Are You Really Ready to Retire?

You Have Earned the Right to Delegate This

If you are reading this, you have probably had a thought you didn’t share at last week’s dinner: “I think I could actually retire.” Then, almost in the same breath, the second thought arrives: “But how do I know for sure?” That second thought is normal. You did not get to where you are by guessing on big decisions. You got here by making careful calls and trusting the right people on everything else.

Here is the thing nobody tells you about retirement readiness: it is not a math problem with one right answer. It is a five-part conversation. We work with successful professionals across Maine and New England who have spent thirty or forty years building something meaningful, and the thing they all have in common is that they are ready to delegate the complicated stuff to someone they trust. They want a clear yes or no. They want to spend their weekends with grandkids, not running spreadsheets. So, the five questions below are the same questions we walk our clients through, in plain English, with no homework. If you can answer them honestly, you will know where you stand.

Question 01: Will Your Money Last?

This is the question everyone starts with, and rightly so. It is also the one most people answer wrong by either underestimating their spending or overestimating how long their savings will hold up. The honest version of this question has three parts: How much will you actually spend each month? Where will that money come from? And will it still be enough in twenty or thirty years, after groceries and gas and property taxes have all gone up?

You don’t need to build a financial model to know the answer. You need to take an honest look at the life you actually want to live, total it up, and compare it to what is coming in from Social Security, any pension, and the savings you have built. If the numbers cover the basics with comfortable room to spare, you are in good shape. If they barely cover the basics, that is a planning conversation, not a deal-breaker. Most of the gap between “barely” and “comfortable” comes down to a few decisions about when to start Social Security, how to draw from your accounts, and what to keep in cash. None of that is something you should have to figure out alone.

Quick Check

If your projected annual income from all sources covers 100%+ of your projected expenses at a 3.5% withdrawal rate, you are in strong shape. If it covers 80–99%, targeted adjustments can close the gap. Below 80% signals more planning is needed.

Question 02: How Will You Handle Healthcare?

Healthcare is the single biggest wildcard in retirement, and the one most likely to catch people off guard. If you retire before 65, there is a real bill to pay every month for coverage until Medicare kicks in. We have seen healthy couples in their early sixties pay $20,000 to $30,000 a year for a good plan in Maine, sometimes more. That is not a small line in a budget.

Even after Medicare starts at 65, the bills don’t disappear. There are still monthly premiums, prescription costs, and the dental and vision care that Medicare doesn’t cover. Add long-term care, which most people will need in some form, and you have a category of spending that quietly grows over time. The good news is that this is one of the most predictable parts of retirement planning once you have a real plan in front of you. The bad news is that most pre-retirees plug in a single guess and move on. A thoughtful retirement plan looks at healthcare year by year, not as one number on a page.

A thoughtful retirement plan looks at healthcare year by year, not as one number on a page.

Question 03: Are Your Bills and Obligations in Check?

This one is uncomfortable to ask honestly, so most people skip it. Are you carrying a mortgage into retirement? Are you still helping an adult child with rent, or supporting a parent, or paying for a grandchild’s school? Do you have a second home, a boat, season tickets, club memberships? None of those are bad things. They are part of a life well lived. They just need to be counted honestly so they do not become a source of stress later.

The simple test is this: if Social Security and any pension you have were the only money coming in, would they cover your essential bills? If yes, your portfolio is doing the fun work of paying for the trips and the gifts and the dinners out. If no, your portfolio is carrying the weight of your basic life, which means a bad year in the market becomes a stressful year at home. That is a planning issue worth solving before you retire, not after.

• A mortgage is fine to keep, especially if the rate is low; it just needs to be planned for.
• Lines of credit and loans for adult children should be on the table for conversation, not hidden.
• Two homes mean two sets of taxes, insurance, and upkeep; both belong in the budget.
• Annual gifts and charitable giving are wonderful and should be sized to your real income, not borrowed from your peace of mind.

Question 04: Are Your Wishes Actually Written Down?

We meet a lot of people who think their estate is in good shape because they have a will somewhere from 2009. Then we look at the will and find that it leaves everything to a sister who has since passed away, names a guardian for children who are now in their forties, and points to a financial advisor who retired a decade ago. The documents are technically there. The wishes inside them are no longer accurate.

Retirement is the natural moment to do a quiet, complete refresh. Make sure the will still says what you want it to say. Make sure the people you have named to make medical and financial decisions on your behalf are still the right people. And, most importantly, take ten minutes to look at the beneficiary lines on every retirement account, every life insurance policy, every annuity. Those lines override your will. More family disputes after a death come from outdated beneficiary forms than from anything else we see, and the fix takes about an hour.

Question 05: What Are You Retiring Toward?

This is the question most articles about retirement skip, and it might be the most important one. The retirees who thrive are the ones who knew, before their last day of work, exactly what their first six months of retirement were going to look like. Not vaguely. Specifically. The ones who struggle are the ones who answered the question with a shrug and said, “I’ll figure it out.”

If your retirement vision today is “stop working,” that is a starting point, not a plan. The next step is just to think about the rhythm of your week. What are you looking forward to? Who are you spending time with? What is going to keep your mind engaged once the meetings, the deadlines, and the people you have worked alongside for decades are no longer in the picture? You don’t have to have it all mapped out, but you do need to be honest with yourself about whether you are actually excited about the chapter ahead, or simply tired of the one you are in. Those are different feelings and they deserve different conversations.

Two Couples, Same Numbers, Different Outcomes

Two couples sat across from us last fall. Both had about the same in savings, both owned their homes, both wanted to retire within the year. On paper, they looked identical. In the meeting, they could not have been more different. The first couple had thought through every one of the five questions above. They knew what they were spending. They knew what their healthcare was going to cost. They had told their children where the documents were. They had a list of three things they were excited to do in the first month. The second couple had the same balance sheet but had not really had any of those conversations. Same money, very different probability of a smooth, happy retirement.

Readiness is not a number. It is the depth of preparation behind the number, and the good news is that the preparation itself is something you do not have to do alone.

Your Next Step, Without the Homework

If reading those five questions raised more thoughts than answers, that is exactly the right starting point. The whole purpose of working with an advisor is to take this list off your plate. You bring the life you want to live; we bring the math, the tax considerations, the Medicare research, the document review, and the calm second opinion that helps you sleep at night.

Download our free Retirement Readiness Scorecard if you would like a simple, structured way to walk through these questions on your own. Or, if you would rather hand the whole thing to someone who does this every day, schedule a complimentary 30-minute conversation with our team. We will tell you honestly whether you are ready to retire this year, or whether you have a few small things to clean up first. Either way, you will leave the conversation with the one thing this decision deserves: real clarity.