Want to retire early and never work again? Here’s the catch

January 27, 2026 — 1:46pm

“Can we not use the word ‘retirement’?” I was in the middle of a private coaching call explaining the role of investing in the context of his long-term goals when my client interrupted me. “I don’t plan to stop working,” he continued.

“No problem.” I smiled. This man was talking in my language. I don’t love the word ‘retirement’ myself. It’s a loaded word that people have too many preconceived notions about.

The truth is – he was already living ‘the dream’. Not the dream you’re usually sold, to build wealth so you never have to work again. But the real dream – the one where you enjoy working enough that you never want to stop – but if you had to, you could afford to.

You don’t have to hang out in the personal finance world for long before you find some guru selling you some variation of that dream: invest in assets that make ‘passive income’ so you never have to work again – and then, then you will finally be able to live your real life.

This sounds like a great idea, at first. No more dreading Monday mornings, no more commuting, no more dealing with office politics, no more insufferable managers. Sounds great, right?

But if your driving force for building wealth is not having to work, you are subtly creating a negative relationship with work. You start to see work as something to avoid.

Trying to build wealth to avoid working is like trying to get fit to avoid exercising.

Here’s the catch: everything takes work

Learning to invest takes work. Managing an investment portfolio takes work. Increasing your income takes work. Building your own business takes work.

Even when you reach the holy grail of ‘retirement’, you will have to do the ‘work’ of figuring out how to find fulfillment without traditional forms of work. Incidentally, for many retirees, this looks like going back to or finding new forms of work because after a while doing nothing gets boring.

So, trying to build wealth to avoid working is like trying to get fit to avoid exercising. The thing you’re trying to avoid is the very thing required, to achieve the outcome you want. Ironically, this mindset often ends up leading to a harder, slower journey.

You look for short-cuts and quick-wins. You hop from one strategy to the next, wondering why nothing is ‘working’ – when you’re just not sticking with it long enough. After months (maybe years) of trial-and-error, you exhaust yourself, and think perhaps it’s just a hopeless pipe-dream.

Or maybe you are focused and disciplined. You know your goal, you know your strategy, you’ve got your eye on the prize. But you’re suffering now, for a future pay-off. You’re gritting your teeth through a career or business you are disengaged with, you’re sacrificing the little luxuries in the name of minimalism. You’re paying for your future freedom, with your current experience of life.

Either way, it’s a hard slog. This, you tell yourself, is the price you have to pay for success. But is it? Or is it just a reflection of what you believe ‘work’ has to be – draining, difficult, unfulfilling?

Escaping work isn’t the solution

The solution isn’t grinding it out for another 10-20+ years or hustling for quick riches, so you can finally quit. The real solution is figuring out how to make work something that is energising, meaningful, and sustainable long-term.

This won’t be easy. You might realise you’re only working in your current career for the money, but it will never bring you fulfillment. It might involve figuring out what business model, industry or company will enable you to have the lifestyle that feels good to you.

It might mean taking a few steps back financially, short-term. If you’re optimising for creating a work-life that feels good, instead of whatever pays you the most, there may well be a period of readjustment as you discover what that looks like to you.

It might even mean making adjustments in areas of your life outside of work. You’d be surprised how many people leave their jobs, only to realise they’re still not happy.

Maybe it’s your lifestyle (sleep, food, exercise) keeping you tired? Maybe it’s that long commute? It takes some courage to ask yourself – is work really the driving force of my dissatisfaction? The answer might be yes. But it might be no.

The solution I’m offering isn’t sexy. You’re not going to see many gurus selling you on this. It’s not going to make for a best-selling book. I’m doing the one thing I shouldn’t be doing – telling you that transforming your relationship with work is going to take some work.

But if that’s a journey you’re willing to go on, you might create something better than just a number in a bank account – a life you don’t need an escape from.

Paridhi Jain is founder of SkilledSmart, which helps adults learn to manage, save and invest money through financial education courses and classes.

• Advice given in this article is general in nature and not intended to influence readers’ decisions about investing or financial products. They should always seek their own professional advice that takes into account their own personal circumstances before making any financial decisions.

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