Social Security is the largest source of retirement income for a majority of Americans. For about 1/3rd of them, Social Security makes up 90% or more of their retirement income.

Depending on your assumptions, the “lump sum value” of your Social Security benefits is somewhere between $300,000 and $700,000. (Source: Kitces)

Even this large figure ignores the fact that your Social Security income is guaranteed to rise each year with inflation, something no other private annuity company in the world even offers any longer at any price!

Therefore, spending a little time and money in order to consider the many options for Social Security (especially for those married, divorced, widowed, or disabled) can really make a difference. This NYT article (free, gift article) lists a number of services that help you navigate the rules (at a variety of service levels and price points). In no particular order:

• Maximize My Social Security (starts at $40 a year)
• Social Security Solutions (starts at $20 one-time)
• Open Social Security (free)

I don’t have any in-depth experience with any of these online tools, but when the time comes I’d probably pony up the money (adds up to less than $100 for all three) and compare the results. If they are properly programmed, they should all agree, right?

The tools below go beyond Social Security claiming strategies and more into overall retirement income planning.

• Maxifi Planner (same company behind Maximize My Social Security)
• NewRetirement.com
• Income Strategy

Even if you’re still far away from claiming time, be sure to sign up for your official mySocialSecurity account (before a scammer does) and take a peek at your stats each year. For those that like tinkering, try copy and pasting your anonymous data into the SSA.tools website (free) and play around with different future scenarios.

In the end, you may not follow the software recommendations exactly, but simply knowing about the different options and factors can be helpful. In my experience, many people just end up claiming earlier because they want “their” money sooner rather than later without understanding the potential drawbacks. A retiree may want to have their “own” paycheck again if their partner still works.

Most people must rely on the power of smaller, regular investments from work income to build up their retirement nest egg. In the latest Sound Investing email, Paul Merriman shared a new Lifetime Investment Calculator that helps you see how these gradual investments (dollar-cost averaging) would have added up during various periods, using actual historical returns from 1970 to 2020.

I’ve already tried to illustrate how regular investments of $250 or $500 a month can add up over time. But instead of having to manually gather performance numbers from a Vanguard Target Retirement fund in a spreadsheet, this fancier calculator lets you adjust many more variables. You can choose different asset allocations, stock/bond ratio, investment amounts, and so on. Importantly, the calculator uses actual historical returns, so you can see what would happen if you invested through the 2001 dot-com bust, 2008 financial crisis, and so on.

You can start the sequence of returns from any of the 51 years to replicate your financial picture as if your decisions were available in the past. For example, you could simulate the role of luck by starting or ending your journey in a bull or bear market. It is not a financial planning calculator per se, nor meant to be a complete planning tool, but it allows you to customize both growth (accumulation) and distribution phases based on your personal timeline and investments.

If you aren’t familiar with Paul Merriman, he is an advocate of adding a bit of complexity to index fund portfolios via additional exposure to smaller and value-oriented companies. For a test run, I went for the “Ultimate Buy and Hold Worldwide (70% US/30% International)” portfolio, alongside a simple S&P 500 portfolio.

Here is $10,000 invested every year for 15 years, with small ~3% increases each year with inflation (ideally corresponding with a higher paycheck), starting in 2005:

Here is $10,000 invested every year for 15 years, with small ~3% increases each year with inflation (ideally corresponding with a higher paycheck), starting in 2000:

Here is $10,000 invested every year for 15 years, with small ~3% increases each year with inflation (ideally corresponding with a higher paycheck), starting in 1995:

You can see that an internationally-diversified portfolio may not be the best in some periods, but it also may not be the worst in others. (I admit I am a bit confused as to why the performance numbers for any given year are slightly different for each test run, perhaps someone out there can explain that to me.)

Even in the 1995-2010 period that contained both the 2001 dot-com bust and the 2008 financial crisis, your ending balance would still have ended up much higher than your total contributions with the internationally-diversified portfolio.

You’ve probably heard of the “4% rule” when withdrawing income from a retirement portfolio. I think using such a rule is fine when you are early in the accumulation phase, although I like the “3% rule” better for early (long) retirements. But heck, reach 25x expenses first and then reassess. However, when it’s actually time to spend down that money, the execution can be tricky. If you start out taking 4% on a $1,000,000 portfolio ($40,000) and then the market drops 50%, will you really take $40,000 (8%) out of your sub-$500,000 portfolio the next year?

Being flexible in your withdrawals works better with both theoretical backtests and natural tendencies. If my portfolio drops 50%, I’m going to tighten the belt and spend less money the next year. Some people may not want to admit this, but I would consider taking on a part-time job again in a severe event. I collect part-time job ideas as part of this Plan B.

On the flip side, if you’ve used a lot of portfolio simulators like FIRECalc and Engaging Data, you’ll notice that your portfolio sometimes gets crazy huge. If your portfolio doubles in size, you might decide to live it up a bit and spend more than 4% of your original amount (inflation-adjusted).

Accordingly, I was impressed to see that Portfolio Charts updated their already-useful Retirement Spending Tool to account for flexible portfolio withdrawals. Everything has been elegantly simplified into four variables:

Withdrawal Rate: the percentage of the portfolio you withdraw every year to fund your retirement expenses

Change Limit: The maximum amount that a withdrawal can increase or decrease from year to year

Account Trigger: A simple rule for when you’re allowed to increase or decrease spending based on how the portfolio is doing relative to its original value

Withdrawal Limit: The minimum or maximum withdrawal you realistically need to pay the bills and live a happy life regardless of what a flexible spending strategy might recommend

Keep in mind that the spending is already inflation-adjusted, i.e. it increases each year with inflation even with no change. Here’s a screenshot:

Take some time to play around with the many combinations. You could see what happens if you let the withdrawals vary wildly. You could see what happens if you only allow the withdrawal amount vary within a tight range. How does your portfolio balance change? For example, I thought about starting with a relatively conservative number like 3% base withdrawal rate, but also be willing to drop it to 2.7% (10% less) if the portfolio drops by 10% in value. Meanwhile, I’d wait until the portfolio increases by 50% before I start paying cash to fly business class everywhere (#goals).

If I were to have a wish list for a new feature, I would like it to show me the minimum balance that the portfolio reached during any of the scenarios. This would let me know the maximum drawdown experienced using my set of variables, as the chart is a little hard to read.

If you have researched retirement at all (early or otherwise), you’ve probably ran across various retirement calculators online. You input how much money you have (or plan to have), your asset allocation, and it spits out some numbers. This Vanguard Retirement Nest Egg Calculator is a good example of a simple version.

Let’s try an example. If I am 40 years old and thus assume I have up to 50 years left in retirement, and I want to maintain a 4% withdrawal rate ($40,000 a year from a $1,000,000 portfolio that is 65% stocks/30% bonds/5% cash), the tool uses Monte Carlo simulations to calculate that I have an 80% chance of lasting 50 years.

There is effectively one output: the odds of not running out of money. Either you still have at least a dollar, or you don’t. In my example, I have an 80% chance of having $1 or more at age 90.

But what if you also considered the odds of running out of time? Yes, that’s a euphemism for dying. (Ever notice how many of those we have?) In another neat tool from Engaging-Data.com, Will Your Money Last If You Retire Early? adds some helpful nuance to this analysis. You input the same types of information, but now in any given year you are provided the overall odds of each of these things happening:

• Red – You are alive, but ran out of money.
• Light green – You are alive, with less money than you started with. (Kinda nervous?)
• Green – You are alive, with between 100% and 200% of what you started with. (Nice and comfy.)
• Dark green – You are alive, with over 200% of what you started with. (In hindsight, I didn’t need to save so much…)
• Grey – You are pushing up daisies. (In hindsight, maybe should’ve retired earlier…)

Here are sample results for the early retirement scenario above at 4% withdrawal rate (age 40, retirement horizon 50 years, $40k from a $1m 65/35/5 portfolio). I picked the female mortality table – if you have a male/female couple, it’s safer to pick the person likely to live longer.

There’s an angry streak of red where I’m broke. Of course, there’s a bigger streak of grey where I’m not breathing.

Here’s the same scenario, except with a lower 3% withdrawal rate ($30,000 a year from a $1,000,000 initial portfolio):

That change got rid of the red, but there is a lot of dark green. (1% makes a big difference.)

Here are sample results for a more traditional retirement scenario: (age 65, retirement horizon 25 years, $40k from a $1m 65/35/5 portfolio)

As a financially conservative person, these charts help illustrate why I prefer working with a 3% safe withdrawal rate for early retirement (50 and under) and 4% safe withdrawal rate for traditional retirement (closer to 65).

My favorite part of this tool is that it makes you take into account your mortality. It’s not all about staying above $1 in the bank, but also about maximizing your years of freedom. If you’re 40, you have a 10% chance of dying before even reaching 65. (This is why most people know someone who died shortly after retirement.) Is it better to have zero chance of broke and be 70, or 5% chance of broke and 60 with 10 more years of retirement (and 10 fewer years of work)? It is better to live a little more luxuriously for shorter time, or a little more frugally for a longer time? Playing around with all the different input variables might help you weigh the options.