Six Financial Questions Men are Afraid to Ask

Photo by Caleb George on Unsplash

There’s a lot of pressure for men to have all the answers, particularly when it comes to finance. It may seem like we’ve come a long way since the “men are the head of the households” days, but women couldn’t even get a credit card without a male co-signer until the 1970s. There was, and still is, a TON of pressure for men to have all the answers. Which means that it can often be embarrassing to ask questions.


So this week we are answering six financial questions men are afraid to ask, at least out loud. But they did whisper them softly into our DMs. Even H.E.N.R.Y.s™ have questions.


1. I’m living paycheck to paycheck, can I still save?

YES! We get asked this a lot. Saving can seem impossible when you’re living paycheck to paycheck. Bills, groceries, and the basics of living your life can make it seem like you’ll never get ahead. So here’s our best advice (and it isn’t depriving yourself of all lattes and brunch bevvies until you have a down payment saved). Get a high yield savings account at an online bank like Ally or Simple and save a little bit out of each paycheck. Put it away before you can spend it. And you can start really small, and then build up as you learn what you can and can’t afford without that bit you’re saving.

At Stash Wealth, we also joke that if you ever meet a life insurance salesperson, run the other way.

A few more tips to really level up your saving:


  • When you get a raise, start saving more immediately, before you feel the bump in your lifestyle to avoid becoming a victim of #lifestylecreep.
  • Consider a side hustle to boost your income, rather than trying to save more out of what you’re already making.
  • Don’t ever carry a balance on your credit card. Saving gets way harder when trying to pay off credit card debt.

2. Is it bad if I’m in my 20s and I’m not saving at all?

Also, yes. #SorryNotSorry We’re here to give you the facts, and the truth is, the money you save in your 20s just has more time to grow, particularly if you invest it and take advantage of compound interest. Saving and investing are all about time, and you’ll never have more time than you have in your 20s. Take another glance through the previous question if you’re worried about how to save in your 20s.


Real talk, you’ll never have a higher tolerance for roommates, ramen, and cheap beer than you do in your 20s, and hopefully your salary will increase as your career progresses. So think how much of a pro you’ll be at saving by the time you really have money to spare if you start saving in your 20s.


At Stash Wealth, we joke that “we don’t like taking on clients in their 40s, because we don’t like delivering bad news”. Harsh but the truth is (and the math behind it proves) that the sooner you start saving, the less you’ll have to save overall.


3. How much should I be spending on life insurance if I’m in my 30s? And do I really need it?

The real kicker here is “Do I really need it?” At Stash Wealth, we also joke that if you ever meet a life insurance salesperson, run the other way. We have a lot of jokes at Stash Wealth, not all of them are Trevor Noah material. Truth is, H.E.N.R.Y.s™ are prey to the life insurance industry. As a High Earner, they will almost never tell you that you don’t need it. We feel very strongly that you shouldn’t get life insurance just for the sake of it. There really has to be a need. That need comes into play when


  1. Someone’s dependent on your income (a child, a significant other, a relative) or
  2. You own property with someone else.

This isn’t what the life insurance industry wants you to think, but it’s the truth. So if one of those conditions don’t apply to you, you don’t need it. Period. As far as how much you should be paying, that’s a question for another day and another blog post. But the short of it is, you should shop around for term insurance and select the provider that offers the best coverage at the best rate.

Trading and investing both have to do with giving your money to companies or debtors, but there is a key difference.

Typically, we see rates around $40/month (that’s per million dollars for a 20 year term policy) for a healthy 30-something. People often wonder if waiting to get insured makes it more expensive later. Yes, but not by enough to change our thinking here and as long as your health doesn’t change significantly – but that’s a risk you’ll want to be comfortable assuming.


Have student loans? There’s one caveat to our rule about who does and doesn’t need life insurance. If you have a cosigner to your student loans you don’t want to leave them stranded if something happens to you. Look for insurance that covers the amount of your loan balance. And if you already have life insurance through your employer, just make sure your cosigner is the beneficiary.


4. How do I calculate tip without using my phone?

It is amazing how many people can’t do this. And some people may argue that you don’t need to. But if you want to calculate tip without reaching for that old calculator Mrs. Johnson said you’d never have in your pocket when you need it, here are two super easy ways.


Option 1: Move the decimal place over to the left to easily get 10% and then double it, that’s 20%. The middle between the two is 15%. It doesn’t have to be exact. How much you tip is personal. Whether you can look yourself in the mirror after you decide how much to tip is also personal.


Here’s what this looks like. Say your total for your dinner and a couple cocktails at Nobu is $123. Move the decimal place one spot to the left, and you have $12.30. Double that, and you have $24.60. That’s your 20% tip. $18 is about 15%.


Option 2: Double the tax and then add some. This works best in places where tax is higher. You may need to triple or quadruple if you live somewhere with low sales tax. And if you’re in Montana or Oregon and you don’t have sales tax, well you’re damn lucky and go back to option 1. In NYC, sales tax is about 9%. So whatever the total for tax is on your bill, double it and you have an 18% tip. Then add a couple bucks.


5. What’s the difference between trading and investing?

Trading and investing both have to do with giving your money to companies or debtors, but there is a key difference. Investing is a long-term strategy for growing your wealth, trading is something you should leave to the professionals, particularly if you are asking this question. That may be #harsh, but it’s also true. Day trading is buying and selling stocks, bonds, and options in a market with the goals of short term gains. It’s what you see on shows like Billions. It’s for trained professionals with a complex understanding of market influences, and enough time to spend researching investments and tracking them on a day to day, and sometimes minute to minute, basis.


Yes, there are books, Youtube videos, and plenty of podcasts that claim they can teach you to trade, and maybe they can. But we’re here for solid, reality-based financial advice, and we keep it real. Trading is for the pros, and it’s crazy hard to beat the market. In fact, studies show that even the professionals rarely get it right. You really will do better in the long term with a solid, diversified portfolio – boring, but brilliant. But really, pros get it wrong all the time. Trading is like gambling, and if you want to gamble, you might as well go to Vegas. They give you free drinks, which makes it more fun – especially when you’re losing money!


6. Is it embarrassing if my girlfriend makes more than me?

Hell no! You’re dating a badass, get proud! But we also get it, men are raised with the expectation that should be able to provide, and when your S.O. makes more than you, that can feel embarrassing. You may not want to admit it to your friends, and it can become a point of tension in your relationship. Here’s the good news, those are only feelings, and they’re feelings based on bad data. Celebrate your partner and her wins, and if she is the one pressuring you to make more money, send her to us, our CEO and founder Priya Malani can set her straight. You’re one team with one dream. Dating and marriage are about partnership, and the more money she makes, the more money you both have to save, invest, and splurge! If you find yourself falling prey to outdated social norms about money, remember, we are all the products of our childhoods and grew up in a world where the man was portrayed as the breadwinner. Man was the rescuer and the woman was the one waiting for rescue. If we are dissatisfied with that narrative (and let’s be honest, we are), it’s up to us to shape new narratives for the next generation. No pressure parents!

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