Why I Wrote Retire-ish

December 2, 2025

If you’ve been in practice for any length of time, you’ve likely had that moment when you catch yourself wondering: How close am I to being done? And what does “done” even look like?

In twenty years of working with doctors, I’ve heard variations of these questions again and again.

The two wonderful reasons WHY I wrote Retire-ish?

It was never to talk about investments, to promote a product, or to add yet another generic “retirement rule” to the pile of already conflicting and confusing advice out there.

First, I wrote it to give you things you haven’t been given enough of: clarity, confidence and a way to connect your money to the life YOU actually want.

Second, because I wanted you to step fully into the ISH part of retirement!

So What Does The ISH mean in Retire-ish?

Many talks with doctors – some clients, some not – helped to create Retire-ish. In those conversations over focus groups, McCaig’s corridors, or your homes, the only consistency in the response to my asking “What keeps you working?” was the inconsistency of the responses!

And with that, a pattern began to emerge.

Doctors weren’t afraid of retiring. It was what came with retiring that was of concern.

Some were afraid of getting it wrong. (After all, they’ve never BEEN retired before!) Some worried about retiring too early or too late. Some wondered what they’d do next, and leaving their teams. Some just loved what they do, while others were ready for a new challenge

For most though, they were so busy looking after others that looking after themselves kept getting bumped down their list.

Tension between your head (math) and the heart (meaning) is the real story behind Retire-ish.

Your retirement shouldn’t feel like a leap of faith.


I wanted to bring you something grounded in reality, but rooted in both math and behaviour. Something that acknowledged your fears but also honored your dreams. Something that reflected what I’ve actually implemented and seen work for doctors over decades.

Retire-ish was my answer.

A framework where your savings aren’t just numbers, with a pretty graph showing rates of return, taxation, and an always-going-up-never-with-surprises cash flow and market prediction.

By far the most common error I see in financial plans isn’t with the numbers, it’s missing connecting your savings with the PURPOSE those savings will do for you in retirement.

Doctors weren’t afraid of retiring. It was what came with retiring that was of concern.

And with many different purposes, you have many different ways to allocate your savings to allow you to step forward into retirement confidently. A successful retirement is one where your ever-changing purpose is met. Retire-ish was written to help you create your 5 buckets with your 5 purposes.

So you can stop “should-ing” yourself. When you finally say you’re ready, you’ll know it with both your head and your heart.

Retire-ish took 2 years to write, to encapsulate 2 decades of experiences of other doctors like you.

I hope you’ll enjoy reading what I’m so passionate about – YOU!


Enjoyed this article? I’d love to hear from you! I’m always interested in hearing about the unique financial situations doctors haveSend me a note! And please check out my newest Amazon bestselling book, Retire-ish: What Doctors Need To Know Before They (Sort Of) Retire

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