Planning in the “BER” Months: Why you should think differently now

As we enter the “ber” months—September, October, November, and December—we naturally begin looking toward year-end. These months also tend to be family months, starting with Back to School and then working our way into the holidays. However, they also provide some of the most strategic opportunities for financial planning.

This season is ideal for:

• Year-end tax planning before deadlines close.
• Estate and legacy reviews to ensure documents reflect current wishes – very common due to the amount of extended family interaction.
• Retirement income adjustments before new contribution and distribution rules reset – This comes as increases in Social Security is released.
• Charitable giving strategies to maximize both impact and tax efficiency.
• Big-picture reflection on whether your wealth is aligned with your values and long-term vision.

In my experience, the “ber” months are when most people gain clarity around what they want. Clients can see both what the year has produced and what they want the next to look like. It’s a powerful window to make thoughtful decisions where you can maximize your wealth for the current year and set the stage for the coming year.

I’ve also found that it’s not always just about the quantitative approach of things. As a matter of fact, most of the time what we think weighs more than what the numbers say.  For over 20 years, I’ve worked with successful business owners, retirees, and families who have accumulated substantial wealth. What always strikes me is this: financial planning is rarely about the math. The numbers matter, but the way we think about money—and the hidden psychology behind our decisions—plays an even bigger role in long-term success.

Here are some of the psychological truths that I’ve learned over the years that a designation or credential didn’t teach me. These are a few of the qualitative items to be mindful of when making financial decisions, yet determine whether a financial plan truly works.

1. Your Spending Reveals What You Value
Every bank statement tells a story. Whether consciously or not, how you spend reflects what you care about most—family, freedom, experiences, or security. The challenge is ensuring that your money habits align with your stated values. Sometimes this realization is surprising, other times, we see alignment. Ultimately, what you say and what you do may not always line up and it’s important to determine what’s important.

2. More Money Doesn’t Guarantee More Happiness
Clients often assume that crossing another wealth milestone will finally bring peace of mind. Yet research—and experience—show that beyond a certain level, money doesn’t automatically create fulfillment. True satisfaction comes from aligning resources with health, relationships, and purpose. A well-crafted plan should honor these priorities, not just chase returns.

3. Risk Tolerance Isn’t Fixed
People often view risk tolerance as a static number determined by a questionnaire. In reality, it shifts with age, market conditions, and even life events. A sudden downturn or health scare can dramatically change what level of volatility feels acceptable. This is why ongoing planning, and not a one-time snapshot, is essential.

4. Emotions Often Override Logic
We like to think financial decisions are rational. In practice, fear and greed move faster than spreadsheets. Markets drop, and the instinct is to “get safe.” Markets soar, and the desire is to chase returns. This is an area where a disciplined plan acts as a stabilizer against these powerful emotional swings.

5. Confidence Can Be Misplaced
Many successful people are rightfully confident in their professional or personal lives. But that confidence often bleeds into areas where expertise is less secure, like financial planning. Because we all spend money daily, it’s easy to believe we intuitively know how to manage wealth. In truth, crafting a multi-generational, tax-efficient, and customized plan requires specialized skill and perspective. Overconfidence in this area can quietly erode wealth over time.

6. Money Squabbles Are Rarely About Money
When couples or families disagree over finances, the real issue is usually not dollars and cents—it’s what money represents: control, freedom, security, or legacy. Skilled planning involves surfacing what underlying values are at play and creating strategies that address them, rather than treating the discussion as purely financial.

7. We Undervalue the Future
Humans are wired for immediate gratification, which makes it difficult to prioritize long-term goals like retirement or legacy planning. Waiting and procrastinating are common themes when addressing your own financial plan.  Why? There really aren’t any deadlines for when you have to accomplish these things. The result? Under-saving, under-planning, and unnecessary stress later in life for ourselves and usually our families as well.

8. Values Drive Sustainable Wealth
At the end of the day, financial planning isn’t about squeezing out another half-percent of return. It’s about ensuring your money supports the life you want to live and the legacy you want to leave. When wealth is aligned with values, clients remain engaged, motivated, and fulfilled—even through market cycles.

As we make our way through the “ber” months, there are a number of financial strategies we can employ.  It is critical to ensure that the strategies alone don’t drive our actions and that our values also come into play. Understanding the psychology that accompanies our decisions is important. Communicating with your spouse or partner along the way to ensure you have consensus prior to making a decision may even outweigh the decision itself if it’s not handled with care. Again, we are in the last few months of the year and it’s a great time to do planning. As you go through the exercise this year, try to consciously match that planning with your values to ensure your actions speak louder than your words. For those who have built substantial wealth, this exercise helps define the difference between financial success and financial significance. After all, the numbers provide structure, but behavior determines outcomes.