Why I Can’t Forget About My First Boss

Cherry Whipped Cream
Soul Magazine
Published in
5 min readMay 16, 2024

He was kind.

You rarely hear about kind bosses. Nice, sure. But kindness is hard to come by.

You can pretend to be nice, but you can never pretend to be kind.

There was something about him that radiated positivity. He was someone who didn’t care about hierarchy, even though he was the CEO of the company. It was clear that he treated everyone equally.

I vividly remember our first meeting nearly a decade ago. I landed my first full-time job a year after graduating, following an internship and six months of freelancing, which I believed enhanced my resume as a new face.

I was waiting in the lounge on the couch when he entered with a grocery bag to buy milk. He made quiet eye contact, stored the milk in the fridge, greeted me, and went to his office. Soon after, he returned and started the interview. It was pleasant, and I landed the job shortly after as the first hire for the role.

Soft skills matter

Your character and daily interactions shape others’ perceptions of you.

From the start of my career, taking initiative and asking questions until I fully understood my tasks has been important to me.

Emotional intelligence (EQ) also makes a significant difference. I’ve encountered people with no self-awareness, resulting in poor social relationships and chaos.

Interpersonal relationships

People don’t remember your actions, but how you make them feel.

It’s true when they say to work smarter, not harder.

I learned this the hard way over the years, but hard work still pays off, especially when it comes to recognition and rewards. However, it’s important to have self-recognition. It doesn’t mean you’re not doing well when no one says anything. People see what they want. As long as you’re delivering the work and not receiving biased feedback, you’re already doing much better than you think!

Learn how to form relationships outside of the workplace. My first boss liked to make jokes and took an extra step to make us feel comfortable at work, at least for me. Since we had frequent meetings as a startup, I had to converse with him a lot and coordinate tasks between different teams.

Trust played a big role too; getting the work done and being proactive helped me achieve success at my job.

He made me feel special and appreciated

Was he extra nice to me compared to others because we got along well? Perhaps. He once told me I was also like a personal assistant to him.

This is probably not going to happen to most of us, especially in a work setting. I treasure the dynamics we created and maintained. He was consistent. He never blamed his employees or took his anger out on us, even if he was having a bad day. That’s why I admired and respected him.

Now that I think about it, he was like a silent mentor.

I never once felt drained or reluctant to go to work. It was a bonus that the workplace was close to my neighbourhood. I made a good friend there as well. During that time, I was probably the happiest and also quite naive.

Be willing to take a chance on others

He took a chance on me, and I will never forget it.

How could I?

It left a huge impact.

To be honest, I miss working together with him after all these years in society. I always looked back at the times we shared in a professional workplace, and it comforted me to know such places do exist when we hear of horrible and toxic environments.

I struggled after leaving my very first job back then. I managed to land a temp role as an English tuition teacher, but I know that wasn’t my calling. I contacted my ex-boss and he was so genuine and willing for me to return. But the other people in management weren’t so keen since I left. I guess there was a silver lining. I couldn’t see it then but I am thankful for how it turned out. Otherwise, I probably will still be stuck in a rut. I left because I wanted to grow and be out of my comfort zone, yet I almost returned. Phew, sometimes rejection ain’t’ always a bad thing.

I joined an SME for a year, and it was great for my experience, but it had poor career progression, support, and a low salary, even though I was single-handedly managing a brand creatively. However, if I choose to look at it from another perspective, it helped me land a better job, a higher salary, and most importantly, progress!

I cherished those two years I had there. It wasn’t a long time, yet it wasn’t short. It was an amazing first job. Not many can say their first jobs were great and that they met good bosses. I still yearn to work with my first boss one day, although the chances are low. However, I can only continue to become better at what I do and as a person! I look forward to the future with optimism and gratitude each day.

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