The start of a new year naturally invites planning. But for most people, planning quickly turns into optimization – more efficiency, better returns, tighter projections.
The more meaningful work often starts earlier than that.
Before adjusting numbers, it’s worth stepping back to ask whether your financial life is aligned with the life you want to live. As we look ahead to 2026, with several new planning rules and legislative changes becoming active under the OBBBA framework, this is an ideal moment to reset both direction and strategy.
As a kid of the ‘90’s and a David Letterman fan, I always waited for the part of the show when he revealed his (sometimes crazy, but almost always funny) Top 10 List. Here is my attempt and a nod to Mr. Letterman with 10 financial and life planning considerations worth reviewing as you prepare for the year ahead, with a particular emphasis on building margin, clarity, and adventure into 2026.
1. Define What You Want 2026 to Feel Like
Before reviewing accounts or projections, clarify the experience you want the year to deliver.
Do you want 2026 to feel spacious or packed? Grounded or mobile? Predictable or exploratory?
Financial plans are most effective when they support a clearly defined life vision. Without that anchor, even strong financial results can feel disconnected.
2. Plan Adventure First, Not Last
Adventure is often treated as optional – something to squeeze in if time and money allow.
In practice, that usually means it doesn’t happen.
Whether adventure for you means extended travel, meaningful family trips, endurance events, or simply more time outdoors, plan it intentionally. Block the time on the calendar. Estimate the cost. Create a dedicated savings bucket.
When adventure is designed into the plan, money becomes an enabler rather than a gatekeeper.
3. Understand What’s Changing Under the OBBBA
Several provisions tied to recent federal budget and benefits legislation are now becoming relevant for 2026 planning. While the specifics vary by household, common planning areas affected include retirement contribution limits, including updated catch-up provisions for certain age ranges; required minimum distribution rules and beneficiary timelines impacting inherited retirement accounts; income thresholds for tax credits and deductions, with tighter phase-outs at higher income levels; and sunsetting provisions from earlier tax law, increasing the importance of proactive, multi-year tax planning.
The key takeaway is that understanding these changes early creates flexibility. Waiting until year-end often removes good options.
4. Revisit Your “Enough” Number
As income and assets grow, old targets often linger long after they stop serving your life.
Revisit what level of income actually supports your desired lifestyle, how much work is enough, and which trade-offs are no longer worth it.
Clarifying “enough” is often the most powerful financial decision you can make.
5. Align Cash Flow With Experience, Not Habit
Instead of asking where to cut spending, ask where your money is working well for you.
Which expenses consistently add meaning or enjoyment? Which ones feel automatic or outdated?
Redirecting cash flow toward experiences, travel, and flexibility often improves quality of life without increasing overall spending.
6. Strengthen the Safety Net
Adventure is easier to pursue when the foundation is solid.
The new year is a good time to review emergency reserves, insurance coverage, estate documents, and beneficiary designations.
These items rarely feel urgent – until suddenly they are. Proactive review reduces stress and creates confidence.
7. Simplify Where Complexity Has Crept In
Over time, financial lives naturally become more complex.
Multiple accounts serving similar purposes, legacy strategies that no longer apply, and complexity that adds confusion without value can quietly accumulate.
Simplification improves clarity, reduces friction, and makes decision-making easier when life changes quickly.
8. Use Tax Planning to Support Lifestyle Decisions
With updated thresholds and evolving rules, tax planning for 2026 should align with life choices.
This may include timing income around travel or sabbaticals, evaluating Roth strategies during lower-income years, or coordinating charitable giving with tax efficiency.
The goal is not minimizing tax in isolation, but ensuring tax decisions support the life you want to live.
9. Decide What to Stop Doing
Borrowing from the annual review approach popularized by Tim Ferriss, one of the most powerful planning exercises is deciding what to stop.
What commitments, habits, or financial behaviors create stress without meaning, consume time without return, or reflect an outdated version of you?
Stopping often creates more freedom than starting something new.
10. Build Margin Into the Plan
Finally, leave room.
Margin in your calendar allows spontaneity. Margin in your cash flow absorbs surprises. Margin in expectations builds resilience.
A plan with no margin may look efficient, but it is fragile. A plan with margin can flex and support opportunity when it appears.
Final Thought
Planning for 2026 isn’t about predicting every outcome. It’s about creating a framework strong enough to support responsibility and exploration.
When financial planning is aligned with experience, when adventure is treated as essential rather than optional, and when decisions are made intentionally rather than reactively, money becomes what it was always meant to be – a tool in service of a well-lived life.
