Interview with ‘The Canny Contractor’

Imagine a lifestyle that allows you to work on exiting projects all over the world. A lifestyle without the routines of the 9-5 office job. Not having to report back to the same boss again and again. A lifestyle with a high degree of independence and freedom.

This is the lifestyle lived by independent contractors. But it’s not always rainbows and sunshine to achieve this kind of life, it takes a lot of hard work and willingness to take big risks and step outside of one’s comfort zone over and over. And there’s always the possibility to fail big time and not having any projects or clients for months.

In this blogpost we’re going to hear from ‘The Canny Contractor’ a guy from the UK who’s been working as a contractor for many years and have experienced some of the ups and downs that comes with the lifestyle. You can check out his blog at

The WWE: Hi Canny Contractor. Thank you`so much for doing this interview. I know from your blog that you’re working as an independent contractor all over the world. How did you get into your field? I assume you’ve been a ’normal employee’ at some point what let you to pursue a career with more independence? Also can you tell the top 3-5 best things about working as a contractor?

The Canny Contractor: “I discovered contracting during my first job after University, after graduating with a Chemical Engineering degree in the summer of ’98.   I guess I was lucky in the respect I applied for some junior engineering position, in a niche that was in its infancy.

It was on that job, I met some contractors/ consultants for the first time.  Their lifestyle really intrigued me.  They had traveled to far-flung places (for project work) and I admired how they were in control of their own financial affairs (and destiny).

I subconsciously knew I was never meant to be part of a system, so contracting was the perfect answer. But it felt a million miles away, a pipe dream at that stage (as I didn’t have the experience.)

After two years in the junior position, I was itching for something else. So, I moved to the South of England for a staff role in an Engineering Consultancy.

It was a bit of a jump and I was thrown into the deep end, but it was the only way to learn fast.

It wasn’t until a project in Ireland (in early 2002) that I felt I really found my groove. Also, for the first time in a while, I was exposed to lots of independent contractors again.

During this project, I had to do some shift work.  At that point, I found out my fellow contractor’s terms and conditions (and pay!) overshadowed mine.

We both had the same boss and did exactly the same work.  However, these guys made triple what I was making….and paying less tax.  That was the trigger for me.

After a ton of research and soul-searching, I turned contract in Autumn 2004.

I’ve listed 3 Reasons, Why to Turn Contract:

  1. Maintain a good work/ life balance:

If you play your cards right, you will have fewer meetings and work the hours that suit.  You can take advantage of extended holidays (at the end of a project) and time off with the family and friends.

  1. More independence:

There are more options from working at home these days. The client can also expect less from you, compared to a permanent role.  Finally, you have more of a say with regards to your future i.e. where you want to go, what sort of company you want to work for…which of course, leads to more job satisfaction.

  1. Opportunity to Retire earlier:

On average, you have the potential to retire in a third of the time, as full-time employees.”

The WWE: I can relate to what you say about not wanting to be a part of a system. Can you elaborate how this subconscious feeling manifested itself in your younger years and now? Did this ‘need’ to have a high degree of independence and freedom come at a cost?

Also, can you describe how it is to be part of a project, what’s your life like doing periods of work? And can you tell us what you’ve learned about work-culture in different countries?

The Canny Contractor: “The first time I started to challenge society/ the system was in ’93, my final year of high school.

It was then I discovered ‘The Prisoner’, a late ’60s TV series broadcast on Channel 4.

It was a stylised metaphor for the attempt to escape the strictures of society.  Individualism versus collectivism.  I started to realize what category I belonged to…

7 years later, I remember feeling trapped in my first job and not having a clue what to do about it.

It was the first time in my adult life I felt really down and helpless.  It was a signal that things weren’t right and not wanting to be part of this system. It was time to make a major change in my life.  But, I couldn’t pinpoint exactly what or where.

What I did do, is take action. Eventually. Although I shouldn’t have waited so long.

After a bit of a struggle, I got accepted for 2 job interviews I attended.

One was a local, more stable role.  The second position (staff consultancy role I mentioned earlier) was on the other side of the country and felt a bit outside my comfort zone. But the second position offered more freedom.

It was one of those ‘sliding doors’ moments, but you know what happened next.

The same thing happened at the end of 2003, after nearly 3 full years at the consultancy.  I felt I was drifting again and was desperate for change.  I needed to be closer to full independence. I wanted to be a master of my own destiny and sample the world and everything in it.

So, I put the wheels into motion that new year, set up a Ltd Company and turned contract.  By the end of 2004, I secured my first contract and was renting a beautiful apartment (close to the canal), opposite the Anne Frank House in Amsterdam.

In some ways, this need for independence and freedom can come at a cost.   Don’t get me wrong, the independence part is liberating and life-changing. But I got used to a high standard of living and people doing things for me, during some of my stints abroad. Hence, it can be an arduous process adjusting back to normality.  You can also lose your identity by being away from home so much.  I can be more in-depth/ give examples later on in the interview…

Being part of a project is challenging and rewarding, some more than others.  But, what really makes a memorable and happy project are the people.  They can make or break a project.  Having a reasonable boss/ project manager is also key.  Half the battle really. Landing a decent project is sometimes luck of the draw or your gut feeling. You can only do so much research on a project, or take so much BS from the agent.

Life is a little more exciting during a project.  I’ve experienced the whole driving back home every night when I procured local contract work in the Republic of Ireland (it was my base/ home for over 4 years).   So, I could build community, a good network of friends, play sports, build relationships, drive the nice car etc.

It was a wonderful experience, but I eventually got restless after a few years. The recession ultimately took care of that when I couldn’t find any local work anymore. Then I did (and I’m still doing) the overseas thing.   It stems back to my very first job, where I had these feelings of doing my own thing and ‘living the dream’.

For the more ‘middle of the road’ projects overseas, they are generally more relaxed. It’s really rewarding to experience a brand new lifestyle and immerse yourself in new cultures. There’s scope to learn new sports, meet new people and experience new food etc. I’ve personally learned how to snowboard and windsurf through contracting in Sweden and Israel respectively.  I’ve learned/ been certified with 1st level Russian by integrating myself into the project over there (and attending lots of lessons).  I’ve experienced and witnessed some incredible stuff, which is priceless.  Working and living in other countries will change your outlook on life.

For the big money projects, the vibe on site is generally more competitive.  Big money is going to attract big talent and big personalities (egos). So, you can either have very challenging (sometimes stressful) work ahead of you and/ or work in a very cut-throat environment, where its a game of survival. Kind of like, who can last the longest, which is very much like the Big Brother House!

However, I’ve come to the conclusion that working overseas is more laid back.  Whereas, British and Irish clients want things done ‘yesterday’.  Overseas countries have the whole life balance thing off to a tee.  In fact, I’m quite adamant in doing mainland Europe/Asian projects only now, where possible.  But, I’m more inclined to do ‘middle of the road’ projects paying fair money.”

The WWE: I can relate so much to what you say about feeling down and helpless in a job and not really being able to put the finger at what’s wrong. In my case, I think it was due to feeling trapped and not in control, exactly as you wrote. The thing is, it’s so easy to get comfortable in a stable job with a monthly salary. If you don’t watch out your expenses will go up and suddenly you don’t have much freedom left to choose a different lifestyle.

Also, I think that the more settled a person is, the less likely they’ll be to take risk, and it seems to me that taking on risk is crucial to get independence and freedom. I have to fight this myself, I can still get way better at taking on risk and not be so goddamn afraid of the consequences. In the worst case scenario, I’ll fail but that’s just a massive opportunity to learn. What are your thoughts about taking risk, in career choices but also in life in general?

It’s interesting what you wrote about getting used to a high standard of living and how difficult it is to go back to a more ‘normal’ lifestyle. Luckily(?), I’ve never experienced a high standard of living myself and so far I’ve been able to avoid the worst lifestyle inflation, but I still find it very hard to keep my expenses low. Can you tell us more about your experience with cutting back on the high standard of living? What was the hardest? Are you currently where you want to be in this regard or do you still have to work on certain areas?

I’d very much like to hear more about how you cope with being in new countries and with new people so often and how that affects your identity? Also can you elaborate on what you mean about how working and living in other countries change your outlook on life? It’s something I’ve heard many expats say, but I haven’t tried living abroad for a longer period myself so I’d like to hear your thoughts on the matter.

The Canny Contractor: “With regards to risk, I experienced a worst-case scenario in mid-2009.

I was close to 18 months into a lucrative contract in Ireland, a senior position with some project management thrown in. I was driving the car of my dreams to and from work every day and got to spend valuable time at a new apartment I purchased a few years earlier. My social life was thriving and life tasted sweet. It was then I took 3 weeks off to travel South America with friends.

I was living the holy grail of contracting.  The 2009 version of me was the best that ever existed.  But, what do they say? All good things must come to an end.

It was during my travels I received an email from my then boss.  The good times were officially over…the consultancy started to let people go during the financial crisis.

The phone never rang for months.   It was like someone pulled the plug.  I had just taken on a second property (short-term rental) and needed to get it off the ground. The timing couldn’t have been worse.  Two mortgages, no income (and no hope of future work) and a gas guzzler of a car to maintain.

As FI’ers, we like to talk about that infamous Emergency Fund.  Well, it came in handy during that financial disaster.

After 5 months I was thankful to secure another contract.  However, the hourly rate was slashed, the hours were capped, the pension tanked to over half its value and I had to move back to the UK.

It was only then I realized, how important passive income is. I never wanted to get caught out again in a downturn…relying on one income stream is actually quite dangerous.

Contracting is unpredictable, and there are forces that are beyond our control.  But, contracting is a commitment. You just have to roll with the punches and get back on your feet.  Sometimes when you’re hit with a juggernaut, you have to come back twice as hard.

The bottom line is if you want something enough (be your own man), you’ll do it. It’s as simple as that.

As Peter Thiel says, “In a world that’s changing so quickly, the biggest risk you can take, is not taking any risk.”

It was then, I started to sow the seeds for geographical arbitrage. Starting with renting out my apartment (as I was now in the UK).  I also knew I had to secure contract work abroad to mitigate the downturn (and reduced rates) to fast track my way to FI…

In 2014, I broke a contract with a blue chip client in the UK, as well as a steady relationship (that was fizzling out).

Why? I secured a 6-month contract in the Russian Federation.  My colleagues thought I was nuts. Yes, it was another risk. However, it was the start of a new roll and having the big three paid for by the client…and living beyond my means for a short spell.

I had my own driver to take me to my hotel in Moscow/ airport.  When in Moscow, I stayed in one place reminiscent of Scarface.  There was the gaudy white statue/ fountain centerpiece.  Everything was decked out in marble and gold trim. The hotel had its own mall accompanied by Faberge egg shop and Ferrari car dealership! There was even a freakin’ harpist playing at the breakfast buffet. Nothing exceeds like excess in Moscow.

What”s more, I was wining and dining beautiful young Muscovite ladies most weekends, courtesy of an infamous dating app. I was just an ordinary punter who was lucky enough to experience an extraordinary world.

Anyway, my contract extended to 16 months. The risk had paid off and my savings rate was fairly intact (thanks to the client).  But, I had to deal with the lifestyle creep issue.  The issue being, how do you sustain that lifestyle.  You don’t. You can’t.

After crashing back down to earth with a bang (after my adventures in Moscow), I had some kind of rude awakening.  I knew I had to change my ways.  I was living in a bubble.

So, I battened down the hatches and went ‘Early Retirement Extreme’ (based on Jacob Lund Fisker’s book) in early 2016. I notched my savings rate up to 80% and have sustained that level since.

I’ve been in a good place with savings for a few years now, but I need to find a base and start building a new life (not a bubble).

With regards to my outlook on life, it’s gradually changed over the years.

I used to think growing up in a suburb, with the fancy car and big house was the path to tread.  It’s what everyone aspired to (certainly where I lived).  But having traveled and experienced so many different ways of living, I know I don’t want that life anymore.  The cookie cutter life isn’t for me.

Living and immersing yourself in these countries change you as a person.  Meeting different people changes you.  You just realize there are better versions of your life you can live. Better environments you can fit into.

Being in various new countries with lots of different people doesn’t affect my identity per se.  But, having to leave these social scenes (I’ve put heart and soul into) behind is tough. And building up an exciting life in a new city, then having to leave?  It’s not easy. That’s when you lose your identity.  That’s why you need a base, a common denominator. Something solid to go back to…”



5 Comments on “Interview with ‘The Canny Contractor’”

    1. I’m happy you found it interesting!
      I agree that it’s not for everyone, but for those who have a taste for adventure I think it’s worth considering. I think it would be nice to do contracting for 3-5 years before settling down.

    2. First of all, thanks for the interview World’s Worst Employee. It’s a pleasure to be featured on your blog and be part of the FI community.

      I appreciate your feedback Mrs Smelling Freedom. I would like to elaborate on one of your points. You don’t have to uproot every 18 months or so, this was the consequence of giving up my base in Ireland. I traded the base for a life of adventure and excitement, where I made some solid friendships across the globe. People I still see on a regular basis. What’s more, contracting overseas has enabled me to fast track the FI process (albeit some off the rail moments).

      In today’s market, you could easily base yourself in the UK or Ireland and travel home (back to base) every evening. Worst case, drive or fly back every weekend.

      But you’re spot on, it really isn’t for everyone. It’s a single or young person’s game. I’ve seen it work for folk with families, but I’ve also seen a high divorce rate (and witnessed some extramarital affairs).

      It’s worked for me and I’m blessed with what life has thrown at me. However, at this particular point, enough is enough. I’m ready to go back to some normality, building more relationships and doing day to day stuff on a regular basis.

      1. It sounds like you built a life that works for you 🙂 I’m a bit of a boring homebody and it would have driven me crazy, but I do see that it is exciting and most important of all, pays very well 🙂 Good luck with the next phase of your life!

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