Let's look at the question: "When should I retire?"

When you can afford to retire. No one wants to move from employment into poverty. They shouldn't spend everything they earn, putting themselves in the position of never being able to stop working. Everyone should have goals. Enjoying a comfortable retirement is a great goal. It can motivate the client to put money aside on a regular basis. They need a roadmap indicating they have a decent chance of reaching their goal, if they stick to the plan.
When there's another job to slide into. Some professions are more dangerous or intense than others. Law enforcement is one example, but some civil service careers fit into this category. They might work for a government agency. They reach the age when they are eligible to start claiming retirement benefits. The state has a similar agency. There's the private sector too. Assuming there are no legal restrictions, they might leave the federal position and start working full time in a state position. Don't want to work full time? Consulting might be an option.
When the family needs you. Let's assume the client is close to retirement age. Their finances are in good shape. They have money put aside. Their parent or child has developed a life-threatening medical condition. They can live at home, yet need constant care. This might be the time when the client leaves the corporate world and becomes a caregiver within the family. they know it's the right thing to do.
When you've topped out your benefits. They have the type of job with a defined benefit pension plan. If they've spent their entire career in this job, they might find the benefits reach a maximum level. They can work longer, but the income they can collect in retirement has hit a ceiling. This might be a good time to hang up the spurs.
When the business can be transferred to your children. This might apply in your own profession. You started the agency. You grew the agency. You brought your children into the business. They have learned all aspects of the operation. This might be a good time to step away, transferring day-to-day operations to them.
When someone offers you a huge amount of money for your business. Your client runs their own business. They own their building outright. Someone comes along and wants to gain market share by purchasing their company. Maybe it's the real estate they are after. They offer a very fair price. The money received can keep the family comfortable for generations.
When your employer offers early retirement. This was more common in the past. The client has worked at a firm for years. The firm might be relocating the headquarters across the country. They might be merging with another firm. They will accelerate the client's retirement, allowing them to leave earlier than expected and start collecting from a very generous defined benefit pension plan.
When you have health issues. This can be a wake-up call. Everyone has a story about someone who put off having any fun until they retired. Once they left employment, something happened and they died. They never had that fun. Perhaps your client had a health scare. They have a new appreciation for their time on Earth. It might be time for them to retire.
When your spouse has a great opportunity elsewhere. Your client is close to retirement. They like what they do, yet they can afford to stop working. Their spouse got a great career break. The job of their dreams is now within reach, but they need to move to the other coast. Your client can be supportive, stop working and encourage them to seize the opportunity.
When your client really can't stand what they do. They have saved like they should. They are in decent financial shape. For some reason, something has changed in their work situation. The firm was bought out and new management has a different way of doing things. Maybe they feel the firm's approach to treating customers has changed. They dread going to work every morning. If they can afford it, this could be a good time to step away.

Retirement often isn't a question of "hit an age, hit a number." Other factors can be involved. It's important to understand your client's situation and be able to offer professional advice. Approach it from the mindset "How can I help make this happen?"

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Ever get asked: "When should I retire?"

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