Part 1 of 3 — A Season of Check-Ins
By Mark Zembo, Wealth Management Advisor
Over the last few years in late summer, my family has run the same ritual. One kid was heading back to college, and the others started a new school year. At some point in the middle of packing lists and school shopping, I would find myself standing in the driveway wondering how the year went by so quickly. “Where did all the time go,” I’d ask myself. And then came the more useful question: “Where am I now, compared to where I meant to be back in January?”

September has a way of making us take stock, whether we intend to or not. The last stretch of the year comes into view. And a run of decisions that are easy to put off and expensive to get wrong starts showing up in mailboxes and HR portals, usually without much warning.
So, over the next several weeks, we are writing a short series built around the financial decisions that tend to surface for many of us this time of year. This is the first installment.
Open enrollment is a natural place to begin.
Workplace benefits deserve a closer look than a quick click-through. Comparing your options means looking at deductibles, out-of-pocket limits, employer contributions, expected healthcare needs, and the tax advantages that may come with an HSA. If you have access to an FSA, consider how much you are likely to spend on eligible healthcare expenses during the coming year and how your plan handles unused funds. If you have dependents, the cost and structure of family coverage add another layer to the decision. Used thoughtfully, these benefits can help you manage healthcare costs while supporting your broader financial plan.
The same enrollment window usually puts your retirement plan back in front of you, too. Are you capturing the full employer match? Have you checked your vesting schedule since the last time your role changed? Does it make more sense to direct new contributions to a Roth account or a traditional account this year? These may seem like small decisions, but their effects can compound over time. Additionally, use open enrollment as an opportunity to confirm beneficiary designations on your plans. Are the right people and the right distribution percentages recorded?
Life and disability insurance also deserve another look. Coverage that was more than adequate at 35 with no children may be insufficient at 45 with a mortgage and two children. A brief review can confirm whether last year’s selections still fit your life today. And don’t forget to ensure beneficiary designations are properly recorded here, too.
When considering everything available to you through an employer’s benefits plan, a good workplace benefits guide can help you compare your available options, identify what may have changed, and know which questions to ask before your enrollment window closes. Some decisions are straightforward. Others can have implications for taxes, retirement savings, insurance protection, cash flow, and the rest of your financial plan. When the tradeoffs are not clear, a qualified financial professional can help you evaluate how the pieces fit together.
The choices you made last year may still be the right ones. The important question is whether they still fit where you are now.
Important disclosure: Investing involves risk, including the possible loss of principal. Past performance does not guarantee future results. This reflects our current assessment and may change as conditions evolve. Questions about anything in this post? Write to us at info@elevagepartners.com.