5 Career Lessons I Learned from 5 Memorable Bosses

Do you remember your first boss?

I remember mine very well. He told me that your first boss is crucial in determining your career success. And as true as his words were, it’s not just the first boss that’s crucial.

It’s every single one of them.

Over my relatively short eight-year career, I’ve been blessed with some amazing people to report to. All of them have taught me invaluable career lessons.

Here are five of the best ones. 5 career lessons I’ve learned from 5 of my most memorable bosses:


1. The Genius

My fifth boss was an Australian.

He was also a genius. An engineer and tinkerer — like a mini-version of Tony Stark. He could help you fix complex engineering problems without even looking away from his computer screen. Just by nonchalantly throwing verbal suggestions at you.

He often sent me away from home for weeks at a time. To be involved in an overseas project I had totally no experience in. He expected me to figure things out. Once, when I asked questions without first doing my homework, he commented “Sometimes I think you must have had a very sheltered childhood. Figure it out yourself.”

While that project never became very successful commercially, it was a great character building process for me.

My fifth boss taught me that in life, you learn things quickly by plunging straight into them — not by peering over someone’s shoulder taking notes. Real world experience beats theoretical knowledge any day. That the hallmark of the Malaysian education system: memorization without understanding, is useless.

And not to shy away from setbacks, but to use them as learning tools to get better.


2. The Devoted

My seventh boss was a Malaysian Chinese.

He was the most passionate and dedicated person I’ve ever met in the corporate world. He took his job very seriously.

He would sometimes reply emails within a few minutes despite that it was three* in the morning. (Don’t ask me why I was writing emails to him at 3am). In fact, I don’t recall him ever not replying a single email I sent him. And this was a guy who probably had at least a hundred emails a day to attend to.

I would eventually take his position and understand why he was always so stressed. And also get the hundred emails a day to read.

He taught me how dedication to your work is necessary, if you want to succeed. And how it can also break your heart and drive you crazy — especially if you work with people who aren’t as serious about work as you are.


Picture of working on Macbook


3. The High-flier

My sixth boss was an American. He was a director in the company by his mid-thirties.

He was also the one who gave me my first promotion.

I once asked him what the secret to his success was. First, he told me had a great mentor. Then, he explained how he always listened extremely carefully to his superiors. And every single thing that they asked for, he made sure he delivered.

It made me think about how we often like to “forget” things that our bosses ask us for. Especially things that we’re reluctant to do. Well guess what, they may forget about those “little” things — but if you deliver, your bosses will always remember you.

My sixth boss taught me that age is no barrier to success. How respect and authority comes from competence, not just years of experience. That mentors are incredibly valuable. And that listening is perhaps the most important skill of all.


4. The Unconventional

My third boss was a Malaysian Malay. The first time I met him, I thought he wasn’t very intelligent. It didn’t help that he made me do all the tedious paperwork.

He’s also the least handsome guy on this list.

Some colleagues thought of him as an ass-kissing, attention-seeking, lying manipulator. But he had a way of getting improbable things approved by higher management. It helped that he seemed to have amazing self-confidence and was a great storyteller.

One time, the resident office bully spread word that he wanted to pick a fight with my second boss. By this time, we had become close — so I laughed it off and did what all weak men do: I made fun of the office bully behind his back.

But my third boss was having none of that. He went straight up to the bully and asked him gently:

“I heard you may have something against me. Shall we talk about it?”
The bully replied “No, nothing.” and backed off like the coward he was.

Today, my third boss is an entrepreneur, established author, and on his way to becoming a local celebrity.

He taught me that boldness, drive and ambition beats natural intelligence and appearance. That in chasing your goals, you may have to defy societal expectations and conventions. That it will often make people uncomfortable, because it crosses the “safe” mental barriers they put around themselves.

And that’s OK.


Picture of the Petronas Twin Towers


5. The Noble

My eighth boss was a Scotsman. He traveled over to this part of the world to further progress his career.

And progress it did. At one point of his career, he was getting promoted to more important roles every few months.

But he was also a genuinely nice person. A total opposite of the stereotype that corporate ladder climbers are scheming, backstabbing bastards. When he spoke to you, you realized he generally cared for you as a person, and wanted to help you develop your career.

He taught me that you could be a good boss by caring for people, and that is how loyalty is built. That making money for the company should co-exist with treating your employees well.  And even if you have to make difficult, heartbreaking decisions — it can be done respectfully and honorably.

When he left, it was a quiet departure. Without any grand farewells, announcements or emotional emails. In fact, he slipped away just as quietly as the day when he first arrived.

And with that, my eighth boss taught me one final lesson:

You don’t have to be loud to make an impact in people’s lives.


What are your favorite boss stories? Comment below, I would love to hear from you!

*Dedication is important. But that doesn’t mean you have to be replying emails at 3am every morning. There are more efficient ways of doing that.

Pic Credit:
“Suit and Tie” by johnhope14

“Writing on the Macbook Pro Close-Up” by Victor Hanacek
“EXPLORE 2011-05-05 standing tall” by Dave_B_

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  • You are so blessed to encounter such motivating mentors. Oh! how I wish I had such good superiors in my career. But anyway I don’t regret how life treat me because I will some how find a way out. Amazing good read.

  • Nice work Aaron. I recognize some of these people. I particularly like the story about Will R. That’s a very important lesson.

  • Reading your stories about your boss makes me wanna share about mine. I worked under the same boss for 5 years and suffice to say he was super instrumental in shaping my character ( work and career wise) and they way I perceive things around me. When things were hard, I remembered him saying ” Don’t worry, I’m here and I aspire to inspire you before I retire”.( pretty sure it was quoted from someone, hehe) but at that point of time, I never would have thought I’d say this to an old man other than my biological dad but -I love you Mr Chia. Thank you so much for your guidance and now I’m proud to say I’m ready to fly on my own.

    Btw Aaron, I’m a budak baru in here , learned about you from a BFM podcast. BTW, your definition of frugality resonates well with the values I believe in when it comes to money and spending. Kudos Aaron and keep writing for us!

  • I stumbled into your website and find it interesting and insightful.
    Keep up your great work.

  • I like this article very much.
    I worked with few bosses too, and some of them taught me very good lesson.
    The dedicated boss, the ass-kissing colleagues, the weak boss.

    I like the part about the bully.
    Your writing is excellent.

  • Hey, man, i know its been years since this article is released, keep it going, good stuff, we millennials need it !!!

  • Hi!

    I’m wondering do you feel demotivated if your articles are not shared or less people commented on it.

    Would like you to know that there are silent reader like me who love your articles and learning so much from it. Just decided to drop by and thank you for your sharing and effort!

    Keep it up and looking forward to more posts of yours!

    P.S. Lately I have been filling my free hours reading up your articles. I’m a new fan ????????

    • Hey Wai Kin,

      Thanks for your kind words and support! It means a lot to me.

      I used to worry more about if people liked/shared/commented on my articles. But after doing it for a while, I’ve become more accepting of my place in the universe. I’m just one voice out of 7.4 billion people today. If someone likes/shares/comments — it’s a huge blessing. But if not, I’ll just continue doing my best. There is some beauty in loneliness. 😉

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