As someone who’s been writing about retiring early since 2009, I want to talk about the best occupations to make lots of money that will allow you to retire early.
I personally wanted to make as much money as possible when I was in high school because I grew up in developing countries like Malaysia, Zambia, and The Philippines. Poverty was all around me, and I didn’t want to end up poor.
Given my desire to be rich, I went to a state university and went into investment banking in NYC at Goldman Sachs in 1999. I worked in banking all the way until 2012, saving and investing 50% – 80% of my income in order to generate enough passive income to retire early.
At 34, I negotiated a multiple six-figure severance and had roughly $80,000 a year in investment income to cover my desired living expenses. Thanks to my severance, I really didn’t have to touch any of my investment income until six years later.
If you’re thinking about retiring early, you should see if one of the below best occupations to make lots of money suits your interests and talents. Going into banking is a smart move. After 10 years in banking, I’m pretty sure you can retire early if you save at least 50% of your after-tax income.
The Best Occupations So You Can Retire Early
I found this very insightful thread on Reddit by “Careerthrowaway10” discussing the best high-paying careers to help you retire early. The discussion evolved around probability and income potential.
Let’s take a look at the various combinations and careers that comprise the best occupations to make lots of money. I’ve added my commentary as well.
High Probability / Lower Income Potential
Physician, Doctor, Dentist
Physician salary ranges from $200–800k. Primary care physicians earn around $200–250k. Specialists earn a median in the $300,000 and surgeons often earn half a million or so.
Of course, long hours, lawsuits, bureaucracy, lots of student debt, starting your career late, high stress, future governmental uncertainty etc. are major downsides, making it a bad career to choose purely for the income. Also note, the top-earning physicians earn far more, especially if they are in a lucrative surgical sub-specialty and/or have related business ventures.
Once you start your own business, you can make over $1 million as a physician. The problem with being a physician is that it takes four years of school and three years of residency AFTER a graduating from a four-year college. Despite the long haul to become a doctor, it’s definitely one of the best occupations to make lots of money.
Big Tech Employee
FAANG (Facebook, Amazon, Apple, Netflix, Google), Microsoft, Salesforce, Linkedin, Oracle, Paypal, Ebay, Adobe, Pinterest, Palantir, Slack etc. are some of the largest tech companies in the world. Hence, the offer some of best occupations to make lots of money for those who like fast paced jobs.
Total median compensation at the top 20-30 is about ~$200k. If you get promoted and have lots of experience, you can earn $300–500k+. Even fresh engineers/product managers etc. at Google earn high #100s. If you can become an employee at a FAANG company, especially in engineering, product management, strategy, data science, sales, UX it’s a solid path towards upper-income.
The big downside about joining a FAANG company is cost of living. The SF Bay Area, where I live has a median home price over over $1 million. If you want to live in San Francisco, the median home price as of 2022 is $1.85 million. Engineering is one of the best occupations for sure.
Becoming an executive – whether it be at a F500 or a growing mid-market company, or a hospital or university, or even a museum or other non-profit – is likely on the lower end of higher probability.
Getting into an executive position at many companies is very remunerative because you have a valuable skill set intrinsic to revenue generation. These job titles include Director, VP, C-Suite, etc.
Getting into an executive (VP-level) position at a F500 typically takes 15+ years and involves the stereotypical “climbing the corporate ladder” which could mean engineer -> MBA -> senior engineer/engineering manager -> IT director -> VP IT -> CTO.
A little more surprisingly, executives at hospitals, universities, and other larger non-profits pay six or even seven-figure salaries to executives. This data is actually pretty easy to find because tax information is generally online for not-for-profits.
The range of income is extremely difficult to come up with because on one hand you could have the VP of Marketing at a local construction company making $100k and you could have the CEO of Google crossing 9 figures in total compensation. Anecdotally, the CFO at a major rehab hospital in a large city earns $1.5M.
Finally, becoming an executive means being adept at playing company politics. You must build a large enough support network to ascend.
Moderate Probability / Moderate Income Potential
Sales reps who sell enterprise software (e.g. Microsoft, IBM, Google Cloud, AWS, etc.) to Fortune 1000-type companies earn a median of ~$300k. These jobs are easily some of best occupations to make lots of money if you’re a great people person. The range is between $200k-millions. A lot of reps work remotely and some in great situations have little travel and very reasonable hours. But others have constant travel, crazy hours/stress, etc.
So, if you are able to become a top performer at your job (ideally, beating quota most years), business-to-business sales is a great option. Of course, it’s a competitive environment, and you have to be good with both technical skills and understanding the product and good with people. The last thing you want is to grind out long hours day after day and feel unappreciated at work.
Another option with very high potential is commercial real estate sales/brokerage (this is on the lower probability side). Med device sales as an alternative to tech that can also be quite lucrative.
Land the big accounts, make sure you don’t lose em and you’re set for 4-5 years or more. Skill set: you’re an athlete. The playbook is established, you know the best use cases, your best strength is hustling for every single meeting, deal, and account. This is where you can make the most imo.
The behemoths: Oracle, IBM, MSFT, etc. Get the right install accounts and you’re good. Skill set: political savvy. Selling yourself internally is more important than externally. You have an army of resources, it’s up to you to quarterback them and keep the install acts happy.
The business happens here no matter who the rep is, your job is to keep everyone aligned and happy. You’re a traffic cop in a lot of cases. All three you can consistently make $200-400k/year and at the latter two can have years of $1M+.” Also, for every top rep, there are several more who burned out/couldn’t hit quota. So, if you aren’t very skilled, probably not the greatest choice.
I was in Asian Equities Institutional Sales. My compensation depended on my average ranking with top clients and the revenue I helped generate for the firm. My compensation was going great until the financial crisis. Then I got zeroed one year, despite being a top producer. Again, playing politics matter.
Investment Banking, Private Equity, VC, Hedge Funds
Investment banking used to be the #1 destination for motivated graduates from top schools. Pay starts around $80 – $90,000 base and increases to seven figures after 10-15 years, depending on if you can survive or not.
For those who can survive, investment banks, private equity shops, venture capital companies and hedge funds easily provide many of the best occupations to make lots of money. Watch the Showtime series Billions for fun and you’ll get a glimpse into the crazy money that is out there.
A common path is top undergrad -> investment banking -> MBA -> private equity/hedge funds etc. The career, however, is less steady/certain than other paths and requires extreme hours (up to 80+) especially in the beginning years. Also, it is extraordinarily difficult to break in from a non-elite school.
I was able to get into Goldman Sachs out of The College of William & Mary because I got on a bus at 6am on a Saturday morning to attend a career fair. I went through 55 interviews over 7 rounds and five months to finally land a job.
Management Consulting, Accounting, Law
Consulting & Accounting highly experienced management consultants and CPAs at top firms can earn very high incomes. Top firms include Bain, BCG, an McKinsey. Consulting is definitely one of the best occupations to make more money.
Big Law As One Of The Best Occupations
Big law is big bucks and highly competitive. You need to go through through three years at a top law school in order to land a big law job from a Pillsbury, Skadden, Wachtel, and so forth. Starting salary is now $180,000 for a first year, 26-year-old associate.
The big problem with Big Law is that the hours are brutal, a top law school is costly, and many people burn out quick. I play in a Big Law softball league and many of my teammates have switched jobs or gone in house because they didn’t like Big Law, or couldn’t make partner.
Small Business Owner
The top 1% of America (who earn a bit under half a million per year) are predominantly composed of small to medium sized service business owner/managers. These include physician/dentist offices, accounting firms, law firms, consulting firms, engineering firms, specialty trade contractors, and even professional bloggers like myself.
While it’s certainly a much less straightforward path than becoming a physician or engineer or even investment banker or top salesperson, it’s possible if you have enough grit and business savviness.
A great entrepreneur doesn’t quit, but keeps on going no matter what. Owning a small business is certainly one of the most rewarding choices in my list of the best occupations to make lots of money.
Not a day goes by where I’m not happy I started Financial Samurai in 2009. It now makes enough money to comfortably provide for a family of four in San Francisco.
Early-stage startup employee
You can get lucky and join an early stage startup. But you are taking excess risk because your equity is not commensurate with the risk. You’re basically busting your butt to make the founders rich. Please sleep with one eye open if you play to join an early-stage startup.
The optimal risk premium is to either join early as one of the first 20-50 employees (Series A timeframe) or join at a senior level (VP) at a pre-IPO company (Series C,D+) where you know the company is likely to go public.
The problem is IPOs are rare these days. If a company does IPO, expect to wait 10-15 years from the start of the company to go public. More often employees are stuck essentially working for a small company whose exit strategy is an acquisition.
Often these companies are ‘over valued’ and the employees effectively get very little, or even wiped out equity wise when the company is finally sold.
What’s worse, is it can take ages for a company to even have a liquidation event. I’ve seen employees working insane hours for nearly a decade, hoping to finally cash out. Meanwhile they’re getting older, having kids, and getting really burned out in general. It’s not a pretty picture.
Most startup employees will end up poorer than those who work at large, more stable companies who pay higher wages. Thus, it’s definitely not a guaranteed job choice to get rich amongst the best occupations to make lots of money.
Low Probability / Highest Income Potential
Founder/CEO Of A Fortune 500 Company
The founder and C-Suite of giant & fast-growing companies earn the most, period. For example, the Uber CEO got a package for over $250 million. The Google CEO made about $100 million from selling stock in 2018. These are absolutely outrageous numbers.
But the probability of becoming a Fortune 500 CEO is extremely low. So, generally not a recommended path for those who want a decent chance at making good money.
Enjoy Your Financial Independence Journey
Being retired since 2012 has been nice. I get to do what I want, when I want. I love to write on Financial Samurai. And I definitely appreciate being able to be a stay at home dad while my kids are young.
But I equally enjoyed my path to financial independence. If you dislike your job, it behooves you to keep on looking for a job that pays well that you enjoy. Don’t just accept a bad situation, especially with such a strong economy.
Actively build new investment income streams. I’m personally heavily investing in the heartland of America through a real estate crowdfunding site like Fundrise because valuations are cheaper and net rental yields are much higher in non-coastal cities.
I believe there’s going to be a multi-decade trend towards lower cost areas thanks to technology and remote work. Fundrise is free to sign up and explore.
It feels wonderful to not have to manage as many properties in San Francisco anymore. Tenants and maintenance issues can be a real pain. As an early retiree, I want easy.
Once you get to financial independence, remember to hold onto your money. You only need to get rich once! Enjoy the journey!
Money Management Recommendation
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For more nuanced personal finance content, join 100,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. Everything is written based off firsthand experience. The Best Occupations is a FS original post.