Sean O'Leary
4 min readJan 22, 2016

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Why is “Why?” the most important question to ask yourself every day?

I was a super annoying kid. Whenever I was told something my stock answer was why? I wasn’t trying to be a smart arse or deliberately be annoying, I genuinely wanted to understand everything I was told and everything I was told to do.

You’ve got to go to school Sean. Why? So you can pass your exams. Why? So you can get a good job. Why? So you can have a nice life. Why? You get the picture!

At some point and I can’t remember when, I stopped asking why. I’m not sure of the reason, maybe I got one too many a clip around the ear for being annoying. So when I was told I should get a profession, that’s what I did, I qualified as an accountant. What’s the problem with that? It’s not really a problem, more of a distraction. You see, I was an OK accountant, I made partner at 26 and set up my own successful firm by 29 but being an accountant or running an accounting firm wasn’t really my purpose. I was materially successful and enjoyed creating and developing the business but it didn’t make me tick!

Listen, when we ask why, we are asking for what purpose? What’s the purpose of an instruction or something we are encouraged to do or even of something we decide we want to do. Why did I become an accountant? Because my parent’s thought it would offer security and status and I didn’t question that. The thing is, security isn’t a big thing for me and whilst at the time status mattered at lot more to me than it does now, it wasn’t a driving motivation.

At an intellectual and analytical level, being an accountant was a smart move, on an emotional level it was not so smart, as it left me feeling unfulfilled and a bit of an impostor.

So what’s my tale got to do with you? Well my question is how many aspects of your life would benefit from asking the question why? What’s the purpose behind them?

Run your own business — why? Ah, you run it to make a profit — wrong answer, making a profit is a consequence, a by-product of what you do. Try again — why? Ah, you run your business to sell widgets. Sorry, wrong again, selling widgets is what you do, not why.

Why you own or run your business is a fundamentally important question, in fact it’s the first question for businesses. What’s the purpose of your business? Who are you serving? What value do you add? The most successful, long term sustainable businesses have a very clear purpose, they know why their business exists, its higher purpose and crucially every-one involved in the business knows why also. If you want a long-term business, one to hand on, that perhaps lasts for hundreds of years, the “why” or “purpose”, is the starting position. You can read my previous post on long term businesses here.

We can take this “why” question into all aspects of our life. Why do you eat as you do? What’s the purpose of your food, is it to nourish you or distract you? The way we eat, our food habits are often unconscious habits or patterns that are handed down from parents or perhaps arise in our relationships. Once you ask why you eat what you eat and consciously choose your food with a conscious purpose in mind your relationship with food can alter dramatically.

What about your fitness, how do you keep fit? You go to the gym. Why? Oh, everyone goes to the gym don’t they? Nope. Look, depending on what your fitness purpose is, going to the gym may be exactly right for you, but equally it may be a terrible decision. You need to ask yourself why, why do you go to the gym, why do you cycle, why do you run, why, why, why?

Another day at work today — why? Well it’s what you do, right? Wrong, you want to be interested in why you do what you do. Are you fulfilling your higher purpose? Are you part of something bigger than yourself, adding value and making a contribution? You are — great. You’re not — why?

I think it can serve us all to re-connect with our earlier, somewhat annoying, childish self and start to ask why — every day!

This article was first published on the blog of Sean O’Leary. Sean O’Leary is a coach, entrepreneur, yogi. Sean writes on Purposeful Business, Purposeful Living, Conscious Health, and Midlife Mastery. www.seanoleary.net/blog

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