Crossing the Threshold Into Startup Land – Founders’ Journey Series

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“Such custodians bound the world in the four directions…standing for the limits of the hero’s present sphere, or life horizon. Beyond them is darkness, the unknown, and danger…” Joseph Campbell

What gets somebody across the threshold into startup land? As we’ve outlined in the previous instalments of this series, there’s a few needed steps and characters involved in opening a founder’s mind to the possibility of startup land. Once the concept is incepted into a person’s mind, it’s actually all too easy to daydream fantasize about quitting your day job for the life of the income-less startup founder without actually making the leap. So what does it feel like to leap and start building your parachute on the way down?

“The first day in start-up territory was a mix of elation and caution. I’d been anticipating this journey for a few years and knew it was the right move.” Hugh Cameron, Founder ChckBx

You finally quit your day job. The next time you get a dollar of income will either be from your customers or clients or else from the day job you have to fall back on. It is crucial to have a life plan that aligns with your startup runway plan, i.e. you know when you have to fold in this game.

As Jeff Paine, founder ResponSight put it, “I was confident I could always get another job if it all went wrong, but there was still the “oh shit” moment when you realise that no money will appear in the bank any time soon.  And then the realisation that starting a business will actually cost money!”


As much as I’d love to tell you every founder that embarks on this quest becomes a successful startup founder, the numbers aren’t in your favour. They are getting better though. The best way to stack the odds in your favour is to know what’s ahead and how you’ll be ready to tackle the challenges.

So how do you plan to maximize mental comfort, create structure, start planning for the vast unknown new world you’re about to immerse yourself in?

“It was fear and doubt early in the day, then excitement across the middle of the day while ‘doing stuff’, and then more fear and doubt by the end of the day when I realised how much work actually needed to be done!” as Jeff puts it.

The big thing is, don’t think you can suppress the fear and doubt. You can’t kill your own internal beasts. You have to acknowledge them and learn to make them work for you. Get as much as you can finished each day. Recharge yourself with your friends and family then get back to work the next day. Just realize that most of the people around you from your ordinary life will not understand what you’re going through in startup world. For that, you’ll need a different set of people.

Don’t make the leap till you’re sure you have the right people around you to deal with propping you up in the ‘oh shit’ moments as well as calming you down in the ‘hell yeah’ moments. Left to your own devices, as you descend into a new and intense reality alone, you’re sure to go mad quite quickly.


Ask for help. Get suggestions for a good mental health professional along with all your business support services. Find founders who are honest and able to speak with confidence about their dark and vulnerable times productively. Only surround yourself with company that recharge your drive to build the best damn startup you possibly can. You’ll have more than enough drama naturally.


From here on out we’ll be curating a conversation on these topics in a dedicated Slack team. You can request an invite and join the conversation by emailing with Founders Journey Slack in the subject line.