1 Truth about “Being Your Own Boss” I Wish I Knew Before Dropping Out to be Self-Employed.

It’s cool, it’s tempting — but it’s what got me into many cycles of depression. The only thing I needed to master first is…

Saran Roy ↴
ILLUMINATION
4 min readNov 2, 2023

--

Image created by the author.

Being your own boss, deciding what to do and when to do it — it all sounds so good and attractive.

Well, it is good and attractive.

Freedom of time is liberating.

Independence is liberating.

Having the power of choice is liberating.

But what most of us don’t understand is it’s a double-edged sword.

For someone uninitiated (like me), this power can be overwhelming — eventually becoming the reason for own demise.

Why is it so hard being your own boss?

The only difference between having and not having a boss is the external constraint of time and a distinct fear.

If you’re employed by someone, you usually get constraints of time for the work you’re expected to do.

And if you fail to do what you were expected to, you may (mostly, will) lose the job. Or, worse, you may be humiliated.

This time-constraint and fear give you the motivation to do the job. It keeps you from deciding to “do it later” — even if you’re tired AF.

But, when you’re on your own, you don’t have the privilege of a pre-made choice anymore.

That constraint of time is no more.

And because there’s no time-constraint, there’s no distinct fear.

Yes, you fear going broke, but you can always “do it later” and delay the inevitable.

There may be project deadlines too — but “there’s time” (until “shit, it’s tomorrow!”)

It’s when you don’t have a choice you crave the power to choose. When you have that power, you realize just how hard making the right choice can be.

I desire to be a full-time writer. I have great strategies and ideas, and decent writing skills.

And I need to do it. Because if I don’t, I don’t know what I’ll do.

So, the only thing left to do is to write daily and consistently, no matter what.

But I don’t. Because “there’s time.”

I am genetically adventurous. I daydream about getting lost alone into the nature. I’d love to document it too and share it with the world.

And I need to do it. Because if I don’t, I know I’ll regret it on my deathbed.

The only thing left to do is to practice photography and really get out there.

But I don’t. Because… you know… “there’s time.”

Instead, I (temporarily) quench my internal thirsts with digital contents and by creating fake goals and plans when motivated.

I do it repeatedly until my dopamine levels hit rock bottom, and I proceed into another cycle of a depressive state of mind.

Here’s what you need to do before going on your own:

Before trying to become your own boss — before quitting your job or dropping out of that course — learn to be self-disciplined first.

You can have all the power you want. But you need to make sure that the power doesn’t overpower you.

You need to be worthy of that power — you need to be self-disciplined.

Being your own boss isn’t about doing whatever you want to do, whenever you want.

It’s about really doing what you need to do. It’s about making the right choices at the right time.

Being the boss is cool — but it’s not easy.

So, become self-disciplined first, my friend.

Conclusion:

Dropping out or quitting your job is cool.

Being self-employed and becoming your own boss is cool.

It brings you the power of free will.

With it, you can achieve remarkable feats, for sure.

But the same power can break you too, unless you’re pre-equipped with the shield of self-discipline.

As our favorite superhero has been told, “With great power comes great responsibility.”

With the power of freedom and free will, your responsibility is to become self-disciplined — capable of making the right choices at the right time.

Because if you don’t, that power may soon overpower you and drag you to the bottom, without you even noticing.

And why listen to me, you ask?

Well, because often there are the nights I spend uttering, “I needed to, but I didn’t.”

I don’t want you to be it.

And, yes, I have been a frequently-depressed self-employed dropout for the last couple of years.

“The road to success and the road to failure are almost exactly the same.” — Colin R. Davis

So, be careful.

Like what you just read?

I’ve just started to try my hand at writing for people other than me.

A follow and feedback will really mean a lot to me.

See ya.

--

--