I've had this conversation at least a dozen times in the past few months. Usually, it starts something like this:
"The market keeps going up. We have to be near the top, right? Should I be getting out now before it all comes crashing down?"
It's a fair question, especially when the Dow broke 48,000 for the first time this month. It's natural to feel nervous when you see your portfolio at record levels and wonder if you're about to watch it all evaporate.
But here's what I've learned after years of having these conversations: "Are we at the top?" is the wrong question.
And acting on it can cost you real money.
Here in Bridgeport, West Virginia, I've been having these conversations with clients across the state—from Morgantown to Charleston, Huntington to Parkersburg. Whether you're a retiree in the Eastern Panhandle or a business owner in the New River Gorge, the question is always the same: "Are we at the top?"
The Market Can't Go Up Every Day
I find myself saying this to clients a lot: "The market can't go up every day. If it did, I wouldn't have a job. No one would need me."
It's true. If investing were as simple as buying and holding while stocks climbed forever in a straight line, you wouldn't need a financial advisor. You could set it and forget it, never look at your statements, and retire wealthy with zero stress.
But that's not how markets work.
Markets go up. Markets go down. Sometimes they go sideways for years. There are bull markets and bear markets, corrections and crashes, rallies and pullbacks. The volatility and the uncertainty is a big reason why people like me exist.
Our job isn't to predict when the market will peak or crash. Our job is to help you build a plan that works regardless of what the market does next.
Time in the Market Beats Timing the Market
Let's talk about what happens when investors try to time the market.
You've probably heard the phrase "time in the market beats timing the market." It sounds nice, but what does it actually mean?
It means that historically, staying invested through ups and downs has produced better results than trying to jump in and out at the "right" times. Why? Because:
- Missing the Best Days Destroys Returns: A huge portion of the market's gains happen on just a handful of days. Miss those days because you're sitting in cash waiting for a pullback, and your returns suffer dramatically.
- No One Knows When the Top Is: Even professional fund managers can't consistently predict market tops and bottoms. If they could, they'd all be billionaires. They're not.
- Getting Back In Is Harder Than Getting Out: It's relatively easy to sell when you're scared. It's much harder to buy back in after the market has already recovered, because by then, you've missed the rebound.
Here's the reality: The S&P 500 has historically closed at an all-time high 6.6% of the time, about 1 out of every 15 trading days. In other words, all-time highs are normal. They're not warning signs. They're what happens in a healthy, growing market.
Early in my career serving West Virginia families, a technical analyst at RBC named Bob Dickey told me something that's stuck with me ever since: "The market will always go farther and longer than anyone anticipates, both up and down."
That's wisdom worth remembering when you're tempted to sell at what feels like a peak or buy at what looks like a bottom.
Buy Low, Sell High (It's Harder Than It Sounds)
Everyone knows the golden rule of investing: buy low, sell high. It's simple. Obvious. And incredibly difficult to execute.
Why? Because buying low means investing when everything feels scary and uncertain. It means putting money to work when headlines are screaming doom and your gut is telling you to hide under the covers.
And selling high? That means taking profits when everything feels great, when your portfolio is hitting new records, and when everyone around you is convinced, the party will never end.
The emotions work against you at every turn.
This is where having a disciplined strategy and an advisor to help you stick to it becomes invaluable. Because while you can't predict the market's next move, you can position yourself to take advantage of opportunities when they arise.
Shaving Cream Off the Top: The Case for Strategic Profit-Taking
Here's something worth considering when markets are at or near all-time highs: harvesting some gains to keep dry powder on hand.
I'm not talking about selling everything and sitting on a cash stockpile. That's market timing, and we've already established why that doesn't work, but strategically trimming positions that have run up significantly? That can be smart portfolio management.
Think of it like shaving some cream off the top. You're not abandoning your strategy. Rather you are:
- Taking some profits while they're available (that's the "sell high" part)
- Creating liquidity that gives you flexibility if the market pulls back
- Positioning yourself to buy quality investments at better prices if opportunities emerge (that's the "buy low" part)
When the market does eventually correct, and it will, you'll have cash ready to deploy. You'll be the investor who can take advantage of the pullback instead of the one panicking and selling at the bottom.
This isn't about predicting the top. It's about being prepared for whatever comes next.
Remember Bob Dickey's wisdom: the market goes farther and longer than anyone anticipates, both up and down. So when your portfolio has had a strong run, consider whether it makes sense to lock in some gains and build your reserves. That way, whether the market continues climbing or takes a breather, you're positioned to benefit.
Quality Over Quantity
One of the most valuable things we do during uncertain markets is help clients evaluate what they own, not just how much they own.
When markets are hitting all-time highs, it can actually be a great time to do some housekeeping:
- Trim low-quality positions: Maybe you're holding onto a stock that's underperformed for years because you "don't want to sell at a loss." But if that money could be working harder elsewhere, holding on is costing you opportunity.
- Rebalance to your target allocation: When stocks surge, your portfolio can become overweight in equities. Rebalancing back to your target risk level protects you if there's a pullback.
- Upgrade to higher-quality investments: If you own funds with high fees or poor performance, replacing them with better options can improve your long-term returns, even if it means realizing some gains now.
None of this is about timing the market. It's about positioning your portfolio for long-term success regardless of short-term market movements.
It's Not About Getting Rich Quick
Here's the uncomfortable truth: there's no shortcut through the markets.
You can't outsmart decades of market history by jumping in and out at the "perfect" times. You can't avoid every downturn. You can't capture every rally.
What you can do is:
- Build a plan based on your goals, risk tolerance, and timeline
- Stay disciplined through market ups and downs
- Make adjustments when your situation changes, not when the market scares you
Investing isn't a get-rich-quick scheme. It's a get-rich-slowly process that rewards patience, consistency, and discipline.
The Entry and Exit Point Myth
Clients often ask: "When should I get in? When should I get out?"
The honest answer? It depends entirely on your situation.
Your entry and exit points aren't determined by what the market is doing today. They're determined by:
- Your timeline: Are you retiring in 2 years or 20 years?
- Your risk tolerance: Can you stomach a 20% drop without panicking, or does that keep you up at night?
- Your goals: Are you saving for retirement, a home, or college tuition?
- Your tax situation: Do you have capital gains to offset? Are you in a high tax bracket this year?
Two people can look at the exact same market and make completely opposite decisions, and both can be right, because their situations are different.
This is why personalized financial planning matters. Cookie-cutter advice doesn't work. What's right for your neighbor might be wrong for you.
So, Are We at the Top?
I don't know. And neither does anyone else.
What I do know is this:
- In two of the four previous years when the S&P 500 set 55+ all-time highs (1964 and 1995), the market gained the following year. In the other two years (2017 and 2021), the market eventually pulled back.
- Over the long term, the stock market has consistently climbed to fresh all-time highs, even after bear markets, and often sooner than you might think.
- Valuations are elevated, but analysts forecast S&P 500 companies will report earnings growth of 15.1% for the full year 2025, which could justify current prices if those forecasts come true.
The point is: we can't control what the market does next. We can only control how we respond.
The Better Question
Instead of asking, "Are we at the top?" here are better questions:
- Does my current investment strategy still align with my goals?
- Am I properly diversified for my risk tolerance and timeline?
- Have I revisited my financial plan in the last 6-12 months?
- Do I have adequate cash reserves or dry powder if opportunities arise?
- Am I making decisions based on my plan or based on fear and headlines?
These are the questions that lead to better outcomes. These are the questions that help you build wealth over time instead of chasing performance and reacting to market noise.
Final Thought
The market will eventually pull back. It always does. But it will also eventually recover and reach new highs. It always does.
The investors who succeed aren't the ones who perfectly time the market. They're the ones who stay invested through the noise, stick to their plan, and make adjustments based on their life, not based on what CNBC says today.
If someone can do it better than me on their own, I absolutely support them. They don't have to pay me, and they could get better returns. But usually, they don't have the time to monitor their accounts to the extent that I can, nor do they have the experience or insights that come from doing this full-time for years.
That's not arrogance. That's just reality.
So if you're sitting there asking yourself, "Are we at the top?" let's have a different conversation. Let's talk about your plan, your goals, your risk tolerance, and whether your current strategy still makes sense for where you are in life.
Because that's the conversation that actually matters.
Ready to stop worrying about market timing and start focusing on what you can control? Let's talk. Together, we can build a plan that works for you—no matter what the market does next.
This information is for educational purposes only and should not be considered investment advice. Past performance does not guarantee future results. Please consult with a qualified financial advisor before making investment decisions.