I’m now 6 years into my financial journey (which has certainly been filled with various financial mistakes and challenges), and I think it’s always important to stop occasionally and look backward. As humans, we are naturally wired to focus on the gap. We tend to obsess over what we still lack rather than appreciating how far we’ve already come. Dan Sullivan calls this “The Gap and The Gain,” and I think about that concept often.

Because if I only focus on where I still want to go, I miss how dramatically life has already changed. Six years ago, my net worth was around -$500,000. Like many physicians coming out of training, I had massive student loan debt, limited investing knowledge, and a lot of uncertainty about the future. At that point, financial freedom honestly felt very far away.

Fast forward to today, and things look completely different.

Our net worth is now over $2 million. We’ve built multiple streams of 6 figure cash flow. We have a written financial plan that works and automates our investing in index funds. We’ve invested heavily in real estate. We’re approaching financial independence much faster than I ever thought possible.

And yet, despite all of that progress, there are still financial challenges

That’s something I don’t think gets talked about enough in personal finance circles. There’s this underlying assumption that once you “make it,” the problems disappear.

They don’t.

The problems simply evolve.

So I thought it would be interesting to reflect on the 6 biggest financial challenges I still face 6 years into this journey. These are in no particular order, but they are all things I actively continue to work on.

1. Not Tinkering With Things

This is probably the one I struggle with the most consistently.

One of the strangest truths about personal finance is that once you’ve created a solid financial plan, your job becomes mostly not screwing it up.

That sounds easy, but for people like physicians, it really isn’t.

As doctors, we’re trained to optimize. We adjust medications. We tweak treatment plans. Sometimes we order more testing. We intervene constantly in an effort to improve outcomes. That mindset works beautifully in medicine. It can work terribly in investing.

Our financial life now is highly automated. Money automatically flows into retirement accounts, brokerage accounts, and investment properties every month. Most of the time, I barely notice it happening. And honestly, that’s exactly how it should be.

But there’s still a part of me that occasionally wants to “improve” things.

I’ll catch myself thinking:

• Could I optimize our asset allocation more?
• Should I be investing slightly differently?
• Is there a more efficient strategy?
• Am I missing some opportunity? (AKA investment FOMO)

The problem is that constant optimization often becomes counterproductive.

I think boredom is actually one of the most dangerous things for investors. Once the system is working, many people feel the urge to do something simply because doing nothing feels too passive.

Even now, six years later, I still have to resist that urge.

One thing I’m proud of is that our written financial plan really hasn’t changed meaningfully in the last 2 years. We continue to execute the same principles over and over again because consistency matters far more than constant reinvention.

That sounds boring. But boring is often what works.

2. Spending Money

Ironically, after years of learning how to save money, I now find spending money more difficult.

Early in our financial journey, this wasn’t a problem at all. We had a very strict budget because we had to. There was only so much money available, and every dollar had a purpose. At that stage, spending decisions were simple.

Now things are different.

We use what I would describe as more of a backwards budget. Our savings goals happen first. Investments happen automatically. Retirement accounts are funded. Real estate investments are handled. Then we spend what’s left.

The funny thing is that there’s often more left over than we actually know what to do with. And after years of training yourself not to spend freely, it’s surprisingly hard for me to flip that switch.

I don’t consider myself a particularly frugal person, but I absolutely still feel resistance when it comes to certain purchases. Even when those purchases are intentional and would clearly improve our lives, there’s still a mental hurdle sometimes.

Things like:

• Paying for convenience
• Outsourcing tasks
• Taking nicer vacations
• Upgrading experiences
• Spending money on services that reduce stress

For example, we recently returned from an amazing vacation as a family. Years ago, taking trips like that would have felt completely unrealistic financially. Now we can do them comfortably, yet there’s still a part of me that mentally hesitates before spending the money.

I think that scarcity mindset lingers longer than people realize.

One positive development has been charitable giving. As our financial situation has improved, being able to give more intentionally has become one of the most rewarding parts of the journey.

But overall, I still think spending money well is a skill I’m learning.

3. Continuing to Pay for Insurance

Every year when I pay our insurance premiums, I go through the exact same internal debate.

We still carry both term life insurance and own occupation disability insurance. Those premiums are not cheap. And every single year, as our investments continue growing, I question it a little more.

I know logically why we still have the policies. They are necessary. We’re not completely financially independent yet. If something catastrophic happened tomorrow, that protection would still matter significantly.

But emotionally, it becomes harder to write those checks when you can increasingly see a future where you no longer need the coverage.

I literally just paid our premiums last week, and I remember sitting there thinking again: “How much longer are we going to keep doing this?” For disability insurance especially, I suspect we’ll continue carrying it longer than life insurance. Since I’m still actively working, protecting future income remains important.

Still, it’s fascinating how your relationship with risk changes over time.

In the beginning, insurance feels absolutely essential because your entire financial life depends on your ability to work. Later, as your investments grow, you start realizing your portfolio is slowly replacing your human capital.

That transition creates a strange psychological tension that I still haven’t completely adjusted to.

4. Trying to Keep Our Kids Grounded

Of all financial challenges, this may be the one I think about most deeply.

My wife and I recently had a conversation after returning from a family vacation. We were reflecting on how many incredible experiences our kids have already had at young ages. And honestly, many of those experiences are things that took us most of our lives to experience ourselves.

That realization hit both of us pretty hard.

On one hand, we feel incredibly grateful to provide opportunities and experiences for our children that we never had growing up. On the other hand, there’s a real concern about habituation. Kids adapt quickly. Things that initially feel extraordinary can become normal surprisingly fast.

I don’t have some perfect formula for how to keep children grounded while also providing them with a great life. I don’t think anyone truly does.

We talk a lot about gratitude in our home. We try to emphasize experiences over material possessions. And we discuss hard work openly.

But I still worry about it.

I want our kids to appreciate opportunities without feeling entitled to them. I want them to understand how fortunate they are while still developing ambition and resilience.

That balance feels incredibly difficult sometimes. And unlike investing or taxes, there’s no spreadsheet or formula to solve it.

5. The Ongoing Headaches of Real Estate Investing

Real estate has been a huge part of our financial growth.

The cash flow has been tremendous. The tax advantages have been powerful. The long term appreciation has accelerated our journey dramatically. But let me tell you something that social media influencers often leave out: Real estate can absolutely be a pain.

We currently own 9 rental properties and still self manage them ourselves, with my wife handling the majority of the operational side because of her real estate professional status.

Even with systems in place, there are constantly little things that pop up.

• Tenant messages
• Maintenance issues
• Repairs
• Contractors
• Unexpected problems (And sometimes very unexpected problems)

This past winter, we dealt with frozen pipes at one property that caused a major leak. In the middle of handling situations like that, it’s very easy to question why you continue doing it. There are moments where you think, “We’re already doing well financially. Why are we still dealing with this?”

But eventually we zoom back out. We remember the cash flow pipeline we’ve built. And we remember the tax benefits. We remember the long term wealth creation.

And suddenly the headaches feel more manageable again.

Still, I think active real estate investing requires more emotional energy than many people appreciate beforehand.

6. Taxes

Taxes continue to be one of the most frustrating parts of personal finance for me. I’ve said before that taxes are often a physician’s largest expense, and that is certainly the case for the majority of physicians.

The frustrating part is that good tax planning requires constant work.

Every year, it feels like we reevaluate everything:

• Income structure
• Real estate losses
• Business deductions
• Retirement contributions
• Tax strategy coordination

It often feels like jumping through hoops endlessly. Now to be clear, I firmly believe people should pay the taxes they legally owe.

But I also firmly believe that we are not obligated to pay more than necessary.

As Judge Learned Hand famously said, there are two tax systems in America: one for the informed and one for the uninformed.

Being informed takes effort. And honestly, sometimes it’s exhausting. Still, the financial impact is too meaningful to ignore, so we continue putting in the work every year.

Final Thoughts

One of the biggest mindset shifts I’ve had over the last several years is realizing that life is not what happens after all your problems disappear.

Life is the process of solving problems.

There will always be challenges:

• Financial challenges
• Family challenges
• Career challenges
• Mindset challenges

The goal isn’t to reach some magical point where nothing is difficult anymore. The goal is to build a life where the problems you have are problems worth having.

Every one of the financial challenges I listed above exists because of something positive we created:

• Investments
• Financial freedom
• Real estate
• Family opportunities
• Wealth
• Cash flow

The blessings and the challenges are intertwined.

So wherever you are in your own financial journey right now, I think it’s worth taking a moment to zoom out and appreciate the gain instead of obsessing over the gap. Because chances are, you’ve already come farther than you think.

What do you think? What are your biggest financial challenges right now? And what were they 6 years ago? Are you surprised by how far you've come? Just imagine how far you will go in 6 more!