#758: Q&A: “I’m 26 and No Longer Motivated by Money. Am I Unemployable?”

Anonymous (let’s call them “Maria”) asks: I’m 26 years old, living in the United States, and my net worth is roughly 10 times my annual spending. There is plenty of advice on how to work your way to financial independence, but what I can’t find is how to work after achieving it. While I haven’t reached full financial independence yet, I have enough that I am no longer motivated by money. I don’t find working on someone else’s schedule acceptable, and I want to determine what projects I work on rather than having an employer decide. It feels like I have a negotiation advantage that other employees don’t have, but potential employers can simply avoid hiring me in favor of workers who are motivated by money and forced to work on someone else’s schedule. I am not at a place in my career where entrepreneurship is a good option yet. Because of my investments, I don’t think I can accept a job doing anything other than what I want to do, which is clearly not what my coworkers are doing and not what employers expect of me. I’m starting to worry that I am becoming unemployable.

Matt asks: I have a question about target date funds. I know Joe is not a fan, and I’ve heard him rant about that many times over the years. However, several people I respect—such as YouTuber Rob Berger, Bogleheads leader John Luskin, and financial advisor Peter Lazaroff—invest most or all of their money in a target date or all-in-one fund and speak positively about them. I know Joe disagrees, but these are people I trust. I don’t invest in a target date fund myself, but I’m intrigued by the idea. I would love to hear your point of view on them.

Lucas asks: I’d love your perspective on the timing and financial risk of a career change. My wife and I are both 35. We have a two-and-a-half-year-old daughter who has special needs and a six-month-old son. My daughter will likely need lifelong support, so we’re trying to plan responsibly for future care costs that are still hard to estimate.

We both work in IT consulting at large professional services firms. Our combined compensation is about $375,000 annually, including salary, bonuses, and ESPP. We spend roughly $110,000 per year today, but we expect that number to rise to about $130,000 starting in 2027 as daycare and other kid-related expenses increase.

Over the past four or five years, we’ve paid off our mortgage and saved an average of about $5,000 to $6,000 per month into our taxable brokerage account. We still get our full 401(k) matches, max out our HSA and dependent care FSA, and have a little over $840,000 across our 401(k)s and IRAs. By the time I expect to make a career move, we think we’ll have about 12 months of necessary expenses in cash reserves, and we also plan to purchase a new vehicle before then.

The complication is that I’m considering a transition into financial planning around late summer 2027. I’m comfortable starting near the bottom of the ladder and expect my income could fall by roughly 60% initially. That would bring our household income down to around $250,000, just as we have two kids starting in daycare and our expenses are at their highest. I’m not really happy in my current role, and I feel confident that financial planning is the right long-term move for me, but I’m struggling with whether this is the responsible timing. Should I make the switch in 2027, accepting a temporary step back in income, or stay in IT consulting another year or two to build a bigger cushion?

As far as the timing of the transition, I’ve already taken major steps over the past few months to position myself for the switch, including completing a financial planning externship, networking with local CFPs to gauge the market in my area, and studying for my Series 65. I’m also taking my last block of paternity leave in January and owe my company 30 business days after returning. By that time, it will be performance discussion season, bonuses are paid out in late May, and 401(k) matches are in late June, so it’s worth staying into the summer.

What blind spots do you see, and am I accounting for the right things, especially given our children, higher near-term expenses, and the uncertainty around our daughter’s long-term care needs?

• Not chasing money can make you more employable: When I hire, I look for two things: a drive for mastery and a belief in the mission. Someone who isn’t there just to collect a paycheck is exactly who I want on my team. Money motivation would be the wrong fit.
• Small businesses reward results over seat time: Joe pointed out that big corporations often care whether you’re at your desk from 8 to 5, while small businesses care whether the work gets done. My caveat: in a tiny company, one or two personalities shape your entire experience.
• Look for founders who are humble but confident: The best small-business leaders know what they’re bad at and hire people better than them, without letting ego get in the way. A quick test before any job or career change: would you want to spend an eight-hour airport layover with these people?
• A good target date fund is harm reduction: Joe argues most people can learn to build a simple three-fund portfolio, and that many target date funds are packed with high-fee leftovers. I see a low-cost one from Vanguard, Fidelity, Schwab, or T. Rowe Price as a smart default for anyone tempted by crypto or individual stocks.
• Your savings exist for moments like this: Lucas has spent years paying off his mortgage and building a taxable brokerage account. To me, funding a career change into work he actually wants is exactly what all that saving is for. Waiting “one more year” just delays the clock.
• Make your career change while your kids are young: Joe started his financial planning career when his kids were small and says getting that pain out of the way early was worth it. Time, not money, is the bigger currency in any career change, and leaner years can still be rich ones.

Free Asset Location Guide
Building your own mix instead of a target date fund? See which account each fund belongs in.
Download the guide

Episode #709 with Keith Wargo
Planning for a child with special needs, including special needs trusts and ABLE accounts.
Listen to Episode #709

Episode #755 with Rob Berger
Our interview with Rob Berger, one of the target date fund fans Matt mentions.
Listen to Episode #755

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