The Dark Side of Entrepreneurship Suman April 4, 2023

The Dark Side of Entrepreneurship

I was slumped on my couch. Like literally, slumped. It takes a lot for me to reach that level of demotivated state.

I get lazy, I loll but never slump with dejection!

I was in a call earlier this week where I was being pitched to take up lead gen services.

Although the person made all fair points, the tone was condescending, pointing out everything that I was doing wrong.

I felt like being admonished by a teacher for not getting the homework right.

The points made were valid! As a business run by a single person, I accept that things fall through the cracks.

But judging someone without appreciating the journey they’ve been through isn’t the right way to gain clients.

While I’m learning new things and trying to build something more permanent in the post pandemic times, this came as a sucker punch!

Now if you’ve ever been an entrepreneur, you know the soul crushing self-doubt that comes with the territory. We don’t need others’ subjective opinions about things slipping through the gaps.

I started questioning everything I am doing. I didn’t even want to get out of bed yesterday.

The prospect of facing work seemed like a lot. And if I got out of that bed, I’d have to work at some point in time.

Not because I have to but because, well! What else would I do with my day, my life. And then it just spiralled into an existential crisis.

But then I woke up today and got to work!

What is being an entrepreneur if not living to fight another day! Getting up, dusting ourselves off and going to battle, hoping to win the war.

Not letting minor setbacks like other people’s opinions veer off course.

As an entrepreneur, there are good days and bad days. Days when you love the heights of freedom working on your own.

And days feeling down in the dumps with no hope in life and future.

Yet, it’s about soldiering on even when you don’t see light at the end of the tunnel. And even when you can’t see it, you have to believe that it’s there!

You’ve got to keep moving to get closer to the light!

It’s a peak you wish to reach. It’s a different one for each one of us. I am not even sure if there is a definition of what the peak looks like.

But most of us spend a lot of time at the bottom – thinking, doubting, mustering the courage.

And even when we begin our ascent – we fail, despair, doubt.

We fall, scrape our knees, lose our hold and slip lower.

But we nurse our wounds and forge on! Climb through the pain.

One step at a time. One milestone at a time.

We may change paths, we may change the goals but the important thing is to keep moving.

To not let the algae of self doubt freeze us at one point.

If you feel alone, you reach out and grab the others who are dealing with the cold, hard truths of working alone.

As someone who’s not a natural at it, I struggle with the concept of “building a business”.

Send me to a room full of people to train and I can dazzle them in no time!

It’s the lonely, anonymous life of an entrepreneur that I’m uncomfortable with. It’s working alone in the trenches that gets to me!

It’s like a great marriage – it comes with so much fun and freedom but also encumbers us with burden and obligation to keep going!

You can’t have one without the other!

And through all this chaos, some things work as a life boat when waves of self doubt threaten to wash my plans away.

Entrepreneurship is a mindset

It changes you at a personal level. You make rules. You follow your vision.

Having been rule oriented all my life, I am learning to colour outside the lines. Try things just to fail. Step way out of my comfort zone.

Despite the dissenting opinions about how things should be, it is the unwavering conviction that we have in our mission that keeps us going.

And that’s a heavy cross to bear…most times.

1. Entrepreneurship is hard

Especially when done solo.

The fast pace of change makes it harder to stick to one set of rules that define reality.

Reality is a fluid concept in the post pandemic world and evolution with the times is imperative to stay afloat.

Things are bound to take time. Or slip through the gaps.

2. Its a marathon not a sprint

This has been the hardest to get used to. I am more of a destination person – let’s check every thing on the to-do and be done.

But working on your own isn’t a task that can be checked off! You can’t finish everything in a day.

Consistency is the key and success is incremental in nature.

My recent trick: Pick tasks for the day and forget the rest

But like I said, forge on!

3. There are different paths to success

Just choose your own path.

I have gone through the blueprint of enough coaches to know there’s no right or wrong.

Find a way to reach your goals defined by who you are and what you want your life to be.

It’s okay to leave some things out and focus on what works for you

4. Finally, it’s okay to wallow 

Doubt is a part of this world. Will you make it or not, who knows!

It’s okay to take a sicky in the middle of the week. Wallow in self pity.

Pout about the hard path you’ve chosen.

Give in to self care! Don’t hold it all in!

And after the catharsis of a good cry, you’ll find more clarity at the bottom of a bottle of wine! Well! once the booze wears off! 🙂

In conclusion

I am not saying that the landscape is all bleak and all’s left at the end are bleeding soldiers who didn’t make the mission.

Like everything else in life, entrepreneurship is also taking one giant leap of faith.

And hope we fly!


This is the only post where I’ve been so open and vulnerable in the hope that there are kindred souls out there! People who’ll be bold enough to shed the facade of control and share their stories of struggle in business.

If you resonate with any of this, tell me in the comments! I am confident you wont hang me out to dry!