Money Q&A: “Is there a top 10 list of conventional finance advice you’d avoid?”

#5: "Pick up a side hustle"

written by oz chen

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Coach and healer @stegdrew made use of the AMA and asked:

Is there a top 5 or top 10 list of conventional financial advice you’d avoid, and why?

Let’s start by asking: what is “conventional” finance advice anyway?

Something might have become a convention because it is generally good practice or advice.

“Don’t get into debt. Work hard. Invest in your retirement.” We all know these things.

By the same measure, any conventional advice is also generic. It’s not personalized to your unique financial situation. You live a big life, and your finances reflect just 1 aspect of that big life. This is why I find money coaching and financial writing so fun—there’s rarely just one “right” answer.

The financial conventions I’m going to bust today are not bad advice; it’s that they lack nuance and personalization.

Using my principle that generalizations hide; specifics reveal, I’ll analyze 10 common pieces of conventional advice and reveal an area where they might fall apart if we get more specific.

Let’s break some conventions!

#1: “If you skipped buying lattes and invested the difference, you’d have a bajillion dollars someday.”

The good aspect of this “latte advice” is that anyone can start investing without a lot of money. But now it’s been perverted by personal finance gurus to shame people out of taking small personal pleasures for themselves.

Most people focus on $10 problems when they should be focusing on $10,000 opportunities.

Instead of cutting out small joys, it’s more motivating to focus on big wins like switching to a higher paying job or negotiating down credit card interest.

#2: “We should all be transparent with finances.”

People assume that “talking about money” means that you have to share your salary or how much money you have.

Nope, here’s why that’s horse shit. There are many good reasons for being private with your finances.

The burden of transparency shouldn’t fall on individuals—the burden should fall on companies and industries to make their pay transparent. Luckily, pay transparency is starting to happen in states like California, Colorado and New York where companies have to list salary ranges for jobs.

#3: “Go to college”

A college education is one of the biggest investments someone can make. With federal student loans averaging $37K, more prospective students should question college before they attend, not after.

  • What am I going to get out of this investment?
  • Which majors have the highest return on investment?
  • Is there something more valuable I can do with my time than going to college?

As a college grad, I lucked out and ended up in a high-paying career unrelated to my college major.

I wish I thought more critically about the identifying marketable SKILLS to develop early on, rather than just getting to the finish line of getting that college diploma.

#4: “Invest as much as possible, as early as you can.”

Have little? Invest in yourself. Have lots? Invest outside yourself.

Example: $1000 invested earning a great 10% return will only net $100. One has to ask: “How much does that extra $100 make a difference in my life?”

The same person with only $1000 is better off investing it to learn new skills to help them land a new job, which can result in thousands of dollars in pay increase.

I go more in-depth in this article, which expands on the principle of focusing on big wins.

#5: “Pick up a side hustle”

If you talk about your side hustle in a cafe, I will probably want to talk to you and blog about you.

As much as I love multiple streams of income, I dare say… one stream of income can be enough.

The metaphor I like is this: create one significant enough income stream first, then divert that stream into other experiments. Avoid distraction and double down on high return on investment opportunities.

#6: “Buy real estate, it’ll never go down.”

I’ve talked about the psychological reasons why real estate is such a “popular” investment. The real estate industry is just like any other—incentivized to promote its investments.

To zoom out of investment myopia, it’s fairer to think of real estate as ONE asset class in your portfolio, and not THE asset class.

Some people love the RE game and have a portfolio that looks like 80%+ real estate. Great.

Others love passive investing and intentionally diversify away from their primary residence into the stock market.

#7: “Track every expense and budget closely”

Okay class starting tomorrow we’re going to track every single calorie and start new strict diet. Who’s in?


Strict budgets are like crash diets. They work in principle but are a pain to stick to. Explore different budget styles until you find one that you can stick to sustainably (just like a diet).

My recommendation: remember that guilt free spending is the holy grail of budgeting. Your systems are always in place so that after your savings and investments, you can just spend the rest without overthinking it.

#8: Don’t just move in together to save money

There’s a standout lesson from the behavior-science-meets-dating-advice book How to Not Die Alone : Decide, don’t slide.

  • Sliding: making relationship transitions without conscious thought, like “Oh your lease is coming up? Mine too. Should we move in to save money and because I love you?”
  • Deciding is the opposite—intentionally having a conversation with your partner about what it means to move in together. Is it a clear indication of marriage? Or is it another relationship step?

Choosing intentionally pays off in the long term too: couple who decide instead of slide end up in longer, happier relationships.

#9: “Live in a low cost city”

Sometimes to pursue your dreams you have to move to where the action is. There’s intangible value to being in a certain place, with a certain energy, with certain people who can inspire you. This probably applies doubly for you if you’re extroverted and ambitious.

There’s also a practical element to living in a more expensive city or part of town: commutes are one of the leading causes of life dissatisfaction. One of the most miserable times of my life was a 1.5 commute from Orange County to Hollywood for 2 months when I was switching jobs…

So if you can have a short commute or no commute, the extra happiness boost is worth paying for.

#10: “Be frugal”

America as a whole needs a frugality check. Collectively we’re in massively debt and overspend. We love to consume.

So it’s hard to argue with frugality. For those who are predisposed to be money vigilant types, they wear frugality as a badge of honor.

But frugality for frugality’s sake is just stupid. I’ve been there, in the grocery aisle, debating the $2 difference between organic and normal berries. The cost is minimal, yet the cognitive load is maximal.

Here’s what I find to be more true: focus on value.

“What do I truly value, and does my finances align with my values?” That’s the lead domino that leads to conscious finance.

I hope you enjoyed that Money Q&A. This is the power of using my Ask Me Anything form – your question can be featured in a long, in-depth article like this.

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