Eight Lessons from the Bosses

In 30 years of life, I’ve been very lucky in many ways.

But one way in which I’ve been incredibly fortunate is the bosses I’ve had, the managers I’ve worked for.

Ever since beginning my corporate career proper in 2017, I’ve had four bosses at three workplaces. From each, I’ve learned not only how to do the work better, but also how to live better. Which I think is far more important.

My four bosses have literally changed my life. Here’s how.

Boss No. 1

My first boss in corporate managed me as I began my career as a Learning & Development specialist. His nurturing and loose reins led me to gain confidence in my skills, exactly what you need as you begin a new career in a new field.

But from him, I learned two things that have had a lasting impact on my life.

Lesson No. 1

How to hold a conversation and get to know someone.

My boss’ trademark sentence that everyone thinks of when we think of him is undoubtedly: “Tell me more.”

We’d be talking about a topic—be it work or personal—and he would pause with a glint in his eyes and deliver his famous line: “Tell me more.”

Up until recently, I didn’t have much confidence in my social skills (I do now). I wasn’t confident that I could hold a conversation, be it with friends or strangers. But this phrase, these magical three words, changed everything.

It changed my mindset in a conversation to be that of curiousity. Now the goal in every conversation isn’t to talk about things, but to get to know the other person.

It gave me a phrase I can use in almost every occasion. I love the gentleness of it. “Tell me more.” It’s an imperative that feels far less threatening and probing than a question. I always felt invited to “tell him more” whenever he said this to me. And I hope my conversation partner feels the same when I say this to them.

Lesson No. 2

Two words: financial management.

Growing up, I never received consistent and well-informed advice on how to manage my finances. And I also never thought to educate myself and take the reins. Almost all of my savings were sitting in savings accounts, fast losing their value to inflation, not being worked for gains.

After two separate conversations with him, I did two things:

First is I applied for a credit card. I’d always been against the idea of credit cards—irrationally because I never had or came up with a valid reason to support my opposition. But if I remember correctly, my boss once mentioned in passing that one benefit of a credit card is it gives you a credit history. And immediately I saw a value in it.

So I got a credit card. And I pay it off every month when prompted. And I get points and cashbacks. It’s great.

The second thing I started doing—and this is far more important—is investing in the stock market.

I remember that day as vividly as if it happened yesterday. It was after work. We were sitting in the meeting room. I’d just been made an offer for a new job elsewhere (my boss was in on the process from the start—which is a bit unconventional but I didn’t feel comfortable with not letting him know that I was interviewing for a new job). We were talking about the jump in salary I’d get from the company switch, and he said in all earnestness: “Invest all the increment in an index fund. If there’s one thing I regret, it’s that I didn’t start investing earlier.”

As with the credit card comment, his advice stuck. And some months later, after considerable procrastination, I started investing in the stock market. I also began to educate myself about different types of investments and risks. For the first time, I tallied up all my assets and allocated them to different investments, based on the recommendation I was getting from banks.

This was a watershed moment. I finally took the reins and now I feel more financially secure than ever, whereas in the past I didn’t really give financial management much thought. Now a portion of my money is actually working for me. And I will continue to educate myself on the matter and optimise my investments. It’s a lifelong journey that will hopefully lead me to a secure and comfortable retirement.

Thank you, Chris, for your insights and earnest advice, and for being a role model for curiousity and openness.

Boss No. 2

My second boss managed me as I was rising in the world of Corporate Learning & Development. By this point I was being given far greater responsibilities than I had in my initial months, and she was skillfully helping me navigate the often choppy waters.

Lesson No. 3

The lasting impact she’s had on my life isn’t so much something she told me. It’s how she lives.

She is one of the most inspiring individuals I ever came across. Her work ethic is exemplary, and on top of that—and this is the key—she lives a most full life.

We worked together for quite some time, but it wasn’t until late in our time together that we began to know each other on a more personal level. I began sharing my personal self with her, and she did the same.

Through knowing her, I’m constantly inspired to live a thoughtful life. This is one thing I’ve always tried to do since a long time ago—I want to be remembered posthumously as someone who’s “lived a thoughtful life,” but no one more than her gives me an impetus to do so.

Until now, we have long WhatsApp conversations where we share updates and reflections on our respective lives. Her endeavours constantly remind me of what we can accomplish in life, of what we can push ourselves to do if we’re willing and disciplined. And her unerring belief in me is a great motivator, to know that she completely believes that I will live a fulfilled and successful life gives me belief in myself.

And on top of being the model of how to live, she also gave me one of the biggest gifts I’ve ever received: she introduced me to the person who’d become my Boss No. 4. But more on that later.

Thank you, Agnes, for always being an inspiration. I’m very lucky to know you and continue to feel privileged every day that you choose to have me in your life.

Boss No. 3

My third boss managed me in the new company I moved to. It wasn’t a long stint, just under a year. But from her I learned two very important life lessons.

Lesson No. 4

Not so much a lesson as something she repeatedly suggest I start doing. And thanks to her genuine persistence, I did. And it changed my life.


I don’t know if you meditate, and I’ve certainly had conversations with many people who don’t get meditation. Hell, I was one of those people.

But within a few days of beginning meditating, I noticed a seismic shift in myself.

Suddenly, I had a very strong desire to stop multitasking. And I mean that in the most literal sense. Since I began meditating in March 2020, I’ve stopped multitasking. I only do one thing at a time.

Right now, I’m typing this. And I am wholly focused on this. I’m not absent-mindedly picking up my phone to check if it’s fully charged (it’s being charged at the moment). I don’t stop to check my messages. I just type and focus on writing the best version of this article that can be.

When I walk to and from places, I don’t message people. I just walk. Many days I don’t even listen to music or a podcast on my phone. This is something I used to do impulsively: leave the house, put on earphones. But I’ve stopped doing it impulsively. If I do it, it’s because I choose to do it. It’s because I’ve thought about it and realised I was in the mood for music, or for a podcast.

But many times, I just walk. I focus on where I’m putting my foot down. I observe the sights around me. I listen to the sounds of life. I just be. I’m at one with my environment.

As well as stopping multitasking, I also started doing another transformative thing: being intentional.

I used to waste hours on Facebook and Instagram, mindlessly scrolling, and feeling shitty afterwards.

After starting meditation, I began to catch myself when I do something on autopilot. And I began to stop myself from doing it.

These days, if I do something, it’s because I’m intentionally doing it. Yes, I still spend some time on Facebook and Instagram, but I do it consciously. I think: Hmm, I’d like to see what’s on Facebook now, then I spend some time on it. And when I feel I’ve had enough, I stop. And I no longer feel shitty when I do this. It’s great.

This might sound a bit hoo-ha to you, and you’ll make of it what you will. But meditation has changed my life.

It’s been over a year, and I still meditate almost every day. Usually ten minutes, but occasionally twenty.

I love it. It’s the time in my day where I just stop and re-charge. And sometimes when I skip a session, I actually miss it.

Meditation has helped me slow down, improved my focus, made me more patient and aware of the fleetingness of emotions. It’s grounded me.

In short, it’s transformed me into a far better version of myself than I was, both for me and for the people around me.

Lesson No. 5

Energy management.

I used to think of productivity as managing your time well. But from my third manager, I learned that it’s not so much about managing time as managing energy.

I learned to not do things when I’m tired, to take breaks, to know my limits and expand them. Energy—unlike time—is after all limitless.

As someone with a full-time job plus two side jobs, this is a skill that has come in handy.

I’ve also applied it to my personal life: Don’t have important conversations when I’m tired. Prioritise sleep. Eat well, exercise.

Just like meditation, energy management has improved my life for the better. If the former makes me a more balanced person, the latter makes me a more productive one.

Thank you, Joy, for teaching me these wonderful lessons and truly changing my life.

Boss No. 4

And now we come to Boss No. 4, i.e. my current manager. As alluded to earlier, it was my second manager Agnes who introduced me to my current boss. My current boss is one of her favourite authors, and she first introduced me to him by recommending me his best-selling book, and then also gifting me (and the whole team in fact) his follow-up when she left the company.

Thanks to Agnes, I began reading my current manager’s work. And it instantly spoke to me.

My manager is a (I think it’s save to say) well-known self-development author. And I joined his team in September 2020.

On top of feeling on top of the world to be working for one of my favourite authors, for being part of his creative process, you can imagine he’s imparted to me many life lessons through his writings. He’s a self-development author after all.

Instead of listing all of the things I’ve learned from him and applied to my life, let me give you the top three that have had the most impact.

Lesson No. 6

The title of his breakout book is The Subtle Art of Not Giving a F*ck. And that’s the most important thing I’ve learned from him: not giving a fuck to things not worth giving a fuck to.

All of us have problems and worries. Often we let them consume us.

But if we take a closer look, we’ll realise that many—if not most—of those problems and worries are mere inconveniences and frustrations. Things not really worth making a fuss over.

This idea of not giving a fuck to things that are not “fuckworthy” resonated strongly with me the second I learned about it in his book. And it’s a principle I’ve lived by since.

Why get worked up over things when you can just get on with solving them (when you can) and continuing with life, or just forget about them (when you can’t solve them) and continuing with life.

Life is too short to be spent constantly worrying and fussing over things.

Lesson No. 7

One of my boss’ principles is: “Fuck Yes, or No.”

This rule basically applies to all things and relationships in life. If we don’t feel something is a “fuck yes” for us, then the course of action is simple: we don’t do it. If we don’t feel “fuck yes” for someone, then we don’t invest in a relationship with them. And—most importantly for me—if someone isn’t a “fuck yes” for us, then don’t pursue a relationship with them.

This last point has been crucial in helping me weed out the relationships in my life where the other person is hot-and-cold, where I’m sometimes not sure whether they want me in their life at all.

As someone who has a lot of hang-ups about relationships, this principle has served me very well. It’s helped me avoid hours of agonising over whether or not “they want to be my friend,” “I should send them that text,” “I should invite them out for X, Y, Z.”

If I don’t feel they’re a “fuck yes” for me, then I just don’t do anything. One hand doesn’t make a clap. I put in an initial level of investment, and if that level of effort isn’t reciprocated, I walk away.

It’s made my social life far more pleasant to navigate.

Lesson No. 8

I studied Economics at university, and the concept of opportunity costs isn’t new to me.

But it wasn’t until I read my manager’s writing on decision-making that the point was really hammered home. In one article on his website, he writes that the goal in all decision-making in life should be to incur minimum costs for maximum benefits. Or if you look at it in risk terms, to take the smallest risks in exchange for the largest potential benefits.

This is a lesson that can be applied in any area in life, but I’ve been using this in the one area of life where I have the most hang-ups and that you may notice has come up regularly in this article: social life.

When I’m hesitating to reach out to get to know someone new, I tell myself: What are the risks involved? The person may reject my advances, but that’s that. The potential benefits, though, are huge. I may gain a new friend, another enriching relationship.

This is something I think I’d been doing even before being introduced to my boss’ writing. It’s basically how I got together with my partner who I literally sat down next to in a bar one evening and decided I wanted in my life.

Most recently, I applied this thinking only a few days ago. I’ve moved to a new city to be with my partner and know only a few people here. There’s a Facebook group for people moving to this city, and I decided (risk #1) to give a shout-out to others quarantining at the same hotel. One person commented “hi” back, saying not only are we staying in the same hotel but also we were on the same flight.

The conversation could have ended there, but I decided to risk rejection (#2) and reach out to them privately to see if they’d be happy to keep the conversation going and trade notes on our hotel. That led to a pretty engaging conversation where they seemed happy to share details about their life, not a stilted conversation where every question is answered with one word.

So before I left quarantine, I decided to take risk #3 (and I thought a lot about this) and ask if they wanted to have coffee in person sometime after we gain our freedom. And they said yes. And now I have potentially made a friend of my own in the city. It wasn’t easy to outright ask a stranger out for coffee, but I’m very glad I did.

So this thinking—minimal risk for maximum benefit—has truly served me well time and again.

Thank you, Mark, for the work you put in to re-package complex philosophical maxims and psychological concepts in a way that is accessible to the world. I—and million others around the world—thank you sincerely for your work.

These are the eight life lessons I’ve learned from my four managers over the past three years and a bit.

As I said, I’ve been extremely lucky in my professional journey to have had managers who have made a positive, lasting, material impact on my life.

I couldn’t, and wouldn’t, have asked for better.

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