You’re Living Longer Than My Planning Software Allows

retirement chart

The Age 100 Assumption

As I’ve been going through my annual State of the Union meetings with clients, one topic keeps coming up in my mind:

What if we’re still dramatically underestimating how long we may live?

Most financial planning software, including the tools I use, stops at (or around) age 100. Historically, that seemed more than sufficient.

That said, over the last century alone, average life expectancy has nearly doubled. Yet some researchers and futurists believe the progress made over the next 100 years could make the previous 100 look quaint.

That sounds like science fiction.

Then again, so did the internet, smartphones, and artificial intelligence.

Longevity Escape Velocity

Recently, I listened to a fascinating conversation between Peter Diamandis (+ his “Moonshot Mates”) and Brian Armstrong, CEO of Coinbase, discussing the work of futurist Ray Kurzweil.

Kurzweil has become famous for his long-term predictions and claims an 86% accuracy rate across nearly 150 forecasts. Among his most provocative ideas is “longevity escape velocity” – the notion that medical advances may eventually add more than one year of life expectancy for each year we age.

Some believe this threshold will be reached not just by Ray’s predicted date (2033), but imminently. Whether these timelines proves correct is anyone’s guess. But even entertaining the possibility changes the conversation.

After all, some scientists have suggested that the first person who will live to 1,000 years old may already be alive today.

Before You Roll Your Eyes…

I can already hear some of my retiree clients lol’ing with an eyeroll and a “here he goes again.”

Fair enough.

But I would simply ask that we remain open-minded.

Every generation has been tempted to believe that the future will largely resemble the present. Historically, there were times when this may have been true. Not anymore.

If these ideas sound far-fetched, that’s okay. The goal isn’t to convince you.

It’s simply to challenge our assumptions.

Treating Aging Itself

Perhaps the most fascinating aspect of longevity science is that the goal is no longer merely to age more slowly.

Increasingly, researchers are exploring ways to repair and reprogram the biological processes underlying aging itself (i.e. reversing aging).

Technologies involving epigenetic reprogramming, cellular rejuvenation, AI-driven drug discovery, gene editing, and regenerative medicine are moving from the realm of speculation into active research.

And the pace of discovery is accelerating at an insane rate, with no slowdown in sight.

Implications for Retirement

Last year at wHealth Advisors HQ, we hosted a cocktail party for our New Jersey clients and gifted copies of Die With Zero – a book many of you have since told me you enjoyed.

Its central message is to recognize our mortality + spend our time, health, and money accordingly.

Longer lives do not invalidate that message.

In fact, they make it even more important.

As I wrote in Kiplinger last year:

If living to 100 or beyond is a real possibility, it’s worth considering how this might reshape your life decisions today, including your work and financial decisions.

A few key questions to consider:

Are you investing enough in your physical, mental and emotional well-being?

Is your career set up to provide fulfillment over a potentially longer working life?

Are you saving enough to support a retirement that could last decades?

Should you adjust your investment strategy to account for the financial implications of a longer lifespan?

Simply put, let’s remain open-minded about our assumptions regarding aging, retirement, and what’s possible.

Perhaps:

  • retirement won’t consist of a brief “go-go” phase followed by decades of inevitable decline.
  • sixty-five will someday feel young.
  • a traditional 30-year retirement won’t seem particularly long.

Time will tell.

But history suggests that betting against human ingenuity has rarely been a winning proposition.

Final Thoughts

If humanity is entering an age of radical abundance (I personally believe we’re directionally heading that way), extending our healthspan may prove to be one of the greatest opportunities (and planning challenges!) of all.

The future has a way of arriving gradually, then suddenly.

And the assumptions we hold most rigidly today are often the ones history enjoys humbling the most.

Tax Alpha: The Most Overlooked Investment

In investing, “alpha” refers to excess returns. Few opportunities may offer more of it than thoughtful tax planning.

This week I’m in Las Vegas attending the AICPA Engage conference, one of the largest gatherings of CPAs and tax professionals in the country.

The reason is simple.

Tax planning is one of the fastest-moving areas in personal finance.

Markets don’t care what conference I attend. Evidence-based investing is largely passive by design. The best investment decisions often involve doing less, not more.

Taxes are different.

Tax laws change. Families change. Businesses are sold. Children leave home. Retirement begins. RMDs start. Charitable goals evolve. Congress passes new legislation. (The recently enacted OBBBA legislation being just the latest example.)

In other words, tax planning is not an annual event. It’s an ongoing process.

And over the years, I’ve become convinced that proactive tax planning may offer some of the highest returns available to affluent families.

Not because taxes should dominate every financial decision – but because taxes touch almost every financial decision.

The Difference Between Filing Taxes and Planning Taxes

Most people think about taxes once a year.

They gather documents, send them to their CPA, sign the return, and move on.

That’s tax preparation.

Tax planning asks an entirely different question:

“What can we do today that might improve the outcome years from now?”

Preparation looks backward. Planning looks forward.

One records history. The other attempts to shape it.

The Opportunity Isn’t One Big Decision

Many people assume tax savings come from finding some obscure deduction or exotic strategy.

In reality, meaningful tax alpha is often created through dozens of relatively ordinary decisions made consistently over time.

Questions like:

  • Which account should we spend from first?
  • Should we recognize income now or later?
  • Does a Roth conversion make sense?
  • How should charitable giving be structured?
  • Which assets belong in taxable accounts versus retirement accounts?
  • Should we harvest gains or losses?
  • How do Social Security and Medicare interact with taxable income?
  • How should stock compensation be exercised?
  • What’s the most efficient way to transfer wealth to children and grandchildren?

None of these decisions exist in isolation, they’re all interconnected. And small improvements, compounded over decades, can produce surprisingly large differences.

Tax Planning Evolves With Life

What makes tax planning so valuable is that the opportunities change throughout life.

Accumulation years bring one set of decisions.

Retirement introduces another.

Business owners face entirely different considerations.

Widowhood, inheritances, charitable intentions, and estate planning create new opportunities again.

The goal isn’t to chase perfection. It’s to continually recalibrate as circumstances change.

Good Tax Planning Is A Team Sport

No single professional sees the entire picture.

The best outcomes often occur when financial planners, CPAs, and attorneys work together.

Investment decisions affect taxes.

Estate plans affect taxes.

Charitable strategies affect taxes.

Business decisions affect taxes.

Everything is connected.

Which means tax planning is rarely about finding loopholes. It’s about coordination.

The Biggest Risk May Be Inaction

Perhaps the greatest irony is that many tax opportunities have expiration dates. Once December 31st passes, many decisions are gone forever.

You cannot retroactively decide to perform a Roth conversion.

You cannot go back and harvest losses.

You cannot revisit a charitable strategy after the fact.

Which is why some of the most valuable conversations we have with clients happen long before tax season arrives.

Because by April, we’re often simply documenting decisions.

The real value was created months earlier.

Final Thoughts

Unlike markets – which we largely cannot control – taxes represent one of the few variables where thoughtful planning can still meaningfully improve outcomes.

Not through clever tricks. Not through aggressive schemes.

But through consistent, intentional decisions made year after year.

And in my experience, that’s where some of the most tangible value in financial planning is created.