A Meaningful Career By Design

[5 min read]

[This post was first published in the middle of 2017 as I left leadership consulting with Heidrick & Struggles to join a University.]

To design a meaningful career, uncover the synergy between your interest, traits, desired lifestyle and values.

I recently had a switch of jobs and people around me seem to have noticed a spring in my step. This has invited many conversations – six in the last two weeks to be exact – with friends and people I’ve just met about what to look for when building a meaningful career. I am neither a career advisor, nor have I the experience and the professional training in the field but the great conversations have inspired me to articulate my thoughts on this topic that I care deeply about. My opinion – admittedly simplistic in this early stage in my career – is this: designing a meaningful career is about finding the synergy between your interest, traits, desired lifestyle and values.


As someone starting out for the first time, seize the chance to work in an area you like. There are far too many people out there, bored, uninspired and living a 9 to 6 because it’s all they know. Getting older, with a mortgage and a family depending on you, quitting a job you don’t like to dabble in something more promising becomes increasingly difficult. So the least you can give yourself is an attempt at starting someplace you like. Unlike our parent’s generation, many inour generation no longer need to settle for the first job that comes. Let’s make use of this freedom.

It’s okay if you’ve not found your passion. Pursue your interest, play and you might just find it, so says Angela Lee Duckworth in her bestseller, Grit. So the earlier you start dabbling in different things – be it through hobbies, small side jobs, internships or clubs and societies – the sooner you will get clearer on what it is you like and don’t like.

What’s vital is the curiosity to say yes to new opportunities that come your way and see what that teaches you about yourself.

Interest can come at many levels. It may be interest in the subject matter – such as education or it can even be an interest in the medium of service such as designing teaching apps on the iPad for educators. The latter combines two of your interest – digital technology and education – and that’s entire possible.


I wanted to title the section ‘skills’ but that sounds very finite and perhaps a little premature for those just finishing university. You may have the traits and personality to be a great sales person but it doesn’t necessarily mean you have the skill to do so right now.

There are a bunch of personality tools out there that can help you identify your traits but the best way in my opinion is to simply get out there, accumulate many different experiences and give your best. Then, be honest with the feedback you give yourself.

Whether you are serving in the Singapore army or in a club at school – take the opportunities presented to step out of your comfort zone, do your best and see how you fair. Did you display potential despite limited experience at it? Did you do well by objective standards? What feedback did you get from people you trust? Did you enjoy it – perhaps theres some synchrony here with your interest.

As a teen, I had the good fortune to have sisters that threw me into the the role of group leader to a bunch of 10 year olds at a Sikh camp they organised. Then in university, I raised my hand when a professor was looking for a volunteer to moderate a discussion as part of a class exercise. Its through experiences like these that I learnt about my potential to effectively teach people and facilitate learning. Admittedly I still have not realised that potential but I’m joyfully on the path.

Keep a journal of these experiences you jump into and title each entry with, ‘what I learnt about myself today is…’, you’ll be surprised by the insights you create.


Visualise the life you want.

This is the fun stuff to dream about. What are the people around you like? Where do you hangout after work and on weekends, and with whom? What hours do you keep? How much autonomy do you want in a job and what culture do you want to work in?

This line of inquiry may reveal that you might be better off in a high paying job that supports the lavish lifestyle you desire, or it might suggest you want a job that let’s you work remotely and so that you spend as much time with your family as possible. Don’t be afraid to design your life. You can start by reading this book of the same title.

Organising my thoughts before a workshop in Johannesburg, South Africa. My old job let me combine my desire to travel with my love of facilitating workshops.


Another way to look at this is to ask yourself, ‘what’s important to you?’ This is usually influenced by your own moral compass – perhaps shaped through your religious upbringing or the environment your grew up in. Perhaps you value leaving a legacy more than anything else and you are happy to strive along until you create that breakthrough innovation. Maybe it is important for you to have a job that helps people on a daily basis. Or maybe you are motivated to ensure your family has the best money can buy. Do not let people tell you that you have to choose between the two. There are people out there everyday who are doing good for people everyday and making a significant amount of money at the same time. Business schools teach entrepreneurs to ‘Create Shared Value’ – i.e – make money by doing good for the world.

While it is not everyday that people find jobs that demonstrate the synergy of these four pillars, I find myself privileged to be surrounded by people who have. In my family, my previous team at Heidrick and in my current team on campus, I’m surrounded by people who have taken the time to design and redesign their lives so they can thrive authentically in their jobs as they do at home. Like my hockey coach used to say, ‘if you don’t shoot, you won’t score’ – so go ahead, take that journey of self exploration and discover what’s possible.

A great guide book by a couple of folks from the Stanford design lab.

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