How to quit your full-time job to pursue your dreams

mandela impossible until it's done quote It’s been some time since I went on A Slice of Life Hour on 938LIVE to talk about my learnings on transiting from a full-time job to the life of a freelancer and first-time entrepreneur. Since then several people including friends of friends have been asking me for tips on how to build up the courage to quit and manage the transition.

As such, I’ve decided to post up my notes for the session with a few more tidbits that weren’t covered. These are just my little learnings and this list definitely isn’t exhaustive nor is there necessarily a right answer. But hopefully this will help others in a similar situation in some way or other. If you’ve been through this yourself and have other tips, feel free to comment and add on! :)

If you’ve been toying with the idea of quitting your full-time job to become a freelancer or start your own business but haven’t built up the courage to quit just yet:

  • Dream big, start small, but most importantly, START.

Stop creating excuses and start carving out time to explore your vision. Stop spending your weekends and after-work hours doing more office work or watching TV and start taking small steps in doing research on your market opportunity or building up on your relevant skills. I know I was really guilty of working after office hours and it wasn’t until I decided to get together with some people to collaborate on photoshoots that I made deadlines for myself to finish some dresses. If you’re toying with pursuing a creative dream, start on a project to add to your portfolio. Stop dreaming and start doing!

  • Focus on baby steps instead of getting overwhelmed by the big picture.

I’ll admit that I’m a dreamer and sometimes the dreams just get so crazy that it gets overwhelming at the start and doubt starts to creep in. What I’ve learnt is that while keeping the big picture in mind is a good thing, what really works is to focus on baby steps and tasks that can be accomplished in a short period of time and that can be checked off a list. As you move along and check things off that list, you’ll find yourself feeling more confident to take hold of the opportunity.

What’s more, small achievements help to convince people close to you (and yourself) that you are serious and that your mid to long term goals are realistic and can be accomplished. People who previously doubted you may even become your supporters! In my case, my parents who never thought my love for fashion design was anything very practical or serious, started to take notice when they saw photos of my work and the dresses being made. Perhaps their daughter wouldn’t become a starving artist after all!

  • Surround yourself with positive people who want to see you succeed.

By this I don’t mean idealistic people who encourage blindly even if you’re about to throw yourself into a burning building but people who understand you and believe in your ideas and potential. They are also honest enough to warn you if they feel you are heading in the wrong direction. But while they are there to listen, they are not quick to put you down and sometimes offer different perspectives and solutions in a gentle manner. I’ve been very blessed to have friends around me who are just wonderful and this journey would have been much, much harder without them.

If you’re someone who has trouble keeping to your deadlines, sometimes it also helps to have one or two close ones as your “accountability partners” to keep you on track and prevent you from slacking off or getting distracted by the daily grind.

  • Create buffers for yourself.

While it would be awesome to live on dreams alone, you’ll need to feed yourself. Unless you are a free-spirited brave soul (of which you’d already have quit that full-time job), you’d probably want to know that you have enough to live on while actively pursuing your new dream.

Work out the numbers for your business or freelance work, the time it’d take to start making money as well as how much you’d need for your own upkeep. Double or even triple that and then see if you have enough. If you don’t, start looking at ways you can save more in the meantime, relook your monthly personal budget and figure out other ways to generate income when you may start to run dry. That way, when other people try to question you and place doubt in your mind, you’ll know you can afford to take this risk and it’s now or never!

For those who are looking to leave their full-time jobs to plunge into an even more exciting world of purpose and fulfillment, you’ll probably find that it’s worth trying some point in your life and it’s better sooner than later, better late than never.

Most people I’ve spoken to who have done so have had no regrets despite the challenges! (In fact it’s probably the challenges that keep them psyched come to think of it…) Coming up in a later post I’ll share what I’ve learnt from managing the actual transition from a full-time job to crazy crazy freedom for those who have made the leap!


  1. says

    It’s not often in our society that people encourage others to step out of their comfort zone. I have to admit I’m a super conservative person, but sometimes I feel like just doing things that I want to, yet have reservations due to responsibilities. Thanks for this post!

    • says

      Hi Nueyer, thank you for sharing your thoughts. I hope you’ll be able to find some time to do what you want and hopefully make your dreams a reality! It’s definitely scary at the start but the more you work on it the less daunting it gets :)

  2. Nat says

    Hi Michelle. This is great!
    How did you decide that it was finally the time for you to ‘threw the paper’ to your former boss? Cos in my case that’s is always the dilemma. It seemed that there’s always an excuse to postpone, whether it’s the projects that i feel responsible for, the colleagues that i’ve grown with, the promotion & salary increment (ha!). Or it’s just me, getting cold feet.

    • says

      Hi Nat! That’s a really good question and I think all of us can definitely relate :)

      With regards to the promotion and salary increment, I guess that’ll be a personal decision you’ll have to make as to whether the next option would be worth foregoing your current promotion and pay grade. At the end of the day, you’ll want to live with no regrets and have tried what you wanted before it’s too late yes? ;)

      I’ve also found that the colleagues that I’ve grown close to remain friends for life. In fact, we still meet up to catch up once in a while even though we’re no longer in the same workplace. Perhaps it could work the same way for you? :)

      To be honest, there is never really a good time to quit considering work portfolios can be ongoing and there’ll always be project after project. One of the ways you could leave responsibly is to speak with your boss and inform him/ her of your intention to leave. But instead of leaving within the exact notice period (or earlier if you clear leave), you could offer to stay on longer in order to finish outstanding work and allow more time for the team to find a replacement and for you to do a proper handover. Even after I left the company, I was still helping to update colleagues on some things that weren’t clear because they were essentially my friends anyway!

      There are pros and cons to staying longer of course, but it’s pretty much what I did and just my two cents worth! :) Hope this helps and I wish you all the best Nat!

  3. says

    Hi Michele,

    Thank you for sharing your story, it’s really inspiring. Maybe one day, I’ll have the courage to take a leap of faith and pursue my dreams :)

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