Before you quit your job to become an entrepreneur

Understanding the why

On three occasions in the past month friends have asked me whether they should leave their corporate jobs, and pursue the independent free life of an entrepreneur. My response on each occasion has been to repeatedly ask a simple question: “Why”?

It is a real privilege to be on sabbatical. The ability to see the world with a new perspective and to create a new vision for the future is something that everyone should do at some stage of their career.  Including you!   As a corporate employee, no matter how balanced and well integrated your life is; you will always remain constrained in your vision unless you take a deliberate step away from the coal face and look at the bigger picture.

A weekend in the mountains is refreshing; but sadly not enough time away. Even 3 weeks leave is not enough. Unfortunately most corporates do not offer employees a meaningful break, a period for recovery and growth of 6 months or more.  Educational institutions are better at this, academics can sometimes enjoy sabbatical; a tradition that in my view needs to be nurtured and protected, even if it appears to come at great cost.

Over the past few months I have enjoyed meeting up with several friends and ex-colleagues. In my own micro business I have been fortunate to continue to stay in contact with several people in my previous company; and enjoyed many meaningful discussions over coffee or lunch.

These discussions can only take place when you no longer work in a company, couldn’t care less about the corporate politics and truly have no vested interest.

These discussions are of necessity confidential because friends will confide in you their thoughts, frustrations, aspirations and dreams.

I am honoured to be the sounding board, to be able to listen. I am energised through these journeys of discovery and frequently draw on the experience for new energy to help me in my own search for the “why”.

Three key questions to ask

In my recent experience I have encountered three groups of people who are seeking change in their lives.

(1)  The first group is concerned with the “what“. What should they really be doing in their jobs? What is the best job for them? What are the options? What type of work is the most fulfilling?

(2)  The second group is concerned with the “how“. How should I plan my exit from this 9-5 job? How will I set up my new company? How do I start a business? How do I make more money?

(3)  The third group is concerned with the “why“. This is often the group where the challenging discussions take place. Why am I dissatisfied in my work? Why do I do what I do? Why should I start up a new business and why should people take notice?

People’s questions are of course not constrained to any one category. Each person asks questions in each of the three groups; but depending on where they are in their journey, some question types become more predominant than others.  The interactions I enjoy because they get to the heart of the matter are the ones where we discuss the “why”.

Looking to change your job?

When I encounter someone who expresses a need to change their job I now respond by asking the question: “Tell me why”.

If they know they will have a clear answer.

Because you are “miserable and dissatisfied” is not always the best reason. Carrying your miserable dissatisfaction into an entrepreneur job or another company can be fatal. You need to get to the heart of the “why”, and it is probably deeper than that.

If the person does not have a clear answer then they have probably not had the opportunity to really go through a process of reflection, goal setting and envisioning the future for themselves. Sabbatical provides this opportunity for some, but not everyone has this privilege. You might need to create this answer for yourself on the job, so to speak.

As someone who is on sabbatical I am sometimes seen as an expert in career planning and a soundboard for those that feel trapped in their demanding jobs. I don’t feel that I am necessarily the best role model; but I can certainly share my personal experience.

My own experience

Frankly, by the end of last year my own “why” had been eroded by years of corporate life to the point where it was unrecognisable from the aspirations I had when I had just graduated. I would not have been able to answer my own question “Tell me why”.

On graduating I had dreams and aspirations like all of us; and realistically anticipated a period in my life where I worked to gain experience. I was fortunate to have worked for a great company which offered exceptional opportunities to young engineers.

I had also anticipated creating something new in my career. After 8 or so years gaining experience I found the opportunity to create a software business to be very fulfilling and enjoyable.

But after the software business was sold to new owners, my “why” needed to change again. The business was successful and established. For various reasons I was no longer feeling as fulfilled. I felt the need to create and build again. To do something brand new, from the ground up. To prove to myself that I still had value to contribute.  This required me to get off the corporate treadmill for a while. Hence a sabbatical to answer why.

My own “what” is actually proving to be difficult because of the abundance of choice. Somehow I want to make a positive impact in the lives of others through creating a brand new enterprise.

I know that I want to create a business that succeeds not because I invest thousands of hours into it, but because it is founded on a great idea that meets a need in society. I have written of the importance of a product mindset before, because when you sell too many consulting hours you end up working in the business not on the business.

My new business will not start out to grow to become an empire because I believe (with some experience) that a small group of committed people can make more of a difference than the largest companies can,  and be far more agile and satisfying to work with.

I am still working on the “how“. This is for me the easy part. Experience makes the difference for me.

But as for my own “why” – this is something that sabbatical is helping me clarify.


3 Lessons learned on sabbatical

The first thing that you must learn is patience.  The process of developing a new vision for your life does not happen overnight. You need to be intentional about creating the opportunity to work through this.

The second thing to learn is to realise just how valuable relationships are in supporting your new goals. From ex-collegues, friends and family – all play a vital role.

The third thing is to realise that time is not money.    This association of time and money comes from the corporate worlds of finance and consulting and must be challenged. In real life time can fly by or grind slowly on. Not all hours are equal and cannot be ascribed to a single unit of currency. The wealthiest people in the world have just as many hours in the day as you and I. They are wealthy not because they sell hours but because they sell good ideas. They understand their why. Think Steve Jobs and Bill Gates. I can’t offhand name a single full time consultant that had as much impact.


Time is a gift which has great value, far in excess of the counting of hours.

Great ideas create wealth.

The greatest ideas do take time to formulate.  Ideas are not measured in hours invested, they are measured by their impact.

The wealthiest people have the same number of hours on this planet as the poorest labourer.    What sets creators of wealth apart is not money but their sense of purpose – they have good ideas and they can answer “why” in a way that you and I can easily understand and identify with.

Time is not just money.   That is a superficial analysis. Great ideas that create wealth are however born out of time, so time has value far beyond money.

Creating wealth is something that invokes a higher purpose than making money.

If you can answer your “why” with clarity, simplicity and purpose you are set to spot great ideas, make good decisions; and move from just making money to creating your own wealth.