How I Quit My Job To Follow My Startup Dream

In October 2014 I took the plunge and entered the wonderful world of self-employment. It was an exciting time in my life and I have never looked back. My life just keeps getting better and since I quit the Corporate Dream.

I strategically planned my exit from the corporate world from the day I stepped foot into the foyer at the law firm I was working at. Having a rough plan of where you plan on heading will take the edge off of the uncertainty and fear that comes with quitting your job.

Here is my personal checklist for quitting your job:

You need a plan. Seriously.

You need to know why you’re leaving and you need to set a deadline.

Are you leaving to spend 12 months on your startup? Do you have plans to travel during that time? Will you be taking a break from the world to grow vegetables in your garden? I planned to launch a startup, move cities and see some of the world over a 12 month period.

If you’re going to launch a startup, have you given enough thought to your idea? How far into your business are you? Will you still be in love with your business idea 12 months from now? Is this business viable? These are all important questions that you need to answer before you take the leap.

Do you have a business plan? If not, I recommend that you at least figure out your lean canvas. It will help consolidate your business idea. You can (and should) revise your canvas often.

Can you handle the heat?

You need to carefully consider how much risk you can handle. Will you be working on a part-time or casual basis while you try and launch and run your business? Will you need to move back in with your parents? Will you work full-time and moonlight as an entrepreneur?

The above questions took me a while to answer. I tried the full-time and part-time arrangements but, ultimately, realised that I’d need to work on my business on a full-time basis in order to really make my entrepreneurial dream happen.

My solution was to quit my job entirely, rent my place and move back home to my mum’s house. What is your solution?

Budget and sacrifice — two dirty words in my book

Does you startup business require capital investment? If so, how will you go about acquiring those funds? Family, personal savings and bank loans are all viable sources that you will need to consider for funding.

Do you expect that your startup will be making money initially? Regardless of the answer, you need to set yourself up so that you’re not reliant on your startup to feed (or clothe) you.

You will need to sit down and draft up a budget that will assist you before you quit and after you quit. You need to know what your expenses will be for the next 3, 6 and 12 months. You will then need to find ways to slash those expenses further but still include a buffer for small luxuries like a meal out with friends and the odd coffee.

Who got your back?

Do you have the right team of people backing you to succeed in your startup dreams? I wouldn’t have made it this far if it wasn’t for my incredible family and some great friends. I’ve also been helped along the way by wonderful mentors.

Don’t forget that your startup isn’t just about you. You need to build a team of the best lawyers, accountants, psychologists, physiotherapists, designers etc. that will make your life easier.

The Art of Networking

Start building your personal brand and your network well before you leave your job. I started approximately 2 years before my departure. Your network will be invaluable in the coming years and it is something that must be nurtured.

Also have a careful think about your personal brand. What sort of message are you putting out into the universe? Do you act, dress and present yourself in a way that accords with your personal brand? Do your Linkedin and Twitter profiles accurately reflect your personal brand?

What’s your worst case scenario?

Your worst case scenario is usually never as bad as you imagine.

I have always considered life as a lawyer to be infinitely more painful than attempting to launch a startup and run my own business. I remind myself of this constantly.

Take the time to redefine your definition of failure. For me, ‘failure’ is not taking a chance when an opportunity presents itself. Growing, learning from mistakes and taking a risk should never fall within your own definition of failure.

Don’t burn too many bridges along the way

Be strategic about your exit. Duh! Don’t lose your sh*t at your boss one day and resign on the spot. I had my very difficult moments but the knowledge that I had a strategy for quitting made the months leading up to my exit more bearable.

Take a break

You may not get a break for a while once you start your own business. I spent 4 weeks traveling around the US after I quit my job. Best. Decision. Ever. I came back with a clear mind and renewed sense of adventure.

Financial Planning

Nine months before I left I found myself a financial planner. I sat down with my planner and came up with a strategy.

I made the following strategic steps thanks to my planner while I was still a full-time employee. Do not leave this until you are part-time or have already quit your job. I’d recommend that you consider the following:

  • Appropriate life, permanent disability and income protection insurance.
  • If you have assets, consider borrowing again them. I have set up loan facilities against my home. It gives me comfort knowing that I can tap into a low-interest loan if I need to.
  • Extend all of your credit cards limits while you’re a full-time employee.
  • Take the time to visit your accountant who can assist you in choosing the business structure that will best suit your needs.


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