August 2026
Featuring
Chris Galeski, Director of Growth & Advice and Partner, Morton Wealth
Mike Rudow, Wealth Advisor and Partner, Morton Wealth
What if I lose my job? What if inflation stays high? What if I run out of money? What if I get a raise and do not know what to do with it? These are the questions people type into Google and AI tools at two in the morning, and they rarely get a straight answer.
In this episode of Financial Commute, Chris Galeski and Mike Rudow pull the most common financial what-if questions and work through each one with the kind of honest, practical perspective that does not show up in a search result. The scenarios are different. The underlying framework that answers all of them turns out to be the same.
0:00 – Intro: the most common financial "what-if" questions people ask AI and Google
0:51 – What if I lose my job or have a major medical expense?
1:44 – Emergency funds, account diversification, and paying yourself first
4:19 – Only 63% of adults can handle an unexpected $400 expense
5:03 – Home equity lines and margin accounts: tools to set up before you need them
6:59 – What if inflation stays high for a really long time?
8:45 – What if I run out of money or live longer than expected?
9:50 – Shame vs. guilt: why putting your head in the sand makes it worse
12:46 – The two types of education, and credit card war stories
14:54 – What if I get a promotion or a bigger bonus?
18:01 – Closing framework: the three buckets that answer almost every "what-if"
What should I do if I lose my job?
The best time to prepare for job loss is before it happens. Mike lays out the structure: a single-income household should have six or more months of non-discretionary spending in a liquid, low-risk account. A dual-income household can get by with three to five months. Beyond the emergency fund, having a taxable brokerage account gives you a second layer of liquidity that does not carry the tax penalties of a retirement account. A home equity line of credit, set up in advance with no intention to use it, can also serve as an emergency backup if both of those are exhausted. The goal is to have options ready before you need them so you are not making emotional financial decisions under pressure.
What if inflation stays high for a long time?
The protection against sustained inflation is owning assets that tend to appreciate alongside rising costs: stocks in companies with pricing power, real estate, and other real assets. Mike describes the core purpose of investing as keeping your dollar from depreciating. A dollar today buys more than a dollar will in ten years if inflation continues. Holding too much in cash or fixed-rate instruments over the long term is not a conservative strategy. It is a slow erosion of purchasing power. The portfolios most vulnerable to long-term inflation are those built around a fixed income pension or Social Security without meaningful investment assets alongside them.
What if I run out of money in retirement?
Chris's answer is direct: this almost never happens without warning. Spending trends, account balances, and the trajectory of a financial plan are visible long before a crisis point. What keeps people from acting on the signals is usually shame or avoidance, not ignorance. The practical answer is to run financial projections regularly, understand your burn rate, and make adjustments, lifestyle, spending, asset allocation, before the situation becomes irreversible. Waiting until the problem is acute means the only options left are drastic ones.
What should I do with a raise or a larger bonus?
The instinct most people have is to upgrade their lifestyle immediately. A nicer apartment, a better car, more vacations. Both Chris and Mike describe making those exact decisions earlier in their careers and wishing they had waited. The advice they give now: keep living the way you were living for six to twelve months after an income increase. Bank the difference. Think through what the money actually means for your goals before committing it to a new fixed monthly expense. If there are no short-term purchases on the horizon, prioritize retirement accounts, taxable investment accounts, or gifts to family and community. Pay yourself first before the lifestyle expands.
What if I have a large unexpected expense like a medical bill or helping a parent?
This is one of the scenarios most directly addressed by financial planning. Chris and Mike both describe modeling these scenarios in advance: what does my retirement look like if I absorb a $50,000 medical expense over four years? What if I need to support a parent for an extended period? A financial plan can run those projections and show you whether your current trajectory can absorb the impact, or whether adjustments are needed now to create more cushion. Having a HELOC, a taxable brokerage account, or other accessible liquidity outside of retirement accounts gives you options that are not dependent on selling long-term investments at the wrong time.
How do the three buckets work in financial planning?
Chris describes the framework near the end of the episode. Bucket one is your emergency fund: liquid, low-risk, enough to cover unexpected expenses without going into debt or disrupting investments. Bucket two is income: enough stable income from investments, pensions, Social Security, or other sources to cover your lifestyle expenses. Bucket three is growth: money invested in assets that appreciate over time, designed to outpace inflation and fund the later stages of retirement. When bucket two is generating more than your lifestyle requires, a recurring unexpected expense in bucket one barely registers. The framework is simple. The discipline to build and maintain all three is where most people need help.
The what-if questions people search most are not obscure edge cases. They are the scenarios that keep real people up at night: job loss, inflation, outliving their money, not knowing what to do with a windfall. This episode works through all of them using the same practical framework, and does it in a way that feels like a conversation rather than a lecture.
At Morton Wealth, the what-if conversation is one of the most valuable ones we have with clients. Running the projections, toggling the scenarios, and seeing the impact before it happens is exactly what financial planning is for. If any of these questions are on your mind, that is where the conversation starts.
Watch Previous Episodes
The Fed Isn't Cutting Rates: What it Means for You
How to Pay Yourself in Retirement: Strategies to Help Make Your Money Last
