If you expect to retire within the next five years, now is a reasonable time to begin interviewing financial advisors. You do not have to make an immediate decision. The purpose is to understand your choices before retirement decisions become urgent. Interviewing several advisors also helps you compare their services, costs, planning processes, and communication styles. Ask each advisor the same five questions. 1. Will you act as a fiduciary at all times? A fiduciary is requi

Artificial intelligence is getting increasingly good at reading information. It can review documents, summarize reports, organize data, explain financial concepts, and help people research questions faster than they could on their own. But there is an important limitation. Knowing the information is not always the same as understanding the decision. That distinction matters in financial planning. A financial plan can show income, assets, liabilities, savings rates, insurance,

Vitalik Buterin, one of the co-founders of Ethereum, recently used a phrase that caught my attention. He was talking about the advantages and dangers of concentrated power. A dictator can make decisions quickly. There are fewer committees, fewer negotiations and fewer people who have to agree before something gets done. But, obviously, there is another side to that power. Without boundaries, accountability and consequences, concentrated authority can become destructive. Buter

Part 3 of 3: Three Questions That Reveal Your Financial Strength Financial planning can become complicated quickly. Investments, taxes, retirement, insurance, debt, estate planning, and changing markets all compete for attention. However, before evaluating individual strategies or financial products, PlanAssist begins with three questions: Is your lifestyle aligned with your income? Is your income diversified and resilient? Are you making progress on both? The questions sound

Part 2 of 3: Three Questions That Reveal Your Financial Strength Financial planning can become complicated quickly. Investments, taxes, retirement, insurance, debt, estate planning, and changing markets all compete for attention. However, before evaluating individual strategies or financial products, PlanAssist begins with three questions: Is your lifestyle aligned with your income? Is your income diversified and resilient? Are you making progress on both? The questions sound

Part 1 of 3: Three Questions That Reveal Your Financial Strength Financial planning can become complicated quickly. Investments, taxes, retirement, insurance, debt, estate planning, and changing markets all compete for attention. However, before evaluating individual strategies or financial products, PlanAssist begins with three questions: Is your lifestyle aligned with your income? Is your income diversified and resilient? Are you making progress on both? The questions sound

Political arguments about money usually begin at the top. What should government do? How should businesses behave? Should taxes be higher or lower? Who should pay for what? Those can be legitimate questions. But they can also distract us from a much more immediate question: What am I responsible for? That is where first-principles thinking becomes useful. Remove the Politics Milton Friedman spent much of his career debating economic systems, incentives, government, markets, a

Financial decisions can become complicated quickly. Investments. Taxes. Retirement. Social Security. Insurance. Real estate. Debt. Estate planning. Each subject has its own rules, terminology, strategies, and opinions. Add financial news, market predictions, social media, and well-meaning advice from friends, and it becomes easy to mistake more information for greater clarity. That is why I believe good financial decision-making should start somewhere simpler. Start with what

Most financial principles are not new. Living within your means is not new. Diversification is not new. Maintaining liquidity is not new. Preparing for risk is not new. Seeking qualified counsel is not new. These ideas have been taught, tested, forgotten, and rediscovered for generations. PlanAssist does not claim to have invented them. Its purpose is to bring established principles together, show how they are connected, and organize them into a practical framework for buildi

Why Building Your First $100,000 Changes Everything When someone begins earning a steady income, the financial conversation usually starts with investing. Which funds should I buy? Should I invest aggressively? Should I use a Roth IRA or a traditional 401(k)? Those are reasonable questions. However, they may not be the most important questions at the beginning. The first challenge is simpler and more difficult: How quickly can you build your first $100,000 of invested assets?

I watched a video from Cody Gunn, CFA, on eight assets that wealthy retirees often avoid. The point was not that every item on the list is always bad. The better point is that many things people call “assets” can quietly become liabilities once you account for cost, complexity, liquidity, and opportunity cost. That matters because retirement is not just about owning more things. It is about having more freedom. If any of these items are part of your financial picture, the que

Most people spend too much energy focused on things they cannot control. They cannot control the economy. They cannot control inflation. They cannot control interest rates. They cannot control tax law changes. They cannot control what their employer does, what their adult children do, or what the market does next. Those things matter. They can affect your life and your money. However, they are not where financial progress begins. In my opinion, most financial progress starts

Why Successful Investors Forgive Fast and Plan Forward Most investors spend a great deal of time thinking about what they should have done. They should have bought that stock sooner. They should have sold before the decline. They should have contributed more to their retirement account. They should have started planning years ago. The problem is that financial success is not built on perfect decisions. It is built on making the next good decision. Behavior expert Chase Hughes

Some retirement products solve real problems. Others introduce complexity, high costs, limited liquidity, or tradeoffs that are not fully understood until years later. Retirement planning often happens during periods of uncertainty. People worry about taxes, market volatility, healthcare costs, income stability, and protecting what they have spent decades building. That uncertainty can make guarantees, protection strategies, and specialized financial products sound extremely

The Timeless 80/20 Rule, Proven Across 2,000 Years Opening Thought Today, economists often point to the 80/20 rule. A small percentage of people typically produce a disproportionate share of results, wealth, leadership, innovation, and long-term progress. Modern retirement data reflects this reality clearly. A relatively small percentage of households hold the majority of retirement assets, not necessarily because they earned dramatically more, but often because they consiste

Every year for the past decade, the market handed investors a seemingly logical reason to step aside. Brexit. A trade war. A global pandemic. Bank failures. AI bubble fears. Tariffs. And now, in 2026, geopolitical tension in Iran and an oil spike. The list reads like a highlight reel of anxiety — and every concern was real. Yet investors who stayed the course through all of it saw the S&P 500 return +200% plus over that ten-year period, dividends reinvested. The List Here ar

In the 1950s, Earl Nightingale delivered his iconic speech The Strangest Secret , painting a stark picture of financial outcomes for 100 young people starting out even at age 25. By the time they reached 65, he observed: only 1 would be rich (truly affluent), 4 would be financially independent (comfortable without struggle), 5 would still be working, and 54 would be broke or dependent on others for life's necessities. The math didn't add up perfectly to 100—likely reflect

Simple principles that guide better financial decisions Most successful investing does not come from predicting the next market move. It usually comes from following a small number of disciplined habits over many years. Markets change. Headlines change. New technologies appear. However, the core behaviors that lead to long-term success tend to stay the same. Below are seven habits widely practiced by experienced investors. Each one supports the same goal. Make thoughtful dec

Artificial intelligence is improving at an extraordinary pace. Tools like ChatGPT and Grok today are dramatically more capable than they were just two years ago. At times, it feels almost effortless. AI can draft emails, summarize reports, explain tax rules, compare investment strategies , and walk through retirement scenarios in seconds. It can translate complex topics into plain language and help users explore ideas quickly. That is real progress. Some headlines suggest

Elon Musk often describes “first-principle thinking” as breaking a problem down to its most basic truths and building back up. The same idea applies to personal finance. When you strip away products, predictions, and noise, nearly every financial decision rests on three first principles. These principles explain why some choices support long-term stability while others create unnecessary stress. They do not change with markets or headlines. They form the foundation for bette