A Different Kind of Retirement
My parents retired in an era where retirement account information arrived by mail (mostly), once a quarter, and was read exactly once and then put into a physical binder or hanging file of some kind. I mean, not that long ago, financial “research” consisted of monthly (weekly at best) periodicals and microfiche. Yes, that is how old I am — I remember microfiche… even though I am really more of a macrofiche guy.
Fast forward to today, where a person approaching retirement has access to more financial information before their morning coffee than my grandfather encountered in a decade. Account balances update in real time. Market commentary is endless and mostly free. There are calculators, forums, podcasts, newsletters (ahem), and an entire economy of people on the internet explaining exactly how you should handle your money — most of whom have never met you, and many of whom have never met a client.
This is, in many ways, wonderful. Information used to be a barrier to good decision-making; now it rarely is. But the barrier did not disappear; it moved. The challenge is no longer access to information. It is filtering it. And filtering is much harder work than searching.
More Information, Less Clarity
Here is something I have observed over the years: the people who check their portfolios most often are not usually the calmest investors (no judgment, and not universally true, but generally). That might seem counterintuitive, as more data points could mean more comfort. But daily portfolio checking does not give you more information about your retirement. It gives you more information about noise. Retirement is often a multi-decade question. A single trading day (or even week) tells you approximately nothing about retirement — yet it feels like it tells you something, and feelings are what often drive behavior.
This is one of the more subtle costs of the Internet age. Not misinformation, exactly, just a far greater volume of data. When everything is available all the time, it becomes very difficult to distinguish between what is urgent and what is merely recent (or, what is even true).
The old constraint — quarterly statements, a phone call, a scheduled meeting — was frustrating, but it had an accidental benefit: it forced patience. Today, patience has to be a choice you make on purpose. I assure you, nothing in the design of a modern phone will make that choice for you.
Enter Artificial Intelligence
All of this brings us to whatever “age” we are actually in right now. The online age? The age of the Internet? The AI age? None of those monikers capture it — most likely because by the time I settle on a term, someone releases a product that makes the previous name obsolete.
Regardless of the name of this age we are in, artificial intelligence has arrived in personal finance, and I want to be balanced here, because I think both the hype and the panic are overdone. AI tools are genuinely useful. They are fast, they are patient, they never get tired of explaining what the required minimum distribution rules are, and they are available at 11pm when you cannot sleep because you are wondering whether you saved enough. There is, potentially, real value. I use these tools in my own work (mostly for research, but for time management as well). But there is a meaningful difference between information and advice, and the line gets blurry when the information sounds so confident.
A tool can tell you the general rules around a Roth conversion, but it cannot tell you that your brother is going to need help in three years, that your business partner is thinking about selling, that your daughter is considering a career change, or that you have a deep and completely non-financial aversion to carrying debt into retirement that will override every optimization I could put on a spreadsheet. It does not know that you cried when you sold the house (or your rookie Pete Rose baseball card, accidentally). It does not know what you are actually worried about.
Good planning lives in those places. The math is the easy part… but the math has been the easy part for a long time.
The New Risks That Were Difficult (or Unexpected) to Plan For
I would be remiss if I did not at least mention that there are also some genuinely new risks in this era, and they deserve a mention because they rarely show up in a traditional retirement planning discussion.
Fraud has gone industrial. Financial scams targeting retirees have become more sophisticated, more personalized, and — with AI-generated voices and images — far more convincing than they were even two years ago. Many scams used to require a decent impression; they no longer do. If you take one practical action from this article, make it this: establish a verification habit with your family. A code word, a callback rule, something. It sounds a little silly right up until the moment it isn’t.
Digital estate planning is real. Make sure you pass on your accounts, your passwords, your policies, your subscriptions, and your two-factor authentication tied to a phone number nobody else can access. I have watched families struggle for months with this after a loved one has passed. A password manager and a documented access plan may be the single most underrated estate planning tool of the last decade — not glamorous, but extremely useful.
Subscriptions are the new leak: small, automatic, invisible, and permanent. Fixed retirement income meets recurring charges nobody remembers authorizing. It’s worth an annual audit, as the “subscriptions” line item can end up as a major part of your monthly outlay if you are not careful.
What Hasn’t Changed
Here is the part I find reassuring, and I hope you do as well. Underneath all of it — the apps, the algorithms, the endless commentary — the actual principles of a durable retirement have not moved much. Spend less than you earn, own productive assets, diversify your overall portfolio, stay invested through the uncomfortable parts, know what your money is for, and, last but not least, be intentional.
The above list is not new. It was not new 40 years ago, and it will not be new 40 years from now. The delivery mechanism keeps changing, but the arithmetic does not. Technology has made executing those principles dramatically easier. It has also made abandoning them dramatically easier, because it has never been simpler to make an impulsive financial decision at two in the morning based on something you read on a screen. Both things are true at once.
So my honest advice for retiring in whatever age this is: use the tools. Genuinely, use them, as the tools themselves are generally good. But decide in advance what role they play. Let technology handle the information, but let a real conversation — with your spouse, your family, your advisor — handle the decisions. Plan, but be nimble. Because the goal was never to have the most information about your retirement. The goal was to actually enjoy it.
