HabitStrong Newsletter #63 - Rajan Singh

When I started my first startup, I thought I was being bold and visionary. And here was my plan: We would build a differentiated learning platform, raise a seed round in 6 months, and take off like a rocket ship.

But three months later, the product wasn’t ready. Six months later, still nothing we could really sell. At that point, I was thinking: this was supposed to be flying off the shelf.

So we added some more features, and tried getting customers, but they didn’t come running. So I told myself: “Maybe we just need one more thing. A few more tweaks. Then it’ll click.”

That one more thing became another, and then another. My confidence kept dropping. But instead of facing the harsh reality, I stayed busy – building, polishing, rationalizing. Three months became six. Six became a year. Then two.

During this period, I would often wake up with a pit in my stomach, dreading the daily calls with my tech team. Every delay felt like a punch in the gut. Did I know what I was doing? But I couldn’t bring myself to say the words: This isn’t working.

At some point, we ran out of money. So I asked my technology vendor if he would work for equity – no cash. He said no (thank God for that).

Many nights, I remember sitting alone, staring blankly at my laptop screen. I wasn’t even thinking anymore. Just frozen. Exhausted. Ashamed.

But still, I couldn’t face the truth.

My mother could probably sense my struggle even though I never told her anything. Very early in my journey, one day, she gently said this to me, “See, you left your job and gave it your best. Not many people have courage to do that – that is in itself a big deal. But there’s no shame in walking away from something that isn’t working. Don’t hesitate to do that.”

I wish I had the wisdom to listen to her. But I did not.

And so began another detour. I said, “Fine, this idea didn’t work. But here’s a sure-shot one: let’s build a tech-based science and math learning platform in collaboration with a big coaching brand in Kota.”

We signed a Joint Venture, and started building again. And thus went another five years.

Five more years of denial. Of telling myself stories. Of clinging to anything that would prevent me from saying, “This is not working.” Eventually, I lost crores, and more painfully, years of my life – all because I couldn’t do the hardest thing: accept the truth.

The hard and sad lesson

We all run from unpleasant truths – that’s human. But the real danger is when we start running from ourselves. Because when we start evading the truth, change becomes impossible.

The turning point in any life, in any career, in any situation, is always the same: Admit the truth. Even if it hurts. Especially if it hurts.

I kept telling myself, “Just one more chance, one more tweak, one more iteration.” But underneath it all, I was just scared to admit I had failed. Scared of the shame. Scared of, “What will I tell my investors? What will they think?”

And ironically, that fear kept me stuck for far longer than failure ever could.

What I want you to take away

I don’t want you to ever go through what I did. So I will leave you with a few things:

1. We all make mistakes. Big ones, small ones – no one is exempt. The problem is not the mistake. The problem is what we do after.
2. Don’t double down on denial. The longer we avoid the truth, the deeper the hole gets. Don’t try to “fix” your way out of something you need to walk away from.
3. Facing the truth won’t break you – it’ll save you. It may sting, but it’s the only path to freedom. To resolution. To peace.

If this story can give you the courage to face a hard truth – to stop hiding from yourself – then writing this newsletter was worth it.

I wish someone had told me this years ago. So I’m telling you now.

Rajan

PS: If this resonated with you, or if there’s someone in your life who might need to hear it, feel free to forward it.

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Rajan Singh I'm the founder of HabitStrong. In my previous life, I was an IPS officer, McKinsey consultant, and a private equity investor. Now, I’m an entrepreneur, helping people be more successful, more focused, and build better mental and physical health.

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