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How Difficult Is the Transition From Employee to Entrepreneur


Do you know what is the most challenging part of being a first-time entrepreneur?

The majority of the answers I have received to the above question revolve around marketing, sales or raise funds.

I differ from popular opinion. My answer to the above question is something that you would have never even thought about because it is not taught in any of the best small business courses or entrepreneurial courses.

The most difficult part of being a first-time entrepreneur who has just quit a job is to get out of the “employee” mindset.

Now, why would I write something so different? Well – I have 12 years of entrepreneurial experience and it took me a good time to figure out this challenge. All along my employee mindset was affecting the work I did as an entrepreneur.

Consider this – before starting your entrepreneurial journey, you were busy working in a specific role as per the KRA provided to you and now suddenly, you are in a role where there is no clear definition of what you have to do.

You are learning the difference between Employee and Entrepreneur – the hard way. In my first venture, it took me months if not weeks to get rid of the Employee Mindset.

The challenges faced by an Entrepreneur are on a different wavelength than what an Employee faces.

I am not saying that the life of an employee is any easy or job does not teach you anything. On the contrary, the learnings from a job are always there to become a better entrepreneur. My first and only job lasted a few years. Some of the learning from the job is still a part of my daily life. I use them to relate to the employees who work for me.

So when I make a decision, I try to put myself in their boots and then be empathetic.

Has it always helped?

Not always. I have taken some very stupid decisions by being over empathetic that has led to me losing money and time.

I had to fine-tune myself to understand the difference between entrepreneur and employee.

It was only a matter of time before the transformation happened and this is what I learned during the transformation :

  • The luxuries you took for granted are no more the luxuries you can afford:

The yucky coffee you threw in the dustbin nonchalantly without even thinking once about the cost is suddenly a cost – you want to control.

Earlier, you threw it because you didn’t like the coffee. The taste was too sweet for your taste buds and you went as far as to write a complaint to the HR about the coffee that sucks.

You never gave a damn about the cost. The company was there to take care of your likes and dislikes.

You always went to an air-conditioned office with AC running even when you were not in the room. You took the office cab even when you could have easily taken public commute because the office paid for all the above.

What I mentioned above are just very few examples of the luxuries we take for granted working in big enterprises.

Fast forward to your life as a first-time entrepreneur and you get a reality check. Now you run a bootstrapped business started with your savings.

Now your company’s expenses are your own expenses that will go out from your personal savings. You want to control every damn expense.

All of a sudden there are no luxuries to splurge on. You are always on a lookout to cut office expenses and your expenses (if you are left with any money to spend on them).

Don’t be surprised if the maddening e-commerce sale does not appeal to you. You will be the Hermit away from life’s temptations with only your work to worship.

You will now travel by public commute. Every cup of coffee thrown by your Employees in the dustbin will be a stone hurled at you.

I won’t be surprised if you will calculate the number of cups wasted every month :).

And the coffee is just the tip of an iceberg- Think about electricity costs.

You have no idea – How hard I tried to keep the electricity expense in check.

Speaking of electricity, I still cannot forget an incident that had me arguing with my marketing lead. It so happened. Our electricity bill had hit the roof during summers and I was looking at ways to bring the cost in check.

Now my marketing lead came from a big enterprise and was a pampered guy who had this bad habit of leaving his cabin’s light and AC switched on even when the cabin was not in use.

We were a company of 10 employees bootstrapping the tough times. We had still not hit break-even and were surviving off our past savings.

Not to make a fuss, when I found it switched on and the cabin not being used – I would switch it off myself. One day, he confronted me about this habit of mine.

I won’t go into what happened next but yes, it did make me realize the difference between employee and entrepreneur’s thinking.

As an entrepreneur, you must look at the methods to control the expenses and keep the cost in check. Big companies do not look for small expenses because it is too minuscule an expense for them to take care.

On the other hand, every single penny counts for you.

Learn to brace up to the transformation.

Learning to be “the responsible one”:

As an Employee, you always have someone to look after your failures. A senior person who can help you when things go south.

And if your failure is unacceptable to the current organization, you can just quit the job or get kicked out of the existing job. Sooner or later the market allows you to move to the next job.

When you are an entrepreneur, every failure has serious repercussions. For a growing company or a startup, your mistakes can lead to immeasurable losses.

If it’s a financial loss – You end up missing your salaries, office rent. Worse, you might not get paid yourself for months.

From being an employee who always has a senior to cover his a**. you will soon be the responsible one who has to cover everyone ‘s a**.

Entrepreneurs are the responsible ones. You might be the most responsible employee in your company but in this job, you are responsible for a lot of things which do not come under your “KRA”.

The job responsibilities you will be expected to handle will be way beyond your imagination.

From the job-specific Employee to the all-rounder:

How well do you understand your taxation structure? How do you hire employees without HR?

Have you ever done sales in your life?

How will you handle the business development team?

Please do not blame Google for not giving you enough information on all the above. Google has its limitations. At the end of the day, it is merely a search engine 😊.

On a serious note, what I wrote above are just a few of the small things you are expected to do.

The heavy lifting where you have to handle the government departments, face disgruntled employees, arrange money for your startup is not even the part of the list.

Now you can’t crib and tell your boss “this is not a part of your profile”.

As an Entrepreneur –  Everything under the sun is a part of your profile.

And this is the most difficult transformation you will have to make from being “the best of the best employee” to an Entrepreneur who has no choice but to be the best.

One of my startups failed because of the allergy I had with finance. I avoided the finance divisions. The numbers made me dizzy.

Guess what? The numbers made sure I landed in a ditch.

This is why I put – “the inability to move outside the comfort zone” as one of the topmost reasons why startups and small businesses fail.

Swallow your ego. Get out of your comfort zone and learn the tricks of the trade before your venture sees the despicable “closed” sign.

Other than the above, you should be ready to look at the other side every time you want to make an expensive purchase. The initial years of your venture won’t give you the luxury of only purchasing necessities. Luxuries are for later years.

There will be no family time or weekends

Your family can kiss goodbye to the precious “family time”.

And you can officially change your marriage date to the date of incorporation of your company. Do not forget. Your office is in your house. Employees are your kids and work is your wife.

How do you make the successful transition from an employee mindset to an entrepreneurial mindset?

To start with – do not get confused with the Employee vs Entrepreneur mindset every time you have to make a tough decision. You are running a company not a charitable organization.

You are there to feed a lot of families but if you don’t get paid for months, who will feed yours? It is a question we, the entrepreneurs forget to ask ourselves from time to time.

Lastly, always remember – you are here because your dreams are bigger than the petty joys you enjoyed as an employee.

The greater joy in life for you is around achieving success and building something bigger. Something that will survive for long and will give you the emotional satisfaction of being an Entrepreneur.

Author bio


Jasmeet is a founder of Lessons at Startup – A blog where he shares entrepreneurial stories. He specializes in Digital Marketing and Content Writing. He is addicted to Google News, Netflix, Good Coffee, and Quora ☺.

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