Should I become a hawker? – applying strategic thinking to solve a dilemma

“Dear Ian, I have been a technician in several MNCs and government organisations over the past 9 years. I have come to a point where I don’t see any progression in my career and have been wondering for the past 1.5 years if I should start a new business, perhaps in operating a hawker stall? Can you help me make a decision?”

Tired Technician

Dear Tired,

I am sorry you have come to the zenith of your technical career and are looking for a new experience. Change is always good, I suppose. While I don’t have enough information in your email to offer you precise advice, I would like to apply the strategic thinking protocol to help you come to the right decision.


I can’t help but wonder what your intent is? Is it to run away from your current career, to make a living or to offer a differentiated product in an already crowded space? Although you didn’t articulate it, I am sure that you know what you are looking for. If you don’t, then apply the Five Why’s technique.

Related: The Five Whys – It is still the best tool to identify strategic intent

Success Factors

Your success factors will further explain your intent. If your intent was to offer a totally differentiated product, then your success factors would include the number of people coming to taste it, the response from it, the number of referrals you get, and ultimately the revenue you generated from it. Success factors can be seen as your metrics towards meeting your end goal.


Obviously, from your intent you can derive different options; although I suspect that the number of options may be limited for some of them. For example if your intent was to offer a differentiated product, then the options really are the various products that you can offer. That will of course depend on your culinary skills. However, if your intent was to make a living, then you widen your options. You can of course go into hawking, but you could just as well do photography, teach children, become a dance instructor and the like. These are only limited by your skills and your passion.


Having been working for almost a decade, I am sure that you have built your life around certain people, certain activities and certain responsibilities. You may have gotten married, you may have had children, you may have a mortgage to service, you may have a vehicle to maintain. These are all elements that can add to your constraints. You may even have other social responsibilities that you need to fulfill regardless of what you did. These need to be articulated so that you frame your decision beyond just what you wanted and how you were going to get there. For some, it is their constraints that they find too constricting to allow them to do any other thing but stay the course (and yes, become very unhappy along the way. Look around you. There are many people like that in Singapore!)

Related: Don’t have a clue? Plan your actions with your constraints!


After you have dove deeper into your decision, you might want to take an alternative frame. Ask yourself this question, “If I were the world’s expert in food hawking career transitioning, what would I say to myself?” Go ahead. Try it. You will find that you might already have the solution within you and if what you said makes sense, then add that to your list of options!

Balancing options with constraints

It is now time for you to whittle your options down to the final two. Draw a table that has all the constraints of your decision at the top, each constraint taking up one column, and all the options available to you at the side, each taking one row. Then, working down the column, assess whether each option can meet the constraint or not. If it can, put a tick in the box, if it cannot, a cross. If you didn’t know, put a question mark. Do this for all the columns, and when you are done, the two options with the highest number of ticks will be your final two options to choose between.

Making the decision

Finally, before you make the commitment of the decision, take each of the two options and identify all your assumptions surrounding them. Then, play the worst-case and best-case scenarios in your head. The worst-case would be when all your assumptions were wrong; and the best case would be when all of them were right. The intent here is to see the variability of your options and assess if you could stomach that. It also asks what other actions you could take to minimize the downside, as well as how you can accentuate the upside. At this point, you can now safely come to the conclusion that one option was better than the other, for reasons such as less risk, lower downside or greater upside; and that should be your decision.

The grass is always greener

Dear Tired, what I have shared with you is the process of getting clarity for your decision. Along the way, you might just bump into the question of jadedness; “Are you making this decision because you are tired of your current job?” Sometimes all you might need is a movement to another organisation, or to learn new skills, or to develop a hobby. This will come out from your intent. And be mindful that the grass is always greener on the other side.

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