Afford Anything

Tag: ask paula

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#583: Q&A: Everyone Is Arguing About Roth IRAs And We Have Thoughts

Contrary to recent discussions, Jesse has concluded that a traditional IRA is the smarter way to go for most people once marginal tax rates are factored in. Is he missing something?  

An anonymous caller is four years away from early retirement but she’s unsure if her portfolio allocations are in the right place. How and when should she start converting equities to cash?

Luz is confused about how to handle company stock options. Is there an ideal spread between the exercise price and the stock price? And, what should she do once the stocks are exercised?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#575: Q&A: The Roth Decision at Every Income Level (And Why It Matters Now!)

Krish is fascinated by cryptocurrency and its impact on global investing. What opportunities should he capitalize on, and how?

Apar’s income has more than doubled after he started his own business. His advisor recommends Roth contributions but he’s skeptical due to his high income. Who’s right?

Keith is frustrated by the conflicting advice he’s heard about Roth conversions. Is it better to do it while he’s young and earning a lower income, or should he wait until closer to retirement?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#561: Q&A: Why Your Retirement Math Isn’t Adding Up

Joanne is confident that her short and long-term financial plans are set, but she’s not certain about the medium-term. What’s the proper way to allocate money for different time horizons?

Jessie is intrigued by Paul Merriman’s simple portfolio recommendations but wonders about his lean away from growth stocks. Are value funds generally better for everyday investors?

Nancy is worried she’ll miscalculate her financial independence number because her net worth includes pre and post-tax money, plus liquid and illiquid investments. What’s the right approach? 

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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#559: Q&A: Should We Ditch Rental Properties Entirely?

An anonymous caller, whom we name “Samantha,” and her husband are financially strained and feeling torn. Shortly after purchasing two rental properties, their income dropped dramatically. Should they sell?

Tina is a full-time environmentalist. She’s worried that her index funds don’t align with her values on sustainability. Is there a world where she can be a savvy investor and fight climate change?

Another anonymous caller, whom we name “Sarah,” is excited and uncertain about her growing business. Should she hold steady or invest more resources into it? And how does she know if she’s making the right call?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#557: Help! The Money is Good … But My Dream Life is Different

Imagine saving nearly your entire paycheck while your rental properties cover your bills. That’s exactly where real estate investor Andrew finds himself — and yet he’s at a crossroads.

At FinCon, a personal finance conference, former financial advisor Joe Saul-Sehy and I sit down with Andrew and another attendee who bring their money dilemmas live on stage.

Andrew’s question seems simple at first: should he sell his index funds to pay off his rental mortgages? But the real story runs deeper.

He feels called to entrepreneurship and wants to quit his corporate job to pursue it full-time. He could achieve minimal financial independence (lean-FIRE) if he pays off the properties, but that might limit his options.

Next, Chris, a Gen X dad, opens up about his Gen Z kids’ gloomy money outlook. His 22 and 24-year-old children, especially his daughter, believe their generation “will never retire.” They see high inflation, expensive housing, and low wages as insurmountable obstacles.

This sparks a deeper conversation about generational perspectives. We note that similar fears existed 15 years ago when millennials entered the workforce during the Great Recession. Joe shares how he helped his own kids develop healthier money mindsets by introducing them to financial voices they could relate to, like Broke Millennial author Erin Lowry.

The discussion evolves into how today’s young people actually have more opportunities than previous generations — they can work remotely, start online businesses with minimal capital, and create multiple income streams through platforms that didn’t exist before. Chris’s daughter, for instance, sometimes makes $35/hour driving for DoorDash during peak times.

We wrap up by talking about the importance of focusing on what you can control and finding purpose beyond just retirement planning. As Andrew points out, it might be worse to spend the best years of your life doing work you don’t care about than to face uncertainty in retirement. The key is taking action on the things within your control while building toward long-term security.

Throughout the conversation, both guests share personal stories that illuminate their situations – from Andrew’s experience at an oil refinery that pushed him toward entrepreneurship to Chris’s daughter storing cash for taxes from her DoorDash earnings, showing she’s more financially aware than she might think.

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#549: Am I Wrong to Worry About Retirement, with $2 Million Saved?

Steven is stuck on the question of financial stability. How do you know if you have it? Is there an objective answer based on net worth? Or is it a calculation relative to your income and age?

Jack isn’t sure how to factor his house into his net worth. It’s an asset, but he has a mortgage against it, and there are transaction costs associated with selling it. How should he frame it?

Patricia and her husband are debt-free with a $2.2 million net worth, but she’s constantly stressed about their finances. Are her concerns valid? Or is she a financial hypochondriac?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#535: Ask Paula: Is Your DIY Investing Strategy Holding You Back?

Melissa and her partner are preparing for the best earning years of their lives. Could they benefit from automated tax-loss harvesting and transition from DIY investing to a robo-advisor?

An anonymous caller just learned something surprising about their Roth 401k and feels squeamish about making future contributions to this account. What’s Paula and Joe’s advice?

Hampton is following up on a question from Episode 524 to spark an intriguing discussion on the generational tax advantages of a Roth IRA.

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#533: Q&A: My Insurance Bill Jumped 60 Percent – Should I Drop It?!

Kristin is floored by the 60 percent increase in her homeowner’s insurance this year. Should she cancel the policy and self-insure instead?

Susana and her husband are torn. They bought their dream home last year but now need to relocate indefinitely. What should they do with the house?

An anonymous caller wants to help his soon-to-be wife invest a five-figure gift she received in another country. How do they untangle the complexities of managing money from abroad?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#529: Q&A: The Unintended Consequences of Early Retirement

Anonymous, 60, recently lost her job and is worried about retirement. She owns a paid-off triplex, living in one unit and renting the others for $30,000 a year. She used her 401(k) funds to buy the triplex and now has $50,000 in retirement savings and $150,000 in cash. She expects only $2,400 a month from Social Security at age 67. After losing her son two years ago, she’s seeking advice on managing her underfunded retirement.

Noelle, 40, and her husband, 49, want to cancel his whole life insurance policy. They are debt-free, own their home, and plan to retire soon, relying on Noelle’s $80,000 income. They have $504,000 in retirement savings. Should Noelle keep her $100,000 term life policy until she retires?

Sleepless in San Antonio, age 35, plans to retire at 45 but is concerned about how this will affect Social Security benefits, which is calculated based on the top 35 earning years. Should they work longer in order to boost their Social Security benefits?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#527: Q&A: Can They Be Financially Independent in Five Years … By Breaking the Rules?

Christina is worried. She’s retired with a paid-off condo in Florida. But rising fees, insurance rates, and a major HOA assessment are killing her cash flow. Is it time to become a renter?

Les is surprised by Paula and Joe’s allocation recommendations for international equities. Based on market capitalization, it makes no sense. What’s he missing?

Luke and his wife are breaking some personal finance rules in the name of financial independence. Are they right to take this approach or is there a better way?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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