The Finish Line Is in Sight. Do Not Blow It Now.

You have done the hard part. You showed up for decades. You worked, you saved — maybe not perfectly, maybe not always as much as you wanted to — but you kept going. And now retirement is not this distant, abstract concept anymore. It is a date on a calendar. It is a conversation you are starting to have seriously with your spouse, your advisor, or the voice in your own head at two in the morning when the house is quiet.

This is the season that separates the people who retire with confidence from the people who retire with anxiety. And I am going to be direct with you about something: the decisions you make in the next five to ten years matter more than almost anything you have done before. Not because the earlier years did not count — they absolutely did — but because right now, at this stage, there is no long runway left to recover from a serious mistake. What you do with this window is what determines whether retirement looks the way you always imagined it, or whether you spend those years managing the consequences of decisions you wish you had made differently.

This is not meant to scare you. It is meant to make sure you are paying the kind of attention this moment deserves.

You Have to Stop Thinking Like an Accumulator

For the past 30 or 40 years, the goal was simple: put as much money in as you can, invest it in growth-oriented assets, and let it build. That strategy made sense because time was on your side. A down market at 35 meant a buying opportunity. A bad year at 42 was just noise in a 30-year story. The math forgave a lot because the horizon was long.

That changes now. When you are within ten years of your retirement date, a severe market drop is no longer just a dip in a long-term trend. If it happens at the wrong moment — say, the year you retire or the first couple of years into retirement — and you are forced to sell investments to cover your living expenses while the market is down, you lock in those losses permanently. You never get that money back. Your portfolio shrinks faster than it should, and suddenly the projections that looked comfortable do not work anymore.

This is called sequence of returns risk, and it is one of the most misunderstood threats to a retirement plan that looks perfectly fine on paper. The average return of a portfolio over 30 years can look great. But if those returns arrive in the wrong order — bad years up front, good years later — the real outcome for someone drawing income from that portfolio is dramatically worse than the average would suggest. This is why shifting your strategy from pure accumulation to something more balanced and protected is not being overly cautious. It is being smart about the risk that actually matters at this stage of your life.

This does not mean abandoning growth entirely. Your money still needs to work. You may have 25 or 30 years of retirement ahead of you, and inflation will erode the purchasing power of money that just sits in cash. What it means is building a thoughtful allocation — enough stability to cover near-term income needs without being forced to sell equities in a down market, and enough growth exposure to keep your long-term purchasing power intact. The specifics of that allocation depend on your full picture, and getting it right is exactly the kind of conversation you should be having with a financial team that understands your whole situation.

Social Security Is Not Just a Check. It Is a Decision That Follows You Forever.

If there is one decision in your pre-retirement years that people consistently underestimate, it is this one. When you choose to claim Social Security is one of the most financially consequential choices you will make — and it is permanent. You do not get a do-over.

Here is what you need to know. You can claim as early as 62, but doing so means accepting a permanently reduced benefit — up to 30% less per month than if you wait until your full retirement age, which is 67 for anyone born in 1960 or later. And for every year you delay claiming beyond your full retirement age, your benefit increases by 8%, up until age 70. That means the difference between claiming at 62 versus 70 can be as much as 76% more per month — for the rest of your life.

Let that sink in for a moment. If your full benefit at 67 would be $2,500 a month, claiming at 62 might net you closer to $1,750. Waiting until 70 could bring that number to over $3,100. That spread, over a retirement that lasts 20 or 25 years, is not a rounding error. It is the difference between financial comfort and financial strain — especially in your later years when healthcare costs tend to rise and other income sources may shrink.

Now, delaying Social Security is not the right move for every person in every situation. Your health, your other income sources, your spouse's benefit, and your overall financial picture all factor into the optimal claiming strategy. The point is not that you should always wait until 70. The point is that this decision deserves real analysis — not a gut call based on wanting to access the money as soon as you are eligible, which is what most people end up doing. Most people claim early and leave significant lifetime income on the table without ever running the numbers.

Run the numbers. Then make the decision.

The Healthcare Gap Is Real, and Most People Are Not Ready for It

Here is a scenario that catches a lot of near-retirees completely off guard. You decide to retire at 62. You feel good. The finances look workable. And then someone asks you: what are you doing about health insurance until Medicare kicks in at 65?

For three years, you are on your own. And individual health insurance is not cheap. Depending on your age and where you live, you could be looking at premiums of $700, $900, $1,200 a month or more — before deductibles, copays, and prescriptions. Over three years, that healthcare gap can cost you $30,000 to $50,000 out of pocket if you have not planned for it. That is money that comes directly out of your retirement assets, often right at the beginning of retirement when you can least afford to drain the portfolio.

This is one of the most important arguments for a Health Savings Account, or HSA, if you are still eligible to contribute to one. The HSA is the only savings vehicle in the tax code that gives you a triple tax advantage — contributions are tax-deductible, growth is tax-free, and withdrawals for qualified medical expenses are tax-free. After age 65, you can use HSA funds for any expense, not just medical ones, though non-medical withdrawals are taxed as ordinary income. If you maximize your HSA contributions in the years leading up to retirement and resist the temptation to spend it down along the way, you can arrive at retirement with a meaningful medical reserve that was built entirely with pre-tax dollars.

The healthcare cost conversation does not stop at 65 either. Medicare covers a lot, but not everything. Long-term care — the kind of care you might need if you experience a serious illness, a stroke, or cognitive decline later in life — is not covered by Medicare in most circumstances. The average cost of a private room in a nursing facility runs over $100,000 per year. Long-term care insurance, hybrid life insurance products, and other planning strategies exist to address this exposure, but they require you to plan for them before you need them. By the time you are already in declining health, the options narrow significantly.

Your Estate Plan Is Either Ready or It Is Not. And "Not" Has Consequences.

You have spent your entire working life building wealth. Savings accounts, retirement accounts, a home, maybe a business, maybe investments outside of retirement. The question you need to answer honestly right now is this: if something happened to you tomorrow, does all of that go exactly where you want it to go, to exactly the people you want to have it, in a way that protects them and honors your intentions?

If you do not have a current will, a financial power of attorney, a healthcare directive, and beneficiary designations that are up to date on every account, the honest answer is no. It does not. And the cost of that oversight is not just financial — it is emotional, relational, and sometimes irreversible.

Beneficiary designations on retirement accounts and life insurance policies override your will entirely. That means if you named your ex-spouse as the beneficiary on your 401(k) 15 years ago and never updated it, that is where the money goes. Your current spouse, your children, your intentions — none of it matters if the paperwork says something different. This is not an edge case. It happens constantly, and families are torn apart by it.

Now is the time to do a full review. Pull every account. Check every beneficiary. Make sure your will reflects your actual wishes. Make sure someone trusted has the legal authority to act on your behalf if you cannot act for yourself. These are not morbid conversations. They are the most loving, responsible things you can do for the people who are counting on you to have done them.

This Is Your Moment to Get It Right

The years just before retirement are not a time to coast. They are a time to build, protect, and align everything with the precision that this season requires. The accumulation phase of your financial life was about momentum. This phase is about intention.

At Black Mammoth, this is exactly the kind of comprehensive, everything-connected work we were built to do. Not just investment management. Not just a Social Security calculator. A full picture — your income plan, your tax strategy, your healthcare coverage, your estate plan, your legacy — all mapped together in a way that actually makes sense for your life and your family.

You are too close to the finish line to leave this to chance. And you have worked too hard to let poor planning be the reason it does not go the way you always imagined.

Let's make sure it does.