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

An episode of [Masters in Business](https://invisiblenetwork.ai/podcast/730188152), 29 May 2025, 14 min.

Audio: https://podtrac.com/pts/redirect.mp3/traffic.omny.fm/d/clips/e73c998e-6e60-432f-8610-ae210140c5b1/4e4cd910-40a1-4619-a5f3-ae2b0012ffff/b1cd6cbb-60d0-4394-a3f9-b2ec0169483e/audio.mp3?utm_source=Podcast&in_playlist=5873a3cb-298f-40bc-b71f-ae2b0013000d

What does it take to undertake a significant career change? How can you shift from a safe but unsatisfying job into one that you love? Successfully navigating a major career change requires some skill, some hard work, and a bit of luck. Morgan Housel is the author of the best-selling “Psychology of Money” (8 million copies sold worldwide), We discuss how he shifted his career into being a writer. Each week, “At the Money” discusses an important topic in money management. From portfolio construction to taxes and cutting down on fees, join Barry Ritholtz to learn the best ways to put your money to work. See omnystudio.com/listener for privacy information.

## Transcript

[0:02] Speaker 1: Bloomberg Audio Studios, podcasts, radio news, Pay the.
[0:09] Speaker 2: Rides remarks based on enough time job at the.
[0:36] Speaker 1: How often have you thought about making a major change
[0:40] Speaker 1: in your career. You're gonna give up time, effort, money, education,
[0:45] Speaker 1: but in the end, if it pays off, it could
[0:48] Speaker 1: be very worthwhile to be true to yourself. On today's
[0:52] Speaker 1: at the Money, let's bring in Morgan Housel. He is
[0:55] Speaker 1: the author of the Psychology of Money, a book that
[0:58] Speaker 1: sold over seven million worldwide.
[1:01] Speaker 2: His new book, The Art.
[1:02] Speaker 1: Of Spending Money, arrived in October. So, Morgan, I know
[1:08] Speaker 1: you've had a bunch of jobs and even a bunch
[1:11] Speaker 1: of careers Ski Patrol valet, Like, what was the original
[1:16] Speaker 1: career plan.
[1:17] Speaker 3: With you when I was When I was a teenager,
[1:20] Speaker 3: my first job was well, my first job was a
[1:22] Speaker 3: was a host at Denny's.
[1:23] Speaker 2: That was that was a glorious job.
[1:25] Speaker 3: And then so I grew up as a ski racer,
[1:28] Speaker 3: so then it was it was a natural flow for
[1:30] Speaker 3: me to get a job in the ski industry. I
[1:32] Speaker 3: worked in a in a ski rental tech place for
[1:35] Speaker 3: it for a while, and and then I got my
[1:38] Speaker 3: first kind of quote unquote real job was as a
[1:41] Speaker 3: valet at a high end hotel that was on a
[1:44] Speaker 3: ski resort, so that was cool. But all throughout my
[1:46] Speaker 3: kind of like uh, late teenage college years, I really
[1:51] Speaker 3: only thought I had one career path, and that was
[1:52] Speaker 3: how I was going to be an investment banker, and
[1:55] Speaker 3: then maybe later on that changed to I'm gonna be
[1:56] Speaker 3: a hedge fund manager. I didn't really know anything about
[1:59] Speaker 3: either of those careers, but nineteen year old Morgan loved
[2:02] Speaker 3: the idea that they appeared to make a lot of
[2:03] Speaker 3: money and have a lot of power, and so that
[2:05] Speaker 3: was appealing to me because I was all that I knew.
[2:07] Speaker 3: And then, haphazardly, not not on purpose, and kind of
[2:12] Speaker 3: with a sense of shame, I stumbled into a job
[2:15] Speaker 3: as a writer. Because I graduated college in two thousand
[2:18] Speaker 3: and eight, nobody was hiring. The economy is a mess.
[2:20] Speaker 3: The only job I can find that was related to
[2:23] Speaker 3: investing was as a blogger for the Motley Fool. I
[2:25] Speaker 3: did not want to do it. I hated writing. I
[2:27] Speaker 3: had no experience doing it, but I thought I would
[2:30] Speaker 3: do it for six months until I stumbled into it,
[2:32] Speaker 3: but then I ended up loving it. It took a year,
[2:35] Speaker 3: but it was like, actually I was like, oh, this
[2:37] Speaker 3: is this is pretty fun. I actually liked doing this.
[2:39] Speaker 3: And then over you know, that was, you know, seventeen
[2:42] Speaker 3: years ago. And over those seventeen years, I've had several
[2:46] Speaker 3: different transitions doing different things, but they've all kind of
[2:49] Speaker 3: been had this common core of I just like being
[2:52] Speaker 3: an observer of how people think about money and investing
[2:55] Speaker 3: and I want to tell a good story about it.
[2:57] Speaker 3: But there have been several different paths and transitions within that,
[3:01] Speaker 3: within that core that I've gone down.
[3:03] Speaker 1: A blogger for the Motley Fool. I wouldn't even call
[3:06] Speaker 1: that a journalist. You're just a content producer at that point.
[3:11] Speaker 1: How long did it take before you this six month?
[3:14] Speaker 1: I'm going to just put up with this until I
[3:16] Speaker 1: find something better. What was the transition that led you
[3:19] Speaker 1: to realize, Hey, I got a knack for this, Maybe
[3:23] Speaker 1: there's more to this than I realized.
[3:25] Speaker 3: I think what was really good In hindsight, it felt
[3:27] Speaker 3: terrible at the time, but because the job market in
[3:30] Speaker 3: two thousand and eight, nine and ten was so bad,
[3:33] Speaker 3: I didn't have the choice of giving up. There's no
[3:36] Speaker 3: other job for me. I had a rent payment to make,
[3:39] Speaker 3: so even in the first year or two that I
[3:41] Speaker 3: didn't like writing at all. It was like, yeah, but
[3:43] Speaker 3: that's what you're like. Sorry, Paal did deal with it.
[3:45] Speaker 3: That's what you're doing. There's no other jobs out there
[3:48] Speaker 3: that was really good in hindsight, because it took me
[3:50] Speaker 3: a couple of years to kind of find my stride
[3:52] Speaker 3: a little bit, just like anybody in any job. The
[3:55] Speaker 3: other thing about writing online or doing anything online is
[3:58] Speaker 3: that if your work is bad, people will tell you
[4:01] Speaker 3: in no uncertain terms how bad it is and how
[4:03] Speaker 3: dumb you are and how stupid you are. That is
[4:06] Speaker 3: painful in the moment, but it is such a powerful
[4:08] Speaker 3: feedback loop that you're able to learn very quickly if
[4:11] Speaker 3: you're paying attention to that criticism. And so every blog
[4:13] Speaker 3: post that I wrote, I would put it out there
[4:15] Speaker 3: and people would either say this sucks and I'd say, okay,
[4:17] Speaker 3: let me try to learn from that, or Hey, this
[4:19] Speaker 3: is really good and let me try to learn from that.
[4:21] Speaker 3: So the feedback mechanism was so powerful that after doing
[4:25] Speaker 3: it for two years just to make rent, it was
[4:28] Speaker 3: kind of like, oh, this is actually fun, and there's
[4:30] Speaker 3: some readers out there who seem to be enjoying what
[4:32] Speaker 3: I'm putting out and that's so it was good that
[4:34] Speaker 3: I had that forcing function of having to do it,
[4:37] Speaker 3: rather than having an exit ramp where I could have
[4:38] Speaker 3: gone and done something else.
[4:40] Speaker 1: So I'm curious about the transition from blogger and I
[4:47] Speaker 1: have been blogging for one hundred years, so I don't
[4:49] Speaker 1: use it pejoratively, but to a more formal either journalist
[4:55] Speaker 1: or market commentator that was the next tier up. How
[4:59] Speaker 1: did that happen.
[5:00] Speaker 3: I've never considered myself a journalist. I don't think I
[5:02] Speaker 3: ever will.
[5:03] Speaker 1: I don't have it either, but I will accuse us
[5:05] Speaker 1: of being journalist.
[5:07] Speaker 3: Right, you know we are, we are journaling, but I
[5:09] Speaker 3: don't consider myself a capital J journalist. But what's true
[5:12] Speaker 3: is that once I realized that my audience was growing,
[5:15] Speaker 3: and I realized who that audience was, there was a
[5:18] Speaker 3: little bit I struggle to say, sense of duty. That
[5:21] Speaker 3: that sounds like it's too much, but it was a
[5:23] Speaker 3: little bit more of Hey, people are going to read
[5:25] Speaker 3: this and they're going to take it seriously, so make
[5:27] Speaker 3: sure that it's right, make sure that it is is
[5:30] Speaker 3: not dangerous advice for them. And so I look back
[5:33] Speaker 3: at some of the things that I wrote early in
[5:35] Speaker 3: my career, and it's not that it was. It was reckless,
[5:38] Speaker 3: but I would just I would just throw my thoughts
[5:40] Speaker 3: on the table, regardless of what they were, and throw
[5:42] Speaker 3: people under the bus, which I tend not to anymore.
[5:45] Speaker 2: And what is this?
[5:46] Speaker 1: What is this throwing people under the bus? You speak
[5:49] Speaker 1: of it.
[5:51] Speaker 3: You've done it once or twice, and even when they
[5:54] Speaker 3: deserve it. I think there's a there's a principle. I
[5:56] Speaker 3: forget who came up with this of like criticized broadly
[5:59] Speaker 3: and pre individually. So it's fine to criticize an industry
[6:03] Speaker 3: and say mortgage bankers in two thousand and five were reckless,
[6:07] Speaker 3: if not criminal, But once you call them out by name,
[6:10] Speaker 3: even if they deserve it, that's a tougher thing to do.
[6:13] Speaker 3: It's usually the case that when you're criticizing somebody, at
[6:17] Speaker 3: best you have half the story. Sometimes you have five
[6:19] Speaker 3: percent of the story. But praising in the individual is
[6:22] Speaker 3: great because you underestimate how much you can change somebody's
[6:25] Speaker 3: life by praising them when they deserve it.
[6:27] Speaker 1: Huh, really really insightful thought. So take us along the
[6:31] Speaker 1: steps and along the aha moments where you realized, oh,
[6:36] Speaker 1: this is something significant and I could build a professional
[6:40] Speaker 1: career doing writing.
[6:45] Speaker 3: It was interesting for me as a writer. That I
[6:46] Speaker 3: think might be a little bit unique is day one
[6:48] Speaker 3: that I was writing for the Mali Fool, the very
[6:51] Speaker 3: first blog post I ever wrote. I was getting paid
[6:54] Speaker 3: a full time salary. It was not exhorbingan but I
[6:57] Speaker 3: was living off of it from day one. And ninety
[6:59] Speaker 3: percent of bloggers go through years where they're not making
[7:04] Speaker 3: a single cent and nobody's reading their work. And so
[7:07] Speaker 3: I had made a profession out of it from day one,
[7:09] Speaker 3: and there was really no ramp of let's see how
[7:10] Speaker 3: I can make money from this. As the years went on,
[7:13] Speaker 3: it could increase, and then I got into speaking in
[7:15] Speaker 3: books and some other things.
[7:16] Speaker 1: So what was next? After Motley Fool.
[7:18] Speaker 3: After a Mither Fool, I joined the Collaborative Fund, which
[7:20] Speaker 3: is a private equity firm. And my entire job now
[7:23] Speaker 3: ten been dire for ten nine ten years. Yeah, and
[7:26] Speaker 3: my entire job there is writing. It's a home for
[7:28] Speaker 3: my writing. And so it's all that I've ever done,
[7:31] Speaker 3: but finding unique ways to make a living out of
[7:33] Speaker 3: doing it. There's several different ways you could do it.
[7:35] Speaker 3: You can be a full time reporter for Reuters or
[7:38] Speaker 3: for your local news or for the New York Times.
[7:39] Speaker 3: That's one way to do it. You can do substack,
[7:41] Speaker 3: you can try ads. There's a million different ways to
[7:43] Speaker 3: do it.
[7:44] Speaker 1: So let's get a little technical. Let's talk about some
[7:46] Speaker 1: blocking and tackling. What sort of tools did you develop,
[7:50] Speaker 1: What sort of subroutines did you learn that helped you
[7:55] Speaker 1: become a better writer.
[7:57] Speaker 3: Ninety nine percent of being a good writer is being
[7:59] Speaker 3: a good reader. And ninety percent of your time as
[8:02] Speaker 3: a writer is reading. And so the huge majority of
[8:07] Speaker 3: my day, and it's been like this for almost twenty years,
[8:09] Speaker 3: is very casually sitting around in my sweatpants reading reading books,
[8:14] Speaker 3: reading blogs, reading reports, listening to podcasts. And it doesn't
[8:18] Speaker 3: look like work, but that's the work of a writer
[8:20] Speaker 3: because you do that and you start putting the pieces
[8:21] Speaker 3: together of Oh, I read this chapter in this book
[8:24] Speaker 3: and it reminded me of something I listened to in
[8:26] Speaker 3: this podcast, which reminded me of the study that I
[8:28] Speaker 3: read recently. I can tie all those together and come
[8:31] Speaker 3: up with a really unique story myself that I can
[8:32] Speaker 3: write about. And so that's that is what writing is
[8:35] Speaker 3: is reading, and what writing is not is forcing yourself
[8:39] Speaker 3: at the keyboard, forcing the sentences out. That's when you
[8:42] Speaker 3: get the worst writing. You should spend all of your
[8:44] Speaker 3: time reading and thinking and maybe ten percent of your
[8:47] Speaker 3: time actually writing.
[8:48] Speaker 1: I love that. That's really really insightful. Psychology Money came out?
[8:54] Speaker 1: Was that twenty twenty twenty one September twenty twenty, all right,
[8:57] Speaker 1: so twenty twenty, So that's a you know, a dozen
[9:01] Speaker 1: years after you begin at the Motley Fool. What was
[9:05] Speaker 1: a transition like writing a book from writing a bunch
[9:09] Speaker 1: of really short blog posts?
[9:11] Speaker 3: It was. It was interesting because when I started writing
[9:14] Speaker 3: Psychology and Money, I was like, Hey, this is a book,
[9:17] Speaker 3: this is not a blog. I need to have five
[9:21] Speaker 3: thousand word chapters and they all need to be cohesive
[9:24] Speaker 3: and tell a singular narrative. And that's what I set
[9:27] Speaker 3: out to write. And I've told the story before. But
[9:29] Speaker 3: after about three months, maybe six months, I had three
[9:33] Speaker 3: really bad chapters, none of which made it in the book,
[9:36] Speaker 3: because I was trying to do something that I had
[9:37] Speaker 3: no experience doing. And I had to look back and say, look,
[9:40] Speaker 3: for the previous twelve years, I have a skill and
[9:44] Speaker 3: a muscle of writing one thousand word blog posts. I
[9:48] Speaker 3: don't have a skill of writing five thousand word chapters.
[9:50] Speaker 3: It's just not something that I do. And so I
[9:53] Speaker 3: just kind of I threw everything out and I said, look,
[9:55] Speaker 3: I need to leverage whatever little strength that I have
[9:58] Speaker 3: and say I'm good at writing short form blogs that
[10:01] Speaker 3: can kind of live on their own. They're not going
[10:03] Speaker 3: to tie tie into the next chapter. They're all going
[10:05] Speaker 3: to be kind of like standalone, live on their own.
[10:07] Speaker 3: The publisher hated that, said it's not going to work.
[10:10] Speaker 3: People want a cohesive book, and I said, yeah, I'm sorry,
[10:12] Speaker 3: but this is all that I can do, like to
[10:14] Speaker 3: deal with it, And I think it actually worked out
[10:17] Speaker 3: well because it's easy to underestimate how much people's attention
[10:20] Speaker 3: spans have declined in the last fifteen years, and so
[10:24] Speaker 3: the attention to read a three hundred page nonfiction book
[10:28] Speaker 3: that is a cohesive narrative from page one to page
[10:30] Speaker 3: three hundred is very difficult.
[10:32] Speaker 1: It's a big ass these days.
[10:34] Speaker 3: But can you ask people to flip through short chapters
[10:37] Speaker 3: that live on their own. If you don't like this chapter,
[10:39] Speaker 3: just flip to the next. You can start there. That
[10:41] Speaker 3: is a better ask, And everybody knows the nonfiction business
[10:45] Speaker 3: book that could have been a blog post, it could
[10:48] Speaker 3: have been a magazine article, but they stretched it into
[10:50] Speaker 3: three hundred pages. I think the only way that you
[10:52] Speaker 3: could avoid that was by writing short, standalone chapters that
[10:56] Speaker 3: live on their own. Here's my point. Let me tell
[10:58] Speaker 3: an interesting story, and then I'm going to move on
[11:00] Speaker 3: to the next one and not waste your time.
[11:02] Speaker 1: So I find it hilarious. We share the same publisher
[11:05] Speaker 1: for How Not To Invest, that you wrote the forward to,
[11:09] Speaker 1: and your book The Psychology of Money. This is the
[11:12] Speaker 1: first time I'm hearing that they weren't enthralled with your
[11:15] Speaker 1: original concept the have we crossed eight million copies yet
[11:21] Speaker 1: you're like seven million on the way to eight million.
[11:24] Speaker 1: I have a whole section in my book about none
[11:27] Speaker 1: of the professionals know what's gonna sell. Nobody wanted to
[11:30] Speaker 1: do Star Wars. They all passed on Raiders. This et
[11:33] Speaker 1: movie is dumb. We have another Spaceman movie like on
[11:37] Speaker 1: and on it goes John Wick, Squid Games. All the
[11:40] Speaker 1: reviews of the Beatles, initially on ed Sullivan were horrible.
[11:44] Speaker 1: It's I'm shocked to hear that the experts were like, eh,
[11:49] Speaker 1: we're not really impressed with this concept.
[11:52] Speaker 3: There's a Daniel Common quote where he said, the more
[11:54] Speaker 3: outlier of the successes, the more an element of luck
[11:58] Speaker 3: played a role, not that it all luck, but he
[12:01] Speaker 3: phrased it as like there's no exception to that rule.
[12:04] Speaker 3: The more standard deviations it is as an outlier, the
[12:06] Speaker 3: more luck there was period end of story. And I
[12:09] Speaker 3: think that's true for books as well. It's true for
[12:11] Speaker 3: every startup. Jeff Bezos tells a story about how much
[12:14] Speaker 3: he struggled to raise one million dollars to sell one
[12:18] Speaker 3: third of it. I think it was of Amazon in
[12:20] Speaker 3: nineteen ninety four. Could he had to take one hundred
[12:22] Speaker 3: calls to get to raise one hundred to raise one
[12:24] Speaker 3: million dollars for Amazon? So it's it always makes sense
[12:28] Speaker 3: in hindsight, it never makes sense with foresight. I think
[12:31] Speaker 3: that's true. And I think books are very much like
[12:33] Speaker 3: a seed stage startup where even if you do everything right,
[12:37] Speaker 3: it's probably not going to work. So don't look I
[12:40] Speaker 3: don't look poorly at all or criticize the publishers who
[12:43] Speaker 3: passed on a book.
[12:45] Speaker 2: Huh.
[12:45] Speaker 1: And our final question, what's your big takeaway about someone
[12:50] Speaker 1: thinking about either exploring a career that wasn't their original intention?
[12:55] Speaker 1: Or making a career shift towards something that they have
[12:59] Speaker 1: a natural aspleude towards.
[13:01] Speaker 3: One thing about careers is that so many of us,
[13:04] Speaker 3: the careers that we have in our thirties, forties and fifties,
[13:07] Speaker 3: are tied to our college major that we chose when
[13:10] Speaker 3: we were seventeen or eighteen. And when you frame how
[13:12] Speaker 3: absolutely absurd that is that you made a decision when
[13:15] Speaker 3: you are seventeen years old that is now tying you
[13:18] Speaker 3: into a career when you're forty five, it's completely insane.
[13:21] Speaker 3: And so the idea that if you're truly unhappy doing it,
[13:25] Speaker 3: that you should you should move on to something else.
[13:27] Speaker 3: There's a great quote from Tilt where he says, if
[13:29] Speaker 3: you're going to panic, panic early. And I think you
[13:31] Speaker 3: can tie that to careers as well. If you really
[13:34] Speaker 3: realize that this is not for you and you're unhappy,
[13:37] Speaker 3: panic early, quit, move on, cut your losses, move on
[13:39] Speaker 3: to something else, rather than tying it out for the
[13:41] Speaker 3: next forty years of your career.
[13:43] Speaker 1: So to wrap up, if you're thinking about a career change,
[13:46] Speaker 1: if you have an aptitude towards a particular skill, if
[13:49] Speaker 1: you want to just try something different, find a way
[13:53] Speaker 1: to do that. See what you're capable of, see if
[13:56] Speaker 1: you can make a go of it. But be aware
[13:59] Speaker 1: merely pursuing your bliss isn't going to get you anywhere.
[14:03] Speaker 1: You have to develop some tools, some skills, and some
[14:06] Speaker 1: abilities in order to earn a living in your new career.
[14:12] Speaker 1: I'm Barry Ridholts. You're listening to Bloomberg's At the Money

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