At Oak Four, we often draw inspiration from the work of Carl Richards — former financial adviser, author, and widely known as the Sketch Guy. Carl has a gift for making complex financial ideas simple, often with just a few words and a sketch. Recently, he reflected on an idea that resonates deeply with us: perhaps retirement, as we’ve been taught to imagine it, is due for a rethink.

The Old Model

The traditional story of retirement is familiar: decades of work, a gold watch at 65, and years of leisure filled with golf, cruises, and umbrella drinks. But as Carl points out, that model was invented in the late 19th century — and much has changed since then. We’re living longer, working differently, and expecting more from life’s later chapters.

A New Perspective

In practice, very few people transition neatly from “full-time work” to “full-time leisure”. More often, we see clients exploring flexible paths:

• Scaling back into part-time or project work they find meaningful.

• Shifting careers in their 50s or 60s to something more fulfilling.

• Using part-time income to delay dipping into savings, giving investments extra years to grow.

This kind of approach not only helps financially — it also creates purpose and connection long after the traditional retirement age.

Why It Matters

As Carl puts it, if you realise you’re not going to retire in the old-fashioned sense, then perhaps you don’t need to keep working in a job that drains you. Instead, you can choose work that energises you — and plan financially to support that choice.

At Oak Four, that’s exactly what we mean when we say: live rich, not die rich. Retirement doesn’t need to be the light at the end of a tunnel. It can be a new beginning, filled with purpose, balance, and security.

Our Role

We help families design retirement strategies that are financially sound and emotionally fulfilling — whether that means a traditional retirement, a second career, or a gradual transition. The goal isn’t just financial freedom, but life freedom.

If you’d like to explore what your version of retirement could look like, we’d be delighted to talk it through.

With thanks to Carl Richards for sparking this perspective. You can explore more of his work at behaviorgap.com.