Afford Anything

#698: We explore financial decision-making at different stages of life:

A high-earning federal couple debates whether to pause retirement contributions to accelerate a $200,000 down payment.A part-time healthcare provider seeks clarity on balancing a 401k and a traditional IRA.And a longtime listener asks a more personal question: Is there anything we’re still figuring out ourselves?

We examine strategy, trade-offs, tax efficiency, housing decisions, and the long-term thinking that shapes financial outcomes.

(01:36) Hannah and her husband are in their mid-30s with two young children, and are hoping to upgrade to a larger “forever home” in several years while keeping their current home as a rental. They’re deciding whether to temporarily reduce retirement contributions to speed up down payment savings and how a possible cross-country relocation might affect those plans.

(37:15) Amelia is a part-time healthcare provider in New York who earns hourly income and wants to contribute to both her employer’s 401(k) and a traditional IRA. She’s trying to determine how much to contribute to the 401(k) from each paycheck while still maxing out her traditional IRA—keeping the overall approach simple and tax-efficient.

(56:12) Lesley praises Paula and Joe’s thoughtful responses to callers and wonders whether they ever seek advice from their audience. After recently undergoing brain surgery that prompted deeper reflection, the listener asks if there is anything in Paula and Joe’s financial, personal, or professional lives where they would value collective wisdom from their community.

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#697: Most people regret the things they never tried.

Venture capitalist Bill Gurley says that pattern shows up again and again in research on end-of-life regrets — including regret about the careers people never pursued. 

In this episode, Gurley joins us to talk about how people actually discover work they enjoy - and why the cliché to “follow your passion” sends people in the wrong direction.

We start with a question many listeners wrestle with: what if you reach your forties or fifties and still do not know what you want to do? 

Gurley explains that career changes later in life remain possible. Financial flexibility helps. People who spend every dollar they earn limit their ability to shift paths. People who control their spending keep more options open.

Gurley argues that “passion” often appears only after someone spends time exploring a field. A better starting point involves fascination - the subjects that pull your attention when nobody assigns the work. 

Gurley suggests paying attention to what you study in your free time. If you find yourself reading about a topic instead of watching Netflix, that curiosity may signal a possible career direction.

We also discuss how most successful careers involve several stops along the way. 

Gurley studied hundreds of success stories and found that many people move through two or three roles before landing their long-term path. That pattern shows up across industries.

Gurley began as a computer engineer working at Compaq. Even though he enjoyed the work, his curiosity shifted toward investing and business. 

He eventually left engineering, went to business school and started knocking on doors in New York until he landed a job as a Wall Street analyst. That path later led him to Silicon Valley and a 25-year career in venture capital.

Throughout the conversation, we talk about continuous learning, side projects that expand career options and how curiosity often shapes a career more than long-term planning.

Resources Mentioned:

Runnin' Down a Dream by Bill Gurley - https://amzn.to/4loywlQ

The Power of Regret by Daniel Pink - https://amzn.to/4sNwZbQ

Designing Your Life by Dave Evans & Bill Burnett - https://amzn.to/47yfeov

One Up on Wall Street by Peter Lynch - https://amzn.to/4ruPsIX

Atomic Habits by James Clear - https://amzn.to/4bj3cjR

Interview with James Clear - Afford Anything Episode #638

Interview with David Epstein - Afford Anything Episode #206

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#696:

(01:50) Jeremy has been a careful budgeter for years, but a surprise car repair has him tapping his emergency fund. With rates falling, he’s wondering if cash is enough or if he should try bonds or a CD ladder to keep up with inflation.

(22:22) A listener in Canada has a DIY portfolio but is tempted by Dimensional Funds, which requires a pricey advisor. At the same time, she’s thinking about leaving work and returning to school, but also wants to keep financially supporting her parents.

(41:27) Anonymous is navigating the tricky waters of buying a new home while still living in their current one. He is considering a bridge loan to avoid a contingent offer, but he’s worried about the strict timeline and potential financial pitfalls. Is a bridge loan a smart move, or does the risk of being stuck outweigh the convenience?

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#695: The U.S. lost 92,000 jobs in February, pushing unemployment to 4.4 percent.That result contradicts a different report released two days earlier showing 63,000 jobs added, leaving economists trying to square the circle. Many agree that we're in a "low hire, low fire" jobs environment.We walk through several major economic stories using a three-layer framework: the household economy, markets and policy, and long-term forces shaping the future.First, the household layer. Hiring has become uneven across sectors. Health care and education previously drove much of the job growth, but layoffs in those areas now appear in the data.Job openings have also fallen to 6.54 million, the lowest level since the pandemic began. Workers are switching jobs less often, and the pay bump for job-hopping has shrunk.Mortgage rates recently crossed 6 percent, influenced in part by rising Treasury yields and concerns about inflation. Gas prices climbed about 26 cents per gallon in a week, partly due to tensions affecting oil shipments through the Strait of Hormuz, which normally carries about one-fifth of global oil supply.The episode also looks at household finances. Six percent of workers in Vanguard plans took hardship withdrawals from their 401(k)s in 2025, up from five percent the year before. That increase suggests some households are leaning on retirement savings to manage financial stress.At the end of the episode, economist Dr. Ben Zweig, CEO of Revelio Labs, joins us to unpack the conflicting employment reports and explain why the labor market may look weaker than expected. He also discusses why health care hiring may be slowing and how economists interpret mixed signals across multiple labor data sources.

(0:00) February jobs shock(1:02) Three-layer economy framework(2:03) BLS job losses explained(3:12) ADP vs BLS data gap(4:30) Job openings decline(5:39) Layoffs and AI cuts(7:15) Mortgage rates near 6 percent(8:26) Gas price spike(10:02) Markets react to oil shock(16:00) Record 401k withdrawals(19:30) Asset owners vs nonowners gap(21:22) Supreme Court tariff ruling(23:31) AI costs collapse, usage surge(27:03) Fed reactions to jobs report(33:33) Economist Ben Zweig interview

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#694: There are about 90 million unique job titles in the U.S. labor market.

Ninety million.

If you are trying to negotiate a raise, switch companies or launch a side hustle, that number has consequences.

If titles do not line up, you cannot easily compare pay, scope or seniority. You might be doing the same work as someone with a higher title and higher salary - and never see it.

That problem is the focus of Part 2 of our conversation with Dr. Ben Zweig.

Zweig is the CEO of Revelio Labs, a workforce data firm that analyzes millions of job postings and online profiles. He also teaches The Future of Work at NYU Stern School of Business and holds a PhD in economics from the CUNY Graduate Center. His work focuses on how jobs are structured and how they evolve.

We talk about taxonomy - the systems used to categorize work. A title acts as shorthand for a bundle of tasks. Trouble starts when the shorthand breaks down. Two people with the same title may do very different work. Two people with different titles may perform nearly identical tasks.

Zweig explains how large language models can group job descriptions based on actual responsibilities rather than labels. That approach could make it easier for workers to search accurately and for companies to organize teams.

The conversation shifts to management. He argues that managers spend much of their time reconfiguring roles as business needs change. Technology accelerates that reconfiguration rather than replaces it.

We close with stories about bank tellers and typists. Their titles remained familiar. Their tasks transformed over time.

Resource:

⁠Job Architecture: Building a Language for Workforce Intelligence⁠ by Ben Zweig

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