Thinking About a Career Change? You’ll Need Skill, Work – and Luck

Summary

Masters in Business: Episode Summary Thinking About a Career Change? You’ll Need Skill, Work – and Luck Release Date: May 29, 2025

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Introduction

In this episode of Masters in Business, Bloomberg Radio host Barry Ritholtz engages in a profound conversation with Morgan Housel, the renowned author of The Psychology of Money and the forthcoming The Art of Spending Money. The discussion delves into Housel’s unconventional career path, his transition from blogging to authoring bestsellers, and his insights on navigating significant career changes. This summary captures the essence of their dialogue, highlighting key points, notable quotes, and actionable insights for listeners contemplating a career shift.

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Morgan Housel’s Early Career and Initial Struggles

Career Beginnings: From Diverse Jobs to Writing

Morgan Housel begins by recounting his diverse early jobs, which included roles such as a ski patrol member, valet, and ski rental technician. Despite these varied positions, Housel initially aspired to a career in investment banking, captivated by the perceived allure of wealth and power associated with the field.

Quote:

“When I was a teenager... I really only thought I had one career path and that was I was going to be an investment banker. And then maybe later on that changed.”
— Morgan Housel, [02:16]

Unplanned Transition to Writing

Housel’s entrance into writing was serendipitous. Graduating college in 2008 during an economic downturn, he struggled to find relevant employment. The scarcity of investment-related jobs led him to accept a position as a blogger for The Motley Fool—a role he initially despised but ultimately grew to love.

Quote:

“The only job I could find that was related to investing was as a blogger for the Motley Fool... I ended up loving it.”
— Morgan Housel, [01:35]

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Discovering a Passion for Writing

Overcoming Initial Reluctance

Housel emphasizes the importance of perseverance during his initial period as a blogger. Despite disliking writing at first, the necessity to sustain himself financially kept him in the role, allowing him to develop his skills organically over time.

Quote:

“It took me a couple years to kind of find my stride a little bit... I just like being an observer of how people think about money and investing and I want to tell a good story about it.”
— Morgan Housel, [04:07]

The Power of Feedback

A critical factor in Housel’s transformation was the immediate and honest feedback from readers. Constructive criticism, though painful, accelerated his learning curve, enabling him to refine his writing effectively.

Quote:

“If your work is bad, people will tell you... it is such a powerful feedback that you're able to learn very quickly.”
— Morgan Housel, [04:29]

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Transitioning to a Professional Career in Writing

From Blogger to Market Commentator

Housel discusses his evolution from a content creator at The Motley Fool to a respected writer within the financial community. This transition was marked by a growing audience and a heightened sense of responsibility to provide accurate and valuable insights.

Quote:

“There was a little bit... a sense of duty... to make sure that it's right, make sure that it is not dangerous advice for them.”
— Morgan Housel, [06:08]

Evolving Writing Practices

Over a decade at the Collaborative Fund, Housel honed his ability to monetize his writing through various channels, including blogging, speaking engagements, and book publications. This diversified approach ensured a sustainable career built around his passion for observing and narrating financial behaviors.

Quote:

“It's a home for my writing. And so it's all that I've ever done. But finding unique ways to make a living out of doing it.”
— Morgan Housel, [08:23]

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Writing a Bestselling Book: Challenges and Insights

Crafting The Psychology of Money

Transitioning from short-form blogging to authoring a book presented significant challenges for Housel. Initially attempting to create lengthy, cohesive chapters did not yield success, leading him to adopt a structure of standalone, concise chapters that resonate with modern readers' shorter attention spans.

Quote:

“I need to leverage whatever little strength that I have and say I'm good at writing short form blogs that can kind of live on their own.”
— Morgan Housel, [10:16]

Publisher Pushback and Ultimate Success

Despite resistance from his publisher, who preferred a traditional, narrative-driven nonfiction format, Housel’s strategy proved effective. The Psychology of Money became a bestseller, underscoring the importance of adapting to audience preferences and trusting one's instincts.

Quote:

“Books are very much like a seed stage startup where even if you do everything right, it's probably not going to work.”
— Morgan Housel, [12:56]

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Insights on Career Change and Personal Development

Breaking Free from Early Decisions

Housel highlights the often arbitrary connection between one's college major and their eventual career, advocating for flexibility and the courage to pivot when necessary.

Quote:

“The careers that we have in our 30s, 40s and 50s are tied to our college major that we chose when we were 17 or 18... it's completely insane.”
— Morgan Housel, [14:06]

Embracing Skill Development and Luck

Emphasizing that passion alone isn't sufficient, Housel advises that successful career changes require developing relevant skills, diligent work, and a degree of luck. He cites Nassim Nicholas Taleb's principle: “If you're going to panic, panic early,” suggesting that early recognition and action can prevent prolonged dissatisfaction.

Quote:

“If you're truly unhappy doing it, you should... panic early, quit, move on, cut your losses...”
— Morgan Housel, [14:06]

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Conclusion and Final Takeaways

Barry Ritholtz wraps up the conversation by reinforcing the key message: contemplating a career change necessitates not just following one's passion but also committing to acquiring new skills and embracing hard work. Housel’s journey exemplifies how adaptability and resilience can lead to fulfilling professional transformations.

Quote:

“See what you're capable of. See if you can make a go of it. But be aware, merely pursuing your bliss isn't going to get you anywhere.”
— Barry Ritholtz, [14:47]

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Key Takeaways

1. Perseverance is Crucial: Sticking with a challenging role can lead to unexpected passions and career opportunities.
2. Embrace Feedback: Honest criticism is invaluable for personal and professional growth.
3. Adaptability Matters: Transitioning careers requires flexibility in thought and approach, as well as a willingness to learn.
4. Skill Development is Essential: Passion must be coupled with the development of relevant skills to achieve success in a new field.
5. Early Action Prevents Long-term Regret: Recognizing and acting on career dissatisfaction early can lead to more fulfilling outcomes.

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For those considering a career shift, Morgan Housel’s story serves as an inspiring testament to the power of adaptability, continuous learning, and the willingness to embrace new opportunities—even when they arise unexpectedly.

Transcript

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[Morgan Housel]

It took me years to write. Will you take a look?

[Barry Ritholtz]

It's based on a novel by a mat name Lear and I need a job.

[Morgan Housel]

So I want to be a paperback writer. Paperback writer.

[Barry Ritholtz]

How often have you thought about making a major change in your career? You're going to give up time, effort, money, education. But in the end, if it pays off, it could be very worthwhile to be true to yourself on today's at the money. Let's bring in Morgan Housel. He is the author of the Psychology of Money, a book that sold over 7 million copies worldwide. His new book, the Art of Spending Money, arrives in October. So Morgan, I know you've had a bunch of jobs and even a bunch of careers ski patrol, valet. Like what was the original career plan with you?

[Morgan Housel]

When I was, when I was a teenager, my first job was, well, my first job was a, was a host at Denny's. That was a, that was a glorious job. And then so I grew up as a ski racer. So then it was, it was a natural flow for me to get a job in the ski industry. I worked in a, in a, in a ski rental tech place for, for a while and, and then I got my first kind of quote unquote real job was as a valet at a high end hotel that was on a ski resort. So that was cool. But all throughout my kind of like late teenage college years I really only thought I had one career path and that was I was going to be an investment banker. And then maybe later on that changed. I'm going to be a hedge fund manager. I didn't really know anything about either of those careers, but 19 year old Morgan loved the idea that they appeared to make a lot of money and have a lot of power. And so that was appealing to me because that was all that I knew. And then haphazardly, not on purpose and kind of with a sense of shame, I stumbled into a job as a writer. Because I graduated college in 2008, nobody was hiring. The economy's a mess. The only job I can find that was related to investing was as a blogger for the Motley Fool. I did not want to do it. I hated writing. I had no experience doing it and. But I thought I would do it for six months until I stumbled into it. But then I ended up loving it. It took a year, but it was like I actually, I was like, oh, this is, this is pretty fun. I actually like doing this. And then over, you know, that was, you know, 17 years ago. And over those 17 years, I've had several different transitions doing different things, but they've all kind of been had this common core of. I just like being an observer of how people think about money and investing and I want to tell a good story about it, but. But there have been several different paths and transitions within that, within that core.

[Barry Ritholtz]

That I've gone down a blogger for the Motley Fool. I wouldn't even call that a journalist. You're just a content producer at that point. How long did it take before you this? Six month. I'm going to just put up with this until I find something better. What was the transition that led you to realize, hey, I got a knack for this. Maybe there's more to this than I realized.

[Morgan Housel]

I think what was really good in hindsight, it felt terrible at the time, but because the job market in 2008, 9 and 10 was so bad, I didn't have the choice of giving up. There was no other job for me. I, I had a rent payment to make. So even in the first year or two that I didn't like writing at all, it was like, yeah, but that's what you're like, sorry, pal, deal with it. That's what you're doing. There's no other jobs out there. That was really good in hindsight because it took me a couple years to kind of find my stride a little bit. Just like anybody in, in any job. The other thing about writing online or doing anything online is that if your work is bad, people will tell you in no uncertain terms, how bad it is and how dumb you are and how stupid you are. That is painful in the moment, but it is such a powerful feedback that you're able to learn very quickly if you're paying attention to that criticism. And so every blog post that I wrote, I would put it out there and people would either say, this sucks, and I would say, okay, let me try to learn from that, or, hey, this is really good, and let me try to learn from that. So the feedback mechanism was so powerful that after doing it for two years just to make rent, it was kind of like, oh, this is actually fun. And. And there's some readers out there who seem to be enjoying what I'm putting out. And that's. So it was good that I had that forcing function of having to do it, rather than having an exit ramp where I could have gone and done something else.

[Barry Ritholtz]

So I'm curious about the transition from blogger. And I have been blogging for a hundred years, so I don't use it pejoratively, but to a more formal either journalist or market commentator. That was the next tier up. How did that happen?

[Morgan Housel]

I've never considered myself a journalist. I don't think I ever will. I don't neither.

[Barry Ritholtz]

But people will accuse us of being journalists, right?

[Morgan Housel]

You know, we are, we are journaling, but I don't consider myself a capital J journalist. But what's true is that once I realized that my audience was growing and I realized who that audience was, there was a little bit, I struggle to say, sense of duty. That sounds like it's too much, but it was a little bit more of, hey, people are going to read this and they're going to take it seriously. So make sure that it's right, make sure that it is, is not dangerous advice for them. And so I look back at some of the things that I wrote early in my career and. And it's not that it was. It was reckless, but I would just. I would just throw my thoughts on the table regardless of what they were and throw people under the bus, which I tend not to anymore. And what is this, what is this.

[Barry Ritholtz]

Throwing people under the bus you speak of?

[Morgan Housel]

It's. You've done it once or twice, and even when they deserve it. I think there's a. There's a principle, I forget who came up with this, of like, criticize broadly and praise individually. So it's fine to criticize an industry and say mortgage bankers in 2005 were reckless, if not criminal. But once you call them out by name, even if they deserve it, that's a tougher thing to do. It's usually the case that when you're criticizing somebody, at best you have half the story. Sometimes you have 5% of the story. And. But praising in the individual is great because you underestimate how much you can change somebody's life by praising them when they deserve it.

[Barry Ritholtz]

Huh. Really, really insightful thought. So take us along the steps and along the aha moments where you realized, oh, this is something significant and I could build a professional career doing writing.

[Morgan Housel]

It was interesting for me as a writer that I think might be a little bit unique is day one that I was writing for the Motley fool, the very first blog post I ever wrote. I was getting paid a full time salary. It was not, it was not exorbitant, but I was living off of it from day one. And 99% of bloggers go through years where they're not making a single cent and nobody's reading their work. And so I had made a profession out of it from day one. And there was really no ramp up of, let's see how I can make money from this. As the years went on, it could increase. And then I got into speaking and books and some other things.

[Barry Ritholtz]

So what was next after Motley Fool?

[Morgan Housel]

After Motley Fool, I joined the Collaborative Fund, which is a private equity firm.

[Barry Ritholtz]

And my job now, 10 years, been.

[Morgan Housel]

There for nine, 10 years. Yeah. And my entire job there is, is writing. It's a home for my writing. And so it's all that I've ever done. But finding unique ways to make a living out of doing it. There's several different ways you could do it. You can be a full time reporter for Reuters, for your local news, or for the New York Times. That's one way to do it. You can do substack, you can try ads. There's a million different ways to do it.

[Barry Ritholtz]

So let's get a little technical. Let's talk about some blocking and tackling. What sort of tools did you develop? What sort of subroutines did you learn that helped you become a better writer?

[Morgan Housel]

99% of being a good writer is being a good reader. And 90% of your time as a writer is, is reading. And, and so the huge majority of my day, and it's been like this for almost 20 very casually sitting around in my sweatpants, reading, reading books, reading blogs, reading reports, listening to podcasts. And it doesn't look like work, but that's the work of a writer because you do that and you start Putting the pieces together of, oh, I read this chapter in this book and it reminded me of something I listened to in this podcast, which reminded me of this study that I read recently. I can tie all those together and come up with a really unique story myself that I can write about. And so that is what writing is, is reading. And what writing is not, is forcing yourself at the keyboard, forcing the sentences out. That's when you get the worst writing. You should spend all of your time reading and thinking and maybe 10% of your time actually writing.

[Barry Ritholtz]

I love that. That's really, really insightful. Psychology Money came out. Was that 20? 20, 21.

[Morgan Housel]

September 2020.

[Barry Ritholtz]

All right, so 2020. So that's, you know, a dozen years after you began at the Motley Fool. What was the transition like writing a book from writing a bunch of really short blog posts?

[Morgan Housel]

It was, it was interesting because when I started writing Psychology of Money, I was like, hey, this is a book. This is not a blog. I need to have 5,000 word chapters, and they all need to be cohesive and tell a singular narrative. And that's what I set out to write. And I've told the story before. But after about three months, maybe six months, I had three really bad chapters, none of which made it in the book. Because I was trying to do something that I had no experience doing. And I had to look back and say, look, for the previous 12 years, I have a skill and a muscle of writing 1,000 word blog posts. I don't have a skill of writing 5,000 word chapters. It's just not something that I do. And so I just kind of, I threw everything out and I said, look, I. I need to leverage whatever little strength that I have and say I'm good at writing short form blogs that can kind of live on their own. They're not going to tie, tie into the next chapter. They're all going to be kind of like standalone, live on their own. The publisher hated that, said, it's not going to work. People want cohesive book. And I said, yeah, I'm sorry, but this is all that I can do, like deal with it. And I, I think it actually worked out well because it's easy to underestimate how much people's attention spans have declined in the last 15 years. And so the attention to read a 300 page nonfiction book that is a cohesive narrative from page one to page 300 is very diff. It's a big ass these days. But can you ask people to flip through short chapters that live on their Own. If you don't like this chapter, just flip to the next. You can start there. That is a ask. And everybody knows the nonfiction business book. That could have been a blog post, it could have been a magazine article, but they stretched it into 300 pages. I think the only way that you could avoid that was by writing short standalone chapters that live on their own. Here's my point. Let me tell an interesting story and then I'm going to move on to the next one and not waste your time.

[Barry Ritholtz]

So I find it hilarious we share the same publisher for how not to invest that you wrote the forward to and your book the Psychology of Money. This is the first time I'm hearing that they weren't enthralled with your original concept. Have we crossed 8 million copies yet? You're like 7 million on the way to 8 million. I have a whole section in my book about none of the professionals know what's going to sell. Nobody wanted to do Star Wars. They all passed on Raiders. This E2 movie is dumb. We have another spaceman movie like on and on it goes. John Wick, Squid games. All the reviews of the Beatles initially on Ed Sullivan were horrible.

[Morgan Housel]

It's.

[Barry Ritholtz]

I'm shocked to hear that the experts were like, meh, we're not really impressed with this concept.

[Morgan Housel]

There's a Daniel Kahneman quote where he said the. The more outlier the successes, the more an element of luck played a role. Not that it's all luck, but he. He phrased it as like there's no exception to that rule. The more standard deviations it is as an outlier, the more L. Period, end of story. And I think that's true for books as well. It's true for every startup. Jeff Bezos tells a story about how much he struggled to raise $1 million to sell one third of it. I think it was of Amazon in 1994. Could they. He had to take 100 calls to get to raise 100 to raise $1 million for Amazon. So it's. It always makes sense in hindsight. It never makes sense with foresight. I think that's true. And I think books are very much like a seed stage startup where even if you do everything right, it's probably not going to work. So I don't look. I don't look poorly at all. Or criticize the publishers who passed on a book.

[Barry Ritholtz]

Huh. And our final question. What's your big takeaway about someone thinking about either exploring a career that wasn't their original intention or making a career shift towards something that they have a natural aptitude towards.

[Morgan Housel]

One thing about careers is that so many of us, the careers that we have in our 30s, 40s and 50s are tied to our college major that we chose when we were 17 or 18. And when you frame how absolutely absurd that is that you made a decision when you were 17 years old that is now tying you into a career when you're 45, it's completely insane. And so the idea that if you're truly unhappy doing it, that you should, you should move on to something else. There's a great quote from Talib where he says, if you're going to panic, panic early. And I think you can tie that to careers as well. If you really realize that this is not for you and you're unhappy, panic early, quit, move on, cut your losses, move on to something else rather than tying it out for the next 40 years of your career.

[Barry Ritholtz]

So to wrap up, if you're thinking about a career change, if you have an aptitude towards a particular skill, if you want to just try something different, find a way to do that. See what you're capable of. See if you can make a go of it. But be aware, merely pursuing your bliss isn't going to get you anywhere. You have to develop some tools, some skills and some abilities in order to earn a living in your new career. I'm Barry Ritholtz. You're listening to Bloomberg's at the money.

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[Barry Ritholtz]

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[Morgan Housel]

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[Morgan Housel]

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