Five Career-Related Things I've Changed My Mind On

An introspective career post.

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Exactly two years ago to the date, a naive, 24-year-old Jack Raines published his first blog post on Young Money. Two years and 185 blogs later, a slighty-less-but-still-very-naive 26-year-old Jack Raines is still chugging away at

Today, I’m sharing a few career-related ideas that I’ve changed my mind on since I launched this site:

1) Work and “traditional” jobs aren’t prisons you should seek to escape.

From 2020 to 2022, I had a jaded view of traditional employment. This view largely stemmed from the fact that outside of my first four days on the job, I spent every second of my short-lived white-collar career working from a desk in my bedroom (Shout out to that February 2020 start date). After 18 months of responding to emails in my PJs while eating Cinnamon Toast Crunch, feigning interest during Zoom meetings, and rearranging spreadsheets, I came to believe that employed folks such as me only had two options:

  • Work for yourself

  • Escape the labor force entirely

However, over the last year, I’ve had a change of heart. While I (somewhat..?) work for myself, I don’t think it’s for everyone. In fact, self-employment would probably yield a lower quality of life for most people. While serial entrepreneurs love to glorify the “be your own boss” mantra, many have quietly replaced 50-hour work weeks and steady paychecks with 80-hour work weeks and uncertain incomes. If you think an overbearing boss is bad, try managing inconsistent employees, placating unruly customers, and spending 90% of your time chasing and putting out fires that never seem to end. All of that additional stress for no guarantee of a higher income.

On the other end of the spectrum, the FIRE movement, or “financially independent, retire early,” has skeletons in its closet as well.

In a 2021 piece about the downsides of retiring early, Nick Maggiulli referenced a sad post from anonymous blogger “LivingAFI” that covered his life for the six years following his early retirement in 2015. After a short-lived period of care-free euphoria, his life stagnated and his relationships deteriorated as he became more and more alienated from his peers living “normal” lives. An excerpt from this piece:

But peers — people my age that are still working that I’ve been friends with for decades. That situation is another matter entirely. I find this year that I am losing a sense of intimacy with some of them. They work a lot — I do not. We are starting to lose some common interests and activities that helped to create our friendships in the first place.  Some of the threads that bound us together for 20-plus years were perhaps unraveling.  

Not going to lie. These developments bothered me. The first couple of years it didn’t seem to matter, the differences in our lives. Here in the third year, they do.


When you don’t like your current employment, it’s easy to romanticize the idea of walking in your boss’s office, declaring, “I quit!” And heading to some tropical beach to enjoy the rest of your life. But that “enjoying the rest of your life” doesn’t last the rest of your life, and that disdain for work is quickly replaced with indefinite boredom.

Romanian-American writer Elie Wiesel once said, “The opposite of love is not hate, it's indifference.” I would always choose a hated job over an indifferent life every single time.

Yes, some jobs, in fact, a lot of jobs, do suck. But that doesn’t mean that all jobs, by definition, suck. I’m sure most gainfully employed workers could find one that doesn’t.

And let’s be real: there is absolutely nothing wrong with spending 50 hours per week doing a job you like-but-don’t love that pays you enough to support your family and leaves you the free time to pursue activities that you enjoy. Your job doesn’t have to be your whole life; it’s okay if it simply supports everything else.

2) What you want to do is so much more important than what you want to tell people you do.

When I was 22 I had no idea what I wanted to do.

Well, that’s not entirely true: I knew I wanted to make a lot of money, and I knew that going to a top business school would grant me a lot more opportunities to make a lot more money than my prospects coming out of Mercer University.

After getting into Columbia, I figured I would work in one of ~five areas: investment banking, consulting, hedge fund, venture capital, or private equity. Why? Because all offered prestigious paths to make a metric shit-ton of money.

This writing thing that I’m doing now is a fluke. It was never supposed to be a career.

The only reason I started this blog was that I applied for a staff writer job at Morning Brew in August 2021 to make some money while I was traveling, my application got dinged for my lack of writing experience, and I figured that 3 months of blogging would give me a big enough portfolio to reapply.

And yet, here I am two years later, still blogging away. What gives?

Last September, Derek Thompson penned one of the best career advice articles that I’ve read (and I’ve since referenced it a few times). The whole piece is worth a read, but one point that stood out to me was that you shouldn’t do the job you want to tell other people you do. You should do the job you want to do. A quote from said piece:

I told my colleague James Fallows, then a writer at The Atlantic, how excited I was to tell people at parties about this new job title that I would soon carry around, like a boutonniere on my lapel. “Don’t do the job you want to tell people you do,” he said. “Do the job you want to do.” Well, damn, I replied. And that was that. I turned down the position about five minutes later.

The more time that’s passed since that moment, the wiser Jim’s words seem. Work is not a series of words on a LinkedIn profile. It’s a series of moments in the world. And if you don’t enjoy those moments, no sequence of honorifics will dispel your misery.

Derek’s initial excitement resonated with me. For a couple of years, I thought, “Hell yeah, I’d love to tell people that I work for _________.” But in hindsight, I know that I probably would have been miserable working in any of my original “dream jobs.” Worse, I would have used the prestige, and the fleeting dopamine derived from broadcasting that prestige, to justify remaining in one of those jobs.

So yeah, I’m a writer. Blogger. Editor/meme curator. Linkedin shitposter. A lot of things, really. Telling people what I do takes longer than it should, and it usually leads to more questions than answers. But I love every second of it. I wouldn’t be writing this sentence at 1:04 AM, seven hours before you’re reading it, otherwise.

That being said, there is something to the whole “prestige” thing.

3) Prestige still matters.

As recently as May 2022, I was a coin flip away from never moving to New York or enrolling at Columbia. I reached the point that I could see where this whole writing thing was going, I wanted to double down on my current path, and I didn’t exactly need an Ivy League MBA to build a following on the internet. If anything, I was worried that classes would be an unnecessary distraction.

I considered moving to a new city like Austin or Washington with friends. I thought about continuing my travels around the world, maybe spending some time in Australia and Southeast Asia. I figured that the only thing cooler than going to Columbia would be deciding I didn’t need Columbia, and I relished the idea of throwing caution to the wind (and a middle finger to the “system”) and doing just that.

But I wanted to carefully think this through, so on May 5th, I sat down and wrote out the pros and cons of each choice. Anytime I have a tough decision to make, I sit down and write it out. You can’t make a well-informed decision without putting all possible variables on paper.

As I considered my options, I came to an unavoidable realization: prestige still mattered, regardless of what life path I chose.

If I wanted to write a book, specifically a book related to finance, “Columbia graduate and finance writer Jack Raines” is a much easier pitch than “Hostel-hopping vagabond Jack Raines” (though that would certainly be a fun alternative, wouldn’t it?)

What if I wanted to write for a larger publication or one of the many wealth management and venture capital firms that have started producing their own content? Or, God forbid, what if I decided that it might be a good idea to get a real job again with one of these firms? The CBS graduate who writes about finance fits those molds much better than a journeyman who skipped business school to move out west with his friends.

Reputable schools and employers are still impressive, and that isn’t changing any time soon. Prestige is a coefficient that amplifies other aspects of your life. Prestige x 0 substance is worthless, but prestige x career ambitions & proof of work in any field is invaluable.

4) The digital nomad life is fun, but home bases are necessary.

Two years ago, I was planning what I thought would become a year-long trip around the world. I would start in Barcelona in August, move my way around Europe until winter, and figure it out from there. I figured that ~12 months of traveling would be the perfect way to spend my last year before business school.

But after four months in Europe, my sense of wanderlust only grew. I came back to the US for a month, just to hit the road once again, renting an Airbnb in Buenos Aires for seven weeks with a Canadian friend, Mike, that I’d met in Portugal. While in Argentina, I began to hit my stride writing and making money online, and I started to think, “I could do this for years.”

God, it sounds like the adventure of a lifetime, doesn’t it? Two months in Buenos Aires. Maybe a summer in Sydney and Golden Coast. I could spend some time in Southeast Asia, or post up in a Spanish beach town indefinitely.

Even after deciding to move to New York for business school, I still had that travel itch. I thought to myself, “I can spend all of next summer abroad, working from anywhere. And once I’m done with this program, I can hit the road indefinitely.”

But then the funniest thing happened. In November, I decided to skip a week of class and travel to Medelllín, Colombia, where Mike was living for a few months. By Day 4, I found myself… excited to return to New York. And despite my plans from last year, I have spent the greater part of this summer in NYC. And yeah, I’ll likely have the freedom to travel as much as I want when I finish school, but I would prefer to retain my home base in New York.

What happened?

I came to realize that travel is most valuable as a finite experience. I will always cherish my time traveling before school, but it was valuable to me because I knew going into that period of my life that I had one year. And I wanted to maximize that year. To experience anything and everything and enjoy every second of it. Those experiences would have lost their luster if they never ended.

In the cautionary FIRE piece referenced above, Nick also shared a story from one of his Twitter followers about his experience living as a digital nomad indefinitely, and it sounded nothing short of depressing. A quote from this story:

I left my occupation 2+ years ago and now travel around the world living out of Airbnbs for 1-3 months at a time…No matter how one pretends, it’s going to be a lonely existence. For me, I’ve lived and died with each place I’m at. If you are always on vacation, you are never on vacation. You are always seeing people and places that you will probably never see again. You make friends and routines that end with each change of location and relationships are next to impossible.

If you’re always on vacation, you are never on vacation.

It’s a beautiful way to live until it becomes the only way you live. We need a place to call home with our friends and families and loved ones. Familiar cafes with their aromas that we know all-too-well. We need street names that we recognize and restaurant menus that we know like the back of our hand and dive bars where the bartender knows your drink of choice without you having to open your mouth.

We need these things because we need something to look forward to returning to when we’re gone. Otherwise, our travels ring hollow.

I enjoy travel. It’s good for the soul. But while travel is an important part of one’s life, it shouldn’t be one’s life.

5) Success looks effortless, but it takes longer than you would imagine.

Packy McCormick, a fellow writer and friend of mine, writes a massively successful newsletter, Not Boring, that boasts 200,000+ readers.

I remember first reading Not Boring in September 2021 and immediately thinking, “Damn, this newsletter business is pretty simple. Just get, like, 25,000 people to start reading my stuff and I can probably make a living from it.”

And that was the day I decided I wanted to be a writer. I did, however, miss two small details in this naive observation:

  1. It is incredibly difficult to get thousands of people to read your stuff.

  2. It is incredibly difficult to publish every week, without missing a beat, for years.

I figured I could sprint my way to 100,000 readers in six months or so.

That didn’t happen.

In reality, it took me almost six months to hit my first 1,000 readers, and it has taken me 185 blogs, 400,000+ words, and ~two years to go from 0 to 42,000+ readers.

Effortless is earned, and it takes a long time to reach that level.

- Jack

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Jack's Picks

  • “We’ve all heard of the trophy wife or husband — a partner that’s valued heavily as a status symbol, for superficial qualities over substance. Similarly, I’ve started to think about the idea of the trophy job — a job that people covet for its status more than its substance.” Anu Atluru wrote an interesting piece on the role that “trophy jobs” play in our work environment.

  • “And the first question this kid asked me is just … ‘What the heck does good masculinity look like?’” “And I’ll be honest with you: I did not have an answer for that.” Christine Emba wrote about our masculinity crisis.

  • Here’s a cool interactive NYT piece on demographic shifts.

  • Nick Maggiulli raised an interesting argument that stocks may not actually be overpriced, but our valuation metrics could be outdated.

  • Anonymous Twitter account “Sophie” (anon Twitter accounts are some of the highest signal follows on the internet) gave an excellent breakdown of Twitter’s current debt structure and potential financing moves that Musk could make to better align shareholders with company management’s vision.

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