Eight Lessons From the Bosses #1

A simple trick to start every conversation

Before we start, I’d like to thank everyone who wrote back after reading last week’s “I Don’t Want Kids.” Your responses were illuminating and I sincerely appreciate you opening up and sharing your intimate thoughts. Thank you.

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For 30+ years, I can happily say I’ve lived a charmed life.

One way in which I’ve been incredibly fortunate is in the bosses I’ve had, the managers I’ve worked under.

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 work better, but also how to live better. Which I think is far more important and has irreversibly changed the course of my life in many ways.

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

Boss No. 1

My first boss in the corporate world managed me as I began my career in Learning & Development. 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 glimmer in his eyes and deliver his famous line: “Tell me more.”

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

It changed my conversational mindset 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 on almost any occasion. I love the gentleness of it. “Tell me more.” It’s an imperative that yet 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 didn’t receive consistent and well-informed advice on how to manage my finances. I also never thought to educate myself. Almost all of my money was accumulated in savings accounts, fast losing its value to inflation, not being worked for gains.

After two separate conversations with my first boss, I did two things:

First: 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. Until one day, my boss 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 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 on 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 feel more financially secure than ever, whereas in the past I never, to my detriment, gave financial management any 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.

To be continued.

Until next Friday… Stay cool, stay safe, stay thoughtful,

Val