“Life is long” is not something we hear very often. Yet for many of us, it’s becoming increasingly true. So, the real question isn’t just how to save or how to invest—it’s what is enough?
One of my favorite business authors, Morgan Housel, writes that good advice is never as simple as “live for today” or “save for the future.” Good advice is to try minimizing future regret. That idea reframes how we should think about both enough and risk—not as formulas, but as deeply personal decisions that occur at two different phases—saving for retirement and enjoying it in retirement.
The challenge is that we’re balancing two competing realities. We’re living longer than ever and we have more opportunities to spend, experience, and enjoy life1,2. One‑third of young women today may live into their 90s, and some will live past 100. A healthy 65‑year‑old man has a strong chance of living into his late 80s, and a real possibility of reaching 90. Retirement is no longer a brief phase—it can be a 30‑ or even 40‑year chapter.
At the same time, life is uncertain. Health changes. Families change. Circumstances change. Deferring everything for a distant future can lead to a different kind of regret: a life that was financially secure, but emotionally under‑lived.
And that is where risk becomes misunderstood.
In traditional investing, risk is often framed as volatility or the probability of loss. But for real people, risk is more personal. Risk is better understood as the potential for future regret—and that regret looks different before retirement than it does after. Think of it like this:
Under‑saving regret begins with the thought, “I should have prepared more,” and shows up as stress, dependency, or limited choices later in life. This is the form of risk most financial planning is designed to protect against.
Under‑living regret sounds different. It’s that voice that whispers, “I waited too long.” It’s about experiences postponed, time not spent, and memories never made — a risk finance often ignores but can happen often once investors make the choice to flip the switch.
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Under-saving regret
- “I should have saved more.”
- Stress, dependency, or burden later in life.
- The type of risk financial planning protects against.
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Under-living regret
- “I waited too long to enjoy what I saved.”
- Experiences never taken, time not spent, memories left unmade.
- A form of regret that financial planning often overlooks.
So how does one balance all the unknowns but still take time to smell the roses?
This is where thoughtful financial planning helps bring clarity to the anxiety of not having enough, and the risk of postponing life for too long. Financial planning helps people find middle ground between these two very real fears.
Good planning gives structure to trade‑offs. It helps define what’s necessary to protect your future while validating what is possible to enjoy the present. In that space—between preparing and living is where most people discover their true version of “enough”.
That requires clarity on two questions:
- What does a good life look like right now?
- What would you regret later if you failed to prepare?
If you’re unsure whether you’re preparing enough for the future or living enough today, we can help bring clarity to both.
¹ Longevity estimates based on J.P. Morgan Guide to Retirement (latest edition), which shows that a healthy 65-year-old man has a majority probability of living into his mid-to-late 80s and a meaningful probability (over 40%) of reaching age 90; average life expectancy for a 65-year-old man extends into the mid-80s.
² As Morgan Housel emphasizes in his writing, longer lifespans meaningfully extend the timeline for financial decisions. Supporting data from the J.P. Morgan Guide to Retirement indicates that a healthy 65-year-old woman today has greater than a 50% probability of living to age 90, reinforcing that retirement can span multiple decades.