10 things that happen when you go from employee to entrepreneur (that might totally screw you up)

Yann Girard
May 28, 2018 · 12 min read

I don’t know what’s going to happen when you go from employee to entrepreneur. Or what happened to other people. But here’s what happened to me…


I became totally paranoid. I was always and always am afraid that things will stop working all of a sudden. So I’m constantly experimenting and trying to figure out ways to protect myself and the projects I work on to become more resistant against possible worst case scenarios.

Which of course is pretty much impossible. There’s no way to completely protect yourself or the things you work on against a worst case scenario. Simply because no one knows what the worst case scenario really looks like, let alone how you can protect youself against it.

They are called worst case scenarios for a reason. They are usually so bad and ugly that you can’t possibly protect yourself against it. Because you don’t even know what they are yet. And if you knew what they were, how they looked like, then they wouldn’t be worst case scenarios anymore.

But putting aside the fact that paranoia can lead to you spreading yourself too thin over time, it will help you to identify micro trends as well as macro trends in the economy way before most people will ever be able to.

And in my book that’s a win…


One of the hardest things when you go from employee to entrepreneur is the fact that you’d have to completely change your mindset. Depending on how long you’ve been working your job, you’re probably very good at it. Maybe you’ve even turned into an expert.

You probably know exactly what you’re doing. All the ins and outs. And no one is able to tell you what to doanymore, simply because you’re the only one who knows what to do. There’s nobody else who knows as much as you do about the stuff you work on.

And this is exactly what you’re getting paid for as an employee. You’re getting paid for doing the things you know and are really good at. You’re the expert. Sometimes you’re even the teacher that teaches others how to do the things you do.

On the other hand when you’re an entrepreneur you’d have to go back to being a student once again. You’d have to start totally from scratch. Again. Because the truth is that now you don’t know anything anymore.

Everything you think you know doesn’t really matter anymore. Because the market is a whole different story. The market is now your teacher. And you have to accept the fact that you’re now the student.

When you’re an entrepreneur the market is your teacher and you’re the student.

No matter how much you think you know. You have to listen very closely. Because if you don’t, if you ignore the market and think you know better, then all that’s going to happen is that you’re just going to crash and burn.

And it’s hard. Really, really hard.

It’s hard to go from teacher to student.

It’s hard to accept the fact that everything you know doesn’t really matter anymore.

It’s hard to accept the fact that you’re now the student. Again…

It’s hard to accept the fact that the market is now your teacher…


Everything is uncertain. Nothing is stable anymore. Or predictable. Your job description changes each and every day. Sometimes even multiple times a day. Things you did yesterday aren’t relevant anymore today. And things you didn’t even know about yesterday become relevant today.


Everybody says that you’ve gotta take over responsibility for your own life.

That you have to get a job.

That you have to do this and do that.

But this advice has a serious flaw.

Because at the end of the day getting a job has nothing to do with taking over responsibility for your life.

Like it or not but all a job really is, is that you’re outsourcing responsibility for your life to a corporation, your boss and their bosse’s bosse’s bosse’s boss.

So instead of your parents taking care of you in exchange for doing what they want you to do and following their rules, you’re now following your bosse’s bosse’s bosse’s bosse’s rules and exchange your time and workforce for stability, safety and money.

And at the end of the day there are so many different layers involved that you can’t even count the amount of people anymore who can crush you within just a couple of minutes.

People who don’t know you and couldn’t care less about you are now taking over responsibility for your life.

People who can decide about you and your family’s future and change it in a matter of days.

Here’s he thing…

Your boss couldn’t care less about you and will try to get rid of you as soon as there’s a robot, an algorithm or an artificial intelligence that’s cheaper than you, better than you or faster than you…


When you go from employee to entrepreneur you have to go from expert to jack of all trades.

When you’re just getting started you’re essentially the marketing department, the sales department, the design department, the business development depatment, the finance department, the IT department and pretty much every other department out there.

And I know what a lot of people are telling you. They’re telling you to just focus on the things you’re good at. And to outsource as much of the other stuff as you possibly can. So you can just do the things you’re good at and enjoy doing.

But the truth is that when you’re just getting started you don’t really have a lot of money. You can’t just pay ten different people to do this or to do that for you. You probably barely have enough to cover your expenses for the next couple of months.

And that’s the reality when you’re making the switch from employee to entrepreneur. You can’t hire anyone. And you have to do everything yourself. And maybe, but only maybe, you can start to hire people once you make enough money to hire someone.

But then again, every hire will increase your degree of paranoia. Because you’re now also responsible for another human being. And her family. Keep that in mind also…

So instead of outsourcing as much as you can, focus on figuring out how you can do most of the stuff yourself. So you don’t have to rely on people that will charge you every single second you talk to them leaving you totally broke before anyone even has the chance to buy your product or service…

And always try to figure out what the real reason is why someone is telling you to focus on what you’re good at…

A couple of years ago when I was just getting started I hired an accountant.

She told me that I should be focusing on the things I’m good at.

Which made a lot of sense to me.

So I hired her to do my taxes.

And then less than two weeks later I got a $1500 bill from her.

And I made less than $10,000 that year.

Needless to say that I never hired her ever again…


Everybody thinks that being an entrepreneur will help you to make a ton of money.

But the truth is it won’t.

Maybe less than 1% of the people who start a business end up making more money running and maybe even selling their business than they would have made if they just kept their job.

And everybody else is pretty much losing money.

So if the probability of making more money is about 1% why would anyone even start their own business?

I don’t know.

That’s a really good question.

And there are many different reasons.

For me it’s very simple.

I wanted freedom.

And I just couldn’t work a job anymore.

It was killing me.

Every single day I went to work and thought that I could do more than this.

That I had more potential than this.

So one day I decided to quit my job.

To prove it to myself.

To prove it to myself that I was really able to do more than this.

That I really had more potential than this.

Whether I succeed or not doesn’t really matter to me.

What matters to me is that I tried.

And to me this is worth more than money.

A lot more…


Might be the toughest thing out there.

And I’m not talking about being a freelancer. I’m talking about building something out of nothing and then trying to sell that something.

Sure, when you’re a freelancer you’re also selling something. You’re essentially selling yourself.

But at the end of the day being a freelancer is nothing else than a job. The only difference between a freelancer and an employee is that you’re selling your services to many different companies at the same time without the protection, comfort and safety of a job.

You’re selling something that you know the market wants and needs.

On the other hand when you’re an entrepreneur you’re usually trying to sell something that doesn’t exist yet to a market you have no clue about whether it even exists. Whether people even need the thing you’re thinking about selling.

And this is one of the toughest things out there. Going from one thing that doesn’t work to going to the next thing that probably won’t work either. Going from one thing that doesn’t work without losing your motivation, your drive, your ambition and without going crazy.

That’s what making money on your own essentially boils down to.

Sure, you could develop a plan. Just like you’re told to do when you read all of these business books. Or when you go to business school.

But the only purpose of a plan is to hep you feel safe.

A plan helps you to think in job terms. You do this and then that happens.

But this is rarely the case. Plans never work. Especially not when you’re just getting started.

Plans work in established companies with established clients and an established customer base you can sell your products or services to. But even then plans rarely ever work…

And this is what makes it so hard to make money on your own.

You think you know how to do it, but the truth is that you have absolutely no clue how to do it.

And the more you think you know, the less you actually really know…

And understanding and accepting this is the first step.

So what about investors?

Aren’t investors a convenient way to help you make money on your own?


Are just like your boss.

The only difference is that in many cases investors give you their own money.

And whenever someone gives you their own money it’s like they own you. You have to do what they want you to do.

And the more you owe them, the more they own you, your business, the things you do and the things you think about…

If you’ve ever taken money from someone you probably know how it feels.

Every single thing you spend some of the money on that the person who gave it to you doesn’t agree with, might lead to a discussion.

Borrowing money from someone, no matter if they’re close to you or not comes with dozens of small strings attached.

Strings that seem so small that they don’t seem to really matter.

But the truth is that all of these small strings mean a lot more than all the big strings combined.

It’s never the big strings that kill you. Because those are the strings you’re aware of. The strings you try to avoid.

And instead it’s almost always the small strings that kill you. The strings you’re not really aware of. The strings that are so small that you think you can completely ignore them.

But you can’t.

Because it’s always the small strings that will ultimately kill you…


Once you realize and really understand how hard it is to make your own money, then you’ll start to value it lot more.

You’ll stop wasting it for things that make you feel better about yourself, that you probably don’t really need,that you probably buy just to impress people you probably don’t even like that much.

And when I say you, I’m really talking about myself.

I can still remember my first job when I graduated.

I made more than $3000 a month.

What did I really do there?

Well, I don’t really rememeber anymore.

Most of the stuff didn’t really matter.

Or change a whole lot.

But at the end of each month I got a big fat paycheck.

More than I knew how to spend.

So of course I ended up spending money on stuff I didn’t really need.

Because it was so easy.It was so easy to make money at my job.

All I had to do was to show up each and every day, do what I was told and then I got money at the end of each month.


Here’s the thing…

The easier you’re able to get something, the easier it is to just give it away again.

That’s one of the reasons why most people who win the lottery go broke.

Because it was so easy to make all that money in the fist place…

Sure, a job isn’t always easy.

But compared to making money on your own building something out of nothing it’s a piece of cake.

By the way, this doesn’t apply to money only.

It applies to pretty much everything.

The easier you get something, the easier you’ll give it away again.

This applies to friendships.



And on and on and on.

And that’s the real reason why people who made a lot of money working really hard live a relatively frugal lifestyle.

Because they can still remember their first couple of years like it was yesterday where they were barely able to get by.

Where they were working their asses off making less than minimum wage.

And at the same time they’re always paranoid and aware of the fact that it could all be gone again tomorrow…


It’s never been easier to start new things than it is today.

That’s why it’s never been harder to keep working on something than it is today.

We live in a time where pretty much every distraction turns into an opportunity.

An opportunity that will get you to where you want to be.

A lot faster than the old one.

We live in a total mess of opportunities.

Opportunities that can change our lives.

But here’s the truth..

Not too long ago we called these opportunities distractions.

And today we call them opportunities…

A new spouse/girlfriend/boyfriend/etc is always just a few swipes away.

A new best friend is just a few chats away.

A new multi million dollar business is just a few clicks away.

But the truth is that all of these things are even further away than they have ever been before…


When you go from employee to entrepreneur you’ve pretty much signed an agreement that says that you won’t have any free time anymore.

Whether you like it or not, whether you agree with it or not doesn’t really matter.

That’s the reality.

For how long?

Until everything works out just fine.

Which is basically never…

So unless you sell your business or shut it down, you’ll never be able to fully relax. Ever…

Here’s the thing…

The day you start running your own show is the day you take over responsibility for everything that doesn’t work out.

And nothing ever really works out when you run your own show.

Sometimes I’m surprised how small the percentage is of the things that really work out just fine.

There are always things to fix. Things to improve. Things to optimize. Things that don’t work out.

And there will always be things to worry about.

That’s why you’ll constantly be worried about things.

What things?

Well, pretty much every thing….

Even if you think this is something you might never possibly be worried about, you’ll be worried about it.

When you wake up at 6am in the morning after you went to bed at 1am, you’ll worry about it.

When you want to spend your free time with your girlfriend/spouse/kids/etc, you’ll worry about it.

You’ll constantly be worried about things.

And the only way to get rid of the worries is to work on solving your worries.

But the problem is that even if you’re working on fixing these worries, you’ll probably never be able to fix them and make them go away.

At one point you just get used to it…

So essentially your free time won’t really be free time.

You basically won’t have any free time anymore. Ever.

It’s gone.

Possibly forever..

And again, whether you like it or not, whether you agree with it or not doesn’t really matter.

Because that’s just the reality.

No matter what all these self help gurus are telling you.

And you know what?

Leaving my job behind and doing what I’m now doing was the best decision I’ve ever made in my whole entire life.

Despite, or maybe even exactly because of all the struggles I had to go through and still have to go through each and every single day…

Originally published at yanngirard.typepad.com.

Thought Pills

Handpicked thoughts about life, entrepreneurship and…

Yann Girard

Written by

I think, live & breathe here: http://yanngirard.com

Thought Pills

Handpicked thoughts about life, entrepreneurship and business for real human beings. Home to inspiring life lessons, creativity, writing and self improvement stories on Medium.

Yann Girard

Written by

I think, live & breathe here: http://yanngirard.com

Thought Pills

Handpicked thoughts about life, entrepreneurship and business for real human beings. Home to inspiring life lessons, creativity, writing and self improvement stories on Medium.

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