The Investing Questions You Were Too Afraid to Ask (But Absolutely Should)
You know those questions you’ve been meaning to Google but felt a bit silly about? We asked our fb community to share the investing questions they’ve always wanted to ask, and honestly, they’re so real.
From tax confusion to dividend dreams, here are the answers with 0 judgment from us, just the stuff you actually want to know.
Dharshani asked:
"If you invest small amounts consistently, when do you actually stop and start enjoying the benefits? Is there a right time or right purchase?"
There’s no official “finish line” with investing. Some people keep going forever, others pause once they hit a goal like buying a home or retiring. The right time is different for everyone, and honestly, sometimes you do start enjoying the benefits while still investing. That’s kind of the dream.
Beck asked:
"When do you sell, or do you just never sell and hope dividends support you later?"
A mix of both can work. You might sell small chunks when you need the cash, or live off dividends if your portfolio is big enough. It really depends on your income needs and what you're investing for. You’re allowed to change your strategy as life changes too.
Lakyn asked:
"How does tax work on investing?"
Generally, you’ll pay tax when you earn dividends or sell something for a profit (that’s a capital gain). How much depends on your income and the type of account you're using. Most investing platforms give you a report at tax time, and the ATO makes it pretty straightforward now.
Pipit asked:
"Can you give a benchmark for whether I'm doing OK with my investing based on my age and risk level?"
Love this. If you're investing regularly, sticking to your plan, and not panicking during market dips, you're probably doing great. Everyone’s journey will look different, so comparison isn’t always helpful, but checking in once a year to see if your portfolio matches your goals is a good shout.
April asked:
"When should you cut your losses on a share?"
If you bought based on solid info and it's just down because of market noise, maybe hang tight. But if the company is truly struggling or it's no longer aligned with your goals, it’s okay to let it go. You don’t have to marry your investments.
Georgia asked:
"What’s the best way to invest on behalf of your future kids?"
You’ve got a few options: investment bonds (great for long-term), investing in your name “for them,” or using platforms that allow minor accounts. It comes down to how hands-on you want to be and how long the money will be invested.
Nikita asked:
"How do people with average incomes own 5–7 properties? How are banks lending them so much?"
Usually it's the rental income that helps them borrow more. It snowballs a bit — income from one property helps fund the next. But it's not without risk. You need solid cash flow, low personal debt, and banks still stress-test your ability to repay.
Soiz asked:
"Would it make sense to sell a rental after 15–20 years and invest in shares to live off dividends?"
It can totally work. Selling at the right time could unlock a chunk of cash to invest in dividend-paying shares, which could give you more passive income and less maintenance than a property. Just make sure it fits with your lifestyle and retirement plans.
Jessie asked:
"Is it realistic to live off dividends? And how does the money actually show up?"
Yes, it’s possible, but it takes a pretty big portfolio. Like hundreds of thousands to millions invested, depending on your expenses. Dividends usually get paid into your linked bank account, just like a paycheck, either quarterly or twice a year depending on the company.
Sienna asked:
"I do my own tax — how do I declare profits from investing?"
You’ll need to report any income (like dividends) and capital gains if you’ve sold something for a profit. Most platforms give you a yearly tax statement. It sounds confusing but once you do it once or twice, it gets easier. Or grab a tax agent and let them do the heavy lifting.
Aimee asked:
"What even is investing?!"
Fair question. Investing just means putting your money into something (like shares or property) with the goal that it grows over time. It’s not about quick wins, it’s about long-term wealth building. You don’t have to be rich to start, promise.
Niki asked:
"Is it better to invest weekly or monthly to save on fees?"
If your platform charges a fee every time you invest, monthly might be cheaper. But weekly can help average out price changes over time. Either works — the key is picking a rhythm you can stick to.
Katherine asked:
"I still don’t really understand compound interest 😩"
No shame in that — it’s one of those things we hear about but no one explains properly. It’s when your investment earns returns, and then those returns also earn returns. Over time, it snowballs and your money grows faster.
Chen asked:
"How can I invest so I never have to work again?"
This is the FIRE (Financial Independence, Retire Early) dream. Most people get there by living well below their means, investing a lot, and starting young if they can. It takes time and consistency, but yep — it’s possible.
Sandra asked:
"Why isn’t this taught in school or uni properly?"
Honestly, we ask this all the time. That’s exactly why She’s on the Money exists. We didn’t get the education we needed, so we’re giving it to ourselves now.
Lucy asked:
"With the current market, should I invest more while shares are cheap or invest less to be safe?"
If you’ve got a long-term mindset, buying while prices are lower can be smart. Just make sure you're not stretching yourself too thin. The market always has ups and downs, so consistency wins over trying to time it perfectly.
Amanda asked:
"What even are bonds and how do I invest in them?"
Bonds are basically you lending money to a government or company and they pay you interest in return. You can buy them through ETFs or managed funds, and they’re generally seen as lower risk than shares.
Kristine asked:
"How do I set up my tax for US or other foreign shares?"
If you're buying US shares, you’ll usually fill out a W-8BEN form to avoid being taxed twice. Then at tax time in Australia, you report any income you made overseas. Most platforms help you sort it out behind the scenes.
We’re big believers that no money question is too silly. Investing doesn’t need to be confusing or gatekept, and you don’t need a finance degree to start.
If this blog gave you a few lightbulb moments, or if you’re ready to take the next step, check out our Investing Masterclass — we’re constantly updating it to answer your biggest questions.
Got a question we didn’t answer here? Slide into our DMs @shesonthemoneyaus, drop it in the Facebook group, or comment below. We’ve got you.
***Please remember our blogs aren’t intended as financial advice - they’re intended only as a starting point to give you a little extra info! For more in-depth advice catered to your personal financial position, please see a certified financial advisor.