Would you rather have an easy job working for someone else or work for yourself but work incredibly hard? And why?

A student asked:

Would you rather have an easy job working for someone else or work for yourself but work incredibly hard? And why?

This is a false dichotomy. There are a few more possibilities:

(1) Easy job working for someone else
(2) Moderately difficult job working for someone else
(3) Incredibly hard job working for someone else
(4) Easy job working for yourself
(5) Moderately difficult job working for yourself
(6) Incredibly hard job working for yourself

I used to work for myself when I did freelance work quite some time back. And if I compare that with how I’ve been working for other people since graduation, I prefer working for other people, but provided that they are good bosses. And I must stress the importance of good bosses. I’ve had my fair share of not so good bosses, and the experience will definitely make you say, “I’d rather work for myself.”

I have been incredibly fortunate that my two former bosses: (1) the former Vice President (Alumni & Advancement) of NTU and former Dean of the College of Humanities, Arts, and Social Sciences, Prof. Chan; and (2) the Associate Provost for Undergraduate Education in NUS, Prof. Chng. Both of them had been incredibly nurturing. They provided me with many exciting challenges and opportunities to grow and develop as a person. And they set themselves as exemplary role models on how to lead and manage a team, how to lead projects, and how to handle difficult situations. I’ve learnt so much working under them. I am forever indebted to them for moulding me into the person that I am.

And I am more than aware that I would never have gained such a wealth of experience and insights if I were to work for myself. We are limited by our imagination and the people we hang out or work with. And if we don’t have access to incredible people – people who are so much better than us intellectually, emotionally, and even morally – we will not know the heights of how much better we can become. Without such people, it’s very hard to gain new ways of thinking, or new ways of managing one’s self and others.

But good bosses are hard to come by. So if you find that an opportunity presents itself for you to work for a good boss, you should seriously consider it.

As for work that’s easy, moderate, or difficult, I’d choose difficult work anytime because I love the challenge. Easy work gets boring and meaningless quite quickly. Difficult work will mean that there’s always lots of surprises and struggles and obstacles to overcome. It’s like the pleasure of playing a computer game. It’s challenging but satisfying when you complete it, except that it’s you in real life and you have only one live. No respawn.

That said, I think it’s because I have enough challenges in my work that I don’t like having to go through another challenge or struggle when gaming. It’s like working another shift, except that I don’t get paid. Does not spark joy at all.