Before the Year Ends: A Wealth and Well-Being Checklist for High Achievers

In January, I revisited a question I’ve come back to more than once on this blog: What is enough? My answer hasn’t changed. Enough is not a number. It’s a relationship with your money, your purpose, and your life, and like any relationship worth having, it deserves regular attention.

The end of the year is one of the most natural times to give it that attention. Deadlines have a way of clarifying things. Some financial decisions have to happen before December 31 or not at all. Others simply benefit from a pause long enough to ask whether the year unfolded the way you hoped. That’s why I like to begin year-end planning in September rather than December. By the time the holidays arrive, the window for thoughtful action has narrowed, and decisions made under time pressure are rarely our strongest.

Earlier this year, I shared ten questions to help you gauge whether you’re on track financially. Consider this the companion piece. Those questions were about direction. These six are about finishing the year well, by including your finances and your well-being in the same conversation.

How do I assess whether my investments still match my goals?

Markets move over the course of a year, and portfolios move with them. An allocation set carefully in January may look quite different by fall, particularly if one part of the market has had a strong run. Drift can happen quietly, which is exactly why it’s worth checking.

The more important question sits underneath the percentages, though. Have your goals changed? A new business, a career shift, an upcoming home purchase, or a retirement date that has moved closer can all change what your portfolio needs to do. Look at your cash reserves, too. Holding too little can create stress when life surprises you. Holding too much can quietly slow your progress toward longer-term goals.

Your portfolio exists to serve your plan. Year-end is a good time to confirm it still does.

What financial tasks should high achievers complete before December 31?

Several planning opportunities have firm deadlines, and many of them get harder to execute well once December arrives. Depending on your situation, these may include:

• Roth conversions, which may make sense in a year when your income is lower than usual or when you expect to be in a higher tax bracket later
• Tax-loss harvesting, using investment losses to help offset gains elsewhere in your portfolio
• Retirement plan contributions, particularly through employer plans that follow the calendar year
• Required minimum distributions, if they apply to you, and a strategy for how to take them
• Equity compensation decisions, such as when to exercise stock options or sell vested shares

Not every item will apply to you, and the right moves depend on your full picture: your income this year, your income next year, and what’s ahead. These decisions are worth making alongside your advisor and your CPA, early enough that no one is rushing.

Are my beneficiaries and estate documents still current?

This is the item many people tend to skip, and one that matters a great deal. Beneficiary designations on retirement accounts and life insurance generally pass outside your will. An outdated form can override intentions you’ve carefully written down elsewhere.

A marriage, a divorce, a birth, a death, or a change in your relationship with someone you once named can all make a review worthwhile. Take a few minutes to pull up your designations and read them with fresh eyes. Then look at your will, any trusts, your powers of attorney, and your healthcare directives. If any of them were drafted in a different season of your life, it may be time to talk with the attorney who prepared them.

After decades in private banking, working with trusts and estates, I’ve seen how much peace this simple review can bring a family, and how much difficulty its absence can create.

How do I evaluate my charitable giving and community impact this year?

Giving is one of the most personal parts of a financial plan, and one of the easiest to leave to chance. Many of us give reactively throughout the year: a friend’s fundraiser, a year-end appeal, a cause that moves us in the moment. There’s nothing wrong with that. But it’s worth stepping back to ask whether your giving reflected what you care about most. Look at where your dollars went, and where your time went, too. Board service, mentoring, and volunteering are investments in your community, even though they don’t show up on a tax return.

If you’re planning a significant gift before year-end, the timing and structure may matter, from which assets you give to whether combining several years of giving into one makes sense. For now, the question can simply be whether your generosity matched your values this year.

What does a well-being review have to do with financial planning?

In my view, everything. This is the question that turns a year-end review from a chore into an act of care.

Well-being isn’t a luxury. Emotional, physical, mental, and financial well-being shape how we make decisions, how we lead, and how we show up for the people who count on us. For high achievers especially, well-being is often the first thing to erode when the year gets demanding.

So before you close the books, ask yourself a few honest questions. How did I spend my time this year, and does it reflect what I say matters? What gave me energy, and what drained it? Did I take care of my health? Did I invest in the relationships that sustain me? Where did I say yes when I wanted to say no?

The answers often point straight back to your finances. A demanding career may be funding goals you no longer hold. A spending pattern may reflect stress more than joy. Or you may discover you have more flexibility than you’ve been allowing yourself to use. Money can create space for well-being. What you do with that space is yours to decide.

What do I want 2027 to make possible?

Last month, I asked what your wealth is making possible. Year-end is the moment to point that question forward.

Before you set a single financial target for next year, describe what you want the year to feel like. More time with family. A career transition you’ve been considering. A business you want to grow, or one you’re ready to step back from. A trip, a creative project, a cause you’d like to support more fully. Then let your financial goals follow from that picture, rather than the other way around.

Plans built around purpose tend to be the plans people actually keep. When you know what your money is for, decisions about how much to save, where to invest, and what to let go of become much clearer.

A Closing Thought: Finish the Year on Purpose

None of these questions demands a perfect answer. Some you’ll settle in an afternoon. Others may take a conversation or two, and a few may stay open into the new year. That’s all right. As I wrote in January, we revisit foundational questions not because we’re uncertain, but because we’re growing.

What matters is giving yourself time to ask them while there’s still room to act. September offers that gift. December rarely does. If you’d like a thoughtful partner as you work through your own year-end review, I’m here for that conversation.