Career Choice: Good boss or Good work?

Someone asked me this recently:

You have 2 options: Work with a good boss, but the work is some boring stuff, or work on some interesting project, but the boss is not good. Which one would you choose?

My mind jumped to all the boss-work combinations possible, see the picture.

If I make this a generic question, it is really a multiple choice question:

Which is the best option for you to choose?

  1. Bad Work and Bad Boss
  2. Bad Work and Good Boss
  3. Good Work and Bad Boss
  4. Good Work and Good Boss

The questioner was asking which one to choose between 2 and 3, so let’s talk about this first. While there is a scale of goodness, let’s assume black-and-white situation for simplicity – things are either good or bad!


Good work makes life at work interesting, it grows your career, and overall makes you happy. So of course you would want to choose good work.

Good boss gives you opportunities to grow, guides you in your career quest, and removes roadblocks in your work thus making you effective. So of course you would want to choose good boss.

If you have to prioritize between them, it is not easy. My answer was to choose good boss (option 2 above). Here are the reasons I gave:

  1. You can turn boring work into work that helps your career (esp. when you have a good boss), but it is very hard to turn a bad boss into a good one.
  2. Your career depends much more on quality of boss than quality of work. This is because career depends on factors other than quality of work. For example, even if you work on a boring project, your good boss can give you opportunities to present your work to your VP, thereby giving much needed visibility.

This also reminded me one of the hindi couplets from my textbook:

गुरु गोबिन्द दोऊ खड़े, काको लागूँ पाय।

बलिहारी गुरु आपने, जिन गोबिन्द दियो बताय।।

(Teacher and God, both are standing – whose feet should I touch first?

I bow to thee, O teacher! Who made me understand God)

While the analogy is crude, it is worth saying: a good boss is like a teacher, a guide – he/she will help you know and understand the work, the career, the workplace. Good work is great, but not enough.

So what about options 1 and 4? They seem obvious – 1 is strict no-no, and 4 is worth grabbing with both hands. However, it is important to keep in mind that there is no single, or correct, definition of ‘good work’ or ‘good boss’. Work good for one may be painful to another, and boss great for one may be bad for others. So if the definitions are clear, the question becomes more complicated, and even moot. Before answering this multiple-choice question, it is important to spend time on following questions:

  1. What kind of work will be good work for me at this stage of my career?
  2. What kind of boss will be good boss for me at this stage of my career?

These are not easy questions to answer because they rely on your current career stage, career goals, and your self-awareness, but they are very important to answer if the original question is to be answered.

What is your take on this? If you are given a choice between good boss and good work, which one will you choose?


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