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The Five Financial Decisions That Have the Biggest Long-Term ROI
Most people think wealth comes from picking the right investments.
It actually comes from a handful of decisions repeated for decades.
Here are the five decisions that create the biggest long-term ROI.
Sean Rawlings
15 hours ago3 min read


The Hidden ROI of Financial Planning
Most people think financial planning is about investments.
It is really about clarity, confidence, and control.
The biggest return on planning is the way it changes your day-to-day life.
Less stress. Better decisions. More options.
Sean Rawlings
Nov 213 min read


Why Your Cash Flow Strategy Should Look More Like a Business
High earners are often surprised when their income goes up but their stress does not go down.
The missing piece is structure.
Not budgeting. Not cutting back.
A real cash flow system.
Here is how to run your money like a business and finally feel in control.
Sean Rawlings
Nov 143 min read


Why Cash Still Matters (Even When Yields Are Falling)
High-yield savings rates have come down, but the role of cash hasn’t changed.
It’s still the foundation of every strong financial plan.
Cash isn’t meant for growth—it’s meant for flexibility, stability, and peace of mind.
Here’s how to decide how much to hold, where to keep it, and how to make it work efficiently for you:
Sean Rawlings
Oct 313 min read


Equity Compensation: 3 Mistakes That Can Cost You at Tax Time
Equity compensation can change your life — or your tax bill.
It depends entirely on your plan.
Every year I see high earners get hit with five-figure tax surprises because they didn’t understand how their RSUs, ISOs, or ESPP shares are taxed.
Here are 3 equity compensation mistakes to avoid before year-end .
Sean Rawlings
Oct 243 min read


What the 2026 Tax Brackets Mean for You (And How to Plan Around Them)
The IRS just announced 2026 updates that could shift how high earners, business owners, and investors approach their tax strategy.
These changes open new doors for Roth conversions, gifting, and tax-efficient investing—but only if you start planning before 2026 hits.
I just wrote a full breakdown of the new rules and how to position yourself for what’s next.
Sean Rawlings
Oct 103 min read


How to Stress-Test Your Financial Plan
Most financial plans look great when everything is going well. But what happens when life throws a curveball?
That’s where stress-testing your plan comes in. Asking simple “what if” questions—what if my portfolio dropped 25%, what if I lost my job for six months—can show you if your financial plan is truly built to last.
Sean Rawlings
Oct 33 min read


The Psychology of “Enough” in Wealth Building
Making more money doesn’t always make you wealthier. The key is knowing your version of enough.
Here’s why defining it can be the difference between always chasing more and finally building the life you want.
Sean Rawlings
Sep 263 min read


How to Plan a Career Break Without Derailing Your Finances
A sabbatical year often means lower income, and that can open the door to tax strategies like Roth conversions or harvesting capital gains at lower rates.
Taking time off isn’t just possible—it can be smart, if you plan for it.
Sean Rawlings
Sep 193 min read


The True Cost of Lifestyle Inflation (And How to Avoid It)
If every raise you get just leads to a bigger house, nicer car, and fancier vacations — your savings rate never grows. And if your savings rate never grows, your future doesn’t actually get any better.
Here’s the truth: wealth comes from what you keep and invest, not what you earn.
Sean Rawlings
Sep 123 min read


The Real Cost of Homeownership: What the Math Really Says in Your First 7 Years
Buying a home isn’t a bad decision, but it’s often misunderstood. The early years of a mortgage are mostly interest, not equity. Understanding this math is key to making homeownership part of a long-term financial plan instead of your entire plan.
Sean Rawlings
Aug 293 min read


The Hidden Risks of Holding Too Much Company Stock
A lot of high earners I talk to are sitting on a huge chunk of their wealth in company stock.
It feels great when the stock is up… until you realize your paycheck, benefits, and net worth are all tied to the same company. That’s not just investing — that’s gambling.
The truth is, too much company stock creates risks most people don’t see coming.
Sean Rawlings
Aug 223 min read


How to Avoid Surprise Capital Gains Taxes (and Keep More of Your Money)
Most people only think about capital gains when they sell a stock.
But in reality, you can trigger a taxable gain in dozens of ways — sometimes without even realizing it.
From mutual fund distributions, to selling your home, to the way you handle equity compensation, the timing of your financial decisions can mean the difference between a minimal tax bill and a big one.
Sean Rawlings
Aug 153 min read


Why Your First $100k Is the Hardest and Why It Changes Everything
Most people underestimate how powerful the first $100,000 invested can be.
It’s not just a number; it’s the tipping point where your money starts working harder than you do.
Sean Rawlings
Aug 83 min read


Why Cash Flow Is King—Even If You’re Earning Multiple Six Figures
Making $300k+ but still wondering where your money is going?
You’re not alone—and it’s not about budgeting harder.
This week’s blog dives into why cash flow is king, even for high earners, and how to create a system that actually builds wealth (and freedom).
We cover:
✅ The 50/50 lifestyle rule
✅ Why unchecked income = lifestyle creep
✅ How to automate wealth-building
✅ Real strategies to align money with your goals
Sean Rawlings
Aug 13 min read


How to Plan for Kids Without Derailing Your Financial Future
Having children is one of life’s most exciting milestones—but it’s also one of the most financially impactful. From diapers and daycare to college and beyond, it’s easy to feel overwhelmed by the rising cost of raising a family. But with some proactive planning, you can grow your family without sacrificing your financial future.
Sean Rawlings
Jul 243 min read


The 5-Year Rule: How to Set Financial Goals That Actually Work
Most high earners focus only on long-term goals like retirement or short-term goals like saving for a vacation. But the real magic happens when you get intentional about the next five years. Whether you want to take a sabbatical, buy property, or start your own business, your financial plan should support the life you’re building—not just your 401(k). This week’s blog breaks down how to use a 5-year window to align your income, investments, and tax strategy with what actually
Sean Rawlings
Jul 183 min read


The Mid-Year Financial Planning Checklist for High Earners
If you're earning a strong income but not sure if you're truly optimizing it, this blog is for you.
From equity comp and QBI deductions to tax-loss harvesting and the best use of your 401(k), I’ve put together a mid-year checklist to help high earners finish 2025 with confidence—and a smaller tax bill.
Sean Rawlings
Jul 113 min read


How Business Owners Can Pay Their Kids and Build Them a Tax-Free Nest Egg(Part 2)
Not all wealth comes from trust funds and inheritance. Learn how to create a lasting legacy for your children in this weeks blog.
Sean Rawlings
Jul 43 min read


How to Make Your Child a Millionaire (Part 1): The Power of Starting Early
Not all wealth comes from trust funds and inheritance. Learn how to create a lasting legacy for your children in this weeks blog.
Sean Rawlings
Jun 274 min read
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