We all fantasise about being our own boss, but just how viable is living out our dreams?

Portrait of Tammy Strobel

We all fantasise about being our own boss, but just how viable is living out our dreams?

My Reading Room

Kelly Tan, photographer and founder of Studiokel Photography 

My Reading Room

Nison Chan, head purchaser and co-founder of We The People Store 

My Reading Room

Lisa Tan, baker and founder of Ugly Cake Shop 

“Live your dreams.” “Pursue your passion.” “Live life to the fullest.” These platitudes bandied about by motivational speaker types have become rallying cries for overworked office workers everywhere. 

Sure, they sound magical when you’re buried neck-deep in paperwork at your nine-to- five and need them to get through the day; but how realistic and practical is it to drop the “typical” job and chase your dreams? 

Picture perfect?

When Kelly Fan of Studiokel Photography first set up her company, the former disputes lawyer quickly realised it was no walk in the park. “I’d hit the sack sleep-deprived and deflated from the endless hours of shoots, meetings, and everything else that needed to be done to birth a business,” she shares. It required “the complete dedication of mind, body and soul”, and every day was a work day, even some weekends. 

It was incredibly tough, and she often found herself questioning whether it was all worthwhile. “But I knew that a young business needed that push to survive. So I powered on,” she says. 

While her work had been featured in international publications by the end of the first year, her company only broke even after 18 months, and became sustainable after two years. 

“Turning a passion into a business isn’t all fun and games. It involves a lot of sheer grit, and good old-fashioned hard work. And surrounding yourself with folks who believe in you goes a mighty long way,” adds Kelly. 

No piece of cake 

Lisa Tan, who owns Ugly Cake Shop, agrees. She quit her job in corporate communications to run the shop full-time, and says it took her about two to three years for the company to be profitable. “The initial investment needed to set up the shop was quite substantial. It also took some personal adjustment because I had to take a pay cut when we started the business.” 

The business is also “all-consuming”, she adds. “When I was an employee, I only brought work home occasionally. Today, work follows me everywhere, even when I’m overseas on holiday. I have to consciously stop myself from working after a certain time because there’s so much to do.” 

While she considered giving up multiple times, the social mission behind her business kept her motivated. Ugly Cake Shop contributes part of its profits towards funding school meals at Shallom School in Timor-Leste. “The success of Ugly Cake Shop affects not only the livelihood of our staff but also the kids in Timor-Leste. My husband and other friends and family members have also been super supportive.  I don’t think I could have sustained this long without them.”

Breaking mindsets 

Together with three friends, Nison Chan set up We The People Store up in 2016. It was the world’s-first store where people could get hands-on with Kickstarter-funded products. 

Back then, nobody believed in the concept, says Nison. They had to “really go all out” to win over critics, he says. 

On top of that, menial labour was par for the course. “Late nights packing stock, figuring out systems by ourselves… Thinking about those times, I have fond memories. The tough life chose us. But we overcame everything.” The company went on to make its first million in eight months, and there will soon be franchise stores in the US, Philippines and Kuala Lumpur. 

All the logistics 

In 2016, Shaun Wee co-founded Hutan Tropical, which sells tropical goods for outdoor and urban activities. For him, the challenge lay in “striking a perfect balance between being able to retain the essence of Southeast Asia and being internationally accepted, understood and appreciated.” 

Shaun says they’re currently focused on developing a sustainable business rather than monetisation, which may come at the expense of having a brand that “lacks soul”. Self-serving businesses will only cause consumers to lose confidence in the brand, he adds. 

Being the boss 

“A lot of people have the misconception that being your own boss means you get to have more time for yourself – that’s not true,” says Stanley Tan of Windflower Florist. Working harder than anyone is normal, and you have to be constantly on your toes. 

“The good thing about being your own boss is that I have something to call my own. When I look at what I’ve built, that sense of satisfaction and achievement is amazing.” 

Dream a little dream

Thinking about taking the leap and starting your own business? Be prepared to be dunked into the deep end. “Failure is almost inevitable,” says Shaun, and it can come in many forms, such as low sales, poor reception, or just bad decisions. Don’t be afraid of it. Instead, focus on what’s within your control and celebrate small successes. Above all, never make the same mistake twice, he quips. 

For Kelly, it’s all about being patient. “Enjoy the slow burn. Don’t expect to see immediate results. And above all, be kind to yourself. Stay curious. Keep shufflin’.”