The Dark Side of Entrepreneurship

February 7, 2021

A subscriber of Sunday Coffee told me about his struggles with his business, and said how reading everyone’s winning stories could sometimes demotivate him further as he’s struggling to drive results.

He asked if I could talk about the dark side of entrepreneurship from my own journey.

I knew exactly what he's talking about.

On the outside, it might seem like we are just thriving everyday. Or the successful people we read about online are just blazing past every goal effortlessly like an elegant ballet dancer.

The reality is different, and I think as an entrepreneur we learn to internalize it and look past it. But it still very much exists.

It’s not always rosy in entrepreneurship.

Like other humans, I have many struggles in life too. And not everything comes easy to me as it might appear on the outside.

Most recently, I had to work 25 hours straight last weekend and not sleep at all on Sunday night. This was all in order to meet the deadline for Programmatic SEO’s course launch. I had committed to Feb 1, and being the person I am, couldn’t fathom changing that date and telling people "sorry I won’t hold up to my commitment."

In the previous two weeks, we were intensely shipping features for DelightChat, figuring out the Facebook app approval process which had lit a real 🔥 under our ass, especially with the fast approaching timeline for beta launch.

For a brief period, we thought we would have to launch a broken product as the FB app approval hadn’t come through despite our best efforts.

Entrepreneurship gives you anxiety.

Sankalp and I worked long hours each day and night throughout most of January.

Especially Sankalp, who until recently was handling all the backend work by himself with four engineers in frontend waiting on APIs. He would get up at 6.30am to start working on APIs and make himself available during the day for ad-hoc problem solving or doubt resolution.

And while we are self-aware enough that it’s not the end of the world and we are doing everything in our power to make things happen, the anxiety still kicks in. 

  • “What will our users think?”
  • “How can we ship a broken product?”
  • "How will your team members feel if users don't like our product?"

You can’t just relax one day and think the problems will go away. If anything, now you have even more problems to solve piled up.

There’s no boss or manager who faces the brunt of an outcome gone awry. It’s completely on you. Every failure is on you. Even the fear of failure hits you.

Entrepreneurship can be lonely.

I often jokingly say that “I don’t have friends.” And while the absolute statement isn’t true, I’m not Tom Hanks living on an island with Man Friday, but it can feel as lonely as that sometimes.

I don’t have group plans for Friday nights. I don’t meet up with people outside. I don't have people I message during the day to "chat" or casually talk about "stuff".

Fortunately Sankalp has been in town since 2 months, which means I had someone to meet up with. There's another friend living in town who I meet up with, but again it’s once in three months. 9/10 times I’m by myself at a bar or coffee shop with my laptop or notebook or nothing (you might find me in the wild staring into a wall).

Don’t get me wrong - I don’t hate being alone. But this journey can get lonely.

You’re no longer part of “normal” social circles. You don’t have company outings or lunches that large corporates organise frequently. Being a remote team means that applies doubly so. You can’t even hang out with your own team members.

Entrepreneurship is hard to switch off.

I stop thinking about a problem, hurdle, situation, it doesn’t mean my business will run on its own or its problems and challenges ahead would get solved by themselves. While I try and I know I should, it’s hard to switch off.

Things are about to get more intense in the coming weeks when DelightChat has dozens of real users using (and breaking) the app everyday. When that happens, every time an issue pops up even on the weekends, we’ll be there to talk to the user and to resolve their problem ASAP.

We can’t tell our users “oh it’s okay if our app is buggy, we’ll fix it tomorrow, you can ignore replying to your customers for a day”. That won’t work.

Entrepreneurship is uncertainty.

“What if we do everything we can, and yet nothing works out?”

It’s perfectly rational to have this fear and to have some expectation of payoff when you’re working this hard. Especially when the results are yet to present themselves.

In my view, results = $ MRR. Every other metric, while it might be meaningful, is ultimately vanity as compared to making actual $, which is the goal of a business.

Until those results present themselves, we have to wonder if we are headed in the right direction. Whether people will pick us over competitors. If some funded competitor wouldn’t just decide to not make money (they can do that, did you know?) and drop a huge free plan and make us redundant.

There’s N number of things that go wrong, and any one of them is usually sufficient to hurt you hard enough and leave you stranded.

Entrepreneurship is a giant pile of problems with 💩 on top.

And yet, I love it.

I love every freakin moment of this giant mess.

I love the uncertainty, of tackling problems relentlessly and solving them. At some point, you feel like Neo who is deflecting blows effortlessly.

I love that the journey is hard. It lights a fire under my ass. It makes me outperform myself and push my own boundaries on what I know and what I’m capable of.

I love those days when we have to go the extra mile. Like staying up all night, or figuring out video editing and annotations at 1am to submit a walkthrough video for approval. Or waking up at 6am to finish up a feature design so that engineering isn’t blocked by me.

I won’t say I love anxiety, that would be a weird thing to say, but I do love the process of learning how to manage anxiety and funnelling that energy into something useful and productive.

I won’t say I enjoy being lonely, but it teaches me a little more about myself and people each time I’m sitting by myself and lost in my own thoughts, or penning them down, or just observing people in the wild (a bar can be considered wilderness considering we don’t live in jungles anymore).

This journey is all we have.

There are days or weeks when the whole thing feels like a drag. And then there are moments of pure joy that make you feel that all of the work and effort is worth it.

Regardless of the outcome, each day we get to live to our full potential. Each day is an opportunity to learn, to do better, to grow, to thrive.

I love the entrepreneurial journey, despite all its downsides.

Because life is an adventure, and entrepreneurship lets me thrive.

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