Here is to the bosses we sometimes wish we had.

The 5 Reasons I (sometimes) Wish I Had A Boss.

The story usually goes as follows.

You meet an old friend, for the first time in a long time, and you ask “where do you work?”

They tell you they work in an office or the bank. They look a little sad and swerve away from adding any more by returning the question. You reply something like “well, I set up my own startup company and I…

Before you finish, they exclaim, “Whoa, so you are your own boss, jeez that is amazing, I wish that was me!


There is a common belief that being your own boss is a one-way ticket to the happiness express.

These people believe that by working for yourself rather than the ‘suits’ — those who perch above you on their pedestals, directing you, enslaving you and treating you like the shit on their shoe — you will find eternal work satisfaction.

The reality of being your own boss is that while it can provide immense satisfaction, it can also be brutal, for several reasons.


Reason 1. It’s overwhelming.

Who’d have thunk it?

Being the boss of yourself means you have to take control of instructing yourself, scrutinising yourself, trying to make plans and routine for yourself, then sticking to these plans and routines.

If you have employed staff, and become their boss, you will have to sort this out for them.

You have to pay yourself, pay others and pay the tax man.

In effect, you now have to control and organise all the stuff you took for granted when it was laid out for you by that bastard boss you used to work for.

You may have dreamed of ‘sticking it to the man’, but at least this man kept you in check.

Reason 2. The shit.

Being the boss comes with a lot of shit.

  • You have to take the shit.
  • Give the shit.
  • Hear the shit.
  • See the shit.
  • Buy the shit.
  • Sell the shit.
  • Stock the shit.
  • Build the shit.
  • Clean the shit.
  • Shit the shit.

The shit is everywhere, and you will have to be the one to deal with all this shit.

(Note: in most cases, this is metaphorical shit.)


Reason 3. Say goodbye to ‘work/life balance’.

The old rule of ‘leave your work at work’ does not apply here.

You always take your work home with you.

Whether you take physical work home or take it home in your mind, it will linger there. Every day, and every night, the running of your startup will consume your brain.

You will always have that one email to send, that project to price, that material order to complete, that client to visit, that social media post to put up…

When you run the show, it is difficult to switch off from it and leave it in the workplace, because unfortunately for you, you are the workplace.


Reason 4. It’s all on the line.

Being your own boss is like the movie 300, although you probably wear more layers of clothing… and don’t have a CGI six pack, or one at all.

Leading your start up is the equivalent of brave Leonidas standing in front of his Spartans, preparing for battle.

It’s you. Your company. Your project. Your idea.

You are the face and the front, and your battle ahead is against all the odds.

If it succeeds, you can “prepare for glory”. If it fails, it is on you and your ego will fall with it. There is no boss, employer or company to absorb the failings.

You must be ready to commit and fight for your start up.

As Gorgo, Queen of Sparta, said… “come back with your shield, or on it”.


Reason 5. No Money Mo Problems

Money is the be all and end all in most start ups, whether you admit that or not.

Paychecks are a necessity, and unfortunately, sometimes they dry up. Maybe a week goes by without a paycheck. Maybe a month goes by. Maybe you realise you have been working without pay for the last two months.

It is a killer.

It happens for various reasons; delays in project outcomes, problems after installation or a client is slow to pay invoices.

During times like these, you will come out in a cold sweat checking your bank balance, worrying about when rent and bills are due, wages etc. You might consider changing career path immediately…

But don’t.

Being your own boss is not a complete shit show.

(even with all the shit listed in reason #2.)

For every failure, there is a success. For every down, there is an up. Every dog has its day and all that.

There are many advantages to being your own boss.

You control your working schedule. You can abolish the 9–5 routine. You can decide your wage. Take holidays and days off when you require. You can pick and choose your jobs and clients. You are able to take the start up in the directions that are best for you.

So to the friends that exclaim “Whoa, so you are your own boss, man that is amazing, I wish that was me!”, that may be so.

But before you rip off your tie and run out of the office declaring you are ‘done with this shit!’ — be prepared to suffer the joy.

It takes heart, dedication and a dose of bravery to ditch your boss and become your own.

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