Dear Mr. Market:
They say it takes 21 days to make or break a habit.
They also say that by mid-January, most New Year’s resolutions have already been abandoned. Gym attendance drops. Diets loosen. Optimism fades just a bit.
Markets, of course, are indifferent to all of this.
But the timing is still useful. Three weeks into the year is often when clarity replaces motivation. And in wealth management, clarity tends to matter far more.
Rather than broad resolutions or generic financial advice, this is a short list of specific things worth revisiting this year, depending on where you are financially. Not because January demands it, but because these are the kinds of decisions that quietly compound over time.
Five Financial Priorities for High-Net-Worth Families
This is where complexity lives and where thoughtful simplification often creates the most value.
1. Re-underwrite your entire balance sheet, not just your portfolio
Most high-net-worth investors know how their portfolios are allocated.
Far fewer have stepped back and looked at concentration risk across their entire financial life:
- Employer stock
- Private investments
- Real estate
- Deferred compensation
- Human capital
Individually, each decision may have made sense. Collectively, they can create exposures that only show up in stress.
A useful exercise this year:
Ask not “How am I allocated?” but “What really drives outcomes if things don’t go as planned?”
2. Stress-test liquidity, not net worth
Net worth is a flattering number. Liquidity is a practical one.
This year, it’s worth understanding:
- How many months (or years) of spending can be funded without selling risk assets
- Where liquidity actually comes from in a down market
- Which assets are “liquid” only in theory
Liquidity is rarely about return. It’s about control; over timing, taxes, and decisions. Families who understand this tend to worry less, even when markets cooperate less. At My Portfolio Guide, LLC we also offer each client the opportunity to run a live “stress test” on their current portfolio. This exercise is important to run, not just on the assets we may manage for you but on your overall portfolio outside of our purview. We can run an analysis throwing any number of potential market stressors such as Inflation/stagflation, AI bubble burst, Fed independence consequences, record global debt, cyberattacks, rising energy costs, geopolitical turbulence, or commodity inflation, to name several. The value isn’t in forecasting the next crisis. It’s in knowing, ahead of time, where flexibility exists and where it doesn’t.
3. Revisit tax decisions that were made in “temporary” years
The last few years created unusual conditions:
- Abnormally high or low income
- Market dislocations
- One-time planning opportunities
Many tax decisions were made with the intention of revisiting them later.
Later has a way of becoming never.
This year is a good time to reassess:
- Roth conversions done opportunistically
- Entity structures created quickly
- Timing decisions that solved a short-term problem but introduced long-term complexity
Good tax planning isn’t about cleverness…it’s about consistency and follow-through.
4. Clarify who your wealth is for, not just how it’s invested
Most estate plans answer legal questions.
Fewer address the human ones.
This year, consider clarifying:
- What this money is meant to do while you’re alive
- What decisions should be made intentionally and which should not be passed on
- Where financial efficiency conflicts with family dynamics
Often the real risk isn’t taxes or markets, but unspoken assumptions that only surface later. Please also revisit this article that goes beyond the legalese of just creating a will or living trust. We’ve created a template via a “Letter of Final Wishes” that is meant to speak to your heirs in your own voice and also gives them a checklist of everything that is important to you if something unexpected happened. (click here to view that)
5. Simplify one thing—on purpose
Success tends to accumulate complexity.
Multiple accounts. Legacy strategies. Decisions that once mattered but no longer do.
A worthwhile resolution this year:
Identify one area to simplify…not to optimize returns, but to reduce friction.
Simplification doesn’t mean doing less. It means doing fewer things that no longer earn their keep.
If You’re Earlier in Your Career or Just Beginning
A few quieter priorities matter more than market forecasts:
- Automate saving and investing before optimizing strategy
- Understand the difference between investing and speculating
- Treat career flexibility as an asset
- Be cautious about lifestyle decisions that permanently raise your baseline
- Focus less on timing markets and more on staying invested
Time is doing most of the heavy lifting here. Don’t interrupt it unnecessarily.
If You’re Mid-Career or Approaching Retirement
This is often the most financially consequential phase.
Worth revisiting this year:
- After-tax retirement income…not just account balances
- The risks that matter most in your final accumulation years
- Insurance and benefits while employment options are still flexible
- How taxes, timing, and portfolio decisions interact
- Whether your plan reflects how you actually expect to live
Small adjustments here can have outsized effects later.
A Closing Thought
Most financial progress doesn’t come from dramatic changes.
It comes from revisiting old decisions with better information and a bit more perspective.
If you’ve already abandoned a few resolutions this year, that’s normal. Markets don’t reward perfection. They tend to reward thoughtfulness, patience, and follow-through.
Those habits take longer than 21 days…but they last a lot longer too.
Dear Mr. Market: 