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7 Questions to Ask Before You Retire (It’s About More Than Money)

Mar 18, 2026
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Retirement is one of life’s most significant transitions. Asking the right questions before the time comes ensures you make the best possible decisions for yourself and your loved ones. Getty Images

Retirement is about more than finances and superannuation; it’s a time when we often reflect on our identity, purpose and life beyond a nine-to-five role. From experience, the closer I get, the further away it feels. The more you are questioned about it, the more confusing it becomes. The easy answers are “travel, more time with family, hobbies”, and each has some purpose, but nothing prepares you for what you might be losing. What if you enjoy what you do?

Retirement is one of life’s most significant transitions. Asking the right questions before the time comes ensures you make the best possible decisions for yourself and your loved ones. Here are a few key questions to consider.

1. What am I retiring from?

We don’t retire from life; we just retire from something specific: a job or a professional function.

2. Why am I retiring?

This may seem like a silly question, but it’s an important one to consider. Are you genuinely ready to explore life outside the workforce, or do you feel like you’re being pushed out of your current organisation or role? Unfortunately, ageism does exist. Not everyone can retire, or does, from a financial perspective. Some choose to work for as long as possible or work fewer hours. There are no right or wrong answers here; however, understanding your motivation is key.

3. Have I achieved everything I wanted in my career?

We are all motivated by different things. Sure, money is essential, but when mature people speak to me and reflect on their careers, they focus on their proudest achievements rather than money. This is a good question to ponder to avoid regret regarding anything you feel you’d still like to pursue, career-wise.

4. Who am I outside of work?

We spend so much of our lives working and so often, our identities are wrapped up in our work. Of course, we are more than our work and titles. If you’re struggling to answer this question, take however long you need to understand what retiring would look like in reality.

5. What do I enjoy doing that I don’t have time for currently?

What did I enjoy doing when I was younger before work and life responsibilities took over?
Is there something I never got the chance to pursue that feels unfinished that I can still pursue now?

6. If I couldn’t fail, what would I do?

I’ve encountered many mature people who are fed up with workplace inflexibility but who still enjoy the work and engaging with people. While they aren’t necessarily tired of working, they are tired of things like the daily commute, endless meetings, and feeling they must follow directions they don’t always agree with. Retirement may be an ideal time to take up volunteering or explore building that business that was only ever a hobby. Think outside the box and ask yourself what you’d do if failure weren’t an option and you didn’t care about anyone else’s opinions.

7. What are my financial realities?

Although it’s the final question, we can’t ignore it. Many people put off asking financial questions because they’re afraid of the answers but as they say, knowledge is power. Money isn’t everything but we need it to survive. Get the guidance you need to ensure the basics are taken care of and that if you choose to retire, you can do so comfortably, especially if anything unexpected surfaces.

I don’t view retirement as the end of the story. Often, it’s an invitation. Retirement forces us to ask the sometimes-difficult questions rather than allowing our careers to coast along. Be curious about retirement and what it may look like and mean for you. Asking some potentially confronting questions now will ensure that the best chapters of your life are ahead of you. And at the end of the day, if you feel like you’ve made the wrong choice in retiring, you can always return to the workforce. You never know what opportunities may come your way.

Deborah Wilson is a Thought Leader and a Career/Leadership Strategist at OnTalent. She takes a personalised approach to strategic career coaching and transitions, mentoring and leadership development. Deborah provides expert guidance for individuals while supporting organisations through change and connecting people and purpose.

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