Three milestones to reach before quitting your day job

Mid-career entrepreneurs often struggle with the decision to quit their day job.

For many, having spent years crafting a successful career, there is a fear of throwing it all away for no good reason. For others, it’s the prospect of leaving a six-figure salary for an uncertain future that keeps them trapped in a vicious cycle of wanting to pursue their dream but not to the detriment of the lifestyle they’ve come to enjoy.

This is a feeling that my co-founder and I knew all too well when deciding to focus on building full-time.

We had both spent a decade building our careers, progressing to senior positions in blue chip companies before founding our business. To add to the stress of leaving our jobs behind, other factors like hefty mortgages, relationships and family expectations all weighed heavily on our decision to focus on growing our business full-time.

In spite of our demanding day-jobs, we spent almost 12 months worth of countless lunch breaks, all-nighters, weekends and public holidays building our business before we made the leap.

We often get asked what the turning point was for us and when the ideal time to jump ship would be for a budding entrepreneur. Everyone has a different trigger point and there really isn’t a divine, shining moment where the decision becomes crystal clear.

Being the nerds that we are, we penned down a clear set of goals early on in our journey to help make our decision as objective as possible. Only once we had hit all of these milestones would it be time to go all in.

The beauty of these three goals was that when we did go all in, we hit the ground running as our business had some real momentum and we weren’t just wasting time overthinking a pre-revenue idea.

Here are the three signs we held out for:

1. A working MVP

We were determined to build our own functioning MVP and having bootstrapped our build, we were keen to get this out to potential customers so we could fast validate the business’s potential to solve our industry problem.

Once a steady flow of deliveries started hitting our system, we could start to identify and prioritise meaningful features that would need to be built out in order for our business to generate more revenue over time. Before this stage, figuring out the must-haves from the nice-to-haves was a purely subjective task – with that comes a lot of potential to waste time and money.

2. Paying customers

Linked to a functioning MVP is the luxury of having customers who are willing to pay for the service you are providing. Nothing spells validation like a paying customer and early adopters become invaluable sources of critical feedback.

We were fortunate enough to have patient and evangelical customers quite early on. Constant and open feedback meant we were building out a wish list of new features that would ensure customer loyalty to our platform.

Our approach to testing, learning and incorporating feedback has meant that many of our pilot customers are still our most loyal users – it’s also meant our attrition rate has remained at around 8% since launch.

3. The support of friends and family

Once you’ve gained the support of your harshest critics you know it’s time to make the leap.

While not directly linked to revenue, this one is the foundation of the founding team’s emotional well-being. The startup journey isn’t easy for anyone so it’s important to have the support of friends and family when you hit your highs and your lows.

These three milestones may not seem like the biggest indicators of future success, what they do show you is that you’ve got a great idea and it has the potential to deliver revenue.

The only thing that stands between you and generating that revenue is your time and your energy – the two things you give away when you keep your day job.

Rob Hango-Zada is co-founder and director of Shippit.

Do you know more on this story or have a tip of your own? Raising capital or launching a startup? Let us know. Follow StartupSmart on Facebook, Twitter, and LinkedIn.


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