Why High Paying Jobs Aren’t Worth It and What to Do Instead

A high paying job sounds nice, but there are downsides. Here are some things to consider if you want one, or if you’re stuck in a high paying job now.

Also, here’s a better alternative.

“I’m only interested in making $150,000.”

I nearly spit out my iced tea.

… but not for the reason you think. My friend Schoolly C recently graduated with an MBA from Wharton, the training ground for future Wall Street tycoons. No, I was more surprised that Schoolly C wasn’t like his classmates with their lusty ambitions of a Goldman Sachs offer. (To many of us, $150,000 seems like all the money in the world. To a Wharton MBA, it’s usually a starting point.)

Schoolly C was putting a line in the income sand and saying that making above $150,000 wasn’t worth it. Why would someone as talented and ambitious as he is willingly cap his income?


I’ve spent over 15 years in the work force. I know the downsides from my own experience and what I’ve observed with my co-workers and friends who are in high paying jobs.

Once you get past $150,000, something happens. You hit the high paying job level. You’re no longer just an employee hired to accomplish tasks, but one that’s expected to produce income for the company or save it a lot of money. Or else. You have a direct line to your company’s profit and loss. If you don’t increase profit or decrease loss, you’re just taking up (big) resources that can go to someone else who will.

So why are these high paying jobs so tough? And what should you consider if you want to get one or feel stuck in one now? Are there alternatives?

The Downsides of High Paying Jobs

Wouldn’t it be nice to make a lot of money? If you make over $150,000, you’d be in the top 5% (according to DQYDJ). At that income, you have more than enough to start looking rich and possibly enough to help your house envy.  So… then all your worries go away, right?

Nope. You’ve only brought different worries upon yourself.

  • High Stress: Put yourself in your employer’s shoes. If they’re spending more than $150,000 on you, they want results. If you’re not delivering results, why are they paying you that much money? I’ve had to cancel dinner plans with friends (many times) because I had to fly to Chicago (or someplace else) to yell at the CFO. There are times when a big deal goes bad and there’s a mandatory all-hands call with the investors and lawyers at 11pm on a Friday night, too, so you stumble out of bed with a foggy head to get on a call where everyone’s yelling at each other. I’ve had Saturday lunches with friends who just stare blankly at their food while work worries crowd their minds. Work stress is the body odor of life. You can’t shake it off, and it can stink up your relationships and your eating and sleeping habits.
  • Looooong Hours: I know it’s cool to be busy. It makes you seem important. But… imagine hardly ever not working. Almost half of Big Law Associates worked at least 12 hour days (more if you hope to make partner). It’s no surprise when law professor Benjamin H. Barton points out in his book Glass Half Full that only 44% of Big Law associates are satisfied in their career. This figure actually seems high to me. Knowing many lawyers, I’d put it at 0% satisfaction if they’re being honest. I guess even lying on a survey is part of their job? (I kid, I kid!) Columbia Law professor Tim Wu writes in the New Yorker that “in 2006, the top twenty per cent of earners were twice as likely to work more than fifty hours a week than the bottom twenty per cent.” A high paying job is now synonymous with long hours.  And when you’re not “working,” you’re on your phone incessantly checking work email. Trust me, this gets annoying for everyone around you. All the people you care about will move on in their lives… without you.
  • Lifestyle Creep: Your high paying job is really stressful. What do you do? Buy stuff! Hey, might as well get yourself something to counteract the suckiness. It’s sort of this bizarro happiness equilibrium where you try to solve for a big negative with little hits of positive. Isn’t this what big money people are supposed to do? Otherwise, what’s the point? Some of you know where this story goes: Those Nike HyperAdapt 1.0s that you bought on Monday did not help you run from the stink of Tuesday, but you think it’s because you actually need $200,000+ to get bigger, shinier toys. Let me save you the many times you’re going to tell yourself that: If it didn’t work with less money, it’s not going to work with more!
  • It Changes You: Show me the person who, after years of spending their waking hours stressed out, maintains a happy and balanced self. But doesn’t it get better the higher up you go? Professor Wu pours cold water on that theory and says that “the people at the top are often as unhappy and overworked as people at the bottom.” The reality is, you become miserable just like your boss, or your boss’s boss.

(Here’s the unbroken chain of your life in a high paying job: stress-eat-sleep-stress-eat-sleep-stress-eat-sleep…)

Where are the High Paying Jobs?

Still want to see for yourself? I get it. Better to know for yourself than be told. I needed that, too.

Ok, first let’s understand the two types. On the one hand, there is the high paying job as a mid or executive level. The lifestyle there is not too bad, really… it just takes years to get there, and you’re not guaranteed to ever reach it. It’s when $150,000 is the starting point in that career that you have to watch out. These high paying jobs are in the consulting, lawyer, finance, or doctor zone:

  • Consultants: Starting salary for a newly minted MBA is $145,000 for McKinsey & Company, but higher with a bonus. The consultants I know are in a different city 5 days a week. This is fun in your 20s, but gets old fast, especially if you’re married and/or have children. I don’t travel this much, but even I get sick of being on a plane and seeing the same airline magazine the last three trips. The delays and rerouting that get me into Dallas at 1am. The turbulence. The sweaty touching of someone else’s arms and thighs for hours! I can handle this if I know it’s my last flight for a few weeks. Many top consultants don’t have this choice.
  • Lawyers: Associate salaries at the biggest, baddest law firms now start at $180,000. The difficulty is that lawyers haven’t found a way to scale, so they need to bill at least a zillion hours to justify their existence. Those hours aren’t predictable either. They don’t (yet) have a machine that can take my question, consider all of its nuances and respond to me quickly. I know that if I email my lawyer at 11pm, I will get a thorough, well-researched response by 11:30pm. In the end, it’s a client service job, and this is the service you expect if you’re paying them hundreds of dollars an hour. I’ve had plenty of my lawyers step away from one of their kid’s games/plays to take a call (if it’s not urgent, I always tell them to get back to their kids). Another lawyer was on the phone with me all the way up until she went into labor (which I didn’t know about until later)!
  • Finance: Analyst pay (including bonuses) has been as high as $150,000 for top tier analysts fresh out of undergrad. It’s not unheard of to grind out 100 hour weeks, especially if a deal is live. It’s not unheard of to keep a sleeping bag under your desk for naps. It’s not unheard of to take performance enhancing “substances” to stay awake and alert. And the work isn’t all that rewarding. On a per hour basis, you probably make as much as your administrative assistant, but at least they’re not changing margins on pitch books (a glorified PowerPoint presentation) at 4am. Basically, the pay is so high because investment banks squeeze the job of 2-3 people into one–not because you’re doing something 2-3 times more important than anyone else.
  • Doctors: Physicians make $175,000 (although specialists make more) according to data from Glassdoor. The challenge with being a doctor is that you start your high paying job late in life. Your net worth is extremely negative at first, but everyone expects doctors to live a certain lifestyle. You were probably the smartest person in high school and college. You busted your hump to ace the MCATs. You gutted out investment banking-like hours in residency. Meanwhile, many of your less smart, less ambitious friends started saving earlier, got promoted, and established themselves. You feel like you got lapped. Even your accountant friend, who started working before you and has less school debt, will have a net worth you’ll never catch up to (and this assumes this accountant friend never makes partner) if you both save 10%.

(A doctor starts off with so much negative net worth and only starts earning a large salary later in life that, if just judging by money, it’s better to be an accountant. By the time the doctor becomes a millionaire at age 47, the accountant will already be worth $1.6 million. The gap between the accountant and doctor keeps growing, even though by this point, the doctor makes more money.)

Now don’t get me wrong, doctors do great work the world needs. Best and brightest of us, please keep striving to become doctors! Some of you were born to be lawyers. You’re also beautiful, rainbow unicorns.

I’m talking to those of you who want these high paying jobs just for the prestige and money.

7 Tips If You’re Stuck in a High Paying Job or What to Consider if You Want One

You’re beat up. You have no time. You worked the last five weekends and through your vacation. You’re always checking your phone. It’s like a bad romance you just can’t quit. Does this sound like a dream to you?

Shouldn’t life should be better than this?

For some of you, it feels too late. We forget we have the power of choice. So if you’re in a high paying job that’s grinding you down (or want to try it out just to see what it’s like), use it for what it is: you’re there to make money. A side benefit is that you get to impress people with your high paying job while you make that money. That’s it, and that’s all.

  1. Put a number on it. I’ll discuss this more in the next section, but if you can’t quantify Your Number (i.e. your investable assets), no sense going through steps 2-7.
  2. Kick ass and get promoted to accelerate your earnings. Go here to see how I’ve been able to do it.
  3. Save and invest like crazy while the money is flowing so you can retire early or shift into a more relaxed career. Every dollar you save and invest today increases your ability to break free tomorrow. That should be extremely motivating.
  4. In the meantime, start planning your exit by building up a side hustle. In Originals, Adam Grant writes that entrepreneurs lowered their odds of failure by 33% when they kept their day jobs. If you’re going to jump, try to figure out where you’re landing first.
  5. Give yourself an end date. An end date brings an urgency to act. A high paying job is a stepping stone, not the goal. If you don’t give yourself a deadline, then that stepping stone becomes a long, rocky plateau. Write it down in red ink. Circle it. Then have a monthly or daily countdown.
  6. Set up a small motivator along the way. Determine whether you need a carrot or a stick. Then give yourself a small motivator and a big one. The small one can be a picture of the beach where you want to retire (carrot) or listening to that distressing voicemail from your boss once a week (stick). Newly crowned homerun king Aaron Judge keeps “0.179” as a note on his phone to remind him of his low batting average in 2016. These little things are like trail mix for your journey. I have this sticker on my laptop that I got from an open house at the coworking space Indy Hall for when I’m too tired to write, too spent to hustle. It’s four simple letters: JFDI. Three of the letters stand for “Just Do It.” I’ll let you figure out what the “F” is for.
  7. Set up a big motivator at the end. For your big motivator, make it count, or else you’re not properly setting your incentives to help you succeed. If you don’t make your alarm loud and persistent enough, you’ll keep pressing snooze. Here’s a suggestion, inspired by Tim Ferris: set aside $10,000 of that money you plan to put away. If you hit your number by your end date, then you can use it on anything you want, no questions asked. If you don’t hit it, then you have to give it as a donation to causes you don’t believe in or political party you never vote for. Sound too scary? What’s worse, setting up a big motivator or spending most of your waking hours, year after year stressed out but not being able to leave because your lifestyle got too expensive?

A High Paying Job Has a High Cost

Does this mean we shouldn’t have ambition? Not at all. It just means that you should consider things other than money when making your career choice. Transfer your ambition onto things other than making money, like making life better for others.

When young analysts would come into my office and ask me for advice, I wouldn’t sugar coat it. I’d ask them:

“How much would they need to pay you to miss out on your life? How much to miss out on forming deep relationships with loved ones? How much to miss your son or daughter’s childhood?”

Go ahead. Don’t be scared to put a number on it. You’re there for the money, so don’t act coy and pretend it’s for anything else. Not quantifying it would be disingenuous.

I don’t mean how much salary you’d need, although that’s a component. How do you do it?

Let’s assume you take a high paying job starting at $150,000 for 10 years and save a hearty 30% of your gross income (remember, you’re not messing around). You invest your savings in the S&P 500, which gains its historical inflation-adjusted return of 7%. Assume salaries increased 5% year (to account for promotions). For each year of salary, I calculated its future value using the following equation: FV = $ Saved That Year x (1+r)^n.

So if you quit at the end of your 10th year, you’ll be worth $620,128. You’d have to willing to be stressed for 10 years while keeping your expenses relatively low to do this. Is it worth it? Only you can answer. If your reasonable investible asset forecast is materially less than your number, then you should strongly consider other alternatives.

How do you figure out your number without doing fancy equations? You’re in luck!

Here’s an easy way to do it based on your savings rate. Even if you don’t have a high paying job, you can find out what number you’re on track to hit based on my assumptions above about savings rate and investment returns.

Here’s how it works: Take your income, choose your savings rate and multiply your salary by the “Your Number” multiplier. For reference, the “Years of Expenses” column is how many years of living expenses your investible assets will cover. Let’s take 2 scenarios:

  • Scenario 1: Say you have the opportunity to make $150,000 per year. Using the assumptions above, if you save 20% a year, in 10 years Your Number would be $414,000 ($150,000 x 2.76), and it would cover 2.2 years of living expenses if you maintain your living expenses.
  • Scenario 2:  If you have the opportunity to make $75,000 per year, if you save 40%, Your Number would be $413,250 ($75,000 x 5.51x), and it would cover 5.9 years of living expenses at your current spending.

An Alternative to the High Paying Job

Did you notice something from the two scenarios above?

In the first one, you’re in a high paying job working long hours and stressed out. You end up with $414,000 in investible assets that can provide 2.2 years of living expenses. In the second scenario, you make half as much, probably work fewer hours and are less stressed, but you also live simply. You end up with $413,250, virtually the same amount of investible assets, but more than double how far it can take you (5.9 years versus 2.2 years)!

Income is never the most important factor in reaching your financial goals.

Your alternative to a high paying job is the job you have now.  But you need to aggressively save and invest.  That is more important than how much money you make.

If you could get to the same place as someone with a high paying job but stress less along the way and have time to do what you wanted outside of work, would you take it? With rare exceptions: Make. That. Trade. All. Day.

Walking Away from a High Paying Job?

“See you next weekend.”

That’s what my former co-worker’s kids used to say to him on Sunday evening. When I heard that, I knew that my time in that job had an expiration date.

I didn’t take vacations until relatively recently. And when I did, I ruined most of them by being on work calls the whole time. I held off on getting ACL surgery for years because I couldn’t “afford” to take time off of work. I had to negotiate for time off to attend my own wedding and honeymoon (and got work calls on my honeymoon – without any apology from my then Managing Director).

For many of us, walking away from money isn’t even an option, especially if you’re like me and were raised in a household with few resources. But once I de-coupled money and happiness in my mind, I was ready.

So I stepped off that career track onto another that paid hundreds of thousands of dollars less. Soon after, my wife, who also had a high paying job, left her job to be at home with the kids. Then fairly recently, I turned down the chance for promotion that would have paid me hundreds of thousands more than what I make now because it would have involved a move. All told, we’ve walked away from hundreds and hundreds of thousands of dollars. Each year. How are we able to do this?

We know Our Number.

If you’re miserable in a high paying job, it’s not too late.  If you don’t want one (or can’t get one), know that there’s a better alternative.  If you want to see for yourself what a high paying job is like, then go for it. But always know the Number you need in order to take on that stress.  Then walk into it eyes wide open, purposeful, and ready to exit once you hit Your Number.  Have a plan and don’t be scared to walk away from money if your high paying job is making you miserable.


(Tired of your stressful job but scared you won’t meet your financial goals?  Before you make the jump, get yourself financially fit.  Get the resume guide, the easy but powerful budget, and the tool I used to help me hit my retirement number as part of my FREE financial boot camp!)

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  • Ryan July 13, 2017 at 5:22 pm

    Absolutely fantastic post! sooooo many people neef to read this! Especially people who haven’t graduated yet. Thank you for writing this, it really needed to be said. I love that phrase, “decoupling happiness and money”. Yes!

    • JT July 13, 2017 at 7:33 pm

      Thanks so much, Ryan! I wish “I” would have read it before I started my career. It seems unnatural to think that money and happiness can be achieved apart from each other, but it’s possible!

  • Tim Kim @ Tub of Cash July 13, 2017 at 7:33 pm

    You make a lot of very valid points. I make over $150K and a lot of what you say is true. Long hours, brutal accountability to the shareholders, chronic stress. There’s a lot of blessings that come with it, but there’s definitely a tipping point. It depends on the size of the company too. In smaller companies (like mine), the threshold is $100K. Once you make over that you’re typically transitioning into a senior management role. $150K+ means you’re in the top 3 executive positions (like mine, I’m the VP). Sometimes I ask myself why I do it. It doesn’t help though when you’re living in a VHCOL area.

    • JT July 13, 2017 at 9:13 pm

      Totally, Tim! There is definitely a tipping point for when that stress isn’t worth it. Top 3 exec? Congrats on your success! When you feel like it’s time to hang it up, let us know your thought process and why you felt ready.

      • Tim Kim @ Tub of Cash July 14, 2017 at 1:07 am

        Thanks and will do! I’m grateful, because I met the right people at the right time. So I can’t take all the credit!

  • Jasmine July 13, 2017 at 7:37 pm

    Great Post! But isn’t that the whole reason why we go to college and get our fancy degrees. Haha! Well I almost drunk the kool aid. Thank God for kids because they totally shifted my mindset and allowed me to see my real value.

    • JT July 13, 2017 at 9:18 pm

      Jasmine! Funny you use the word “mindset” and fancy degrees. I’m reading _Mindset_ by Carol Dweck (watch out for it in a future post) and it’s totally about that dynamic. There are those who use that fancy degree to validate themselves and those who are lifelong learners (which I know you are). If each were a horse, bet on the life long learner!

  • Cory @ Growing Dollars from Cents.com July 14, 2017 at 1:22 am

    Awesome post!

    What you said is so true. I’ve even seen it first hand in the workplace. Highly paid directors stepping down from their position and taking a lower paying one.

    Usually the reason is stress. Those long hours aren’t easy and what’s the sense of making all of that money with no time to enjoy life?

    • JT July 14, 2017 at 7:03 am

      So true, Cory! I didn’t really want to get into pin my post (maybe I’ll add to it later), but a great deal of these execs are in their 2nd, 3rd, or 4th marriage, so much of their money goes to child support. So to add to your point, “what’s the sense of making all of that money with no time to enjoy life and no money to keep anyway?”

  • Nick July 14, 2017 at 2:33 pm

    Great post! The blog continues getting better with each entry. I look forward to the upcoming topics!

    • JT July 14, 2017 at 3:23 pm

      Thanks Nick! Hope I keep writing about topics relevant to you and provide useful tips. Let me know if there’s anything else you want to read about!

  • Mike Collins July 15, 2017 at 2:16 pm

    People think that earning more money will solve all their problems but that is rarely the case. The higher you move up the ladder the less freedom you have.

    • JT July 15, 2017 at 5:24 pm

      Totally agreed, Mike! The golden handcuffs are real.

  • Inbar July 17, 2017 at 3:13 pm

    interesting points you are making here

    • JT July 17, 2017 at 3:37 pm

      Thanks! And thanks for stopping by Inbar!


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