The 90‑Minute Annual Financial Review: A HENRY’s Guide to Staying Sane
(Part two of HENRY planning series)
When I meet with clients, I like to say, “You don’t need to think about your finances all year, you just need to think about them once a year, on purpose.” I also like to say, “Ponderosa Steakhouse is a national treasure.” But that is for another part of the conversation. Being purposeful and reviewing your process for making decisions is critical once a year. Especially for HENRYs (High Earners Not Rich Yet) A 90‑minute annual review is one of the simplest ways to reduce stress, stay organized, and make sure your money is working for you and not the other way around.
Here’s What We’d Cover in Those 90 Minutes
- Your cash flow Are you saving enough? Is lifestyle creep sneaking in? Do we need to adjust anything?
- Your investments Are you on track? Do we need to rebalance? Is your risk level still right for your goals?
- Your stock options This is where things get interesting. We’d walk through:
- What vested this year and next year
- Whether exercising makes sense
- How taxes will hit you (AMT, ordinary income, capital gains)
- Whether you should sell, hold, or diversify
Most high earners have no idea how much clarity this part brings. Once you understand your equity, everything else feels easier.
- Your taxes We’d look at:
- Last year’s return vs this year’s projections (we find a lot of errors)
- Opportunities to reduce your tax bill
- Whether you need estimated payments
- How your stock options change the picture
Tax clarity = stress reduction.
- Your goals Are you still aiming for the same things? Has life changed? Do we need to adjust the plan? What are your top 10 non-negotiables to plan for?
Why This Works
Because it gives you:
- A clear picture
- A simple plan
- A sense of control
- And 364 days where you don’t have to think about any of it
When your stock options, taxes, and financial systems are aligned, your whole life feels lighter. Reach out if you want us to guide you through this process. We can do this in person or over zoom. Your call.