To quit or not – when and why should you quit

LinkedIn is ablaze with posts that tell you, “Never quit.”

But probably the biggest mistake I have made as an entrepreneur is not quitting when I should have.

Let me share this story which started in 2012 when I quit my job and launched CourseBrew, my first startup. I built a learning platform, which had some truly novel ideas. But there was only one problem – I had zero customers. People didn’t care about the product features I thought would set the internet on fire.

So I had two options: quit and try another startup idea, or keep going.

The problem was that I had never, ever quit in my life. In the past, whatever goals I had set, I had always achieved. So how could I quit now?

My mother told me, “You have tried hard. And if it isn’t working, there is no shame in trying something else or even taking up a job.” But I didn’t listen to her.

Instead, I rationalized, telling myself, “This product is obviously great. All it needs is this ‘XYZ feature’, which is currently missing. Once I build that feature, it will fly off the shelf.”

So I added that new feature to the software, but still, no customers came!

Then I rationalized that the product needed ‘just one more feature.’ And this went on and on: from 3 months, it became 6 months, then 1 year, and finally 2 years. But even after adding lots of new features, the product was heading nowhere.

At that point, I had no idea what to do next. I was deeply ashamed but the more time I invested in the product, the harder it became for me to quit.

So now looking back, what should I have done?

I should have quit between the 3 to 6-month mark and tried a different startup idea. Alternatively, I could have easily taken a high-paying job for a year or two and later tried another startup.

But I just could not bring myself to say, ‘I quit.’

And I was making the same mistake that many others make: I misunderstood the concept of grit and not quitting. So let me explain.

If there is one quality that almost every high-achiever possesses, it is grit. And the underlying reason is that any ambitious journey will have massive ups and downs, and it will take time. These lows will shake your confidence and destroy your motivation. Your emotions will spiral out of control.

And this happens with most successful companies and entrepreneurs. In 2000, if Amazon had delayed its fundraise by a month, it would have gone bankrupt – that is how close it came.

In these difficult situations, when motivation plummets, most people quit. And that is why, they don’t achieve ambitious goals.

So the logical conclusion is – ‘If you want to do big things, don’t quit.’

But I think this advice is too simplistic. Let me provide a more nuanced version of ‘Don’t quit.

When we have a goal, there are many possible paths that can lead to it. And there can be three kinds of quitting:

1. You quit because the journey is hard even though you STILL believe in the goal and the path.

2. You quit because you believe in the goal but feel that the path is wrong.

3. You quit because you no longer believe in the goal. E.g., you quit your startup because you decide that entrepreneurship is not the right fit for you.

Grit is about NOT doing the no. 1 above – it is about not quitting because of discomfort. If you genuinely believe in the goal and the path, then stay on course.

But you can believe in the high-level goal and yet be flexible on the path that leads to it. If you find that one particular path isn’t working out, quit that and try another one.

In my story above, this is what I should have done. My goal was to become an entrepreneur, for which I could have pursued many different startup ideas. I could even have taken up a job for a bit and later tried my hand at another startup.

But I was not thinking clearly.

If you keep doing whatever you are doing even when it no longer makes sense, it is stupidity, not grit. This is what I did not understand.

So my suggestion is that if you believe in your end goal, don’t quit because of discomfort. However, shamelessly change the path if you are convinced that it is the wrong one. In the startup world, this is called ‘pivoting’. And you can pivot even in your personal life and career.

Now, you might ask, should we never quit on our big goals?

Again, I would take a cautious stand here. We humans change, and our goals also evolve. It is a natural part of our growth and learning. So it is possible that a goal that excited you a few years ago now feels meaningless. If so, it is totally fine to quit that goal.

However, when quitting your high-level goals, be very cautious. Make sure that your goals have genuinely changed, and that it is not some mood fluctuations or emotions making you think so. But how do you make that distinction? That is where your personal judgment comes in. That is also why human decision-making can never be reduced to an algorithm.

Finally, is it okay to quit even if you still believe in the goal and path? In general, I would say no – but there would be exceptions. If staying on the path is causing unbearable pain, compromising your mental health, or family life, then prioritize your well-being.

So do I still believe the ‘Never quit’ motto? I actually do.

But everything has to be within the limits of reason. Discomfort and pain are part of growth. Don’t let them distract you from your goals – with the exceptions I laid out above.

The next time you are in doubt, I hope this piece can be of some help.

Nothing worthwhile is easy. And easy stuff is rarely worthwhile. I wish you good luck in your journey. Stay the course, but sensibly.

Thank you for reading this.


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