Want to carve your own path? What strategy might work for you?

Your starting point is gratitude. Yes, your somewhat ungrateful a*s might want to thank whatever higher Being you identify with for having a job in the first place. Zero income is not fun if you’re a functioning adult. As someone with as many attempts at escaping the clutches of 9-to-5 as a delusional Alcatraz inmate, I’m reminded of this from time to time. But as my fellow Escapees know all too well, what a regular job gives in steady income it often takes in insidious ways. If you don’t enjoy your job, it’ll suck your mojo by blunting your creativity, risk appetite or personal growth. If you do happen to enjoy it, the pay may suck, so you’re always a pay check away from broke. Or worse, it actually pays well and you’re trapped by your expanding appetite with every pay rise – a middle-class malaise known as lifestyle inflation. You’re “doing well” but secretly depressed. The other thing to consider is that we could all very well lose our precious careers within a few years anyway with the rise of AI.
Those that decide to make the jump and quit their day jobs usually take one of these three approaches….
The I Never Got Burnt Approach
This is generally the preserve of the young. You’re just out of university or while at uni, you had enough wisdom to look down the road and realise you don’t want to work for anyone. You don’t have any responsibilities, you’ve got balls and oodles of swagger. More young people than ever can afford to take this approach as they rely on willing middle-class parents who, having paid the price, are willing to let their offspring keep their bedrooms well into their late twenties. You may even have access to a garage where you can use for band practice or as a workshop or build your startup. If you can take this approach, go for it. We, as a society, are the better for it. Go girl! Go guy! Go whatever-you-identify-as! The saying goes youth is wasted on the young. If you’re still in your 20s, wake up, start thinking about what your passions are, what the technology and cultural landscape is looking like — and move!
The Burn Your Bridges Approach
Makes for great Hollywood but is generally a recipe for high blood pressure. Who doesn’t like a great story? The guy that punched his manager in the face, grabbed his laptop and marched into the blazing sun, chest out, finally ready to risk it all. Aside from being arrested by security for assault — and theft (that laptop wasn’t his and contains company intellectual property) — he better be ready to adjust rapidly to a frugal life.
The advantage of this approach, of course, is that you are boosted by urgency. The mind does a funny ol’ thing; it begins to think of creative ways to survive and achieve your goal. Prayer and meditation will likely become close companions through this period as it dawns on you the challenges of not having a thought-out plan. Pro-tip: Get a coach/mentor in your domain as quickly as possible.
The Slow Burn Approach
Less La-La Land, more Ta Da! It will seem like magic when you pull your goal off, but you and I know that a lot of thought went into it. A LOT. This approach isn’t very romantic to observers. No one’s writing a script about your quiet struggles.
This approach is also fraught with a few unsavoury bumps as well. You’ll have to cut back and live a frugal life like the bridge burners. But you planned for this, didn’t you? You know how much you need to survive every month. If you have a job that pays well and provides useful benefits like health insurance, training, opportunities to build your network, etc, then there’s nothing wrong with holding onto your job until all the pieces needed are in place to transition. The disadvantage, you guessed it, is that this approach can dull your sense of urgency. Don’t let your well-paid job stop you from working on your dreams at night and weekends. Also, remember that as time passes, complications to leaving your 9-to-5 career behind increase. That’s why the earlier you make that transition, the better. Before you get to a point in your life where you care about the type of car you drive, before you get to the point that vacationing at least twice a year becomes a human right rather than a luxury, one could even argue, before you marry (especially if you marry someone that loves you, but also loves the good things in life), before you have children, buy a house, have to take care of your ageing parents… and on and on… it’s easier to plan your exit, switch and live on hotdogs and garri (Nigerian readers will know this ‘delicacy’).
A good idea is to let your day job be your first investor. Start-up wisdom encourages Founders to bootstrap for as long as possible. The easiest way to do that is to have a job funding your side-hustle. Prove your concept, get your first customer if you can.
Create a solid plan! Think about the minutiae.
You’re more than likely going to throw half of that plan out the window when you begin taking action but make one anyway. Also, think about ways you can pivot if going down a particular path proves to be the wrong one. Also consider finding a mentor.
You may even be able to work on your ideas during breaks at your job but check the rules around doing something like that. Some companies claim proprietary rights on anything you work on if you use their equipment, e.g. a company laptop or phone or while you’re employed by them, period! Check where you stand legally.
It’s decent advice that you shouldn’t leave your job until earnings from your business match your pay but that also depends on how much you earn. A six-figure salary is more challenging to match. At some midway point between your worst frugal nightmare and a workable life you’re still proud to call your own, you got to jump.
Whatever approach you pick, be very aware of the challenges that come with it and execute quickly like someone lit a match under your backside.