For high earners
Your income went up faster than your systems did. That's the normal story here, not the embarrassing one.
Book a 15 to 30 minute call
"I make good money. I just don't feel like any of it is actually under control."
If that sounds familiar, you're not doing anything wrong. You're not alone in it either. Making more money rarely comes with more time, or a better system for managing it. It comes with higher stakes, and less room for small mistakes to stay small.
That's often a load-bearing problem: a lot rides on your continued ability to keep earning, or scaling what you've built. From the outside, that looks like freedom. From the inside, it can feel like the opposite, more locked in, not less.
Your income outpaced your systems, not your judgment. You're good at what you do, the calendar is full, and the financial side has been piling up in the background while you handled everything else first. That's the normal story here, not the embarrassing one.
I write more about knowing what's actually enough on the Money & Happiness page.
Making more has already happened. What's often missing is the margin that was supposed to come with it: money that's actually working for your life instead of locking you into decisions you made back when you had less room to choose.
That's more about the shape of your whole financial picture than the return on your portfolio: how much depends on any one thing continuing to go right, and how much room you'd have if something changed. That's the shift I aim for: less dependency on any one thing, more room to make a change if you wanted to.
Six areas come up in almost every conversation I have with high earners. Rarely does someone need help with just one of them at a time.
One coherent portfolio and strategy, instead of scattered accounts you opened at different points for different reasons.
A second set of eyes before you take on more debt, risk, or fixed costs that lock you in.
Your most controllable cost, and usually the least managed. I don't file returns, but I coordinate closely with your CPA.
A high income doesn't organize itself. One system that actually catches what's coming in and where it's going.
Your income is worth protecting. My default is low-cost term coverage, unless specific circumstances call for more.
Stock options, RSUs, and similar don't manage themselves just because you understand your job.
A quick, useful starting point
1. Named beneficiaries override your will Beneficiary listings on investment accounts override your will entirely. Named an ex-spouse or a late parent? They still inherit, no matter what your will says…
A short, low-key call. We start with where your money actually is today, and go from there.
Very. Income tends to grow faster than the systems to manage it, and most high earners feel some version of this, even the ones who look completely on top of it from the outside. Building that system takes time you likely haven't had, not ability you're missing.
There's rarely just one. The pattern I see most is underinsurance relative to what you'd actually need to replace your income, paired with a portfolio that grew by accident rather than by plan: individual stocks, idle cash, and retirement accounts from different jobs with no strategy tying them together. The checklist below walks through the most common ones.
There's no universal answer, since it depends on what has to keep going right for it to work out. Before taking on a bigger loan or obligation, it's worth asking how many things would need to stay on track, and how much room you'd have if one of them didn't. That's usually a more useful question than whether you can afford the payment today.
Maxing out those accounts is a good habit, but it's not a full plan. The bigger questions, tax-efficient investing outside retirement accounts, insurance that matches your actual income, and making sure everything is coordinated instead of scattered, tend to matter more the more you make.
No. I'm not a CPA, and I don't file returns. What I do is coordinate closely with the CPA you already have, or point you to one if you need it, so the tax strategy and the actual filing stay lined up instead of working against each other.
There's no flat multiple that fits everyone, despite what the rules of thumb suggest. It depends on your income, debts, how many years you're covering, and what you want your family to be able to maintain if something happened to you. My starting point is low-cost term coverage sized to the years you actually need it; more complex products only come up for specific situations, like estate planning or a business buy-sell agreement.
It depends on the type of equity, your vesting schedule, and how concentrated your net worth already is in your employer's stock. A common mistake is letting it accumulate without a plan, so one company ends up carrying more of your future than you'd choose on purpose. We build a plan for exercising, selling, and the tax bill each decision creates.
Often, yes, if your income is above the level where you can contribute to a Roth IRA directly. It's a legitimate, commonly used strategy, but it has to be done in the right order and reported correctly on your taxes to avoid an unexpected bill. We handle the mechanics and the tax reporting together.
Yes. My own household runs two businesses, this practice and my wife's medical spas, so I'm familiar with the cash flow, tax, and planning complexity that comes with owning one. Business owners get the same coordinated approach as any high earner, plus attention to how the business and your personal finances interact.
When insurance is the right tool, I can put it in place as part of the plan. I may earn a commission on a policy, and I will always tell you when that is the case.
Almost always. Everything is handled virtually, so where you live is rarely a barrier. The only exception is a handful of states where I'm not registered yet, and if that's you, I'll tell you on our first call.