Monday Night Finance- Volume 141

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What Happens When Roommates Don’t Pay Their Share

It’s the start of a new school year, and maybe your kids just signed their very first lease off campus. While they might be focused on the excitement of indepdence and worried about things like the perfect decorations, you might be a little more circumspect. Amid the thrill of setting up that new space, there’s a worry most college students don’t consider until it’s too late: what if one roommate stops paying their share of the rent or utilities? It’s a scenario that can turn the fun of shared living into a financial and emotional nightmare, whether you’re a college student, a recent grad, or a parent quietly co-signing the lease.

In many cases, when roommates don’t pay, the only way to avoid eviction is to cover their portion yourself. This can quickly turn into a financial strain, especially if the rent is high.

~ Catherine Reed, The Free Financial Advisor

Catherine Reed’s article, What Happens When Roommates Don’t Pay Their Share, lays out exactly how quickly things can unravel. Landlords don’t care who skipped out… they can hold every name on the lease responsible. This means you could face eviction or collections even if you’ve been dutiful with your own payments. Your credit score can tank if unpaid rent heads to collections, and you may have no choice but to cover the missing portion yourself just to keep the lights on. (Literally, because unpaid utility bills can mean shutoffs and hefty reconnection fees). Beyond the money, friendships can sour fast, and recovering what you’re owed through small claims court is far from guaranteed. Reed’s bottom line is clear. You should protect yourself before problems start. Pick roommates with care, put every financial agreement in writing, and keep a backup fund so one person’s irresponsibility doesn’t derail your budget or peace of mind.

Managing a Workhorse Dividend Stock Portfolio

Ever wonder what it really takes to build a portfolio that quietly works for you year after year? Many investors dream of a nest egg that keeps producing income no matter what life throws at them, but getting there isn’t just about picking a few hot stocks and hoping for the best. It’s about consistency, discipline, and the flexibility to adapt when your goals shift. Over time, a well-built dividend portfolio can become more than just an investment account but instead be a financial partner that supports everything from daily living to big life adventures.

Since becoming a Dad to active kids, an online business owner, and an all-around curious person interested in new things, I lost the motivation to research dividend stocks for my personal portfolio. I now prefer the ease of low-cost ETFs and mutual funds for a the large majority of my wealth, and expect to continue that preference into retirement.

~Craig Stephens Retire Before Dad

This article follows Craig Stephens’ decades of experience creating exactly that kind of “workhorse” portfolio. Starting as a plan for early retirement, his collection of 53 dividend-paying stocks and ETFs has evolved into a steady source of income and a financial safety net. Stephens explains how he uses dividends to supplement his self-employment income, fund Roth IRA and 529 contributions, and cover family expenses, all while carefully managing taxes. He shares the systems he relies on to manage his portfolio which include automated alerts and portfolio aggregators to track performance without spending hours on research. In addition he outlines his strategy to simplify holdings over the next decade, trimming from 53 to about 20–25 positions to reduce complexity while preserving income. He’s candid about potential risks, such as market downturns and erosion of value, and stresses the importance of balancing withdrawals with continued growth. While building a resilient dividend portfolio is difficult, it can provide long-term flexibility and peace of mind.

3 Questions That Determine 99% of Your Retirement Success

Thinking about retirement can feel a bit like standing at the edge of a diving board: exciting, a little terrifying, and full of questions you didn’t know you needed to answer. How do you turn decades of saving into a stable, enjoyable life without constant anxiety? What if a surprise expense or a market dip shows up in year one? Retirement planning isn’t just about hitting a target number, it’s about asking the right questions early so you can make confident choices and actually enjoy the next chapter.

There is a direct correlation between how much planning a person does before retirement (including the non-financial elements) and the resulting transition. The more time you spend thinking about the non-financial elements, the smoother your transition will be.

~Fritz Gilbert, The Retirement Manifesto

Fritz Gilbert argues that nearly everything important boils down to three questions you must answer before you retire: (1) Do you have a reliable cash-flow plan? (2) Have you accounted for healthcare and unexpected costs? (3) How will you spend your time and stay fulfilled? He walks through practical ways to tackle each: build a bottom-up spending forecast and map all income sources (including Social Security timing), create a drawdown strategy and cash buffers to avoid selling in downturns, and use tools or advisors to project longevity needs. For risks, plan for healthcare (especially pre-Medicare), taxes (quarterly payments and Roth strategies), car and home repairs, inflation, and long-term care (through either insurance or having extra money in your portfoloio). But the article also emphasizes the importance of planning the non-financial side of retirement such as purpose, structure, relationships, and activities. In short, Gilbert points out the you should spend the time now to answer these questions well because your future comfort and happiness depend on it.