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How to transition smoothly from being employed to self-employment

By Susan Catherine Keter | May 28th 2020

I am not saying a man/woman can't try. I am not saying that we should settle for less. I am not saying we don't deserve the best. Perfection, after all, is what we are all looking for. The intricacies of relationships are a wide purview of introspection. It is in relationships that we define ourselves. What turns you off? What makes you smile? What is your breakpoint? When do you say enough is enough? How do you know he is the one? Reciprocity is the lifeline of every relationship. Someone said: there is nothing like unconditional love- I agree. Unless you are masochistic (not really in that way), but unless you enjoy pain, your level of affection towards your significant other is largely determined by how far they are willing to go. Many employees are inspired by the idea of no longer being answerable to a boss. The dream of becoming one's own boss is definitely attractive. Still, self-employment is not free of challenges and disappointment, so it is important to be adequately prepared for the road ahead.

Plan for the best but be prepared for the worst

A plan on paper never goes as expected. Think of a plan for a journey. Much as you plan for everything to the minutest detail, there are many different variables that you cannot factor into your plan, such as accidents along the way, traffic snarl-ups, mistakes by other road users, and so much more. As you build a business, it is not all dependent on you and your plans. Many factors are beyond you, such as political climate, currency fluctuations, the entrance of competitors into the market, changes in legislation, and so much more.

The key to surviving as an entrepreneur is having a contingency plan that things could go wrong, and they often do. Cash flow is the most important aspect of this contingency plan. Start a business with adequate preparation that it could fail to earn any income in the first one or two years. Have a concrete plan on how you will finance the business and also continue to meet your obligations during that period.

Learn from the farmer

Imagine if you were to go into self-employment as a farmer. You had just purchased a piece of land and were all set to go into farming. How long would it take you to start earning income as a farmer? How much would you put in before you could begin to earn? What if there were some unexpected challenges such as drought, floods, or crop failure?

The most assured way for your business to survive is to have a reliable source of income as you build your business. If you are in employment, you want to remain in employment for as long as is possible, but at the very least for the first year of your business. Plan your transition very well.


Do not use your employer's time to build your business. That is dishonest and should be avoided at all costs. Give your employer 100% of your time and attention while you are still working there. Build your business in your free time and using your own resources.


Building a business costs. You will, therefore, have the extra responsibility of financing your business while still meeting all your other responsibilities. This will be challenging if you are already stretched financially.

Begin by tracking your expenses for at least three months. The use of personal finance software can make this easy. Identify areas in your budget where you could free some money. You could make sacrifices such as using public transport to work instead of driving, carrying lunch from home instead of spending money in restaurants or doing your hair at home at least some of the time rather than spending money in hair salons. There are sacrifices to be made if you plan to become your own boss.

Avoid quitting your job before you have some reserve, either from your savings or revenue from your business. One of the major causes of business failure in the initial stages is related to cash flow problems, so guard against this.

Medical insurance

One benefit that you will lose when you leave formal employment is medical insurance. Not having insurance can completely crush you should a serious illness or an accident strike, so ensure to have an insurance cover before you leave your job.

Leave as friends

You will still need the networks from your employer as well as the goodwill even after you leave, so do not burn bridges. Your first jobs might actually be referrals from your former place of work, so take care of those relationships.

Give your employer adequate notice, find out how you can be helpful during the transition period, such as in training replacement staff. Minimize hardships for your employer and former colleagues and genuinely wish them well. Be ready to share tips and to be supportive to those who reach out to you.

As an entrepreneur, you are your most important asset, so invest in yourself.

Invest in yourself. Read personal development material. Attend relevant forums and events and expand your networks. Identify the skills you will need as you build your own business and invest in acquiring them. Hang out in the right circles, with fellow entrepreneurs and upcoming self-bosses.

Practice being disciplined. Do what needs to be done, when it needs to be done, whether you feel like or not. Being self-motivated is the key to successful self-bossing.

Work on your mindset. You will need to replace the employee mindset with the entrepreneur mindset. Practice thinking in terms of exploring possible solutions to challenges, rather than seeking the opinion of someone else who is more knowledgeable than you. Identifying the right people to consult about different matters is part of the entrepreneur mindset.

Look at life's challenges with an attitude of 'what could be done to make it better? Where can such information be found? Who can help sort out this situation?' Your ability to solve problems will make or break your business.

Develop a curious mind

Always be curious to know what is happening in the industry and in the business environment as a whole. Evaluate what others are doing and be proactive in conducting further research on the topic. Learning is a lifelong process, so never stop learning.

There are no guarantees that it is going to be easy.

Most people give up their dreams of building their own businesses when they find the journey more difficult than they anticipated. Keep in mind that the price has to be paid sooner or later, and that sooner is better than later. Putting off self-employment until you retire is definitely going to hurt you more so better start early so that you can leave employment on your own terms rather than wait to get desperate when you are forced out without a plan B.

All fairy tales have defining moments when the soft lips are about to the touch the slimy and ugly frog when the golden coach turns into a pumpkin and the stallions into measly mice. However, the untold story of happily-ever-after is a mundane mystery. I love how C.S. Lewis in The Chronicles of Narnia, where the Prince Caspian lives a fairly normal life with his wife the happily-ever-after, fighting, making-up, and fighting again-normal. Perfect partners are all we ever imagined. Tall, dark, handsome, caring, loving, funny, or beautiful, caring, understanding, respectful, curvaceous – or whatever you fancy. Additionally, they understand us and fulfill every economic, social, emotional, and spiritual need we have.

Ladies, the man comes home on time, never drinks, never cheat, never flirts, cleans after himself, remembers everything (birthdays, anniversaries et al.), cooks for you, buys flowers-occasionally, and will always be there for you. They may do all these things but not always. Sometimes he will leave the wet towel on your duvet, or forget to put the socks in the washing basket. Right? No? How do you live with such a man? With such a "clean" record, you will be held to a higher bar. You won't afford to let one hair strand fall out of place. The call for perfection two-way traffic and the compromises in-between are thoroughly negotiated that they- at best- produce a cosmetic relationship. Although few principles should guide any relationship's normal decency, compromise is an active and perpetual ingredient in perfect relationships (pun intended).

The truth is: when two individuals from different worlds and backgrounds decide to come together- it is work. The work of shaping each other necessitates confessions, revelations, acceptance, confrontation, and compromise. It looks ugly, but it's real, and it will be beautiful as time waxes. When one or both individuals are struggling to live up to preconceived expectations orchestrated by the other or both, it ceases to be a relationship; it becomes contract- hypocrisy. Therefore, perfect calls for perfect, but the stakes are high.

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