For years, I’ve talked about the importance of knowing your numbers. And that’s because my own financial journey started from a pretty uncomfortable place. Thinking about an upgraded financial plan wasn't in my mind at all. I didn't even know what constituted a financial plan in the first place…

During residency, I had significant student loan and credit card debt, essentially no investments, and very little understanding of personal finance. Despite knowing that I would eventually earn a high income as a plastic surgeon, I felt like I was staring at an endless financial hamster wheel. My financial well-being was poor and, as I’ve shared many times, that was having a very real impact on my overall well-being.

Learning about personal finance changed that. And one of the first things I learned to do was incredibly simple: calculate my net worth.

I opened a spreadsheet, made one column for assets and another for liabilities, and started adding everything up. At the time, the assets side was pretty sparse. The liabilities side was not. The result was a net worth of roughly negative $520,000.

Strangely, seeing that number was a relief

Before calculating it, my finances felt like this big, amorphous problem hanging over me. Once I had a number, I had a framework. I could see that investing would increase my assets and paying down debt would decrease my liabilities. And while I couldn't change everything immediately as a resident, I could start moving those numbers in the right direction.

That spreadsheet became the foundation of my financial plan. And if you've followed my journey, you know that tracking my net worth has remained a huge part of how I measure our financial progress.

But recently, working with Enpo Tu, CFP®, COO of My Financial Coach, has helped me realize that there is another level to understanding my finances.

My Financial Plan 1.0: The Net Worth Spreadsheet

As our finances evolved and upgraded, so did my spreadsheet and the financial plan it tracked. My wife and I added retirement accounts, including our 403(b)s and backdoor Roth IRAs. Eventually, we added our home mortgage and mortgages associated with our investment properties.

Every six to twelve months, I could update everything and answer a very important question: What is our net worth right now?

That was enormously useful. In fact, I still think knowing and tracking your net worth is one of the most powerful tools in personal finance. It gives you a scorecard. You can see what is working, what isn't, and whether your actions are actually moving you closer to financial freedom.

But there was an important limitation hidden inside that question. My spreadsheet gave me a snapshot. It could tell me where we were at one particular moment, but it couldn't necessarily tell me where we were going with the same level of precision.

And that's where my work with Enpo and My Financial Coach began.

The idea wasn't to throw out the system that had gotten me this far. It was to take the information I was already collecting and use it to ask better questions.

From a Financial Snapshot to a Living Upgraded Financial Plan

The first step was translating my spreadsheet into a real-time financial dashboard. Instead of manually opening every bank, investment, and retirement account and transferring balances into a spreadsheet, we could connect many of those accounts through read-only feeds. Accounts that couldn't be connected automatically could still be incorporated manually.

Suddenly, my financial picture wasn't something I reconstructed every six months. I could see our assets, liabilities, and changes in our financial position in one place and in real time.

But honestly, the dashboard itself isn't the part that excites me most. The real value is what we can now do with that information.

For years, I had believed that our financial plan was working. And it has worked! We went from a net worth deep in the negative to becoming physician millionaires much earlier than we originally projected. But now we could start asking more specific questions. Are we actually on track for our ultimate goals? What happens if we change our savings rate? What happens if inflation is higher than expected? And what happens as our mortgages disappear but other real estate expenses remain? And what happens if we make financial decision A instead of financial decision B?

My spreadsheet helped me understand where I was. This new approach truly represents an upgraded version of our financial plan and is helping me better understand where I am going.

The Real Question Isn't How Much You Earn

One of the most interesting lessons from this process has been reconsidering how we think about retirement spending.

You've probably heard some version of the rule that you should plan to replace a certain percentage of your pre-retirement income. But that can become a strange benchmark for high-income professionals. If you're a plastic surgeon earning well over $500,000 annually, do you actually need to replace 80% of that income every year in retirement?

Maybe. But probably not simply because a rule of thumb says so.

The better question is: What does your life actually cost?

Your retirement contributions aren't your lifestyle. Paying down mortgage principal isn't necessarily your lifestyle either. Your lifestyle is the house you live in, the food you eat, the vacations you take, the activities your kids participate in, and everything else that creates the life you actually enjoy.

And that lifestyle evolves. How I lived as a resident is not how my family lives today. Nor should it necessarily be. I didn't go through all of medical training with the goal of living like a resident forever.

The goal isn't permanent deprivation. It's understanding what spending actually matters to us and determining whether our financial plan can sustainably support it.

This is also why I've increasingly come to view physician finances as being about the finish line rather than winning some imaginary race. The point isn't to save the highest percentage, accumulate the biggest portfolio, or retire earlier than everyone else. The point is to use money intentionally to create the life that you want.

Finding the Expenses Hiding Inside My Mortgages

Our real estate provided another great example of why greater financial granularity matters.

I had always tracked our mortgage balances. I knew the payments, interest rates, and roughly when they would disappear. But a mortgage payment isn't just a mortgage. There is principal, interest, property tax, and insurance. And for rental properties, there are maintenance costs and other ongoing expenses.

Most importantly, some of those expenses don't disappear when the mortgage does.

That seems obvious once you say it out loud. But seeing it modeled across decades was eye-opening. Our current escrow-related expenses were around $61,000 annually. When those expenses were projected forward using a conservative inflation assumption, they nearly doubled by retirement.

Previously, that wasn't something we had explicitly incorporated into our future spending projections.

On the positive side, the modeling also quantified the impact of something we were already doing: making extra mortgage payments on one property. Rather than simply knowing that extra payments were “good,” we could see how dramatically they could shorten the repayment timeline.

And that highlights one of the biggest changes in how I'm now thinking about my finances. I'm moving from “I think this is a good financial decision” to “Here is approximately what this decision does to our financial trajectory.”

That may sound like a subtle distinction, but I think it is a huge one.

Turning Financial Anxiety Into Measurable Risk

Perhaps the biggest benefit of deeper financial modeling is the ability to test assumptions.

Everyone has financial worries. What if the stock market crashes? What if inflation stays elevated? Or what if we buy the wrong rental property? What if we save too little? Or, just as importantly, what if we're saving too much and unnecessarily saying no to things we'd enjoy today?

Traditional retirement modeling often focuses heavily on investment returns. That's important, and tools like Monte Carlo analysis can help estimate how a plan performs across different market environments. But markets aren't the only risk.

Inflation is a perfect example. It doesn't just affect groceries and vacations. It can affect property taxes, insurance, home maintenance, and countless other expenses. And small changes compounded across decades can create enormous differences.

When we modeled a prolonged higher-inflation environment, the lifetime difference in one scenario approached $24 million.

Does that mean we're going to lose $24 million to inflation? Of course not. That's not the point of modeling.

The point is that we can identify a risk, estimate its magnitude, and decide whether it deserves action. A $1,000 potential problem deserves one kind of response. A $10,000 problem deserves another. A multimillion-dollar potential problem deserves serious consideration.

That's very different from vaguely worrying about inflation because you saw another scary headline.

From “Can We Get There?” to “What Do We Want?”

This process is also changing the questions my wife and I can ask.

Earlier in our financial journey, the question was essentially, “Can we ever get there?” Then it became, “Are we probably going to get there?”

Increasingly, we can begin asking a different set of questions. Could we take our foot off the gas? Could we spend more today? Should we accelerate certain goals? Which financial decisions are actually worth our time? And eventually, what exactly are we building all of this for?

That's a pretty cool place to be. Especially because when we created our written financial plan, our goals seemed very far away. The plan gave us a roadmap, but at that stage we were still very much in the process of digging out and building the foundation.

Now, some of these questions lead naturally into estate planning. We have a basic will, but we haven't deeply explored what we ultimately want to leave our children, how we'd want them to receive it, whether the assets we're accumulating are assets they'd actually want, and how much we'd prefer to use during our own lives.

Those aren't really investment questions. They're life questions that happen to involve money. And that's ultimately where I think an upgraded financial plan should lead.

My Upgraded Financial Plan 2.0

Working with Enpo and My Financial Coach hasn't made me abandon the principles that got me here. Quite the opposite.

Tracking net worth still matters. Saving matters. Investing matters. Paying down debt matters. And having a written financial plan absolutely still matters. In fact, our financial plan has continued to evolve as our financial lives have evolved.

My spreadsheet wasn't wrong. It was version 1.0.

What we're building now is version 2.0: taking the financial habits and principles that helped my family move from a net worth of negative $520,000 toward financial independence and adding another layer of measurement, modeling, and intentionality.

And perhaps that's the biggest lesson I've taken from this process. You don't need perfect financial sophistication before you start. Start by looking at your numbers, even when you're afraid of what they're going to say. Then create a plan. Follow it. Measure your progress. And as your finances become more complex, keep improving your understanding.

Because eventually, the goal isn't simply to accumulate the biggest number possible.

The goal is to know what you want your money to accomplish, understand whether you're on track to accomplish it, and have enough confidence in the plan that you can actually enjoy the life you're building along the way.

For me, that's what financial well-being is really about.

What do you think? How has your understanding of your personal financial journey evolved over time? How are you tracking things? Is it helping you understand where you are going in addition to where you are? Let me know in the comments below!