At the ripe old age of [redacted] it’s fair to say that my career trajectory hasn’t panned out quite the way anyone would have expected. Certainly not my teachers, who were certain I’d be spending my days counting chickens when they eventually came home to roost. My parents, while having every confidence in my abilities, were a good deal less confident in my ability to apply my obvious (to them) intelligence and skills in some meaningful fashion.

In the decade or so after leaving school, many of their prophetic warnings were proven right. I couldn’t hold down a job. I didn’t know how to apply my skills. I was heading nowhere fast. But then fast forward a few years, to December 2015, and I’m celebrating the anniversary of the longest career I’ve ever had. 5 years of highly lucrative and for the most part, highly enjoyable, independent contracting!

When I first embarked on this voyage though, I was’t sure whether my career would even last 5 days!

Pushing away from the shore

Lots of people find it hard to make the transition from being employed (permie) to being self-employed (contractor). The main issue in my experience is that the perceived risk of living and working without the safety net of a monthly pay check is too high for many to contemplate. On the other hand though, many have drawn a comparison between having a pay cheque dependency and being addicted to some kind of narcotic. Most famously Nasim Taleb likened working for pay as being like a heroin addiction. While I wouldn’t necessarily go that far, you can probably see what he’s getting at.

Launching out on your own is an opportunity to break the dependency. Rather than being paid for simply rolling into work each day, you have an opportunity to gauge your real value to the marketplace based on what you alone have to offer and the value you add to your clients. This makes it potentially a scalable opportunity too, because the more value you add – the more you can bill your client. To a point, at least.

For me, it took a couple of years for the reality of this to set in. Self-employment felt insecure for a long while, and while I felt insecure I was reluctant to commit to large expenditures (like a mortgage or a car for example), for fear of suddenly finding myself without work and needing to finance an indefinite period of bench-time. Looking back over the last 5 years though, I’ve never spent any significant periods of time on the bench. Even when I’ve wanted to, there’s always been somebody needing some work doing. The problem has always been saying “No!” Not the other way around.

Setting your sail

Over the course of time, assuming that you have a couple of successful engagements under your belt, you begin to realise that the things you originally thought of as risks – the lack of a steady pay check, periods of feast or famine (if the famine part ever actually occurs), not being able to find the next gig – you realise that they’re actually opportunities disguised as downsides.

  • Running your finances becomes an accounting exercise with opportunities to invest in yourself and your business – paying the taxman last rather than first.
  • Work feasts enable you to build a warchest and make some solid financial plans. Feast periods are opportunities for rest and recuperation, reflection, self or business development.
  • Finding the next gig becomes a marketing rather than an unemployment challenge – as you learn to express your unique selling points and value adding propositions in a way that differentiates you from the crowd and the noise.

Again – it took a little while for some of these lessons to sink in. It took some time to adjust to the flexibility that running a business gave me. Particularly in terms of my finances. Ultimately I ended up investing a goodish amount of money in property, but as I mentioned above – there was a strong temptation to leave money in the bank, just in case!

Figuring out where I fitted into the marketplace came a lot sooner. Identifying my unique skills and selling points came naturally to me, and I’ve always been quite good at marketing myself. But things change over time and the way I marketed myself at the beginning isn’t the way I do things now. I’m a lot more likely to rely on word of mouth, referrals, recommendations and repeat business now than I would have been able to at the beginning of my contracting career. I don’t have to try so hard now. So I have a different challenge. Finding new ways to market my services that are congruent with the way I want to do business, and not taking my eye off the ball.

Settling in for the long haul

Sometime down the road – sooner for some, later for others – it becomes apparent that you are in fact running a business, with all of the benefits and potential drawbacks that implies. Your ship is sailing on an open sea. Your direction and velocity a function of the set of your sails. Will you lift them high and sail ahead as fast as you can, or are you content to drift and allow the current to take you where it will – conserving energy for a coming storm?

I think this is a problem many entrepreneurs probably face. You’ve setup your business, it’s ticking along nicely and making you some money. What do you do now? How do you grow it? How do you keep expanding your business into new territory? I’m not quite sure about this myself yet. So if you have some suggestions, or things that work for you – I’d love to hear about them in the comments section below.

A rising tide lifts all boats

My seafaring (or at least, near the sea dwelling) friend says this often. And of course he’s right. In order to benefit from the rising tide – you simply need to push your boat onto the water and allow nature to take its course.

But the reverse is also true. If your boat is too close to the shore when the tide goes out, you’ll be beached. Going nowhere fast until the tide comes back in again, by which time opportunities to do business may have come and gone.

The best thing you can do is get out onto the open sea and get away from the effects of the rising and sinking tide as quickly as possible. But to do that, you have to be committed. Metaphorically speaking, getting out to sea (particularly If your boat is small) is a risky business that requires a lot of effort.

That level of commitment might be new to you. A whole new level of determination is required to push past the incoming waves, and the sea winds that seek to push you back to shore.

You might also be tempted to paddle back yourself – thinking “what’s out there for me anyway?”

That’s where it might help to have some friends along for the journey. Some fellow sailors, many of them more experienced than you, helping you set your sales just so. Helping you navigate the currents of the open sea, and showing you the best places to let down your net for the biggest haul. Funnily enough.

Please remember.

  1. Your vision is your permission.
  2. You are capable of your calling.
  3. You are much more powerful than you realise.
  4. Yes you can get everything you want.
  5. You are loved. You are enough. You are worthy. You deserve the very best of everything.


Now is the time to completely rewire your mindset for increased happiness and prosperity with an immersion in THE ABUNDANCE LIBRARY.


ALL YOU NEED TO DO IS LISTEN to the ever-increasing catalogue of business, spiritual and personal growth programs within the library.


Find out more at and begin your immersion for a dollar. 


Unlock your true potential and take back dominion over your money, relationships and energy right now.


START YOUR 7 DAY TRIAL for just $1.


Much Amazing Love 


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.