Hey everyone,

Whether you're making your first investment or you've been in the market for years, I keep hearing the same questions come up again and again. Should you wait for the market to crash? Are your investment costs too high? Is your portfolio actually diversified? I answer a few questions I get asked most below.

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I'll be honest with you: trying to time the market is so, so hard, even for professionals. There are investors who can maybe do it successfully once or twice but doing it consistently year in, year out is basically impossible.

Most people who wait for the "perfect time" to enter the market and start investing just end up staying on the sidelines too long. Think of it as “paralysis by analysis” - we’re always thinking there’ll be a better time because of this factor or that. Instead, map out a simple, consistent investing plan because, over time, this will beat waiting for the ideal entry point and will be way less stressful too.

Here's something that surprises people: markets spend a lot of time at all-time highs. Just because a market has hit an all-time high, it does not mean it won’t go on to make another new high.

Indeed, multiple studies have found (over the past 70-80 years or so) that investing at all-time highs - versus any other time - will give you roughly the same returns one year, three years and five years on.

So, instead of focusing and stressing about the current level of markets, shift that focus to:

If you're investing for 10–20+ years, short-term highs technically don’t matter and they’re merely just a psychological barrier to you investing.

There is never a perfect time to invest. Just like anything in life, whether it’s getting married, having kids, or switching jobs, there’s never a “perfect” time to do it.

Similarly, in investing, every period has reasons for us to wait to start:

Waiting for "stability" usually means never starting. The key is to:

Both are valid approaches, and I get this question constantly.

Lump sum investing tends to perform better statistically, and historically, if you already have the cash as you’re giving your capital more time to compound in the market.

Dollar-cost averaging (monthly investing), though, is emotionally easier and helps you stay consistent when investing. I like it because it also matches your cash flow.

What matters most is starting and staying invested, not timing it perfectly. If you do have a spare amount of cash and you’re worried about putting it in all at once in a lump sum, you could split it into three tranches.

By putting those three tranches into the market over three to six months or so, you’re sort of dollar-cost averaging but with bigger amounts and in a shorter period of time.

That’s because the maths is simple:

Many ILPs and insurance-based products invest in expensive underlying unit trusts, adding another layer of cost. Over 20-30 years, these fees compound dramatically against you and can end up costing you tens of thousands (if not hundreds of thousands) of dollars.

You can, but I feel like it’s completely optional. If you want to counterbalance US large-cap and tech exposure, adding a global small-cap ETF as a small allocation of your overall equity sleeve is reasonable. Small caps tend to be less tech-heavy and more diversified by sector, too.

Over the long, long term, they also technically provide higher risk-adjusted returns for investors. However, they have underperformed large cap indices given how incredible the returns have been from US Big Tech in the past 10-15 years or so.

Overall, just don’t forget your key rule: keep your overall equity allocation aligned with your risk profile and investing time horizon.

These are just a few of the questions I cover in Investing Made Simple. My course is designed to take you from confused (or frustrated with high fees) to confident and in control.

The course gives you everything you need:

✅ How to build (or fix) a diversified portfolio
✅ Choosing the right platforms and ETFs
✅ Understanding risk, rebalancing, and asset allocation
✅ Avoiding expensive mistakes that quietly cost you thousands

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