6 pieces of classic money advice that might actually make your life worse / 98
Pay off debt as fast as possible. Buy a house as soon as you can. Save as much as possible for retirement.
If you've spent any time learning about personal finance, you've probably heard some version of these money rules. And while they're usually well-intentioned, following them without question has the potential to make your life worse.
The thing is, good financial advice isn't always good advice for you. Some recommendations are based on outdated assumptions, while others focus so heavily on building wealth that they forget money is supposed to help us enjoy our lives, too.
In this episode, we're challenging six pieces of common financial advice (plus one bonus hot take!) and exploring when conventional wisdom might do more harm than good.
Episode highlights
[00:00] Why some of the most common financial advice can do more harm than good
[01:00] Why delaying all your fun until retirement could leave you with regrets
[05:00] Why taking the highest-paying job isn't always the best career move
[08:30] Why you don't need a side hustle or have to monetize every hobby
[13:00] Why buying a home as soon as possible isn't always the smartest financial decision
[18:30] Why paying for convenience can actually be worth the extra money
[21:30] Why paying off debt as quickly as possible isn't always the best use of your money
[26:30] Bonus: Why going to college to get a good job might not be the best advice anymore
[31:00] How to evaluate financial advice and decide what makes sense for your own life
1. Delay all your fun until retirement
Saving for retirement is crucial. With pensions becoming increasingly uncommon, most of us are responsible for funding our own futures. But there's a difference between planning for retirement and postponing everything you want to experience until you get there.
There's no guarantee that you'll be physically able to enjoy all the experiences you've been saving for once you retire. In our conversation with Jillian Johnsrud, author of Retire Often, she explained that certain experiences have seasons of life when they're most possible. She shared how she took one of her parents hiking in Ireland while they were still physically able to enjoy it.
There's also the possibility that after decades of aggressively saving, you might struggle to actually spend the money you've accumulated. If you've spent your entire adult life denying yourself things you enjoy, that mindset doesn't necessarily disappear the day you retire.
A better approach: Save consistently for retirement while making room for meaningful experiences today. Your future self deserves financial security, but your present self deserves a fulfilling life, too.
2. Always take the highest-paying job
Making more money can genuinely improve your life. Cassidy experienced this firsthand when her income increased from approximately $32,000 to $100,000. Having more financial breathing room made a significant difference in her happiness, and there's no denying that a higher income can make reaching your financial goals much easier.
But eventually, you may reach a point where additional income doesn't meaningfully improve your quality of life. A higher salary might also mean longer hours, more responsibilities, higher stress levels, or less time for relationships and hobbies. If you're already comfortable financially, taking on significantly more stress for a modest increase in income might not be worthwhile.
A better approach: Consider what your personal "enough" number looks like. How much income would allow you to comfortably meet your needs, pursue your goals, and enjoy your life? Once you're there, climbing the corporate ladder doesn't have to be your next move. Choosing more free time or less stress over a bigger paycheck can be a perfectly reasonable financial decision.
3. You need a side hustle (monetize your hobbies!)
Having multiple income streams can provide financial security, especially when your primary income isn't guaranteed. But somewhere along the way, the idea of earning extra money turned into pressure to monetize practically everything we enjoy.
While these suggestions are usually well-meaning, turning something you love into a business can fundamentally change your relationship with it. Emily experienced this when she tried turning her watercolor hobby into a greeting card business. Once painting became something she had to do, she lost the joy in doing it.
And the financial payoff from side hustles isn't always meaningful. Data from Side Hustle Nation says that roughly half of side hustlers earn less than $100 per month, despite many spending 11–20 hours monthly on their businesses. Depending on your situation, picking up an extra shift at work might be more lucrative.
A better approach: Evaluate whether a side hustle is worth your time, energy, and potential earnings. Investing in your skills, professional relationships, and health can also support your long-term financial security. And remember, not every hobby needs to generate income to be worthwhile.
4. Buy a home as soon as you can
In the U.S. especially, homeownership is a classic milestone of financial success. After all, why pay someone else's mortgage when you could build equity in your own property?
But buying isn't always a better financial choice than renting. In many cities, renting can actually be more affordable, especially when you account for mortgage interest, property taxes, maintenance, insurance, and closing costs.
Plus, homeownership isn't the only way to build wealth. Investing in diversified index funds has become much more accessible, giving renters another opportunity to grow their money without taking on the financial responsibilities of owning property.
We also think buying a home is as much an emotional decision as a financial one. Before purchasing, consider whether:
You can comfortably afford the mortgage, closing costs, and ongoing maintenance.
You expect to stay in the home for at least 5 to 7 years.
You feel emotionally ready for the responsibilities of homeownership.
Emily recently bought a house after deciding those conditions made sense for her. Cassidy, meanwhile, is happily renting because she doesn't feel ready to buy.
A better approach: Buy a home when it makes sense for your finances, lifestyle, and goals, not because you've reached an age when society says you should own one. Renting isn't necessarily throwing money away, and owning a home isn't a prerequisite for building wealth.
5. Never pay for convenience
Convenience usually comes at a premium. Ordering grocery delivery costs more than shopping yourself, and prepackaged food often costs more than preparing everything from scratch. But sometimes paying extra is well worth it to make your life significantly easier.
For example, in episode 97, Bola Sokunbi shared that she happily pays extra for grocery delivery because she knows she'll spend more on impulse purchases if she shops in person. For her, the convenience fee is worth it because it helps her avoid spending on things she doesn’t need.
Cassidy also described using a prepared-meal delivery service during a season when she didn't have the energy to plan and cook nutritious meals. It cost more, but it helped her eat better and feel healthier, which made the additional expense worthwhile.
And there's another resource worth considering: your time. If grocery delivery saves you two hours every week, those hours could go toward family, friends, rest, or even earning additional income.
A better approach: Instead of automatically choosing the cheapest option, ask whether paying for convenience would meaningfully improve your life or prevent other expenses. Your time and energy have value, even when they don't come with a dollar amount.
6. Pay off debt as quickly as possible
Debt can feel stressful, and paying it off can be incredibly freeing. But treating all debt as equally bad overlooks some important financial tradeoffs. High-interest credit card debt, for example, deserves a different strategy than a low-interest auto loan.
When Cassidy bought her car, she could have paid cash. Instead, she chose to finance because she could get a really low rate. Paying cash would have depleted much of her savings, leaving her with less money available for emergencies. By financing, she could preserve her emergency fund and continue investing for retirement.
The tradeoff was paying some interest over the life of the loan, which felt worthwhile given her priorities and the relatively low cost of borrowing.
Of course, investing isn't guaranteed to outperform the interest you're paying. And for someone who finds debt emotionally overwhelming, paying it off sooner might be worth the peace of mind.
A better approach: Consider your interest rates, available savings, investment opportunities, and comfort with debt before deciding how aggressively to repay it. You might find that paying the minimum on low-interest debt while investing the difference makes sense, or you might prefer to eliminate the debt sooner.
(BONUS) 7. Go to college so you can get a good job
For generations, kids have been told going to college is the most reliable path toward a stable, well-paying career. And college can absolutely be worthwhile — we both value the experiences, relationships, and skills we gained in our college years.
But higher education is also soooo expensive, and these days, a degree doesn't guarantee a particular salary or career outcome.
Cassidy graduated with approximately $18,000 in student loans, thanks partly to scholarships. But many borrowers leave school owing a lot more, and those payments can follow them for decades.
The job market can also change considerably between someone's freshman year and graduation. A degree that seemed like a promising investment when you enrolled might not lead to the opportunities you expected four years later.
Meanwhile, there are career paths, including freelance work and entrepreneurship, that don't necessarily require a traditional four-year degree. Cassidy, for example, has built a freelance career that doesn't require the degrees she earned.
A better approach: Before enrolling, understand the total cost, likely borrowing needs, realistic career opportunities, and potential earnings associated with your chosen program. College might be a wonderful investment in your future, but it's worth making that decision intentionally rather than assuming it's the only route to success.
How to decide which financial advice is right for you
If there’s anything we want you to take away from rethinking this classic financial advice, it’s that not all suggestions will make sense for your circumstances, values, and goals.
The next time you encounter a money “rule,” ask yourself a few questions before deciding whether to follow it:
Who's giving the advice? Consider their background, financial circumstances, and personal experiences. Someone who's built wealth through real estate, for example, might genuinely believe buying property is the best financial decision anyone can make. But their experience doesn't necessarily mean that approach is right for you.
What assumptions is the advice making? Does it assume you have unlimited energy to work a side hustle? That your career will follow a predictable path? Or that building the largest possible net worth matters more than anything else?
Does it align with your priorities? Think about whether following the advice would help you build the life you actually want. A financial strategy that looks perfect on paper might not be worthwhile if it leaves you constantly stressed, exhausted, or unable to enjoy the things that matter to you.
Ultimately, personal finance is exactly that: personal. So don’t be afraid to reconsider the classic advice and make thoughtful decisions that support both your present happiness and your future financial well-being.
TL;DR
Save for retirement, but don't postpone every meaningful experience until then.
A higher salary or side hustle isn't automatically worth sacrificing your time, energy, or happiness.
Homeownership and college can be valuable investments, but neither is the right choice for everyone.
Paying for convenience or keeping low-interest debt can make financial sense depending on your circumstances.
Question blanket financial advice and prioritize decisions that align with your goals, values, and real life.
Resources
Episode 39 with Jillian Johnsrud, author of Retire Often
Die With Zero by Bill Perkins
Rich Girl Nation by Katie Gatti Tassin
Episode 96: Our conversation about buying a home, choosing a mortgage, and knowing when you're ready
Episode 97 with Bola Sokunbi about money and paying for convenience
This content is for educational purposes only and is not personalized financial, tax, or legal advice.
