Waiting for a Better Time to Invest
Hannah reached out last week to say she inherited $350,000 almost a year ago and hasn’t invested a dollar of it.
It’s been sitting in cash since last April.
And to be fair, April didn’t exactly feel like a great time to invest. Liberation Day tariffs had just been announced, markets were sliding, and suddenly everyone was talking about a global trade war. It didn’t feel like the moment to plow a large lump sum into global stocks.
So she did what many investors say they’ll do and waited for things to settle down.
Except they didn’t really settle down. The headlines stayed messy, the outlook stayed uncertain, and yet the market moved higher anyway. Global equities are up more than 30% since they bottomed on April 8th. There was no “all clear” signal for investors to jump back into the water.
Now it’s March 2026.
Hannah is still in cash. The news still isn’t great. And she’s asking whether she should invest now or keep waiting.
I think about this a bit differently.
I own VEQT in my entire portfolio. I see the same prices. I read the same headlines. If markets feel expensive or the outlook feels shaky, none of that information is hidden from me.
And yet I’m not selling.
So if those same conditions aren’t enough to make me sell, why are they enough to keep someone else from buying?
Because staying in cash isn’t a neutral decision. It feels like one, but it isn’t. It’s a shift from a long-term plan to a short-term one where you’re waiting for a better entry point.
That sounds reasonable until you try to define what “better” actually looks like.
Lower prices would do it, but markets don’t tend to announce those in advance. More reassuring headlines might help, but by the time the news improves, markets have usually already moved. The market tends to lead the news, not follow it.
I’ve seen this play out over and over again. People go to cash or stay in cash, thinking they’ll step in when things look clearer.
Instead, they get stuck. The market starts to recover, but the headlines still sound bad, so they wait. Then prices move higher, and now it feels even worse to buy. Eventually they either buy back in at higher prices or they stay on the sidelines longer than they ever intended.
You don’t have to be right once. You have to be right twice. When to get out and when to get back in. That second decision is the hard one, because it rarely feels obvious in real time.
That’s why I don’t try to sidestep the bad periods.
The stretches where markets fall are uncomfortable, even scary, but they’re also part of the deal. That volatility is what you endure in exchange for higher long-term returns. If you try to avoid it completely, you usually end up avoiding part of the recovery too.
Anyone can stay invested when things are going up. The decision that matters is what you do when things feel uncertain, because that’s when people are most tempted to change course.
Hannah didn’t invest because things felt uncertain, and the market went up anyway. Now things still feel uncertain, and she’s wondering if she should wait again.
At some point you have to decide whether uncertainty is a reason to stay in cash or just the normal backdrop of investing.
Because if you’re waiting for things to feel better, you’re probably also waiting for higher prices.
I take it then you aren’t a fan at all of a rules based momentum component to a portfolio?
I’m a fan of evidence and simplicity.
This is the way
Am I correct that the prevailing facts are that 9 times out of 10 it works just to go all in? And the plan B for someone like Hannah is, at the very least, to consider dividing the cash by a number (6, 12?) and DCAing a buyin of some kind (e.g. per month) to at least get in and not sit on the sideline? I would hope that Hannah at least got into HISA or CASH.
I may have a similar decision to make within a year or so and I’ve been wondering about all in versus DCA. Though I have to deal with some shorter time horizon requirements too.
I would just buy assets as soon as the money is available. More likely to gain vs “dividing the cash” but even if you don’t the difference will get lost in the noise over investment horizon. Always deploying cash as soon as it becomes available = the simplest and the best strategy.
This is the way.
I did the same with an inheritance. Went all in. Banks pay almost zero interest on savings accounts, so really, it was a no brainer.
Great article Robb. Very reassuring and true.
Hi Brad, the research suggests that investing a lump sum immediately beats dollar cost averaging about 2/3 of the time. And, importantly, as Mordko mentioned, the 1/3 of the time that it didn’t beat DCA doesn’t mean that it was a disaster – returns just slightly trailed.
And, unfortunately, Hannah’s money sat in a big bank savings account earning very little.
Worse than earning very little in interest. Inflation is the silent thief of her spending power.
She probably lost a considerable amount in real dollar terms.
As they say, the best time to invest is when you have the money. It sounds like this person has the money, so now is the best time for her. It doesn’t hurt that the S&P 500 is down for five consecutive weeks.
Not enough info. Is this money for retirement. How old is Hannah ? Does she have a spouse? Or mortgage ? How long is her investment horizon?
Does not really matter. If she is planning to invest then trying to time it is a bad strategy.
Assume she *wants* to invest in global equities. She knows it’s the right thing for her situation. Behaviourally, she can’t bring herself to do it and she doesn’t have enough knowledge of markets to know that timing this decision is futile.
I see this time and again with folks and when I was earlier in my career I appeased to the emotional salve and delay of DCA, and now I strongly encourage a head first into the deep end approach consistent with the weight of historical data for it.
If she can’t bring herself to do it behaviourally, then a 100% stock allocation is likely not right for her.
Definitely! Never 100% in stocks! May as well go to Vegas!
Hi Sheila, perhaps if you’re picking individual stocks it might be considered gambling (stocks can and do go to zero), but a basket of global stocks has a positive expected return.
That’s a fair point. Though I do find that balanced / conservative investors can be just as skittish as more aggressive investors when markets fall. It’s all about regret minimization, and we feel the pain of losing twice as much as we derive pleasure from an equivalent gain. Not an easy problem to solve, despite mounds of supporting evidence.
Not necessarily. It all depends on her circumstances. You haven’t been reading Robb’s articles or have forgotten. Even with a 50% decrease in the market, she would still have 50%. A Vegas gamble would have her lose 100%. Study the market. Yes it goes down, but it also goes up and goes up more than down over time.
What Robb is trying to get across is that being ultra conservative in the long run is a losing strategy. You buy a GIC paying 3.8% and inflation will take about 2% and taxes will take about 1%. Can you realistically call that an effective investment? No it isn’t Vegas.
Oh dear, oh dear. I hope Hannah is a young investor with a long time horizon and a strong constitution.
Oh Garth, you’ve been quiet lately. Have the bears come out of hibernation? Perhaps we should teach Hannah about cup handles and candle sticks to figure this out instead of relying on mountains of evidence to support the fact that stocks have a positive expected return.
How young is young, by the way? At 60, one might still have 1/3 of their life to live. Should they go to cash?
The reason I’ve been quiet lately is because you unilaterally ended our thread in a huff on April 6, 2025. At that time, I said I’d check back in “18 to 24 months later”. I was going to stay mum until then, but when I saw your post today suggesting an inexperienced investor go full port with $350,000 in a highly volatile market with serious underlying issues I felt it was time to wade in with a PSA. Hannah might want to consider a few facts:
1. All major indices have been in distribution for the past six months. Large institutions have been dumping the whole time. Market breadth is terrible.
2. This past week both SPX and NDX (and VEQT) sliced through major support, closing below their respective 200 MAs, confirming the downtrend. Not exactly an ideal time to go long with $350,000.
3. The U.S. economy is being managed by a deranged lunatic and his servile minions. The current oil supply shock will have lasting repercussions on the global economy if it is not resolved soon. Inflation is rising, and the bond market and financials are showing signs of severe stress.
4. The average intra-year drawdown of SPX in a mid-term election cycle is approximately 17% to 18%. Considering we’re down only 9% from ATH we may have a ways to go still. Will we get there? I have no idea. Will we see new highs this year? I have my doubts.
Whatever the case, I’ve learned to park my opinions on what the market will actually do and just wait for price action to signal when it’s time to buy and sell specific sectors. More broadly, a Zweig Breadth Thrust signal will trigger indicating the worst is over for most sectors and it’s relatively safe to go long. If/when that happens I won’t get bogged down by what I think, or what so-called experts have to say.
Nevertheless, I do owe you a big thanks for posting that self-congratulatory note earlier this year, which nearly top-ticked the market. Whenever I see market participants bragging about their gains I know it’s time to start taking profits and amass a cash pile.
As for my “bearishness”, I did exactly what I said I would in our exchange last year: I went overweight in metals and precious metals, especially gold and silver. Turned out better than I could have imagined. I closed all those positions after they went parabolic, bought the dip, and then sold again on their second parabolic runs. At the same time I rotated heavily into oil and gas. I exited 75% of my holdings when oil spiked to $119. Still holding a modest position, but with a tight stop. Does this make me a perma-bear?
As for VEQT, you are up about 9.5% from last year’s high. Allowing for 2% inflation, that translates into an overall annual gain of about 7% during an epic bull market run. Good for you!
Happy to keep this thread going, or revisit in 6 to 12 months from now as planned.
Imagine mocking the returns of someone who is invested in a sensible global index fund as if he’s simultaneously in the riskiest position possible but also in a boring low return fund.
Did it feel good to type all of that? The Dunning–Kruger effect is real.
I’ve got you on record in early July saying VEQT was forming a “bearish candle”. Did it take eight months to materialize?
Or is it more likely that stock returns are random (with a positive expected return)?
My, my. Someone is getting triggered.
Read what I actually wrote and you’ll see I said a bearish engulfing candle is not a reason to sell, but merely a warning sign. The same can be said of parabolic moves and big rejection wicks. They are conditions, not signals. These signals became extreme over the past few months and so I started taking profits (and cutting losses) in February. Glad I did.
As to your ad hominen insult, you may wish to do a bit of research on what the Dunning-Kruger effect is actually all about because it is one of the most widely misunderstood concepts in modern psychology. The common misconception among the uninformed is that it is a sophisticated way of calling someone “stupid” because they are so over-confident that they are unable to recognize their own ignorance or lack of expertise. However, the actual research by David Dunning and Justin Krueger was about metacognition — the ability to think about your own thinking. I know this because, like you, I used to use “Dunning-Krueger effect” as a facile insult with adversaries, until I realized I was using the term incorrectly and had no business referencing a complex psychological research study. I also recognized it was a rather simplistic and ugly way for me to dismiss people I disagreed with. Does my willingness to research, reflect on, and question my own opinions and change my behaviour suggest I am a poster-child for Dunning-Krueger effect?
Certainly, the most important thing I’ve learned in my trading/investing journey is to manage risk, keep an open mind, admit when I’m wrong, and never listen to financial “experts” who think they’ve got all the answers. Last time I did that was in August of 2022 when a certain someone advised me that bonds had taken the worst of their “bad medicine” and my 80-year-old mother should continue holding a significant amount of her portfolio in bonds. Fortunately, I eventually rejected that financial advice and started using my own research and judgment. Instead of watching her wealth continue eroding I was able to reinvest, rebuild capital and protect wealth. She’s now 84 and I have no intention of gambling her life savings in overpriced equities. That said, my 22-year old son is starting to invest and I’m encouraging him to start scaling in to growth stocks when buying opportunities present and DCA for the next 30 to 40 years, trimming slightly during periods of euphoria and redeploying when opportunity presents.
I know you always have to get the last word in, so I’ll sign off now until we reach our 18- to 24-month milestone later this year or early next. If I am wrong and we’re at all-time highs again at that point I’ll be sure to make a post here about how you were absolutely right and I was foolishly wrong. Are you willing to do likewise?
You go off in a huff and stay away for months based on a short and common sense comment + type 457865788 words… And that means that someone else is “triggered”?
If you like timing the market then good luck to you (you’ll need it).
This reads like a trading diary with hindsight baked in.
You’re describing tactical sector rotations, timing exits on ‘parabolic runs,’ and waiting for signals like Zweig Breadth Thrusts — that’s an active trading strategy, not a realistic framework for an inexperienced investor managing $350K.
The original point wasn’t about predicting the next 10–20% move — it was about long-term allocation. A globally diversified ETF like XEQT (or VEQT) is designed for exactly that purpose: staying invested through cycles, not sidestepping them.
If someone could consistently do what you describe — perfectly rotate sectors, time exits, and re-enter at the right moments — they wouldn’t be coming to great sites like this.
For most investors, the real risk isn’t a 10–20% drawdown. It’s missing the recovery because they’re waiting for a signal that only looks obvious in hindsight.
Different approaches, but let’s not pretend market timing is the safer or more repeatable one
Hannah should buy $87,500.00 in FREEHOLD ROYALITIES. (Fru-t)
$87,500.00 in ChEMTRADE (Che-un)
$87,500.00 in CANOE INCOME FUND (Eit-un)
$87,500.00 in KETEREA (Key-t)
That simple- she will then get an estimated amount of $24,500 in dividends (7% return).
That’s $2042.00 dollars per month.
These are save stocks and I have them funding my retirement.
So Hannaha – open up a non registered trading account and start earning secure income,
That simple- and a very save income and will keep your investment full.
I just did a quick comparison for KT vs MSCI over the last 20 years, total return with divs reinvested. If you had 10k Jan 1st 2006 in KT, in 20 years you got $21,300 (nominal, less in 2006 dollars).
MSCI would have given you $49,600. You left on the table circa 28K. And you did it by taking on more risk and increasing complexity. Future might be different but you are always lowering your expected return while increasing risk. So, you are giving bad advice.
Hannaha
by buying Chemtrade, Canoe Income Fund, Freehold Royality’s and Keyera- you get straight dividends into your account monthly – (Keyera pay’s quarterly. No fees no nothing- just straight cash into your account. Do not wait any longer- every month you wait you lose a dividend payment to you – every dividend missed is your lost opportunity.
So get cracking-
I really do not understand how someone can come to a free BBQ thrown by their neighbour and then do nothing but loudly complain about the food. Robb is a better man than I.
BRAVO! Well said. I’m glad I discovered Boomer & Echo and thoroughly enjoy reading the thoughts Robb passes on to us each week. I am a buy and hold investor, not a trader, and it’s changed how I look at my long term investments. Hopefully Robb will ignore the less than constructive criticism and keep posting these very informative articles.
“I second that emotion.”
Smoky Robinson and the Miracles
I also find it fascinating (and sad) that people come on here to boast about their complex investment strategy that 99% of people couldn’t follow and then keep fighting against the person providing the most sensible content.
Take your thread to a reddit forum, please.
Keep up the great work, Robb!