Learning something new almost always follows the Dunning-Kruger Effect; early learning brings a rush of confidence, followed by the humbling “Valley of Despair,” when we become aware of the limits of our knowledge. That moment of humility is what makes true learning possible and allows us to climb toward real wisdom.

That fancy private-equity dinner? You paid for it. With fees, illiquidity, and risk most investors don’t fully understand. I’ve been there — and I wish I’d leaned harder into the “boring” path. Here’s what I wish I knew sooner.

See the updated 2026 tax brackets, standard deduction amounts, and retirement account contribution limits explained in plain English.

The conversation women aren't having about money- but should be.

If your money is running on autopilot, it might be steering you somewhere you didn’t intend. Here’s how to take back the wheel and build a values-driven financial plan with confidence.

We often overthink and overreact with our finances in a similar way that we do when we parent. Here's how to avoid over-financing so we can focus on the parts of our finances that matter most.

What do you do if you want the excitement of investing a small amount of your money in riskier stocks, such as start-ups, but don’t have the risk tolerance to lose it all? This is where stop loss orders come in. If you’re dabbling in risky plays like a speculative biotech or a small startup, you may decide you only want to risk so much. In that case, a stop loss can help you draw your line in the sand.

Why too much of a good thing (like big tech stocks) can spoil your basket. Many funds look balanced, but under the surface, they’re stuffed with the same thing.

Something that we all have in common is that our financial lives consist of a combination of good decisions, bad decisions, and luck. And fundamentally our ideal outcome is to have the ‘good decisions’ and ‘good luck’ outweigh the ‘bad decisions’ and ‘bad luck’. In my workshops I often talk about how we need to set up our entire financial portfolio from the position of the House at a casino – there will be individual winners and losers, but overall we need to be positioned to

Why a Trump Account isn't the gift it claims to be, and how we could make retirement better if we wanted to.

Today I’m going to let you in on a financial secret of the Ultra Wealthy: Discounting. A few weeks back I wrote about the 3 different...

How the repackaging of luxury shopping as an "investment" is damaging to women.

We live in a broken system that needs fixing, but change takes time, and we can't afford to wait. We need financial strategies that work for our reality. We have to understand how the world has made us think and feel about money, and our role in it. And then we get to rewrite that script.

We see this all of the time. Someone thinks they’ve “made it.” They’ve crossed the magical $1 million net worth threshold, based on their...

Caitlin and I have been out on the Podcast circuit again, guesting on some popular podcasts that will be out soon. Until those episodes are released, I thought I would revisit some of the other podcast interviews we’ve done – the good, bad, and the ugly.

The best time to sell is not what you think it is. There are three important factors to consider, and apply to your life.

With markets swinging wildly, here are three ways to stay in control of your finances.

Let's unpack one of the best tax-saving tools: the Roth IRA conversion. Most people don’t realize there are actually three distinct types of Roth conversions, each with their own rules, timelines, and tax consequences. So let’s demystify the Roth lingo and break down how these moves can seriously level up your tax game.

When colleges lose government funding, they don’t just dim the dorm lights - they start selling off private assets in their endowments, and those moves can ripple down into our portfolios too.

We often unknowingly support companies that don't align with our values, through our investing. Whether it's with a retirement or brokerage account, we may be funding the very actions we vote and protest against. This article breaks down how we can find out where our assets are invested, and what we can do to change those that are not aligned with our values.