Rich Man’s (or Woman’s) Jobs

The young rich man holding whiskey glass and show winning with cards and stack of dollars on green table, white background with business casino concept

I was an English major, as an undergrad, with big dreams of one day being a copywriter, journalist, or some other job that went well with seersucker suits and martinis. But then I realized that it was probably more important to eat and put a roof over my head.

I learned the hard way that there are many jobs out there that appear alluring at first, until you realize that most of them are filled by those with trust funds, subsidized rent, or parents that have condos in the city that they “let them stay at”.

The following are careers primarily populated by the rich – but you wouldn’t readily guess why. These jobs don’t pay extraordinarily well… on the contrary, they are so poorly compensated that only those with inherited wealth can possibly afford to hold them.

Jobs like these have a role in financial independence – but they are there not to get you to financial independence, but to give you something to do once you’ve achieved FI. On the contrary, building a career in fields like this can almost guarantee you’ll never reach FI. So beware of the following:

  • Sports management – any career with the word “sports” in it is a near guarantee that it will be underpaid. These types of jobs are generally given to college jocks whose parents’ connections got them an internship at ESPN or the LA Dodgers (probably the same parents that bribed their child into USC). It doesn’t matter how much (or how little) they pay since Mom and Dad will foot your rent and cell phone bill well into your thirties. If you don’t have such parentage, avoid any “sports” related careers.
  • Writing – another brilliant career option after you have achieved FI. The average freelance journalist gets paid less than $.25/word. At that rate, you’d have to write 400,000 words annually (not including spending time procuring the gigs) to reach a six figure income. A lot of good writers are short cutting their way to profits by blogging, but even that is a long term investment before you see a payout (I of all people should know!).
  • Design – I know that my friends have bagged a rich husband or wife when they announce a career in design; there’s no greater status symbol than a spouse who toils in a field involving fabric swatches and negative returns. Take a look at virtually any designer – they are very rarely the major breadwinner in their family. The most successful designers are born with assets that help nurture their career – family connections or social contacts that help build a client base, ample capital to help launch their business, trust funds that can get them through dry periods, etc.
  • Artist – no matter what the medium – film production, poetry, sculpture, acting, painting, etc., there’s a logic behind the term “starving artist”. Of course, I don’t want to squelch any potential Brandos or Picassos out there. I’m just saying that 1) if you choose to be an artist, accept that it is unlikely you can do that and achieve FI and 2) if you want both, give this a go of say, 2 years and if it doesn’t happen, take your talents into an adjacent (graphic design, film finance, commercial production) field that actually pays the bills.

Honorable mentions: Here are a few other careers that are notoriously low paying due to massive competition from other aspirants, low barriers to entry, or both:

  • Journalist
  • Therapist
  • Short film producer
  • Caterer
  • Jewelry designer

Maybe one day, when you become financially independent, you can partake in the greatest of indulgences – a career that pays close to nothing. Until then, I would recommend a steady paycheck, at least initially, with a side gig that can make you money while you sleep (more on that later) as the most sensible diet to achieve FI – tness.

Have you struggled with a career meant for the already rich? Or even achieved the elusive financial success with a “rich man’s job”? Tell me about it below.

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