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Retirement Planning: How Did We Get Here (And How Do We Get THERE?)

Retirement Planning: How Did We Get Here (And How Do We Get THERE?)

October 13, 2025

The retirement planning landscape changed forever in the early 1980s, and many people today have limited awareness of what we lost in the process.

Before 1978, when the 401(k) was born from a tax provision that isn't exactly a household name, retirement had more of a tendency toward simplicity.

For a much larger percentage of the population, the story was clear: you worked for a company, they promised you a pension, and when you retired, checks showed up in your mailbox until you died. Period.

In this situation, the company bore all the investment risk. The company handled longevity risk. The company dealt with sequence of returns risk. And if this was your setup at work, then your role was primarily to show up to work and not get fired long enough for this to play out.

Following the passage of this act, the percentage of private wage and salary workers who received a "defined benefit" pension was cut nearly in half. When the laws and customs shifted, companies realized they could transfer all that messy, expensive risk to employees. Why would they guarantee lifetime income when you could just match a few percent of salary and call it a day?

The Great Risk Transfer

What filled the gap? The 401(k) – originally designed as a executive compensation supplement, not a replacement for actual retirement security. And of course, in fact, the Economic Policy Institute described 401(k)s as “a poor substitute” for the defined benefit pension plans many workers previously relied on.

What happened here might well have been among the largest transfers of financial risk in American history – from institutions with professional management and deep pockets, who were able to pool retirement risk across thousands of employees, to individuals fending for themselves, with no risk pool, and armed with nothing but a handful of mutual fund options and a quarterly statement.

Suddenly, regular people had to become investment experts. They had to figure out asset allocation, rebalancing, and withdrawal rates. They had to predict their own lifespan and hope the market cooperated during their specific retirement window.

Think about how absurd this is. We expect our marketing professionals, designers, and engineers to master in their spare time what pension fund managers with teams of actuaries, economists, and investment professionals do full-time, often with degrees, designations, and decades of experience.

And here's the kicker – even if you nail the accumulation phase and build a solid nest egg, you still have to solve a significantly harder problem: making that money last for an unknown period while markets do whatever markets will do.

The Investments-Only Trap

Most retirement planning today follows a depressingly simple formula: save money, invest in stocks and bonds, hope capitalism keeps working, and pray you don't live too long or retire at the wrong time. 

It's a one-way bet on economic growth. You're essentially gambling that the general rise of markets will happen to benefit you during your particular slice of history, in the right ways and at the right times.

It's not an entirely terrible bet – capitalism has done pretty well over the long haul. But it's still just one approach to a complex problem. So what's missing? The magic that made pensions work in the first place.

What if something similar to the 2000s happen again – a lost decade where the S&P 500 went essentially nowhere? What if you retire right before a major correction and have to spend money to live your life while your investments are "temporarily" depressed in value? What if you're that person who lives to 95, 96, or 97 instead of 85? Will you be OK running out of money a few years before you die, secure in the knowledge that you got it right "on average"?

The investments-only approach puts you at the mercy of forces completely outside your control: market timing, sequence risk, inflation timing, and your own biology.

Here's what we've asked regular people to become experts in:

  • Asset allocation across market cycles
  • Sequence of returns risk
  • Safe withdrawal rates
  • Tax-efficient distribution strategies
  • Longevity planning (because apparently you need to predict when you'll die)
  • Market timing (even though professionals can't do it consistently)

And that's just the investment side.

Now add the distribution challenge: How do you turn a pile of money into a paycheck that lasts for an unknown number of years, through unknown market conditions, with unknown healthcare costs, and unknown inflation?

Most people are trying to solve this puzzle with a single tool: hoping their portfolio grows faster than they spend it. Like trying to build a house with only a hammer.

There's Actually Another Way

Here's what the retirement planning industry hasn't sufficiently acknowledged since: you can shift much of this risk back to institutions. You have more power than you think.

Pensions weren't just investment accounts. They used a logical and effective approach for their purpose; they used something called risk pooling and the law of large numbers. Instead of each individual bearing their own longevity and market risks, everyone's risk got pooled together, across thousands, hundreds of thousands, or millions of people.

Some people died early (sad for them, good for the pool). Some lived to 100 (good for them, manageable for the pool). Some retired right before a market crash, others retired at market peaks. When you average it all out across a large group, the uncertainty becomes predictable.

Professional managers handled the investments. Actuaries calculated the probabilities. The company promised the outcome.

You can transfer longevity risk back to institutions via insurance companies. You can guarantee income streams that last as long as you do. You can protect portions of your wealth from market volatility while still participating in growth.

Tools Are Available

Here's what many people don't realize – you're not stuck with the do-it-yourself retirement approach just because pensions disappeared from your workplace.

The tools available to create guaranteed income streams? There are forms that exist today. You can transfer some of your risk back to institutions.

I'm talking about things like:

  • Immediate and deferred annuities exist that can convert a lump sum into guaranteed monthly payments for life. Same concept as a pension, except you're buying it directly from an insurance company instead of earning it from an employer.
  • Bond ladders and TIPS that create predictable income streams for known periods, independent of stock market performance.
  • Defined outcome solutions that provide specific, pre-stated return profiles over set time periods. These can take the form of structured notes, buffered ETFs and UITs, or certain index-linked annuity products that provide specific outcomes given an array of possible market outcomes. They may include specific amounts of potential market downside you do not have to absorb, and may provide a set percentage (sometimes 100% or more) of equity upside if the market goes up, for example. Other forms pay monthly or quarterly fixed income percentages, assuming certain index outcomes.
  • Life insurance strategies: While the main purpose of life insurance in the death benefit, some insurance solutions create tax-efficient income and legacy planning simultaneously, while also potentially serving to backstop or replace assets used to create guaranteed income (above).

Importantly, you don't have to choose between "all investments" and "all actuarial guarantees." You can and in most cases should mix and match based on what you can commit to and what you value most.

The tools are there. The question is whether you know they exist and how to use them strategically.

It's About What You're Willing to Commit To

Here's the tradeoff: risk transfer requires commitment. You can't have guaranteed income AND complete liquidity AND maximum growth potential all from the same dollar contributed. Something has to give.

This approach means giving up some flexibility in exchange for certainty. You're trading optionality for your desired level of security.

But here's what matters – whatever you can commit to, you can optimize for. If you know you'll need a baseline level of income no matter what, why not guarantee it and remove that stress from your life? Then you can be more aggressive with the rest.

Every financial decision involves trade-offs. With retirement planning, the big one is usually between commitment and flexibility.

Want more certainty? You'll probably need to commit more assets for longer periods. Want maximum flexibility or a shot at maximum growth? You'll likely need to accept more uncertainty about outcomes.

Neither approach is right or wrong – it depends on your situation, your personality, and what you're trying to accomplish.

But here's what I see too often: People defaulting to maximum flexibility (keeping everything in investment accounts) not because they've thought it through, but because it's the only approach they know exists.

Building Your Own Retirement Income

Here's one way to think about modern retirement planning.

Consider the following: some money goes toward guaranteed income (Social Security, annuities, bond ladders). Some goes toward growth investments (stocks/equity, real estate, business ownership). Some goes toward flexibility, spending, and short-term goals (cash, liquid investments). A number of tools in tandem, including the categories above, will dictate what's available to pass on to your heirs or charities of your choosing when it's your time to go.

The mix depends on your priorities. But having a mix gives you options that a pure investments-only approach can't provide.

You get to decide how much certainty you want to buy and how much uncertainty you're willing to accept. You get to choose which risks to keep and which risks to transfer to institutions that are better equipped to handle them.

We, as employees, didn't choose to be excluded from a once more robust private pension landscape in America, but here we are.

The good news? You have more tools available than most people realize. You can still access risk-pooling benefits available from actuarial science. You can still transfer risks to institutions instead of bearing them all yourself.

The challenge is figuring out which combination of tools makes sense for your specific situation and goals.

Because retirement planning isn't really about investments. It's about creating the financial structure that supports the life you want to live when you're no longer earning a paycheck.

And that's a much more interesting – and solvable! – problem than trying to pick the right mutual funds.

Your Situation Matters Most

A tech executive with equity compensation has different needs than a business owner planning an exit. Someone with strong family longevity should think differently about guaranteed income than someone with significant health concerns.

Got a pension from a previous job? Maybe, all else being equal, you can afford to be more aggressive with your 401k since you already have some guaranteed income.

Expecting a significant inheritance? That changes how much longevity risk you need to plan for.

Own a business that could provide income in retirement? That's another piece of the puzzle that affects how you handle everything else.

The point isn't that everyone should use or avoid any product, solution, or tool in particular. The point is that you have choices beyond the standard "save in your 401(k) and hope for the best" approach.

You can engineer predictable outcomes for the parts of your financial life where predictability matters most. You can shift risks you don't want to bear back to institutions that are better equipped to handle them.

The Real Questions

What kind of certainty is worth paying for in your situation? And what are you willing to commit to in order to get it?

Do you want to spend your retirement years wondering if your money will last? Checking your portfolio balance every morning and adjusting your spending based on market performance?

Or would you rather know that your core expenses are covered no matter what, freeing you to actually enjoy the wealth you've built?

The retirement planning world changed dramatically in the 1980s, but it doesn't have to stay that way for you. You can take back control by using the same risk management tools that institutions use.

You just have to know they exist and how to use them strategically. 

But there's a bigger game available to be played, and you can learn the rules.

 

 

 2025-8495398.1 Exp 10/2027

Past performance is not a guarantee of future results. Indices are unmanaged and one cannot invest directly in an index. All investments contain risk and may lose value. Diversification does not guarantee profit or protect against market loss. The opinions expressed are those of the author and not necessarily those of Guardian or its subsidiary. Investing in the bond market is subject to certain risks including market, interest rate, issuer, credit and inflation risk.

Annuity guarantees are backed exclusively by the strength and claims paying ability of the issuing insurance company.

The primary feature of whole life insurance is the death benefit. All whole life insurance policy guarantees are subject to the timely payment of all required premiums and the claims paying ability of the issuing insurance company. Policy loans and withdrawals affect the guarantees by reducing the policy’s death benefit and cash values. Some whole life polices do not have cash values in the first two years of the policy and don’t pay a dividend until the policy’s third year.