Oakleigh Wealth Services

05/03/2026

Our local elementary school scores below average on the GreatSchools rating that shows up on every Zillow listing. We sent our son there anyway, and what we found was a school that the number couldn't begin to capture.
That mismatch sent me down a rabbit hole on the role metrics play in our lives, and in financial planning specifically. New piece this morning on the numbers worth watching, the ones that quietly start running the show, and how to tell the difference.

I've been thinking about the role that metrics play in life, prompted by a recent Derek Thompson interview with the philosopher C. Thi Nguyen, whose new book is called The Score: How to Stop Playing Somebody Else's Game . Nguyen has a useful term for what happens when a simplified measure quietly t

02/19/2026

02/19/2026

Let's talk about Trump accounts! Putting the politics aside, how are Trump accounts useful for gifting to children? How do they work? When does it make sense? What are the drawbacks?

Check out the full discussion on the Make the Most of Your Money Podcast with Taylor Stewart
https://www.youtube.com/watch?v=OveftDT47mw&list=PLMmN_TKCRBYOuhY2LDTTBu5905mJyeMF_

02/17/2026

Why I love using 529 plans for gifting to grandchildren.

Check out the full episode on giving money to kids on the Make the Most of Your Money Podcast with Taylor Stewart

https://www.youtube.com/watch?v=OveftDT47mw

02/13/2026

02/12/2026

Should you plan for an inheritance in your financial plan?
See how we answer this question on the latest episode of the Make the Most of Your Money Podcast with

02/10/2026

“I want to give my kids just enough so that they would feel that they could do anything, but not so much that they would feel like doing nothing.”
― Warren Buffett

12/02/2024

Can you imagine an economist who states, “There is a 60% chance of a recession next year” getting any air time? We much prefer the certainty of the broken clock, even if it’s only right twice a day.

We live in a world governed by random events, yet humans are terrible at thinking probabilistically. We vastly prefer certainty over probability, narratives of skill and design over luck, and we find all manner of patterns within noise. We listen to the “experts” who talk confidently about the f...

11/05/2024

OWS Retirement Planning Newsletter | November 2024 - http://eepurl.com/i3x3_U

05/24/2024

Helping folks navigate the paradigm shift from saving to spending is one of the core issues in retirement planning. I love addressing the financial questions and discussing the deeper internal tensions at work.

There are a couple of reasons why retirees might find it hard to switch from saving to spending: Fear of running out: Habit and mindset: Loss of regular paycheck: These anxieties are common, and there are strategies to contextualize and address them to develop a healthy spending plan

05/16/2024

Insurance works best to cover risks that are both low in frequency and high in severity (e.g. car accidents, house fires, premature death, or disability). This is why LTC is so difficult to plan for: It’s not all that low in frequency, but it can also wreck your retirement plan. These two things conspire to make LTC much more expensive to insure against (whether that’s self-insuring or purchasing an insurance policy).

Insurance works best to cover risks that are both low in frequency and high in severity (car accidents, house fires, premature death, or disability). This is why LTC is so difficult to plan for: It’s not all that low in frequency, but it can also wreck your retirement plan. These two things conspi...