Three rules on how to raise a happy multi-hyphenate

Which is the job and which is the side hustle? It shouldn’t matter, says web professional Jack Tan, who also runs a digital agency and lectures at a polytechnic. The father of three thinks the ability to pivot and juggle between tasks will set his sons up for success.

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In today’s context, working more than one job is not out of the ordinary. Hustle culture has made it normal for the younger generation to engage in multiple side gigs as they try to make more money and get ahead of the pack.

Some call it being fickle, but in a world that changes fast, this knack of adapting quickly and multitasking deftly is seen increasingly as an asset.

Enter Mr Jack Tan, 46, who wears several hats in a single day. He develops apps, runs digital agency Whooshpro, and lectures in web design at Temasek Polytechnic. But he never set out to be a multi-hyphenate. 

“Growing up, I always aspired to be whatever I was interested in at the moment,” Mr Tan quips. “When I was in school, I wanted to be a teacher. When I went to polytechnic and studied Electronic and Computer Engineering, I just wanted to be an engineer!”

On top of it all, he is a hands-on father to three growing boys aged 13, 11, and 7, and he does not plan to give up any of these roles in spite of the real challenges that come with juggling so much. 

Why? Because being a chronic multi-tasker gives him “the great privilege of experiencing all facets of my work” and is a privilege he hopes for his sons. Here are three strategies he uses to put the multi-hyphenate in them: 

1. Never let failure hold you back – even when you failed most of your modules

In the first year of his polytechnic course in Electrical and Computer Engineering, Mr Tan failed most of his modules. He was disappointed but he did not cower in defeat. 

“In my second year, I was determined to re-do all the modules I had flunked in my first year alongside my second-year modules.” He drew up his own timetable to fit in all the course modules of both years, “and this was even with the Dean telling me that my plan was impossible to execute”. 

The result? “I proved him wrong. I aced them all.”

Years later, as a father, Mr Tan taught the same lesson to his eldest son who was in Secondary 1 and an aspiring athlete. The boy did not do well enough in his CCA trials to qualify for the track and field team.

“I encouraged my son to appeal to his teacher for another chance to try out, and went with him to see his teacher as a show of support and to teach him how to ask for a second chance. When he was given that second trial, I trained with him almost daily, running with him in the evenings. And he got accepted!” he says, beaming. 

His son would go on to breast the tape at a 400m event. “I am so proud of him for not giving up and pushing on.” Sometimes, rejection is inevitable but “I always tell them if they don’t try, they wouldn’t know. If you just accept rejection at the start, you will probably regret not having even tried to make a change”.

2. Never laugh at your dreams – even if you sold just three computers 

Even as a student, Mr Tan was acutely aware of how transient the years were and how he wanted to make the most of every day. 

“Part of the reason why I was so adamant on taking all the Year 1 modules I had failed together with my Year 2 modules, instead of just re-taking them another year and delaying my graduation, was that I did not want to waste any precious time,” he says plainly.

Squeezing more into his day was his unofficial mantra, so he tried his hand at running a business in the hours in between. Together with a close friend, they went to Sim Lim Square to scout for part and built computers to sell to other friends.

He laughs at the memory of the mission. “We made $500 per computer, but we didn’t factor in the after-care service and repairs after each sale. It was very time-consuming but because we sold our computers to friends, we wanted to do our best to make them happy, so we went all out!”

They folded the venture after selling just three computers.

He has no regrets because the experience was the bedrock for his future exploits into being his own boss. He dives into challenges with the intention of getting more out of life, like when he started lecturing a decade ago at Temasek Polytechnic, or trying out new hobbies. 

“I can’t just tell my sons to be open to new experiences, I have to do it too. And they’ve seen me try all sorts of new things with gusto. On top of seeing me juggle my different roles all these years, they also see that I enjoy my hobbies like riding a motorcycle and aquascaping my fish tank,” he says with a spark in his eye.

3. Never underestimate the power of determination – it could make you a multi-hyphenate

For his sons to grow up and enjoy what they do for a living, they need to have designed their vision of the future for themselves, not live out someone else’s dreams, says Mr Tan. 

“Passion and determination must underscore everything they pursue, so that they can give their 100% to whatever they choose to do.”

This was something he drummed into his son when he performed poorly in his mid-year exams at Primary 6.

“He had 22 points then and was shocked. But I told him he has to decide for himself that he wants to do better and work harder of his own choice. And he did, he really did. He more than halved his points for his PSLE and managed to get into the school of his choice,” he says, beaming with pride.

“Excelling in something requires lots of passion and determination. This is a fact of life, no matter how work changes in the future.”

He tells his sons that putting their own stamp on their aspirations, and putting in the effort, is what will take them far and see them through all the obstacles in the future. “I guess this perspective also contributes to me living as I do, juggling all the roles I have. I just want to live life to the fullest.”

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