• Lindi Engelbrecht

3 strategies : Don't quit your day job, until you have to

A checklist for Startup Success

Today we are starting a new series and discussing the first point on the business starter checklist, which you can download for free on our website.

The first point is : Don’t quit the day job until you have to

Is it time to quit my job? 

This is a question we’ve all asked ourselves at one point or another. Most people wait until they feel they must leave their job or organization, and that puts them at a disadvantage.

According to Tony Robbins :


When you don’t quit your day job, you have more access to resources. This capital is particularly important if you are #bootstrapping your business yourself. In early 2017 we founded a Tech Company called DiggerApp and for the first 2.5 years, we bootstrapped our way through, and in this period of the business, resources and capital from our other ventures made it possible to continue on the journey. In Venture Capital circles there is this saying :

"It's not the ideas or innovations of Entrepreneurs that fail but rather that they run out of money".

And since you won’t constantly be bombarded by the idea that you gave up your job for this idea, you will have more flexibility to pivot and figure out what working style fits you best.

Did you know that Airbnb failed four times before it found success? Having a day job affords you the opportunity to fail, as ironic as that may sound, and this sense of freedom is a welcome space for creativity.

The 3 strategies are :



  • WHEN?


First, it gives you time – time to iterate, strategise, clarify, and simplify your business approach and product offering. When you don’t quit your day job right away, you won’t feel the pressure to cut corners, and if you don’t turn a positive cash flow immediately, you will still be able to remain afloat.



Take this time to make your business grow. Too many entrepreneurs are actually “wantrapreneurs.” A #wantrapreneur is someone who does everything except taking the steps to build an actual business.

I call this : The positioning of you business.

Positioning of your business has 2 sides : I refer to it as – Rational & Emotional positioning, like YING AND YANG.

Many of the entrepreneurs that I work with and teach, gets wrapped up in the emotional positioning of the business. They focus on the bells and whistles like slick business cards and impressive websites first, and yes we do require those things but it's wiser to start with and focus on the rational side of positioning first. The Rational side of position is where we are actually building a viable and profitable business, setting up the scaffolding and structure of the business, assessing the TAM (Total addressable Market), SAM (Serviceable Addressable Market), the correct business & financial model & ensuring a minimal viable product that the market needs. So now you ask me, Lindi,  WHEN TO QUIT YOUR DAY JOB Now that you know the reasons to not quit your day job, it’s time to look at the flip side. How do you know when to quit your day job? Unfortunately, there is no easy answer to this question as each entrepreneur and his or her business is unique.

I do want to encourage & champion you to not let fear hold you back from jumping in once it’s feasible. Just make sure you don’t let this ideal time slip away because you’re too afraid to take a leap of faith.

If you think that you need to quit your day job in order to be a real entrepreneur, stop. When it comes down to it, keeping your day job until you are cash flow positive is not only the safest, but arguably the smartest decision you can make.

Please comment or share your experiences from building your side venture and still working in your day job, or if you have learnt lessons along the way.

We are taking a deep dive into the checklist, live on Facebook and Instagram, and Youtube so be sure to follow us on those platforms to not miss out on valuable tools to up-skill yourself for thriving in your business.