How looking back can help move your start-up forward

Whenever you can, take a little time to self-reflect. It is important to understand the influences that have brought you to where you are.

When can or should an entrepreneur take a break? More importantly, what can or should be done during that break?

This is part six in a series where I share my personal entrepreneurial journey in building the start-up business

The following is a brief account of what I did over the Christmas period which, hopefully, provides some insight into the potential upside of a little downtime.

Being relatively new to entrepreneurialism, my work is nearly always top-of-mind. Friends and family may with the best of intentions suggest taking a break, even if it’s just to relax and perhaps catch up on some books.

Unfortunately, rarely are entrepreneurs able – our minds just won’t let us. It’s not that we don’t want to, but building a future in the business takes precedence. We’re perennially drawn to thoughts about how to become stronger, faster and better.

Anyway, in my case an 11-day family cruise to New Zealand aboard the luxury liner Explorer of the Seas was organised.

From past cruise experiences, I knew from the outset that internet access would be akin to the speeds of dial-up, and so without much chance of productive work I planned a rough schedule that allowed time for family, self-reflection, listening to my audio books and visits to the huge buffet that would be offset by working out in the gym.


I’ve just turned 40, and not sure if I’m young or old. But of one thing I am certain: things are changing. In fact, I joke with friends that half my life is over.

On the other hand, this means the remaining half is in my complete control, which is exciting. Also, having reached 40, I now see life in four parts.

  • Zero to 20 years: A period without much control, consisting mainly of following, learning and “growing up”. A time of testing and exploring the possible future, with a feeling that time is on your side.
  • 20 to 40 years: Building a career and getting to know yourself – your skills, attitudes, discovering what you’re good at, testing assumptions, and savouring the joys and energy of youth. Most people start a family.
  • 40 to 60 years: The action years; striving towards and consolidating a solid career and wealth. Becoming the best you can be at what you have chosen to do. Reassessing prior aspirations and perhaps developing new ones. The pedal goes to the metal, combined with a realisation that life is finite and meant to be enjoyed, usually with family. Unfortunately, it can also be a time when older family members, and sometimes peers, pass away.
  • 60 to 80 years: Starting to chill, increasingly health conscious and experiencing what you previously might not have been able. Wondering in amazement at property prices and why you didn’t buy the house 25 years ago that just sold for $13 million.

My journey as an entrepreneur began four years ago, after a fortunate but planned-for redundancy released me from a corporate career that had spanned 17 years and provided a clean sheet to decide my future.

In the six months that followed I astutely used frequent flyer points to start ticking off a bucket list: business and first class to Hong Kong (Chinese New Year); Tokyo (Cherry Blossom Festival); Bangkok (friend’s wedding); Los Angeles; Las Vegas (Consumer Electronics Show); New York; Copenhagen; Paris (Tour de France); and London (Olympic Games).

I had never really paused to reflect on it, but while cruising on Explorer of the Seas I realised how fortunate I was to start iFLYflat. It was done without any real plan and, to be honest, with little idea as to what I was really doing. After all, I had no formal training in the area, relevant networks or even much practical experience.

As a natural introvert, it was something no career advisor would likely have recommended.

However, as a CPA I was trained to understand and apply rules (accounting standards are rules and regulations), to be logical, objective and apply judgement to problem solving. 

In my past role at Macquarie Bank, I had learned how to manage people (teams, peers and upper management), priorities, projects, budgets and build complex and accurate financial modelling.

With iFLYflat, I taught myself how to network and cultivate relationships, become at ease with public speaking, build processes and implement systems, refine and market the sales proposition, inspire and hire and, above all, engender customer buy-in. In other words, I learned how to be confident and comfortable in my own skin and with who I am.

Now, four years on, I still pinch myself when invited to speak about my passion at key travel conferences and corporate events around the globe. Learning how to fly first and business class at economy prices seems to be a popular topic.


Along with a sense of accomplishment, on the ship to New Zealand I realised that the success of iFLYflat could be also be put down to a number of key influences, some dating back years.
  1. The book Rich Dad, Poor Dad by Robert T. Kiyosaki, which I read as a kid.
  2. The open-plan office at Macquarie Bank, where senior executives and known millionaires sit alongside everyone else, prompting me as a young executive to ask one: “Why do you still come to work?” He responded: “I enjoy what I do, I’m really good at it, and what else am I going to do? The beach gets rather boring after a few weeks.”
  3. The Young Entrepreneurs’ Unconvention 2013, hosted by The Entourage, and one particular speaker’s slide that compared running a start-up to a duck – calm above the water but furiously paddling below.
  4. The Key Person of Influence (KPI) seminars run by small business expert and KPI Australia co-founder Glen Carlson, along with entrepreneur Daniel Priestley. It was there I learned that if you are good at something, you need to showcase your knowledge to the world so that people will seek you out.
  5. Watching and being in the long lines outside Mamak Malaysian restaurants. I’m no foodie, but they have got their roti just right and let the whole world know about it.
  6. Earning sufficient frequent flyer points for a personal trip in business class to Hong Kong, the points having been accumulated through a series of flights to New Delhi, where I was setting up an India-based accounting team for Macquarie. It was a “light bulb” moment – effectively scoring a flight worth over $4500 that had been “paid for” by my employer.

So, whenever you can, take a little time to self-reflect. It is important to understand the influences that have brought you to where you are, and if you are still on the right path. If not, it is never too late to realign, to start again if need be, and to learn from scratch whatever it is you really want to succeed at.

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