Is This A Good Time To Invest? (A Tale Of Two Markets)

"It was the best of times, it was the worst of times, it was the age of wisdom, it was the age of foolishness..."

― Charles Dickens, A Tale of Two Cities

[A special note up front: I wrote this post in February 2021 and updated in on 29 July 2025. Any reference to investment gains or losses is relative to market prices at the close of business on Monday, July 28 2025. BUT, I am so confident that the message I want to share is timeless that I don’t care that the exact numbers will be out of date by the time you read this. In fact, as I’ll share, I think that whatever happened in the intervening weeks, months, or even years should hardly matter at all when it comes to how you invest your money.]

A few years ago, after I had moved to Durham NC but before I started my business, I was having lunch with an old buddy of mine. For context, I’ll mention that I always admired how my friend seemed to balance financial responsibility with quality of life, even in his 20s. He seemed to be operating from a different playbook than most of the people I knew.

To the best of my memory, this lunch happened sometime in 2018 – when I happened to be investing a lot of my money – and somehow, probably because of me, the conversation turned to investing. I asked my buddy what he does with his investments and, in a nutshell, he told me that he had been sitting on a fair amount of cash, but didn’t know if it was the right time to invest or not. The markets seemed turbulent and risky and, in fact, there was about a 16% sell-off by the end of that year that most people don’t even remember anymore.

The reason that people don’t remember that late 2018 market decline is because of what happened over the next five and a half years. Hindsight being what it is, we can look back and know that of course 2018 was a great time to invest. Let’s say that by complete coincidence my buddy happened to invest some money in an S&P 500 index fund on the exact date that it peaked in 2018. That investment would now be up about 119%. Amazing, right??? He would have more than doubled his money by investing in a simple stock market index fund and patiently waiting.

So why didn’t he do it? Why did he sit on all that cash instead of investing it? Well, as I mentioned, in the short-term things felt risky. And when the market dropped at the end of 2018, he probably felt pretty smart for sitting it out. But on the other hand, we know that if he had invested his money – even at the peak before that 16% decline – he would have more than doubled it.

This is one of the great paradoxes of investing: it always feels like the wrong time to invest, like danger is right around the corner, while simultaneously feeling like you should have already invested at some previous date that you missed. Right? It feels like the past was a great time to invest, but the present is too risky – the irony being, of course, that the past also felt risky when it was the present.

One of the most common questions I get from people who are nervous about investing is: is this a good time to invest? The fear is that you would invest your hard-earned money, only to watch the market drop and some portion of that money evaporate.

And, if all we're thinking about is the short-term, then yes – investing a bunch of money right before the market crashes is the worst. It totally sucks. So I’m not saying that people should somehow be immune to their emotions. We’re emotional creatures, and it’s been well documented that we feel the pain of loss about twice as much as the joy of gain.

What I am saying, though, is that we are, by nature, a long-term species. With any luck, you will live a long and eventful life, which means that you need to think about both safety in the short-term and prosperity in the long-term. So, while short-term losses certainly hurt a lot, I don't want that security to keep you from making great long-term investments for two main reasons.

The first is that the feeling of insecurity simply will never go away. If you’re waiting until it feels safe to invest, you’ll be waiting the rest of your life. And, like my buddy in this story, you’ll miss out on all the growth that kept quietly chugging away while you were on the sidelines waiting for it to feel safe.

And the second reason I don’t want you to let short-term fears keep you from investing for the long-term is that in the context of the entire rest of your life, what the stock market does in the short-term DOES NOT MATTER. Let me say it again: it truly does not matter what happens to your investments today or tomorrow or next week when viewed in the context of the next ten or twenty or fifty years.

I truly believe that the best time to invest your money is whenever you have extra money.

Everyone should maintain a savings cushion of at least 3-6 months worth of expenses, and you shouldn’t invest any money that you need for short-term goals like a vacation or car purchase or a mortgage down payment. Ok? Never invest money that you need right away.

But if you have more than what you need for the short-term, then you should be putting it to work for you by investing it. You don’t need to put it all in at once, you don’t need to choose the riskiest investments, but you DO need to invest your money for more & better options in the future. And the best time to do that is when you have the money.

Conversely, the worst time to invest is when you don’t have money. If you’re having a hard time keeping up with expenses or you’re up to your neck in debt, don’t invest. That money is needed elsewhere.

Notice, though, that in both of those scenarios – when to invest, when not to invest – I haven’t said a single word about what’s happening in the stock market. Because again, in the context of the entire rest of your life, I don’t think what’s happening in the markets right now matters all that much.

What matters most is that you invest what you can, when you can, and stay invested for a long, long time.

I want to share three historical anecdotes from my own life to put this in perspective.

The Great Recession

I made the decision to leave my job as a recording engineer in favor of more promising (and profitable) opportunities as a touring audio engineer sometime in 2008 or 2009. My recording studio salary had been enough to pay my bills in relative comfort for several years, but it wasn’t until my touring career took off around that time that I really started earning a decent income.

Of course, this was also in the midst of the housing market collapse, which would lead to a stock market collapse, which would lead to The Great Recession. This was a risky time to leave a steady job for an unstable career on the road. If ever there was a time to avoid having money tied up in the stock market, that was it.

Now, I hadn’t actually started investing at this time. In fact, I didn’t even know it was possible for someone like me TO invest. But if I had invested in an S&P 500 index fund on Oct 09 2007 – the market peak before the crash, the absolute worst time to invest – that investment would now be worth over 300% more than I paid for it. To put it in more concrete terms, if I had invested $1,000, I would now have over $4,000. So investing at the absolute worst time in the short-term would still have tripled my money in the long-term, just by being patient and holding those investments.

Now let’s look back a little further back in time.

The Dot-Com Bubble

I turned 21 while playing a concert at Harvey’s On The Mall in Kalamazoo MI, where I went to school. Bands loaded in through the back staircase at Harvey’s, which meant avoiding the ID check at the front door and, because I had been playing shows there since I was 18, the staff knew who I was by this point. And, to cut to the chase, I *slightly* took advantage of that to order drinks that I shouldn’t have been drinking at that age. I remember the look on my favorite bartender's face when we celebrated my 21st birthday from the stage – which was a mixture of amused and angry.

Coincidentally, there was also a massive stock market sell-off on the previous date. See, my birthday is on tax day and a lot of investors were selling stocks to cover the taxes owed on gains realized in the previous year before the tax filing deadline. This was the midst of the Dot-com Bubble, in which the valuations of tech stocks plummeted 78% in seven months. If ever there was a time to avoid having money tied up in the market, that was it.

The NASDAQ 100 index mostly tracks tech stocks, which were the hardest hit in the Dot-Com Bubble. If I had invested in a NASDAQ 100 index fund on Mar 10 2000 – the market peak before the crash, the absolute worst time to invest – that investment would now be worth over 900% more than I paid for it. So if I had invested $1,000 on March 10th of that year, it would now be worth over $10,000. Again, buying at the absolute worst time would still give you more than 9 times your original investment if you were patient and stayed invested for the long term.

Here’s the last anecdote.

Black Monday

I was very interested in post-season baseball in the autumn of 1987. My beloved Detroit Tigers – having won the championship three years prior – finished the regular season with the best record in baseball. Despite having power hitters Chet Lemon, "Sweet" Lou Whitaker, and Kirk Gibson, the legendary double-play duo of Alan Trammell and Whitaker, and all-star pitcher Jack Morris on the mound, the Tigers lost the American League championship series 4-1 to the Minnesota Twins. It was very disappointing for me.

One week later, the Dow Jones Industrial Average would lose 22.6% in a single day, the largest one-day drop for that index up to that point. That date would earn the ominous nickname Black Monday because it was soooo dark. If ever there was a time to avoid having money tied up in the market, that was it.

Now, I was, in fact, too young to invest money in 1987. But if my parents had invested in a DJIA index fund on Aug 25 1987 – the peak before the crash, the absolute worst time to invest – that investment would now be up more than 1,500%, turning $1,000 into more than $16,000.

So what’s the takeaway from these three examples? It’s that what seems like a bad, risky, turbulent time to invest – possibly the absolute worst time to invest – in the short-term doesn’t really matter when you zoom out and put it in perspective to the rest of your life. It’s that paradox again: it always feels risky right now, while simultaneously feeling like the past was a much better, safer time to invest.

So forget about the news, forget about what the stock market is doing today or this week or this month or this year. The best time to invest your money is when you have it, and the best things to buy are investments you can own for a long, long time.

Ok, maybe everything you've read so far makes sense but you STILL aren’t sure if this is the right time. Well, luckily there are ways that you can invest that take some of the stress out of the process.

One way is to choose investments that reduce short-term risk. When I manage investments for clients, I always balance less risky investments like bond funds against riskier investments like stock funds. That way you can get the right amount of growth for you & your timeline while also smoothing out some of the peaks & valleys along the way.

Another way you can minimize the short-term risk is to consistently invest a small-ish amount of money in regular intervals, like weekly, every other week, or every month. So instead of investing $1,000 all at once today, you could invest $100 per month for the next 10 months. By spreading out your contributions, you help reduce the risk that you’ll put your money in right before a market drop. And if you automate those contributions it can feel totally effortless.

Finally, you can make investing easier by choosing investments that you can own forever, like low-cost index funds. If you choose things you can own for the rest of your life, then you’re slightly immune to the short-term trends & fads that get a lot of attention in the financial media.

In summary: short-term stock market drops feel really bad and, truthfully, are unavoidable. There’s no way around that. Less visceral, but much more powerful are the long-term gains that come to those who invest in things they can own for a very, very long time. Instead of focusing on when to buy, just aim to consistently invest whatever you can whenever you can, then do that over and over again for as long as you can. It is not only one of the simplest strategies for investing, but also one of the best.

Timothy Iseler, CFP®

Founder & Lead Advisor

Iseler Financial, LLC | Durham NC | (919) 666-7604

Take control of your financial future. We help you bridge the gap between your creative passion and your financial health with values-based investing & financial planning specifically tailored for artists, creatives, and self-employed professionals. Find out if we're a good fit.