Freelancing is appealing because it presents a change of scene. It offers a fresh start especially if your career has been a disappointment. Freelancing is also a chance to take on a new talent or pursue a different opportunity.
I have a friend who left a nice paying job in a technology company to become a freelance photographer. It didn’t happen overtime for him and he had to go through a lot of preparation – time, money, and self-assessment.
My friend chose to reinvent himself, prepared for it, and succeeded.
Some reinvent themselves because of layoffs or unplanned family situations. Ideally, you don’t want to be forced to make changes in your life. It’s no fun thinking about freelancing after a layoff. If you want a new job (because your current company sucks), you better start finding a new one before you can’t take it any more. As they say, the best time to find a new job is when you don’t need one.
If you don’t want to be in a situation where you are pushed against the wall, you should take a regular review of your current situation and find out the imbalances in your life, upside/downside of your current job, and more importantly, the gulf between who you are right now and who you want to be.
Review yourself. On a piece of paper, list your disappointments and things that stress you on the left side, and things that make you happy or will make you happy on the right. From this alone, you can clearly see what things need to be addressed to swing your life towards the happy side.
Question your fears. Everyone is afraid of something. If you think you can’t afford to start over with your career, that’s normal. However, fear and truth are not the same. List the things that are preventing you from pursuing your dream and start questioning them whether they really matter.
Sometimes, you are looking at the problem from a wrong point of view. If you quit your job and become a freelancer, you are not necessarily starting from scratch because you still have the personal network you have built over the years with you. You may have to start at the bottom with regards to accounting, but you can jumpstart your marketing through your network.
Don’t kill your dream. If you want to travel around the world but you don’t have the resources to do it, would you stop dreaming about it? Just because it is impossible today, doesn’t mean it won’t happen tomorrow. Dreams not only liberate; they also puts us in touch with who we are and who we want to be. If you stopped dreaming today, you will never get around the perceived limitations of money and security. The only way your dream can ever come true is you hold onto it with unwavering belief.
Fill the gaps. If you feel you lack a particular skill or the knowledge in subject you’re interested in, ask yourself how you can fill it. It can be as simple as spending a day in the library, a lunch with a former colleague, or regular chat with a mentor to guide you. There are millions of successful people who are more than willing to help you.
Do it. What’s the point of thinking and planning if you are not going to do it? Every change you do in your life will feel unusual at the start but that’s OK. Just keep doing it and eventually it will feel natural. Being shy, whenever I attend gatherings where I don’t know anyone I always tell myself to say “Hello” and smile. It’s weird at first because I’m consciously trying it yet. Eventually, I got over it.
There will always be moments of doubt and that’s normal. Just remember that if you fail, the worst thing that would happen is you end up to where you are right now. So what are you waiting for?


