insightful article about modern workforces but it morphed into a call to action to anyone with whom this article resonated. If this is a situation you find yourself in, ask yourself honestly: do I want it enough to make it happen? If so, commit fully and you will never regret it.

If by any chance you read this and want to take the leap but aren’t quite sure how, get in contact with me or sign up to my mailing list where I share free tools and resources for finding your inner genius and learning how to monetize it.

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Live the life of my dreams

Wealth Does Not Equal Happiness – The Benefit of Hindsight

No Shit Sherlock

I know, I know, you’ve heard it all before, I can hear you’re ironic cries from here. 

Please hear me out.  This is not just some re-hashed article about a theory that has been publicized ad-nauseam in self development circles…OK well maybe it is but please read on.  I feel I am better qualified than most to discuss this topic -not that that usually stops me!

One Town - One Enormous Disparity

The handful of people who have read the ‘About Me’ section on my website will know that I used to live in Whistler.   

For those unaware, Whistler is a ski resort in British Columbia, Canada.  It is where I cut my teeth as a properly independent adult once my University ‘studies’ were over.  It is also like few other places on earth…for many reasons.

As usual however, for this Ramble I will discuss only one…the disparity of wealth between the local and the tourist; the helpers and the helped; the risk takers and the Risk Managers.

A financial gap between tourist and local is nothing new -we’ve all been on holiday and seen first hand the contrasting fortunes of the two.  However, in the western world this is a far less common occurrence, not least in such a concentrated way.

I must point out right now, that in no way am I suggesting the difference in overall well-being of a college educated Whistler ski-bum and the tourist they are serving beer to is comparable to that of a local worker in the developing world and the western traveller.

Why Is It So?

I put this gap down to a few reasons:

  1. The proliferation of gap years and world travel for pre or post University graduates means that resort towns everywhere are being inundated by low net worth youths in search of fun and frolics on an epic scale. 
  2. Tourism/service jobs in the main, do not command high pay.  Factor in the high labour supply mentioned above and there’s no reason why employers would pay more than they need to for their staff. 
  3. Whistler is a long way to travel.  Unlike skiing in Europe where over 700m people are a two hour flight away,  anything less than a 10 day trip for those outside North America in unviable.  This rules out many financially conscious travellers.
  4. Whistler is very expensive -for both the tourists and the locals.  This does two things.  It cripples the locals and, as with the point above, leaves only the financially fit tourist in attendance.
  5. Whistler is so much fun, workers don’t give a shit what they get paid and tourists don’t care what they get charged.

This theory is backed up by the fact that visitors to Whistler account for 85% of consumer spending despite only representing 50% of the towns’ population on a given day (

A Smile and a G’day

OK, I think I’ve made my point.  Whistler is full of poor workers servicing rich visitors. 

It is safe to assume then that the holiday maker on a two week break from funding hedges would be greeted upon arrival with disdain by an embittered millennial with long hair and no money. 

Not true, well not in one aspect at least…in actual fact, the shaggy haired Australian is delighted to see them and welcomes them with a smile and a chipper tone.  Why?  Because he knows that within 12 hours he will be enjoying the best lines of his life...whatever form those lines come in!

The place is the ultimate playground for the Untamed adventurer.  Passion and energy course through the veins of all who inhabit.  Who cares about sharing a room with four others when the powder is so good? (Snow I mean).   Who cares that the daily wage just about covers a crate of Wild Cat and some pasta and pesto, when awesome parties are on tap every night of the week!

Everyone is living their passion and are damn pleased to do so!

Two Weeks To Unwind 50

And what of the stock broker?  The $300k a year earner who can afford to treat their family to a posh hotel and private ski lessons every day?  Are they as happy as the lifty standing in -10 earning $10/hour? 

In any other world, this wouldn’t even be a question but in the perverse universe that is a ski resort, especially Whistler, the answer generally is no.

Superficially of course they’re delighted to be there.  Delighted to finally enjoy their only holiday of the year.  A break from 15 hour days and the chance to unwind in plush, activity-rich surroundings. 

Dig deeper however and reality is very different.

If You Want To Get To Know Someone, Get Them Pissed

As a ski instructor, I was different from the rest.  Rather than hanging up my boots and spending the night with my peers discussing the best type of ski’s, I preferred the company of the interesting folk I had been teaching all day. 

Once the class was complete I would willingly spend all my wages -and a tiny portion of theirs- in the bar, getting to know them better, sharing stories.

This was the time the truth came out.  3 pitchers of Kokanee in and the tales of stress, overwork and a lack of time off began to surface.  “I wish I had the chance to do what you’re doing” and “it must be great living out here, doing what you love everyday?!” were both common admissions when the lowering of inhibitions allowed it.

Hindsight is 20/20…When You're a Ski Instructor

These daily reminders of the two contrasting life paths served me in two ways.  Firstly it ensured I never took my amazing position for granted: there was not a chance I would leave this lifestyle behind having not made the absolute most of the abundance around me -an abundance that people from all over the world paid thousands to see.

Secondly it provided 20/20 vision as to what might be should I pursue a career based on salary, social status or family pressure. 

Rather than yearning to earn their salaries and be able to afford trips to Whistler two weeks of the year, -as I no doubt would have done in different circumstances- my life was their holiday and I lived it to the fullest, all the while appreciating the relationship between wealth and happiness.

For this I will forever be grateful to the place and all the interesting people I got to meet.

A Viable Life Choice or Merely a Cue?

Hopefully by now you have both realized the theory I am proposing here. 

Whilst living on the ragged edge, both financially and physically, is not sustainable (I lasted five years before the full time shakes set in) there are valuable lessons to be learnt.

Whether you're an entrepreneur relentlessly pursuing growth, or an employee in pursuit of that promotion, think of this tale.  Consider the real reason behind your desires and the possible outcomes.

Will the extra money bring you happiness by affording you more time to engage in your passions?  Will it enable you to spend more time with your family or buy your dream car?  Or will it bring added responsibility, social pressures, stress and workload, taking you further away from genuine happiness than ever before?

There are many drunk holiday makers in Whistler well qualified to answer this one.