Why I Left My 6-Figure Job to Become an Entrepreneur 20 Years Ago

6 min read
Becoming an entrepreneur changed my whole life.Now, almost 20 years later, I can assure it.It’s not an easy decision and, before making it, you should ask yourself some questions.It’s crucial to be 100% sure you do really want to do it before taking the leap.In this article:
  • I will describe what my situation was.
  • Why I decided to become an entrepreneur.
  • What questions I asked myself before leaving the company I was working for.
  • What questions I should have asked myself to truly believe I wanted to be an entrepreneur.

Introduction: My Initial Situation

I started programming when I was 8 years old. It was 1984.Technology fascinated me.I didn’t stop until I became a computer science engineer and started working in large tech consultancy companies.I spent almost 5 years working in these types of enterprises.Why did I decide to quit?I was in such a deteriorated mental and physical state that I had no choice. It was “do or die”.Here I share some of the questions I asked myself before making that huge step in anyone’s life.

Do You Really Want to Quit? Questions Before Leaving

Leaving seems to be the “hardest” part, but today I have to say it was the easiest one.These were some of the questions I asked myself because I was in a very healthy position talking about my career and salary.

Question 1: Do you want to be a professional or a politician?

Whenever you’re inside a big company, you don’t only need to be an excellent professional, you have to look like it, and you have to create contacts.Networking is essential if you want to prosper in any large social organization, such as a major corporation.Are you comfortable being a politician?

Question 2: Do you want to be climbing an endless ladder?

Big companies have an endless ladder you’re supposed to climb, step by step.Can you see yourself climbing all your life?

Question 3: Do you like people who have been in your company for many years, maybe decades?

Look at your future self by watching your co-workers who have been inside the company for many years.Do you like them? Do you like what they do, how they live, and what their work is all about?

Question 4: Do you look like them?

Can you see yourself being one of those veterans?

Question 5: Do you want to be all your life “a number”?

It’s impossible not becoming a number inside such huge companies. There are hundreds of thousands of employees. You are a tiny drop in the ocean.I’m not saying you should look from a negative perspective at the questions above. I’m just saying those were the questions I asked myself almost 20 years ago, before taking the big leap.You may guess what my answers were…

Do You Really Want to Be an Entrepreneur? Questions to Think About

I was so desperate that I decided to create something as far away as possible from the world of technology. My “stupid” idea was this: a stewardess agency.Don’t try to look for logical reasoning because there is none.It wasn’t a smart “movement”, although it finally worked. That’s why I would pay attention to the questions I list below before “running away”.I didn’t think about them before making my decision, and it was a big mistake that could have sunk my project.I didn’t ask myself these questions due to 2 main reasons:
  1. I didn’t know I should think about them.
  2. I was so burned out that I just wanted to leave. Don’t let despair jeopardize your future.
I had to ask all these questions “on the go”, live, suffering their consequences, without being mentally prepared, not knowing they would be produced.Ask yourself these questions. Now it’s the time when:
  • You can think about them.
  • You can look for answers.
  • You can get advice.
  • You can be prepared (mentally and with the infrastructure needed).
You will save time, money, energy, anxiety, and unnecessary unpleasant scenarios.

Question 1: Are you ready to stop receiving your paycheck?

It seems foolish, but when you’re used to receiving a paycheck, you don’t know how lucky you are.As human beings, we don’t appreciate things until we lose them.You can’t imagine how fast time passes whenever you don’t receive a paycheck. Months seem to be days…Be prepared to 0 income if you haven’t planned things (as I did).

Question 2: Are you ready to understand that everything depends on you?

When you’re inside a huge company, many things are done by others, by the system. You take them for granted.When you become an entrepreneur, if you don’t do things, they won’t be done.All you get is all you do. As easy as that.Again, it seems obvious, but it’s not until you feel it in your body when you notice it.

Question 3: Are you ready to create a roadmap and stick to it?

No matter if there are storms, no matter what’s happening, you must believe in your project, the path you defined, your planning.Will you start changing things whenever they may seem they’re not working?Will you be able not to be affected when things start failing?

Question 4: Have you got enough economic resources to live without incomes? For how long?

This has nothing to do with question 1.One thing is being mentally prepared not to receive a paycheck, and a very different one is how long you will be able to last your project with 0 income.I almost gave up after being 6 months without seeing any money at all.

Question 5: Are you ready to receive infinite “NO’s” to your product, services, and proposals?

People are not waiting for your product or services. They have their lives, their problems, their issues. They have not been waiting for you to rescue them.You will receive NO’s in a way you can’t even imagine.Prepare yourself mentally to accept rejection. That’s usually how the story goes.

Question 6: Are you flexible enough to move your products or services to what the market is demanding you, although it might be something that has nothing to do with your initial thoughts?

Some entrepreneurs hold on to their ideas until they die with them.It’s not easy to find out the balance between keep on trying and changing your initial idea.I started with a stewardess agency and ended up being a marketing agency. You have to be a chameleon to survive. To take your mind to the most flexible point you’ve ever imagined.


Becoming an entrepreneur, it’s a very personal decision. Nobody but you can make it.My experience tells me one key factor is how burned out you’re in your current situation.Still, think it through, especially the questions in my second group.Today, I have 4 companies running simultaneously. Everything seems logical and just common sense but, in the beginning, nothing was evident at all (as you’ve seen).We should live our lives from death to birth to really understand them. The natural cycle is everything but logical.My learning process taught me this:
  1. Start. It’s by starting and doing how opportunities will appear. Don’t try to ask all the questions that arise in your head, trying to find out an answer for all of them. It’s impossible. You have to learn how to live without answers to all the questions, but pay attention to those I mention in this article.
  2. Don’t be afraid because of the questions I’ve listed above. Think about the first group, the causes why you’re creating your project. If you’re 100% sure of them, they will give you the energy you will need when the second group of questions invade you (because they will).
  3. Being an entrepreneur has many disadvantages, but it’s a way to really feel free in life.You decide when you work, which tasks you’ll perform, how to organize everything… If you’re looking for freedom, this is your way, no matter how many inconveniences there are.
Photo at the top courtesy of Evan Dvorkin on Unsplash.