How to transition from Employee to Entrepreneur

from employee to entrepreneur

There are many people out there who have been entertaining for years the idea of running their own businesses or starting freelancing. Understandably, the possibility of being in charge of our time and making own decisions seems very attractive to most of us.

If you have recently lost your job due to the pandemic-induced economic crises, you might find yourself thinking about starting a business and developing your own brand even more seriously. You might be inspired to mastermind an online course to share your unique teaching, or create a product or service you think people need, or start an online store or, perhaps, you can just see yourself being able to deliver your services electronically, on a contract by contract basis.

All these ideas can work perfectly well and a great number of people, not much different from you and me, are doing exactly these things very successfully. However, we also know that there is an even greater number of people who start their entrepreneurship journey without getting any closer to the results they hoped for.
What defines our success as an entrepreneur or a small business owner? Why are some people great at what they do, but can still be “hopeless” at managing a business? Why can some of us have a highly sought-after skill set and yet be unable to execute a business idea in any meaningful form?

The answers to these questions are multifaceted and interesting to ponder, and though finding them is not the aim in this article, I want to offer a few reflection points for you to consider before starting your transition from an employee to an entrepreneur.

Your thinking

Being in business on your own will make you realise that it requires certain qualities from you than may have not been sought after by your ex employer. The kind of qualities I mean here are: creative (as well as critical) thinking, tolerance of risk, patience, perseverance, confidence and self-awareness. Many entrepreneurs admit that venturing into business on their own and building their own brand has turned into a journey of self-discovery and self-development.

The transition from an employee to an entrepreneur will also require you to change your mindset. Kris Kluver writes in his famous book “The aspiring solopreneur”: “Rarely, if ever, does a new start-up fail because the person starting the business isn’t great at providing the product or service. Where people falter is failing to adjust their thinking to that of an investor (investing in the business), a manager (managing the business), a business development expert (driving the business), and a technician (proving the product or service)”.
Without the aforementioned qualities and the mindset shift, you could quickly find yourself in the same rut to which you wished never to return at the moment you left your employment.

So, how exactly do you transition from an employee to a business owner (or a solopreneur, if you prefer to work on your own) and where do you start?

Your inspiration

One of the things the best-selling author Simon Sinek teaches in his well-known book “Start with Why?” is to discover what you truly care about and what your main values in life are. This is by far one of the most vital things you can do before venturing into your own business. Figuring out your values will take some work but it would definitely be a worthwhile investment of your time. The reason why this work is important when you transition from being an employee to an entrepreneur is because, in our lives, we are usually infused with energy and enthusiasm when we do something that is aligned with our values. At the same time, we often feel unfulfilled or emotionally disconnected when our actions and values are misaligned.

Sinek says: “The concept of WHY is a deeply personal journey borne out of pain”. He proposes that “to uncover our WHY we must bring together our standout memories – our defining moments – and examine them to find the connections”.
Aligning your busines with your values is extremely important because without it may be difficult for you to push past the times when you just want to give up. You don’t necessarily find happiness in your work every day, but you can feel fulfilled by it because it makes you be part of something bigger than yourself. We may not be always aware of it, but It’s our values that empower us through the challenging times.

Your passion

People who want to go into business often wish to create it based on something that they feel passionate about or strongly interested in. What’s important though, is to ensure that what you are passionate about is also something that people want and, more importantly, will be ready to pay for. There is absolutely no point in coming up with something that you love, but not many others want it or are inspired by it. It’s really about finding a balance.
You may find the Japanese concept Ikagai (meaning “a reason for being”) helpful for finding just that balance. Detecting our strengths is not always easy. Ikagai invites us to find out what lies at an intersection of four important questions that can help us find our path. You can use this concept as a compass helping you identify your most promising business pursuit.

To find your Ikigai, you must ask yourself:

1. What do I love? (passion)
2. What am I good at? (vocation)
3. What can I be paid for? (profession)
4. What does the world need? (mission)

Start working on your questions, and see how your answers fit into the Ikigai fundamental components.

Your personality

Thousands of small businesses out there are ‘one-man band’ companies. Each of these businesses is built by a beautifully imperfect human! The reason why that makes the personality of a business owner rather important is because any solopreneur’s business is unavoidably affected by the personality blueprint, the belief system and, if he or she is not careful, the ‘blind spots’ of its owner.

Every one of us has unique strengths and weaknesses. This character imbalance is what can make us vulnerable or blind-sided in our decision-making process which, subsequently, can make our business vulnerable, too.

Below are just a few of our common (read ‘human’) personality imbalances that can create problems in our business:

  • Overthinking and not producing enough action.
  • Working too much, leading to a burn out.
  • Acting impulsively and getting ourselves into difficult situations.
  • Emotionally overreacting and taking things personally.
  • Feeling overwhelmed when faced with too many tasks which may lead to procrastination.
  • Feeling disheartened, negative or uninspired when things are not going the way we hoped for or as fast as we expected.

You might ask: “But what’s the antidote to personality imbalances?” The way I think about it is this. First, it’s important to start noticing and observing your personality habits without judging them. Secondly, it would be helpful to identify situations which usually trigger an ‘out-of-balance’ response in you. And, lastly, you can let the information you gathered about yourself guide you to finding an optimal structure and strategy for your business operation.

Remember, we are not talking about changing or ‘bettering’ yourself here (though being more self-aware may have such an effect anyway). When geologists start studying a new piece of land, they are not getting upset about or attempting to change the harsh weather conditions they have to work under, but instead, they just take such conditions into consideration and build a strategy to minimise (or sometimes utilise) their consequences.


Becoming “your own boss” is really a transformational journey to be on if you are mentally prepared for it and ready to embrace challenges and surprises it puts in your way.

If you have firmly decided that you want to transition from an employee to an entrepreneur, I suggest you start with the above steps. It will put you way ahead of many who take the leap without doing this important introspection first.

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