Applying Your Examination Skills to Your Investment Philosophy…

You spent a decade learning to think critically.  You were trained to question assumptions, challenge diagnoses, and never accept a conclusion without evidence.  You apply rigorous intellectual scrutiny to every patient interaction, every clinical decision, and every protocol you follow. 

So why do you have an outdated investing philosophy?  

That question should bother you.  

Not because there is anything inherently wrong with being conservative. But because the decision to be conservative may not have been yours to make. It may have been inherited—absorbed quietly over kitchen table conversations, passed along like a family heirloom nobody thought to appraise. 

We talk endlessly about genetic inheritance. We understand that our patients carry predispositions—toward cardiac disease, toward diabetes, toward certain cancers. We treat those inherited risks with the seriousness they deserve. 

But financial behavior is inherited too. And almost nobody treats it with any seriousness at all. 

Research from the National Bureau of Economic Research has demonstrated that parental attitudes toward money—particularly risk tolerance and savings behavior—are among the strongest predictors of how their children will manage wealth decades later.  

The transmission mechanism is not genetic. It is environmental. It is the dinner table philosophy that money is something to protect rather than deploy. It is the unspoken belief that a respectable person works, saves, retires, and hopes the math works out. For physicians specifically, this inheritance is compounded by a professional culture that reinforces it.  

Medical training selects for people who are detail-oriented, risk-aware, and inclined toward caution. These are virtues in a clinical setting. They can be liabilities in a financial one. 

Consider the physician who earns $400,000 per year, saves diligently into a 401(k), holds a diversified portfolio of index funds, carries appropriate insurance, and assumes this constitutes a sound financial strategy.  

By every conventional measure, that physician is doing everything right. The question is: right according to whom? And right for what purpose? 

Your parents’ financial world was structurally different from yours. In 1980, a physician could graduate medical school with manageable debt, enter practice in their late twenties, and spend forty years building wealth through a single income channel. Employer loyalty existed. The social contract between work and security was still intact. The strategy of earn, save, and wait made sense because the math supported it and the timeline cooperated. 

That world is gone. 

Today’s physicians graduate with an average of $200,000 or more in student debt. They enter practice later. They face reimbursement pressures their parents never imagined. Administrative burden consumes hours that used to generate revenue. And the cost of the lifestyle they were implicitly promised—the house, the education for their children, the retirement at 65—has inflated well beyond what a save-and-wait strategy can reliably produce. 

Yet many physicians are still running the 1980 playbook. They save into tax-advantaged accounts, invest in broad market indices, and assume that time in the market will deliver the outcome they need. They avoid alternative investments not because they have evaluated them and found them wanting, but because those investments feel unfamiliar. They feel risky. They feel like something their parents would not have done. And that, precisely, is the problem. 

The feeling of risk and the reality of risk are not the same thing.  

A physician who puts 100% of their investable assets into public equities and bonds is not avoiding risk. They are concentrating it. They are betting entirely on one asset class, one set of market conditions, and one economic paradigm—and calling it prudence because it is what they were taught to do. 

Here is where intellectual honesty demands something uncomfortable. You need to ask yourself what your money is actually for. 

Not in the abstract. Not “security” or “retirement.” Those are inherited answers—default settings from a previous generation’s operating system.  

What does freedom look like for you, specifically

  • Is it the ability to stop practicing at 55 instead of 65?  

  • Is it the option to take three months off and no one notices because your income does not depend on your physical presence?  

  • Is it the capacity to fund your child’s venture, invest in a colleague’s practice, or walk away from a hospital system that no longer aligns with your values? 

If your financial strategy cannot deliver those outcomes, then it does not matter how disciplined you are. Discipline in service of the wrong objective is not a virtue. It is inertia with better branding. 

The physicians who achieve genuine financial autonomy—not just a comfortable retirement, but actual freedom during their prime years—tend to share a common trait. They did not inherit their strategy. They chose it. 

They made a deliberate decision to look beyond Wall Street’s standard offerings and evaluate investments based on a different set of criteria: Does this asset produce income independent of my labor?  

Does it offer tax advantages that compound over time? Does it reduce my dependence on a single market’s performance? Does it move me closer to a life where work is optional rather than obligatory? 

These colleagues are not reckless. They are not chasing speculative returns or ignoring due diligence. In fact, they tend to be more rigorous in their analysis than their conventionally invested peers, precisely because they are evaluating opportunities that require genuine understanding rather than passive allocation. They treat their financial life with the same intellectual seriousness they bring to their medical practice. 

The difference is not intelligence.  

The conventionally invested physician and the alternatively invested physician are equally smart. The difference is the question they started with.  

One asked, “How do I save for retirement?”  

The other asked, “How do I build a life where I decide what each day looks like?” 

Those two questions produce radically different strategies. And only one of them was probably yours to begin with. 

None of this is an argument against saving. It is not an argument against index funds or 401(k) plans or any specific investment vehicle. Those tools have their place and their utility. 

This is an argument against unexamined inheritance. Against running a strategy you never consciously selected. Against optimizing for a version of success that was defined by people who lived in a fundamentally different economic reality—people you love, people who meant well, but people who could not have anticipated the financial landscape you now navigate. 

You were trained to question inherited assumptions in every other domain of your life. You do not prescribe a medication because “that is what we have always used.” You do not follow a protocol because “that is how my attending did it.” You evaluate the evidence, consider the individual case, and make a decision calibrated to the actual conditions in front of you. 

Your financial life deserves the same rigor. 

So ask yourself the question honestly:  

  • Is your investment strategy truly yours?  

  • Did you design it around the life you actually want—or did you inherit it from a generation that wanted something different, in a world that no longer exists? 

The answer may be the most important diagnosis you make this year. And unlike most diagnoses, this one comes with the opportunity to write your own treatment plan