Reader Q&A: Am I Ready to Retire? 12 Questions That Bring Clarity

12 questions I’m asked all the time (with straight answers)

1) “How do I know if I can afford to retire?”

You need three things: a realistic spending picture, a plan for income over time, and stress-testing for “what if” scenarios.

2) “What if markets crash just after I retire?”
This is why planning for withdrawal strategy, cash reserves, and flexibility matters—sequence-of-returns risk is real.

3) “Should I pay my mortgage off before retiring?”
Often emotionally helpful, sometimes not financially optimal. The right answer depends on cashflow, rates, and security preferences.

4) “I’m financially ready, but I’m nervous. Is that normal?"
Completely normal. Retirement is a major identity shift. Planning should reduce uncertainty, not just calculate outcomes.

5) “What will I do with my time?"
This is the purpose gap. If you don’t plan for your weeks, retirement can feel empty—especially in the first 6–12 months. Start planning your retirement lifestyle before you retire, have a test run by taking a couple of weeks off.

6) “My partner and I want different retirements. Now what?"
Talk early. A good retirement plan is a shared plan, even if you keep personal freedom within it.

7) “Is it better to retire gradually?"
For some people yes so they can test the water, it can also help with the emotional and financial aspects. 

8) “When should I take my (state) pension?"
It depends on health, longevity expectations, other income, and personal priorities, but don't default-decide.

9) “How much is ‘enough’?”
“Enough” is personal. It’s the point where your essentials are secure, your lifestyle is affordable, you’ve built in breathing space for the unexpected, and you can genuinely relax about the future.

10) “How do I stop worrying about running out?”
Clear income planning + stress testing + a sensible safety margin. Anxiety reduces when you can see the plan.

11) “What’s the biggest mistake you see?”
Retiring too late and having regrets about what you could have done sooner.

12) “What should I do this month if retirement is 12–24 months away?”
Get organised, get clear on your lifestyle vision, and map out the income plan. Small steps now create confidence later.

As you can see from the questions above, for most people retirement isn’t just a maths problem — it’s personal, which is exactly why I wrote the book.

And it’s rarely one question in isolation. It’s usually a combination: income and confidence, timing and purpose, options and uncertainty, and (if you’re a couple) how two people’s plans fit together.

That’s also why the most helpful approach is to look at retirement as a whole — aligning money, emotions and lifestyle — so the decision feels clear, not rushed or guesswork.