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Being Your Own Boss is Great

In Theory

4 min readJan 2, 2022


I laugh when people tell me they want to quit their job and go freelancing full time. Not because I don’t believe in them but, because I know they’re in for a hell of ride. And they just don’t know it yet.

Everything is better in theory. Life is better in theory. So the dream of being your own boss and not being shackled to a desk is better…in theory.

But, the reality is very different.

More and more, I see articles popping up on Medium on how people are actually quitting freelancing to go back to the 9–5.

And I get it.

Because I tried and failed.

Well, let’s say I actually got very lucky. Before I could really fail, I got a steady contract. A 9–5 that saved me a lot of grief.

You’re not just the boss…

It all start with you suddenly realizing that you’re not just your own boss but, you’re also your own HR, Admin, Accounting, Sales, Marketing, IT… you get the point.

You don’t just do one thing. You have do everything.

In an organization, we tend to forget that we have 10 different departments supporting us. And then suddenly you have to learn to do all of that.

Granted, it’s much easier to do it for one person but, it is time consuming and for freelancers time is money.

And outsourcing these things, also cost money.

You need Strength

Oh boy… you need all kinds of strength when you’re on your own.

Because of all the roles you need to fulfil, you actually work longer hours.

You have no timetable so you tend to do whatever, whenever.

I mean that’s the reason you wanted this right. The freedom of time. But the hours add up and soon, you’re exhausted.

So you’re physically tired, and then mentally tired.

But wait, that’s not all. You begin to realize at one point that despite all the hours you’re working, the bank balance isn’t increasing the way you’d hoped. It’s not like there’s going to be an automatic credit to…



Ayesha Tariq

Mother | Macro & Investment Strategist | Co-Founder, MacroVisor | Contributor on Bloomberg & Fox Business | Ex Corporate Banker