Are You Truly Ready for Retirement? 10 Questions That Can Change How You Plan Your Future

Retirement isn’t just about leaving work—it’s about stepping into a new chapter of life. For many, it’s a time of reinvention, reflection, and yes, uncertainty. Most people haven’t been here before.

You haven’t navigated being work-free, maybe mortgage-free, and figuring out what to do with your newfound time. So, how do you prepare for a life that’s fulfilling and secure once the money piece is sorted?

Research by Susan Bell (Susan Bell Research) identified 10 essential questions to consider before you retire.

While retirement can be exciting—full of adventure and new memories—it can also be challenging. Life takes turns, and retirement rarely goes exactly as planned. These questions help you prepare for both.

Whether to work or not

Will you keep working part-time, start a passion project, or fully embrace retirement?

Some can’t wait to retire and quickly fill their days with activities. Others still want to contribute or keep social connections through low-stress, meaningful work.

• Sam, a professional in a demanding role, plans to sit on a few boards to stay engaged.
• Ray and Joan can’t wait to pack it in and hit the open road in their camper van.

Prompt: What role—if any—should work play in your next chapter?

How will I manage my finances to support my dreams?

Do you have a clear plan for superannuation, investments, and spending?

Early retirement (“go-go years”) is when you’ll likely spend the most: travel, experiences, and family time.

• The key shift: focus less on “how much I’ve saved” and more on “what reliable income will fund my lifestyle.”
• Super, investment property, downsizing—these are big decisions without one-size-fits-all answers. Feeling overwhelmed is normal. A personalised plan brings clarity.

Prompt: What monthly income do you need to live the life you want in the first 10 years?

How will you spend your time?

Without work’s structure, how will you create routines that bring joy and purpose?

There are 168 hours in a week—how will you use them?

Excluding holidays, what rituals will shape your weeks and seasons?

Many retirees say they don’t know how they ever had time to work. Mini-experiments help you find your groove.

Prompt: List 5 weekly anchors (fitness, volunteering, hobbies, grandkids, learning) to build your new rhythm.

How will you parent adult children?

Retirement can be a chance to reconnect. Will you support them emotionally, practically, or financially—and to what extent?

• Dave and Jane love taking their adult kids out for meals and picking up the tab. It matters to them.
• Garry and Sandy, while wanting to help their two daughters enter the housing market, they also want to be there when they need them.

Prompt: What boundaries and traditions do you want with your adult children?

What kind of grandparent will you be?

Will you be highly involved (the doting grandparent) or set a lighter cadence that fits your lifestyle?

My mother-in-law chose to be very involved—school runs, sports drop-offs, and the occasional last-minute pickup. It’s been a joy for her.

Prompt: How many hours a week do you want to dedicate to grandparenting, and what does that look like?

How will you navigate a changing relationship with your partner?

Different timelines, desires, and energy levels can create friction.

• John wants to retire now to enjoy his active years. Sally enjoys work and the security it brings, especially knowing she may outlive John. They had to balance his desire for immediate freedom with her need for continued work.

As one person moves from structured work to more home time, you’ll both need to find a new groove. As one person said, “I married you for love, not for lunch.”

Prompt: What does an ideal week look like for each of you—and where do they overlap?

What kind of carer will you be?

Many are in the “sandwich” phase—supporting adult children and aging parents.

• One couple is navigating a late-50s redundancy and coordinating care for parents on both sides of the country.
• Another client spends mornings managing her mum’s care team in the UK—rewarding but draining. Caring is an act of love—and it’s unpredictable. It should be part of your plan.

Prompt: If caregiving increases, what support systems or budget will you put in place?

How will you make and keep friends?

Work often provides a built-in social life. Retirement requires intention.

Some can’t wait to leave workplace dynamics. Others miss the camaraderie.

Many find maintaining friendships takes effort; men often find this harder.

• James and Sally planned travel around Australia to reconnect with old friends, meet new ones in caravan parks, and through house sitting.
• Jane wants to relocate to be closer to her closest friends.

Prompt: What relationships are important to you and what’s your plan for maintaining them?

How will you grow old? 

In nearly every first meeting, two themes come up: time and health.

You want more time for what matters—and the health to enjoy it for as long as possible. We’re all aging; bodies slow down, aches and pains show up, and certain conditions become more common.

Many of my clients stay active with yoga, golf, cycling, gym work, and even morning ocean swims (shark scares and all).

Prompt: What’s your weekly plan to protect mobility, strength, and energy?

How do you want to present yourself as you age?

Some people don’t focus much on appearance in retirement. Others invest time and money in looking and feeling their best. There’s no right answer—only what’s comfortable and authentic to you.

Prompt: What simple self-care habits will help you feel confident and healthy in this chapter?

Two More Questions to Consider…

What does “home” mean to you?

For many, the home is your largest asset outside super. Once the kids leave, a large house may not fit your next chapter.

You might stay put for a while, or downsize because it makes practical sense—not just to free up funds.

I’ve seen people delay home decisions for years, which makes change harder later. As you age, needs shift.

Can you maintain a large home? Will you hire help, or would a smaller place better support your lifestyle?

Prompt: Are you planning to stay, right-size, or relocate—and by when?

What legacy do you want to leave?

Legacy can be financial, relational, or values-driven. Do you want to maximise experiences now, leave a specific amount, or help along the way?

• Fiona and Sam want to live well and also earmark support for each adult child’s first home.
• Andy and Susie’s children are thriving financially, so they plan to spend on experiences; if the house is left over, that’s a bonus.

Prompt: What impact do you want to have on loved ones—and what’s the plan to make it real?

Retirement isn’t one-size-fits-all

Beyond super, your home, and investments, there are many facets to a life well lived. It takes time, reflection, and planning—but the payoff is a rewarding lifestyle with more confidence and clarity. Don’t leave your retirement to chance. Many people procrastinate and then feel blindsided at retirement. That doesn’t have to be you.

Don’t let uncertainty define your retirement. Book a free Retirement Clarity Call by clicking here.

Imagine waking up with the freedom to pursue what matters—knowing your finances support it. That’s the power of a thoughtful plan. Schedule your call today.

Glenn Doherty – CFP – Financial Planner | Retirement Planning Specialist |Retirement Planning Made Simple for over 55’s within 7 years of retirement

We work with people in Adelaide and around Australia virtually via zoom!

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