A New Season to Imagine What’s Possible

By Ben Wicks, Wealth Confidant

Fall has arrived in the Pacific Northwest, bringing both endings and new beginnings: the end of the Mariners season (a relief this year) and the start of football; the end of warm evenings on the patio and the beginning of our long stretch of PNW “cozy” weather.

The “fresh start effect” is a well-established psychological tendency to feel more motivated after a clear temporal landmark such as a new year, birthday, new season, or start of a school year. These moments create a mental dividing line between who we were before and who we can become next. Past delays or setbacks feel less defining and future progress feels more attainable.

Fall is a particularly useful fresh-start moment. Summer routines are ending, schedules are becoming more structured, and year-end is close enough to create urgency without making change feel out of reach.  It’s an opportunity to consider not just where your finances stand, but whether your time, resources, and priorities are aligned with the life you want to live.

We have heard this theme in conversations at Highland. People are reflecting on what they hoped to do this year, what has actually happened, and what they still want to make time for. Some conversations begin with a financial question; others begin with a life question. The two always seem to intersect.

Maybe you meant to take that family trip but never found a week that worked. Perhaps you hoped to work less, spend more time with family, or set aside more money for something you care about.  Or the year moved so quickly that you haven’t stopped to ask what you want the next few months to hold. In my family, we have been so focused on a kitchen remodel that we have missed other important traditions.  But there is still time.

Start by asking what you wanted more of this year. Was it time with family? Travel with loved ones? The freedom to make a change at work? Then ask what got in the way. Sometimes the obstacle is financial, and you need a clearer picture of what you can afford. Sometimes the money is there, but your plans haven’t caught up with what you want from life.

Or sometimes you may not know what you want yet. When life is full of work, family, and responsibilities, it’s easy to keep moving without finding time to reflect. Couples may discover that they picture the future differently. Families may want their wealth to serve a purpose without having discussed what that means to each person. Individuals may become so focused on achieving goals that they never pause to ask a simple but important question: What is it all for?

You don’t need to have a complete answer. Sometimes simply making space for the question is a meaningful place to start.

We’ve written before about why we prefer reservations over resolutions [check it out here]. A reservation could be a weekend with your family, time away with your spouse, or simply an afternoon you protect from everything else on your calendar. Choosing a date will not answer every financial question, but it can turn “we should do that someday” into a practical conversation about how to make it happen.

This fall, consider asking yourself:

• “What is one goal I would feel proud to advance before year-end?”
• “What has kept that goal on the back burner, and what would make now a better time to begin?”
• “If I made the first step simple, what could I commit to in the next two weeks?”
• “What would finishing the year with momentum make possible for me in the year ahead?”

You do not need to wait for January for a fresh start. Let fall mark the shift from postponing to progressing, and use the weeks ahead to build momentum.

At Highland, we’ve found that the most powerful intersection between money and life often begins with a question about what matters most.

¹ Hengchen Dai, Katherine L. Milkman, and Jason Riis, The Fresh Start Effect: Temporal Landmarks Motivate Aspirational Behavior, published in Management Science (2014). The researchers found that people are more likely to pursue goals following temporal landmarks such as the beginning of a week, month, year, birthday, holiday, or other meaningful transitions. [jstor.org], [faculty.wh….upenn.edu]