Save. Spend. Splurge.

When should you quit and walk away from a high-paying but miserable job?

You know what’s hard?

Saying no to money.

You know what’s REALLY difficult?

Saying no to really good money.

I struggle with this, because obviously.. I make good money. Really good money.

Like $20,000 – $30,000 a month good.

In one instance, I made $100,000 in 10 weeks.

I never got to repeat that again but man that was great. And I worked like a DOG for that money, but I weighed my options, saw the money and bit the bullet.

So I know of what I speak of because I am a loudmouth who likes to get #%* done and does not suffer fools in the nicest way possible and I am always in jeopardy of getting let go because I am not willing to sit back and let bad things happen just because it is the easiest way to do it.

So, when you’re “stuck” in a job, I know how you feel.

Golden handcuffs, amirite?


(I absolutely did not want to add an image of handcuffs, so I chose a golden pineapple instead. You’re welcome.)

A high paying one that was great to begin with, and has now turned into a tunnel of despair, as someone who has been there multiple times, I can help give some perspective.

For me, almost every dang contract ends like this because people get weird at the end.

When I say weird, I mean people start realizing how good you are at your job, they start getting frustrated that they themselves are not that good, or worse, management sees you’re great, and thinks that they can mold someone else to be your doppelgänger and get the same results but for a quarter of the price.

They get really weird, and condescending, they begin treating you like a paid slave, and you no longer have feelings or a life. They say things to you like — You are here to deliver. Why the hell are we paying you so much money if you can’t fix this? FIX IT.

They talk down to you, they get angry that they can’t do what you’re doing (this is happening now, BT dubs), and you have to bite your tongue and smile while raging with fury inside because youz a pro and you need to pay your bills.

Note: This has happened more than 3 times, and each time I had to try and diplomatically explain (as diplomatically as I can, let’s be honest) that I am one person, and their issues run deeper than just a project; they are ingrained in the culture or built into the company itself, and to think I can fix this as one lowly consultant with zero power, is laughable. They usually don’t love this answer because it puts the spotlight back on the way they’re managing their teams.

So yeah.

Not many of my work environments end on a good note. When it does, I’m flipping thrilled.

Consultants are generally not appreciated and looked at as overpaid cash cows, unfortunately. No matter what you deliver for them, what consultant, you’re an outsider. Sometimes this happens at the start of the contract, other times near the end.

On my end, they always end with them overloading me with work, me feeling resentful because I am trying to be a great consultant who delivers and is still pleasant to work with but then a lot of companies just walk all over you when you care too much.

As a result, this is my sage advice if you too, are facing a similar issue and cannot decide if you should say “No I am out” or to stick it out.

(Counting down the days)

1. Give it a year before you really call it quits but stay sharp

It went from great to sour over night. Give it a full year before you start planning anything.

It could go from sour to great, just as easily. Maybe it’s a question of management. Maybe it’s just that they are going to get canned, and things will go back to the way they were, or at least get rebuilt.

Who knows? No one has a crystal ball. Do not make rash decisions.

2. Consider moving to another department / city /area

Can you shift laterally to another department? Under another manager? Under another VP or area that looks better?

Maybe you love the company and everything that comes with it, but you need to work for someone else. It could be as simple as that.

3. Brush up on your CV and start prospecting

During that year before you call it quits, don’t be silly. Take the time to properly (leisurely) brush up on your CV, put feelers out, and start prospecting.

Look at other jobs available.

What’s the market like? Is it terrible? Is this a good time to jump?

(If it is, consider jump ASAP and ignore advice #1. Sometimes you need to be flexible and take an opportunity when you see it, and when you feel it in your gut.)

If you have a serious mortgage or debt, or other obligations, you sometimes need to suck it up, buttercup.

(Look! An actual, sad buttercup!)

You have to make sure you don’t ruin your finances just because of a terrible employer. You can get out of that situation, but you need to be smart about it and plan ahead before you pull the plug.

In addition to all that, do some salary market research. Are you being paid fairly? Overpaid? Underpaid?

Adjust your future salary / expectations accordingly and either ask for more money or understand that you will be paid less because you were getting a stellar deal before.

4. Start saving (now) for a serious emergency buffer

Don’t wait. Start today. Hope spring eternal.

Consider your spending habits and shifting down your spending to prepare for the worst case scenario (I am talking half your salary, beans and rice kind of deal)…

Yes, you should have 3 months saved already, but with a high paying job, prospecting can take longer than 3 months.

Companies are not a fan of paying a lot of money.

If you wanted to go work for half the pay, doing the same job, you’d find one in a heartbeat I am sure, but to get paid what you are worth? You need to be aware of how expensive you are for companies to take on, and that they may not be keen to do so.

I’d say a year of savings should do it.

A good year should be enough expenses saved as an emergency buffer to weather the storm.

As a freelancer, I save up to 3 – 5 years because I am picky AF about contracts and won’t travel, so I limit my own options to gain employment.

If you have already quit, or are unexpectedly ousted, I’d strongly suggest you get an interim lower paying job (retail, minimum wage, whatever) just to stem some of the cash loss as you continue to live, pay your mortgage and eat.

Really though, the ideal situation is that you focus 100% on job hunting.. WHILE BEING PAID.

(That is, to do this while you are still gainfully employed. Not necessarily to do it on company time.)

The worst is to get to a point where you feel forced to quit with no backup cash or exit plan.

5. Map out your exit plans

A good offense is a well planned defense. I am sure that is not a saying, but I wanted to throw in a football metaphor…

My point is to plan what will happen so you have a strategy, even if you have to veer off course, you can riff on the situation as it changes, but you will be prepared to do so instead of panicking at the nth hour.

Work out your main scenarios:

  1. I stay and I quit in a year if things don’t get better – I start saving and trying to see what else is here for me
  2. I stay but I move to another department with a lower salary – how much lower can I take in salary?
  3. I leave but I end up not working for a year – how to handle the cashflow? take another job? how? where?
  4. I quit now (or get fired) – What would do I immediately, Day one?

Those are all the plans I go through.

For me, as a freelancer, I plan on my contract end date and income accordingly.

If that doesn’t go well, and I get canned earlier, I already know I started a good 6 months in advance, so I have less money in free cash saved, but I am not sweating it because if need be, I can bleed my investments to live (I HATE DOING THIS. HATE HATE HATE.)

Ideally, I am already frugal, and living on the bare minimum but if you are a regular reader of this blog, you are laughing your @$$ off right now because I’m too bougie for beans and burlap sack clothing.

So realistically, I budget in fun money at the start.

But when unemployment drags on to 6 months, I shift the spending gears down.

When it drags on to a year, I shift them down again.

When it drags on to 2 years, I start climbing the walls and making burlap sack dresses.

(Just kidding. Sort of.)

You need to do something similar. Plan your spending. Plan what happens if it all runs out. Plan what happens if you lose all your money and/or a $$$ issue comes up and you need to handle it.

Be prepared.

That’s it.

My sage advice on how to let go of a high-paying job.

At the end of the day, you need to mentally be happy with what you are doing.

If you are not happy*, then you need do something about it.

Your job is 40 hours of your week. FORTY HOURS. That is 23% of your life!

(Or more if you do overtime. Ick.)

We only have 168 hours in a week in total, and a good chunk of that is SLEEPING! Really, do you want to spend your life on something you don’t at least feel engaged in, and happy to do?

*Let’s not get it twisted — I am not talking about following your passion of becoming the next breakout Instagram star kind of happiness. I am talking about waking up and being okay, even happy it is a Monday and getting excited to go into work and get stuff done. This is how I feel, even though my job can get very hairy sometimes.

You need to mentally take care of yourself and make sure you are happy.

Don’t feel dumb for not being happy at work and feeling like an ingrate because of your killer salary.

You have a right to not enjoy your work no matter how much they pay you.

These are two separate thoughts and concepts.

What say you? Any other tips you’d like to add?


  • Marc

    Thank you for writing this article. It’s uniquely different from some of the other articles I’ve read on the subject. Fear is the biggest thing to overcome. In reality all of us will survive a job loss or cut in pay. It’s the fear of the unknown that can be debilitating. There are so many things that happen mentally when you no longer like your career/job. I start to question if I’m any good at it anymore. Will I be a failure at my new job? When you have a family and a spouse there is another level of pressure to maintain that lifestyle they are accustomed to.

    I have enough saved to quit and be unemployed for a couple of years but my fear is not being able to find work or becoming to comfortable being unemployed making it super difficult to transition back into the work force and depleting my nest egg.

    Unfortunately there is no crystal ball. I wish there was. I was once told that tomorrow is the first day of the rest of your life. I could be missing out on my best life …out of fear and of course the proverbial golden handcuffs.

    • Sherry of Save. Spend. Splurge.

      I suspect that once you walk away, and get used to being in a good headspace, a good environment, without toxicity, you could realize you would prefer a job with less money, less stress, and living with less to compensate.

      I would save enough for a few years, quit.. and what’s the worst thing that could happen? Figure out the very worst scenario and see if you can live with that, plus its likelihood.

      For instance, my worst case scenario is I could just go pick up a minimum wage job. That pays X amount a year, could I live on that? Yes. I could. I wouldn’t be happy but I could, and I’d have to downsize my life a little.

      That exercise might help you. Good luck.

  • Amanda M

    Great post! It validated that I am handling my situation well. I’ve been taking my time, trying everything within my power to change my feelings about the job, investing my big pay checks, making contingency plans that cover 18 months, looking for other prospects and all of the things you talked about. It will be hard to walk away from the check, but exciting to build another career path and get to that pay rate again in the future. 🙂

  • Ed

    Good article. I’ve been in sales for two decades. Specifically, telesales. I fell into it because I left college with a useless degree. Pretty common, unfortunately. Hating my job is an understatement. Between cold calling all day long and the embarrassment of cold calling at 46 while my friends have real careers is causing anxiety, depression, and insomnia. As I live in an expensive area and I just bought a house, my expenses dictate that I keep doing the only thing I’m good at – sales. If you can tell me how you made $20k/mo, I’d do that. I make about half of that and I still feel poor. I’m considering getting a not so miserable job (they’re all miserable to a degree) and live off my savings at the same time. God damn…how did I get here?

    • Sherry of Save. Spend. Splurge.

      It really sounds like you’re stuck between a rock and a hard place. Is it possible for you to move into another industry or area and use your skills in sales, but sell something else? Another thing is simply to lower expenses. I know you just bought a house (congratulations!) but maybe a lower cost of living area would drop your expenses and you could take on another job that doesn’t pay as much but you’d be happier in.

  • JCT

    Thank you for writing this!

  • Mia

    Is the miserable job threatening your physical and mental health and quality of life outside of work? Because you have to consider that as well. Are you depressed, suffering from insomnia and anxiety, sick a lot, etc.? Those things are often the “breaking point.”

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