5 Questions That Have Shaped My Career

Like many important things in life, often wisdom reveals itself in introspection. During a recent reflection on my career where I reviewed the paths I have taken and the code of conduct I have chosen to adhere to, I realized that my behavior has been largely influenced by five questions that have presented themselves to me through the years.

1. What makes a friend for you?

This question was ironically presented as a joke. I was 13. I had no response. As far as relationships went for a 13-year-old kid, you were friends with the people who accepted your awkwardness and shared the same interests. People who let you sit with them during lunch and hang out after school and on the weekend.

I’ve been thinking about this question ever since the day it was first asked me, and it has taken more than 20 years for its importance to really sink in. It defines what type of people you will let into your life and what values you hold. It is a barometer that dictates what kind of person you want to be, what kind of friend you should exemplify and makes clear what you will not stand for.

The knowledge of what makes a friend for you also identifies what is edifying and toxic in a corporate environment. We are so caught up with job titles and status that it is often a secondary consideration if a company has a culture we want to be associated with. If Company X was a person, would you be friends with it? You are going to spend most of your time there. You will be representing them. If you are comfortable with your decision, so be it. But at least consider the question.

2. How do you know it’s true?

The question of fact checkers. The one thing you assume is true will probably be the thing that gets you in the red. You can’t go around double checking everything (that would just take too long!) but the skill is in having the humility to ask yourself the question in the first place. Asking if it is true throws forth the potential that your assumptions could be wrong. You do not know everything — and neither do they.

The ability to ask this question has added benefits besides ensuring accuracy. You ask the question about statements made by others about you, and statements you make about you to yourself. If you are unfortunate to be subject to thoughtless feedback, asking if it is true is a potential career saver. Especially for those of us who can get crippled by the opinions of others. The key is to remain open to the answer. If it is true – then do something about it. If it is not true – then ask why you were so ready to believe it to be.

3. What are you not facing?

There is a great quote by Nancy Kline that goes “Thinking dies in denial. Information resurrects it.” In her book, More Time to Think she goes through the 3 stages of organisational denial: what is happening is not happening; it happened, but it was not bad; and the bad was good. The problem with this behaviour is that the real issues never get addressed. They are left to live on as corporate lore and in stories told at after-work drinks.

I should have asked this question at every place I have ever worked, and with every client I have ever worked with. Take it as a kind of due diligence. This is also a question you absolutely have to ask yourself if you are managing staff. No one is asking you to go looking for the bad stuff, but at least take an objective view of what is happening and be aware of your biases.

“Thinking dies in denial. Information resurrects it.” Nancy Kline

4. What is the worst case scenario?

This is my favourite question when I’m in the sh*t. I have made a mistake, or something is not going as planned. Or worse, things are going downhill at speed. Asking what the worst case scenario may be forces me to articulate what I imagine to be the bottom of the barrel and confront the potential reality.

Usually it is some form of rejection, a reprimand, disappointment, embarrassment and me feeling like a failure. Envisioning it helps me prepare for what may come. It may even give me an idea to counter-attack the present situation. Strangely it never really turns out the way I think it will, but having a picture of the beast gives me some courage to face it.

I also ask this question when I am afraid to do something. It can range from submitting work, applying for an opportunity to pitch, public speaking or calling a journalist I do not know (just for the record, I hate cold calling but I do it anyway). Asking myself what the worst scenario may be makes me realise that it can’t get worse than rejection – which is pretty bad, but not enough to stop me.

5. What is the most important question today?

I have this written up in my office in red on a whiteboard so I can’t miss it. It is the most recent addition after listening to an interview between Tim Ferris and Josh Waitzkin. There are so many things that consume my mind and time during the day. Some are superficial, some are driven by deadlines and other people’s priorities. Some are existential and a lot of it just stuff that comes through email and the internet. At the end of a work day, I ask myself this question – and it distills the noise into one most significant thing. Then I sleep on it.


A communications strategist and award-winning PR consultant who just happens to also be a photographer and published author. A Penang-born Kiwi living in Singapore. Always looking for the next big thing.

1 comment on “5 Questions That Have Shaped My Career

  1. Thank you for this post. Great food for thought 😊


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