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  • Writer's pictureSophia Chin

HOB-JOBBER: Personal leadership, should I stay or should I go?

Updated: Jun 17, 2020

“Games are life distilled into programmable parameters.
And life is a game where everyone is still learning the parameters.”

You have been switching roles a bit. Seven roles in ten years, to be exact. A two-year stint here, another one there. And then there was that dead cat bounce of 10 months you prefer not to talk about. You have done big stuff; you know how to do big stuff. However, you haven’t quite found your groove yet.




British dialect, circa 1850

a man or boy walking the streets on the lookout for small jobs

You go all sentimental talking about your first job: running multi-million dollar marketing campaigns for some of the hottest electronic gadgets. But there was one problem… the pay sucked. All that marketing budget had to come from somewhere.

So after two years of doing charity, you bounced and landed in another A-lister tech company, running multi-million dollar marketing campaigns for sexy gaming products. With better pay. However, as time went by, you realised what justified the higher pay: the boss was an insane workaholic megalomaniac.

After two years, you had enough, and by the way, another exciting opportunity came along, and you bounced. And bounced. And bounced. You left Marketing. You dabbled in various Sales roles. You had a side business.

But you can’t seem to find that perfect job. Something always goes wrong. From the outside, the job would look like a daydream, but once you got in, it becomes a nightmare. Every time you changed your job, you thought the problem is solved. Problem with salary? No worries, get a better paying job. When you get it, you’re ecstatic! But inevitably, a new problem would crop up, and you’re back to feeling miserable again.

Should I stay or should I go now? Should I stay or should I go now? If I go, there will be trouble And if I stay it will be double So come on and let me know
- The Clash.

You think that by quitting you solved the crazy boss problem. But really, what’s happening here is that you’ve rid your life of this person, but you haven’t gotten rid of your problem.

You’re still miserable.

Seven roles and ten years later, you’re having those familiar thoughts again. But this time, there’s a twitch of worry. You feel like you’ve gone down one too many rabbit holes. You don’t want to do that anymore. You don’t want to run away from your problem anymore. You want a real solution.


The thing is…. Deep down, you know you’re born for greatness. YOU KNOW YOU’RE DIFFERENT. You can feel it in your bones. Even if you don’t have the words for it yet.

You were a precocious child growing up, questioning everything. Your mind is like a sponge hungry for knowledge. You’re a walking encyclopedia of random factoids. You have all these brilliant ideas swimming in your head. You pick up new skills very quickly, that’s why you can bounce from job to job with ease.

You resist being forced into a mould. You want to be yourself, but sometimes it comes into conflict with the job, such as forcing the numbers: “Bring in the numbers or else.” Conformity riles you up to no end because it’s so boring and your mind switches off. When you don’t love what you do, it becomes a job that pays the bills. Your work quality deteriorates; your relationships suffer. And to you, that’s plain stupid and a waste of your potential.

You want to be yourself, but sometimes it comes into conflict with the job, such as forcing the numbers: “Bring in the numbers or else.”

You don’t take things for granted. You need to test it for yourself to see whether it works. You’re always experimenting and looking for ways to make things more efficient and logical. After ten years, the experimentation is stabilising. The experiences of your youthful enterprises have granted you the depth to be truly wise about life.


No job is 100% aligned with who you are and what you want to do. Stop trying to shoehorn yourself into jobs. Instead, find creative ways to tailor the job to take advantage of your best strengths. On the surface, you’re doing everything that’s expected of you. You go about your day-to-day like everyone else. But inside, it’s a wholly different matter. You’re not just a Director leading a sales team across APAC. You are Lilith leading the Crimson Raiders into battle in Borderlands 2. Or the lone, cynical, dark brooding anti-hero hero Geralt of Rivia. Or you forge your own characters. When they are hounding you for numbers, you remind yourself: “I don’t do sales, I do relationships”. To you, life is like a game. And there are so many different types of games to play: games where you need to use all ten fingers and ten toes. And then there are the one-swipe games. Candy Crush your life!

“I don’t do sales, I do relationships.”


If you can be true to yourself, you’ll be a source of positive energy, and it’ll have a tremendous impact on the people who work with you.

According to research by Amy Wrzesniewski from the University of Michigan, there are three approaches to work – job, career and calling. A job is where it is purely to support our financial commitments. It pays the bills. A career is where the focus is to move higher on the corporate ladder. Promotions are the highlight of the work. A calling is where the work is an important part of you, something you take great pride and share fondly with friends and family.

While there is no right or wrong orientation toward work, Wrzesniewski’s research shows that individuals who have a calling orientation report higher satisfaction with their lives and work, and are more likely to “craft” their jobs to fit their strengths and interests.

Most of us were brainwashed since young to pursue a job and career, pushing aside ideas about calling until we’ve paid off the mortgage, sent the kids to university and built a nest egg for retirement.

You took the bullet upfront. It takes courage. You dared to fail. You experimented with different things. You’re a hotchpotch of uncoordinated talents & expertise. There’s none the same. And that makes you supremely unique.


You have a tremendous amount of power to lead change. Your eclectic mix of skills and knowledge means that you see things differently. You see solutions where others see dead-ends. The key to unleashing your full potential is to be honest and articulate what you think. You have to stand up for yourself and make difficult decisions. Don’t beat around the bush or be coy. Don’t wait for people to second-guess what you want. Or hoodwink you into a role that you later regret.

But because your views are so unique, you're afraid of being rejected. You've experienced it many times. Sometimes, you don’t believe you’re good enough, "Who the hell you think you are?" Or you’re afraid people will think that you're conceited or arrogant.

The inner work has to be done upfront. Craft your leadership brand. Tell your authentic story - why you’re uniquely positioned to do the job. That's how you tell people what you think.

That's the real solution to your problem. When you listen to your heart, the money follows.

This is your Work. It's your choice to stand on the edge of greatness. What you find is work becomes more personal. You become more engaged, you concentrate better at work, you go deeper and come up with creative solutions to the ickiest problems.

When you realise it’s time to move on, make the decision to move on and fulfil your duties professionally. Build and maintain relationships. You never know when they will reactivate again in the future.

It’s a journey to find the right fit. Pack your bags. There’s a much bigger game to be won here.

This article is part of a book I'm writing titled Dancing At The Edge Of Greatness: In Pursuit of the Joy of Leadership. I would love to hear your comments on what resonated with you and where I can make things better.

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PERSONNA is a leadership development company focused on the people side of transformation. We hold a simple belief that everyone is an extraordinary and powerful force for positive change. When you make work personal, naturally you become a better leader.

We’re here to help people become better leaders, build highly-effective teams, and create a culture of trust & collaboration in their organisations. We provide leadership branding, leadership coaching and group experiences. If you are curious to learn more drop us an email to

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