The Late-Start Retirement Guide

Let’s say you just turned 50, or 60, and that you’d like to retire.

What can and should you do if you’re a late start retirement investor?

Read this.

Retirement Accounts

If you don’t have a Roth IRA, start one. If you don’t have a crypto brokerage, start one.

If you have multiple accounts, consolidate many of them while trying not to lose good closed mutual funds, like you might have in an old 401K.

Look at the performance and all fees for each fund. Are they worth it? Can you do better?

Are any of your funds closed to new investors? You might keep those. Check and see if the manager(s) of each fund are new to the fund or if they’ve been there for a while, performing excellently.

Liquidate the actively managed stock funds that lag the S&P 500 and add the proceeds to better funds or the S&P 500 (ticker: VOO).

Buy the lows of shares you know and believe in. If a stock doubles, you can sell half and play with the house’s money.

I’d have 10+% of my accounts in cash to take advantage of buying opportunities during panics.

Keep a few thousand dollars’ worth of gold and/or silver as insurance against financial meltdown and power grid meltdown. Have some cryptocurrency as a hedge against disaster, too. Buy the lows when cryptos tank (like they did in Spring 2022).

Cash in low-yield annuities. Consider selling collectibles. Perhaps make settlement offers to people who owe you money. If you have large amounts of cars or guns or other valuable items, you may need to sell some if you’re late in your retirement planning. Scrape the barnacles off your barge.

Options & Speculating

You might speculate with options. If you read, “XYZ Inc. might sign a contract Monday,” buy a call on XYZ if you feel the deal will happen. If you read the market data and conclude x miners are oversold, buy a “call” to speculate, or use a “put” to insure common shares.

If you lose common shares, you lose some life savings. If your option expires “out of the money” you lose what you paid for the option.

I would not buy pink sheet stocks unless a newsletter I trusted advised making the wager. If a pink sheet stock got moved up to the Nasdaq or other index, you’re doing pretty well. Usually, pink sheet stocks just go belly up.

Don’t invest exclusively for dividends if you have little capital. A stock or fund with a low dividend yield is just that, even though the yield slowly but consistently appreciates. This is frequently a marketing gimmick. Don’t get shaken out of good investments by marketers.

Investigate Ticker: CLM at your brokerage or at Yahoo Finance. CLM is a covered call closed end fund that pays about 2% per month. (I own none at this time.)

Spread your money around. If you work 60+ hours per week, I’d let index funds and actively traded mutual funds do most of the work.

If you don’t want to learn to invest, use index funds (and/or rental real estate). Try to buy more when the market is down. As for cryptos: buy the lows. Be alert for scams. See our Glossary page.

If you do invest, stick to a plan. What was the price target of your stock when you bought it? If you hit it or surpass it – sell half of it. Don’t sell too early because of a flash correction or a rumor. If you researched your investment, don’t be shaken out by a marketer. Usually, I aim to hold a stock for at least a year.

Don’t overlook small caps. I’m not talking about pink sheet stocks. How about new restaurant chains, or something Millennials buy for their Zoomer kids or something Zoomers buy for themselves?

Use your circles of knowledge to your advantage. If you have an idea for what will or won’t work in technology, this can be a big help to you. Early adapters of emerging tech sometimes perform really well.

I would avoid high management fees.

Read about new mutual funds. Look for mutual funds started by a high-flying hedge fund manager or an analyst from an excellent investment company going on his or her own. Once I read of a fund manager who took the S&P 500 and simply didn’t buy the stocks in the index he figured would go down. The fund did really well.

A good financial planner is a good resource. But you still need to become financially literate (per Robert T Kiyosaki).

Before every payday, determine what you can contribute to your investments. I wouldn’t deprive myself too much to maximize my savings. Contribute what you comfortably can.

General Personal Finance:

Next, pay off debt if you have any. In my opinion, there is no way to justify having a high interest rate credit card, especially when retirement looms.

You can moonlight. If you’re not doing the “heavy lifting” for your employer, you can start doing some. You can come home from work and mind your own business, as Robert Kiyosaki puts it.

Stick to your plan! But, simultaneously, be flexible. Focus on one step at a time until you’ve completed your preparations. Ignore advertisements and propaganda from people who feign concern for you. All global politics is local.

There are many people who angle for other people’s retirement funds, business seed money, inheritances, and even financial aid funds. The thieves and sleazy marketers are the entitled ones. Try to argue this in a Clown World venue. (All global politics is local.) Financial crime will doubtlessly worsen as (post-modernist) globalist-socialist clowns keep things hummin.

I have heard some awful stories about bad financial advisors. You have-to become financially literate. Our featured books and audios are the best instruction I know about. (You can click the image of the book or audio, go to amazon, and find a used copy of the text.)

Be your own friend in all things regardless of the Clown World nonsense we’re all subjected to.

Your finances need to be closed to prying eyes. Again, shut out Clown World.

You can read practically anything a securities analyst, business professor, or sales professional can read.


If you’re really behind in the game, don’t panic. Keep working. Follow your plan. Don’t listen (buy into) extreme fear, extreme greed, unfounded optimism extreme ideological or social stupidity, or nonsense sales talk. As I hope you’re aware, on the flip side, disruption that’s positive for you doesn’t mean hey, let’s throw all principle and morality out the window.

Stories about elderly people who were encouraged not to save and invest for retirement and told to accumulate bad debt are sad and very real. (Must tell son.)

When asked about missing opportunity, Warren Buffet told a reporter, (other stock) opportunities are like buses. Another will come along.

If you’ve been drifting, it’s time to stop.

A final item is to consult a fee-only financial planner within several months of retiring. This is advisable because it’s good to have objective guidance on the entirety of your finances. Ask for references and check online reviews.

I will also strongly suggest having a will and designating a person to have power of attorney over you and your estate. Although we see elderly billionaires in the media doing deals, the majority of people seem to eventually lose their mental acuity with old age. You can draft a will and testament at Legal Zoom or a competitor of Legal Zoom or go to a lawyer who specializes in Wills, Trusts & Estates.

Disclaimer: This article is not to be construed as professional financial advice.

If you are a late-start retirement investor, the rest of this web site should help too. This site isn’t just for 20-somethings.