Jacques Bolivar

10/26/2026

How many years before you are ready to be “retired”?

It’s one of the most important numbers yet.

TIAA's 2026 longevity literacy research found that workers who expect a shorter retirement save less consistently than those who expect a longer one.

That makes sense, but it also means the people who assume their retirement will be short are the same ones who may be building portfolios with shorter time horizons.

Once someone has already reached 65, the numbers shift.

According to Social Security Administration data:

📌 A 65-year-old man has roughly a 24 percent chance of living past 90

📌 A 65-year-old woman's chances are higher, closer to 35 percent

📌 For a 65-year-old married couple, there is about a 50 percent chance that at least one spouse lives past 90

The practical implication is not "assume you will live to 100."

It’s that a retirement income strategy built around the “average lifespan” often assumes a person will die on schedule. Most people do not.

If retirement is on your horizon, the question to ask is, "What happens to my income strategy if I live to 95?"

10/22/2026

Trust & Will's 2026 Estate Planning Report found that 56 percent of adults don't have core documents in place, including:

📝 A will: who gets what, and who is in charge of making it happen

🏥 A healthcare directive (or living will): what you want if you cannot speak for yourself

✍️ Two powers of attorney, one for medical decisions and one for financial decisions, each naming a specific person

📄 A letter of instruction: the practical map to where accounts live, who your professionals are, and what your kids or pets need

The friction is that estate work forces a family to sit with mortality, name specific people for specific roles, and make decisions that feel too permanent to rush.

Without something in writing, though, families are left improvising during one of the most difficult moments of their lives.

Most say they fully intend to get to it, but too many put it off until it's too late.

Don't put it off. Talk to a financial professional who can help.

10/19/2026

What happens to your cash flow when you stop earning a paycheck?

The 2026 EBRI Retirement Confidence Survey caught something interesting about that shift.

📊 Among workers, 33 percent say they turn to a financial professional for guidance.

📊 Among retirees, that number climbs to nearly 40 percent.

National Retirement Security Week (October 19–25 this year) is a reminder to check whether your strategy is evolving with your lifestyle priorities.

If retirement is within a few years, the practical step is not rebuilding the strategy today.

It's identifying the two or three moving pieces that are no longer theoretical, the day you stop working, and consider working with a financial professional who can help guide you.

10/16/2026

Fidelity's 2025 wealth transfer study found that roughly 67 percent of parents age 55 and older have never told their adult children what they will inherit, or whether they will inherit anything at all.

About 33 percent would prefer the kids are kept in the dark about the amount.

Their reasons should feel familiar:
✔️ Worry that a specific number will dampen a child's drive
✔️ Discomfort talking about money at all

The same study found:

Most adult children say they are ready to handle whatever they inherit and would rather shape things while their parents are still around to explain the "why" behind decisions.

Families who have inheritance strategies share some similar habits:

💬 Kids know who the financial professionals are and how to reach them
💬 Everyone knows where the estate documents are
💬 They try to manage any surprises well ahead of time

So, do you tell your children or not?

There's no single right answer here.

Sharing exact numbers isn't necessary, but most families find that a broad discussion can help with priorities and expectations.

10/08/2026

Stocks finished the third quarter mixed. The S&P 500 gained 2.03%, and the Nasdaq Composite rose 2.47%, while the Dow Jones Industrial Average slipped 2.70%. Halloween is next on the calendar, with U.S. consumers expected to spend \$13.5 billion USD this year and 6.26 million Canadian children in their trick-or-treating years.

Stocks were mixed in the third quarter as economic, geopolitical, and corporate earnings news pushed the broad market higher while weighing on the Dow Industrials.

10/07/2026

There's a reason so many women business owners half-joke that their real title is "everything."

More women than ever are starting and running businesses, and they're doing it at a faster clip than the market overall.

Census data show women now own more than 14 million businesses nationwide, a number that's grown 26 percent since 2012, compared with 19 percent growth for businesses as a whole.

A lot of that growth is happening online, where women-owned businesses tend to be more digitally integrated than those owned by men.

It also means millions of women are managing key decisions from scratch:

💼 How income gets paid (salary, distributions, or owner draws) and what that means at budget time

💼 Which retirement vehicle fits, and how much room there is to contribute

💼 How healthcare, disability, and other insurance get sourced without an employer default

💼 How the business gets valued, and what a sale or transition would actually look like

💼 How personal finances stay untangled from the business's finances

Wearing a tall stack of hats doesn't make entrepreneurship harder than it's worth. Plenty of women running these businesses would say the trade-offs are part of the deal. But it does mean the hats keep stacking up, one on top of the other.

This month is a good time to tip our own hats to the women doing it all at once.

10/02/2026

What's one financial decision you've made that helped you feel more prepared for your future?

For many of the people we work with, it's not a single investment or product; it's taking the time to create an overall strategy.

🗓️ October is Financial Planning Month—which is all about how the pieces of your financial picture fit together to help pursue your financial goals.

It's about putting together a comprehensive approach that manages your investments and retirement, provides for your loved ones—all while staying flexible enough to adjust as things change.

💡 If you've been meaning to update your strategy or to create one for the first time, it's never too late to start.

10/01/2026

Some financial decisions get a second chance. A handful don't.

▪️ When you actually retire. In EBRI's 2026 Retirement Confidence Survey, 46 percent of retirees left the workforce earlier than they expected.

▪️ Stepping into a parent's finances. A 2026 Care.com report found sandwich-generation caregiving duties typically begin around age 34.

▪️ Receiving an inheritance. Ohio State research found nearly one in five people who inherited $100,000 or more had spent or lost the entire amount within two years.

▪️ Selling a business. For a typical owner, roughly 80 percent of their net worth is tied up in the business itself, per the Exit Planning Institute.

▪️ Writing (or updating) a will. Only 24 percent of Americans currently have a will, down from 33 percent in 2022, according to Caring.com.

None of these moments announce themselves on schedule. The families who handle them well are usually the ones who started talking years before circumstances forced their hand.

09/30/2026

Will your future income keep pace with the life you are preparing for?

In October, the Social Security Cost-of-Living Adjustment (COLA) for 2027 will be announced.

The annual adjustment is designed to help benefits keep up with inflation, but the same principle can be applied more broadly.

Your retirement income may need to be adjusted as your life, expenses, and priorities change.

Healthcare, insurance, travel, home maintenance, and support for family members can all affect the income you may need to generate.

Ask yourself:

▪️ Has your expected retirement spending changed?
▪️ Are certain future expenses rising faster than you thought?
▪️ Does your income strategy account for inflation?
▪️ Are you strategizing for the lifestyle that you budgeted for years ago?

A thoughtful retirement income strategy should evolve as your life and expenses change.

09/23/2026

📱 More and more people are now using AI for financial questions.

And with tools like ChatGPT adding bank account integrations, personalized financial guidance is starting to feel more accessible than ever.

So yes, AI can help organize information, model scenarios, and answer technical questions faster than most people could on their own.

BUT… financial insight isn’t just a math problem.

AI cannot talk to you about the pros and cons of making a portfolio adjustment when stock prices are falling. It might struggle to fully weigh your family dynamics, health concerns, risk tolerance, competing goals, or what will actually help you feel confident in your decisions.

🧠 That is where human guidance still matters.

Vanguard’s long-running Advisor’s Alpha research highlights behavioral coaching as one of the most valuable aspects of a relationship.

Not stock picking. Not market timing.

Helping people manage emotion when the stakes are high.

🤝 The future is not AI vs. financial professionals.

The future is for those who use better tools while still bringing judgment, context, and a real understanding of the person behind the strategy.