Designing the next chapter
What Does Retirement Look Like to You?
I’ve been asking people this question for more than 30 years.
And most people don’t answer it straight away.
They’ll tell me when they want to retire. Or how much super they’ve got. Or what they’re worried about. But when I ask, “What does retirement actually look like to you?” there’s often a long pause.
One client once said, “I just don’t want to run out of money.”
Which is completely understandable. But when I gently followed with, “What do you want to run towards?”, that’s when the real planning began.
Because retirement isn’t a short break. For most of us, if we are lucky, it’s 20 to 30 years or more of life. That’s too long to leave to chance.
Retirement is about choice, not stopping
I’ve worked with people who couldn’t wait to retire… and then felt strangely lost six months later. One client once told us, “I’ve painted the deck three times and I’m driving my wife mad.”
He didn’t need a job, he needed purpose.
Retirement doesn’t have to mean stopping work completely. Some people love a clean break. Others are happiest doing a little paid work, consulting, volunteering, mentoring, or contributing to something meaningful.
One client summed it up beautifully: “I don’t work for the money. I work because Tuesday mornings matter to me.”
That’s retirement done well, on your terms.
So, how do you plan for a good retirement?
Here are some practical steps I encourage clients to take, long before they finish work.
- Picture your life, not just your finances
Ask yourself:
- What would a great week look like?
- How much structure do I want?
- Who do I want to spend my time with?
- What gives me energy and purpose?
Money supports the plan; it doesn’t create the life.
“The most successful retirements aren’t defined by a number—they’re shaped by clarity, purpose, and the confidence to make decisions along the way.”
— Jenny Brown, CEO, JBS Financial
- Talk about work, volunteering, and purpose early
Don’t assume you’ll “figure it out later”. Think about whether you’d like:
- Part-time or seasonal work
- Volunteering or mentoring
- Helping family or community
- Learning something new
Purpose doesn’t have to be grand; it just has to be yours.
- Have honest conversations with your partner
I’ve seen couples discover, far too late, that they imagined very different retirements. One wanted to travel constantly, the other wanted routine and home.
Neither was wrong, but no one had said it out loud.
Good retirement planning includes space for individual interests as well as shared goals.
- Stress-test your finances, calmly
This isn’t about perfection. It’s about confidence.
- What income will support the life you want?
- How flexible is your plan if markets change?
- What’s essential spending vs discretionary?
- How will your strategy adapt over 20–30 years?
A good plan gives you options, not anxiety.
- Review regularly, not just once
Retirement isn’t static. Health changes. Family changes. Priorities shift. The best plans evolve with you.
We often say retirement planning isn’t a “set and forget” exercise, it’s a long-term relationship.
Designing the next chapter
I wrote Retirement: The Great Escape Plan because we’ve seen what happens when people plan thoughtfully, and when they don’t.
The happiest retirees aren’t necessarily the wealthiest. They’re the ones who planned with intention, stayed curious, and gave themselves permission to design a life that suits who they are now.
So let me ask you the question I ask every client:
What does retirement look like to you?
And more importantly, have you given yourself the time and space to really think about it?
If you’re not quite sure yet, that’s okay. Most people aren’t at the start. But having the right conversations early can make all the difference.
At JBS Financial, we’ve spent decades helping people turn ideas, questions, and even uncertainty into a clear and confident plan for the next chapter.
If you’d like support shaping what retirement could look like for you, we invite you to start the conversation. Book a conversation here.
Because the best retirements don’t happen by accident.
They’re designed calmly, thoughtfully, and with confidence.
And yes… thriving should be fun. And naps should be epic.