The three-year period from 2021 through 2023 was an extraordinary time in my life. After a career in building financial plans, managing investment portfolios, and advising successful business owners, I took the plunge into entrepreneurship. Stepping away from wealth management, I co-founded VEL. The company’s mission at the time was simple: to help remote workers and freelancers be more productive by addressing pain points, such as lack of privacy, terrible Wi-Fi, long wait times, and wobbly tables, that many of us have experienced while working in coffee shops. We had the solution! (That’s for a different blog.)
While the goal was simple, starting and running the company proved very difficult. In the early days, my co-founder and CEO would stress the importance of being able to “peek around the corner.” You see, in business, success often depends on anticipating change, identifying emerging opportunities, and preparing for potential threats. In a startup, these seem to appear way too frequently. Contractors not meeting expectations, equipment arriving damaged, and delayed permits are just a few examples of factors that threatened to derail our timeline.
After some hard lessons, I got better at it over time. But recently, I’ve been thinking about how this skill relates to financial planning and investing in the stock market. Core planning tenets, such as being honest about one’s spending habits and recognizing current and potential risks, are critical. But when it comes to investing, that same instinct to forecast what’s coming next can actually be one of the most destructive habits an investor can have.
The best investors avoid making decisions based on short-term forecasts, gut instincts, or the latest headlines. Instead, they follow a disciplined, carefully considered plan. They understand that over the long term, markets reward patience, diversification, and consistency, not clairvoyance.
Letting go of the day-to-day control is one of the hardest lessons for successful business owners and professionals to internalize: what works in business often backfires in investing.
Great business leaders are visionaries. Without the Steve Jobs and Howard Schultzes of the world, we would all be living very different lives. They look ahead, predict where markets or technologies might move, and position their companies accordingly. They thrive on anticipating what others can’t see yet. This ability to foresee changes in technology, regulation, consumer preferences, or competitive dynamics can mean the difference between thriving and fading away.
A founder who built an e-commerce platform before the pandemic probably didn’t get lucky. They saw where consumer behavior was heading. A manufacturer who began re-shoring supply chains years before global disruptions was planning ahead and reaped the benefits when others were caught off guard.
This kind of foresight is not only valuable, it’s necessary. Business leaders must plan ahead, make bold bets, and constantly adjust course. When you run a company, standing still is dangerous. So, it’s no surprise that many successful entrepreneurs bring that same mindset to investing. But trying to forecast economic data, move in and out of the market based on valuations, or time interest-rate cycles is a formula for underperformance. Unfortunately, the market doesn’t reward that behavior the way business does. When investing in the great companies of the world, standing still (i.e., holding your positions through various market cycles) actually pays off!
The stock market doesn’t respond neatly to our forecasts. When you attempt to get ahead of the news or data in investing, you’re predicting something that’s already priced in. The market has already digested the known facts and expectations. By the time we’ve spotted an opportunity, thousands of professional investors have already acted on it.
That’s why trying to outguess the market rarely works. Decades of research show that even professional fund managers with teams of analysts and access to real-time data struggle to consistently outperform simple, low-cost diversified portfolios.
When investors “peek around the corner,” they’re usually acting on hunches, headlines, or emotion, and not on actionable intelligence. They might feel confident because their reasoning sounds logical: “The economy looks weak, so I’ll move to cash,” or “Rates are rising, so bonds will fall.” But markets don’t move on logic alone. They typically move on surprises that investors didn’t see coming.
A large part of the challenge is psychological. Successful people tend to be confident, proactive, and comfortable solving problems. They’ve built careers by seeing patterns, acting decisively, and taking calculated risks. But markets aren’t a problem to be solved. They are the culmination of millions of investors’ expectations, both rational and irrational. When you try to “outsmart” that collective wisdom, you’re essentially betting that your insight is better than everyone else’s combined. That’s a tough wager to win consistently.
This is why even brilliant minds fall into the same trap: they conflate intelligence with predictive ability. They believe that because they understand macroeconomics or corporate strategy, they can anticipate how the market will react. But understanding something after it happens doesn’t mean you could have predicted it.
In business, your edge comes from knowledge, experience, and execution. In investing, your edge comes from temperament — from being able to sit still, stick to a plan, and ignore the noise.
An advantage of having a financial plan is that it replaces prediction with preparation. Instead of guessing what the market or economy will do next, a well-thought-out plan aligns your money with your life. A good plan assumes volatility will happen and prepares for it, rather than trying to avoid it. It’s a roadmap that helps you stay invested when others panic, rebalance when others chase returns, and make rational decisions when emotions run high.
The best investors focus on what they can control, like their savings rate, asset allocation, taxes, costs, and behavior. They accept what they can’t control, like short-term market swings.
If you look at long-term market data, the rewards for staying disciplined are clear. Despite wars, recessions, elections, and pandemics, the S&P 500 has delivered roughly 10% annualized returns over the past 100 years. Those returns weren’t earned by predicting each twist and turn. They were earned by staying invested through them.
Here’s the irony: investors who stop trying to “peek around the corner” often end up seeing the big picture more clearly. When you no longer react to every piece of news or every market dip, you begin to see the market for what it really is: a long-term compounding machine comprised of exceptional companies powered by human innovation and productivity. Trying to time the next move distracts you from what truly drives wealth: time in the market.
If you want to build wealth, patience beats prediction every time. Making decisive changes based on accurate forecasts and spotting trends before the competition are survival skills in business. It’s what keeps you competitive, agile, and ahead of the curve. But in investing, it’s a liability. If you have a well-constructed plan that aligns your portfolio with your goals, you don’t need to try to predict the next dip. You need to confidently stay on the agreed-upon path, knowing there will be bumps along the way.
Business rewards action; markets reward discipline.
Business requires foresight; investing requires fortitude.
Business is about control; investing is about confidence in the long-term trend.
For those who built their wealth by being proactive and decisive, this mindset shift can feel unnatural. But it’s also liberating. Once you stop trying to guess the next move in the market, you can focus on what truly matters: enjoying life, running your business, and letting your money work quietly in the background.
Because in the end, the best investors don’t peek around corners. They build a plan, stay the course, and let time do the heavy lifting.