Should I stay or should I go? Wrestling with the decision to quit a career

J.D.’s note: In the olden days at Get Rich Slowly, I shared reader stories every Sunday. I haven’t done that since I re-purchased the site because nobody sends them to me anymore. But earlier this year, Mike did. I love it. I hope you will too.

Earlier this year, I sent my wife a text message: “On a scale of 1 to 10, how freaked out would you be if I quit my job this afternoon?”

My wife and I had only been married a short while, but she’d known since our second date that I didn’t plan to work in my traditional job until normal retirement age. She also knew that I hadn’t been very happy at work in recent months.

We’re very compatible financially — both savers raised in working-class families that didn’t always have a lot. We make a point of having what we like to call “Fun Family Finance Day” from time to time. On Fun Family Finance Day, we do everything from competitively checking our credit scores to discussing questions that get at the root of our money mindsets to help us create our goals.

But this question wasn’t part of the plan. Not then.

And it was never on any of the lists of questions that we’d discussed with each other. It was like a pop quiz, a pothole in the smoothest relationship road I’d ever traveled…and I was the one putting it there.

Dreams Remain Dreams Without Doing

My wife and I rarely argue, but when we do it’s usually about food. It’s the kitchen and the grocery store that are our battleground. Our finances are fine. Thankfully, when you’re confident in the life you’ve created and the person you chose to build it with, it’s a lot easier to be honest about what’s on your mind.

That still doesn’t always mean you get the answer you want. Or the answer you were expecting. She responded: “Wait what. Kinda. What would you do?”

A completely reasonable and fair question. Not to mention one that I’d probably have to get comfortable answering from a lot more people.

I think my immediate reaction was: We talk about this stuff all the time, where is my, “No worries baby, YOLO!”? (I must have watched too many romcoms back before we cut cable from our lives.)

Being a grownup, it turns out, is actually really hard sometimes. I was about to learn that talking about something, and actually doing it, are a world apart.

Life is full of dreamers and doers. Sometimes those two personalities cross over. But there are plenty of people who go through life talking about so many things they’ll never have the courage to try — or the discipline and determination to follow through with.

Which person was I? The dreamer? The doer? Or that fortunate combination of both?

Standing on the Ledge

There’s a quote perched atop my bucket list of long-term goals:

“At some point, you will need to take a long look in the mirror and ask yourself not just if this is something you wanted to do at one point, but if this is something you will want to have done.”

Words are meaningless without action. It was time for me to take that long look in the mirror. I thought back to one of the questions that my wife and I had previously discussed: What does money mean to you? To me, once I grew out of the “stuff accumulation” phase of my early- to mid-20s, my answer had always been freedom. Money meant freedom. To my wife, the answer was security. Money meant security.

You can probably see how freedom can conflict with security. That was the case here. Not only that, but I was asking to change the perfect plan, one that she was comfortable with and excited about.

That’s not one, but two shots against financial security. If I’d thought more about our financial blueprints and how they differ, I might have seen this coming from a mile away!

As I was standing on that ledge, about to quit my job, thoughts started to race through my mind. What did I actually have to lose if made the leap? Lots.

  • A happy relationship and marriage.
  • A secure job with solid income, not to mention a sixteen year investment in my career.
  • Great benefits, including lots of time off, health insurance, 401(k) — even a pension.
  • The ability to afford anything at any time without any real worry. (Our finances were already on autopilot.)
  • My work friends and work prestige.
  • The general day-to-day purpose of a job.
  • The opportunity to create generational wealth. If we worked until 65, the power of compounding would likely make us ridiculously wealthy.

Today at Get Rich Slowly, let’s perform a little exercise. Come stand in my shoes for a minute, won’t you? Join me on the ledge. Do you see the beautiful view? The endless opportunity? The excitement that’s felt only at the beginning of a grand adventure, an adventure where anything is possible?

Or do you get a queasy feeling in your stomach? Do you feel like you’ve lost your balance, like you’re on the edge of some great catastrophe? Do you see a frightening fall from grace? Does it make you want to back away immediately?

Let’s go back to what it felt like to make this decision…

Sitting on the ledge

My Situation

I’m 38 years old. I’ve worked for the same company since I was 22. Corporate insurance is all I know. I’m well paid. I work from home for a solid company with good benefits, plenty of time off, and I really enjoy most of the people I work for and with.

It’s the definition of stability — a solid guardrail protecting me from what lies over the ledge. So what’s the problem?

A year ago, I took a new position that seemed like a great opportunity. Only it wasn’t. The first misstep of my career. A year in, that spot has killed my enthusiasm and engagement. For the first time at work, I’m struggling to get things done.

As an extrovert that derives meaning from helping others, this feels like a prison. My job isn’t hard because it’s stressful. It’s hard because it’s boring me to death! And what are any of us doing thinking about personal finance and early retirement if we aren’t trying to make better use of our limited time on this planet?

There’s a project looming that would require some weekend work once in a while for the foreseeable future, I’ve avoided it in the past, but my luck is running out. My team — and, more importantly, my position — need to take it on. I understand completely. I just don’t want to do it.

At this point in life, my time is way more important to me than money. The weekends and vacations are what I live for. Adventures in the mountains with my friends, quality time with my wife, our dog, and our families – that’s what makes me feel alive.

Insurance? Meh.

No little kid ever said they wanted to work for an insurance company and play with spreadsheets and Powerpoint presentations when they grow up. I wanted to be a baseball player, a sports writer, even a professional forklift driver. (Because what’s more badass than a forklift when you’re a little kid and your dad works at a marina?)

A Glimpse of the Other Side

My wife and I just got back from a delayed honeymoon to Alaska. To say it was incredible would be an understatement. Denali. Kenai. Majestic train rides. Fjords. Glaciers. Bears. Bald eagles. Whales. Hikes.

Life slowed down.

I somehow managed to read five books while doing so many other amazing things. During our more than two weeks off, I got to see what my mind was capable of when it wasn’t drowning in useless information and mundane tasks that consume my braindwidth.

We talked to people who had ended up in this wild place through a history of taking risks. Parents that had hitchhiked cross-country and ended up there back in the 70s. Can you imagine? Where we live, a fair number of people never leave their town or state!

Before the trip, I had tried to apply for a few positions. For whatever reason, it just didn’t work out. I came home from an amazing glimpse into what life could be to a job that seemed like the polar opposite. (Isn’t that every vacation though?) I’ve felt like a square peg trying to fit in a round hole for a while now. Maybe normal life just isn’t for me anymore. Maybe I need something just a little less ordinary.

Should I Stay or Should I Go?

I’ve been practicing the classic tenets of personal finance since I was in my mid- to late-20s. I found an awesome woman in my mid-30s who just happens to be down with this lifestyle as well. We’re probably two to three years short of where we want to be based on our master plan of a fully-paid house and a really comfortable number in invested assets.

We’d likely fall somewhere between Agency and Security on the stages of financial freedom.

I know good jobs don’t grow on trees, especially where we live. The seasons of the economy are always shifting and there’s a chill in the air. Economic winter can’t be too far off. My wife still has a solid job, and we live a pretty simple life — albeit in an expensive part of the country. Our main splurge is travel, but otherwise we live well below our means.

All of this knowledge and preparation comes with a cost. Having options can be a burden too, because then you’re responsible for making hard decisions. And you’re responsible for the outcomes of those choices.

What other options are there?

  • Be a crappy employee/teammate, and still get paid? Plenty of people have played that game. Get a surgery or two, go out on leave, let performance management run its course for however long that takes, and keep cashing checks the whole time. I don’t think I have it in me to put people I respect through that. It’s just not who I am.
  • I work from home, and I still can’t bring myself to abandon my laptop. What if someone needs me?
  • Am I giving up too soon? The finish line seems just around the corner — somehow so close yet so far away.
  • Should I just suck it up and sell a little more of my soul? Slump my shoulders a little bit more as I trade another piece of myself for money I don’t need to buy things I don’t want?

As I go back and forth, sometimes I briefly wish I’d never found the personal finance community. Like Neo in The Matrix, why’d I have to take the damn red pill? Being a mindless consumer wasn’t so bad. I would have invested 6-10% in my 401(k) with a traditional pension on top of it.

Forty years on autopilot would have produced a comfortable life of work, nice things — and maybe some time in old age to relax and travel.

Facing Freedom

The whole point of everything I’ve done since I started this journey was to be in control of my own life. To not be owned by things or circumstances. To have options. Freedom of choice. F-U money.

I have the corporate battle scars and survivor’s guilt to understand why that’s important.

I’ve sat on the phone while I heard that my old department was closing down. The sadness and tears in the room. Everyone that had taken me in, given me my chance, taught me the job…basically gone, casualties of a business decision.

I’ve seen people get laid off who are petrified because they don’t know how they’ll pay their bills in a couple of weeks. People will be okay eventually though, right?

What about my friend who was struggling last year and left the company? He committed suicide a few months later. Maybe everyone won’t be okay eventually. Depression runs in my family. Am I really built for this? That thought is haunting.

It’s been said that one of the hardest decisions you’ll ever make in life is whether to walk away or try harder. Every bone in my body tells me it’s time to walk away, to bet on myself.

The End?

About six months after the text exchange that blindsided my wife, with her support, I hit send on the scariest, most exciting and important one-line email of my professional career. It would also signify the unofficial end of it: “I will be resigning from my position effective Wednesday, June 26th.”

To combine a few lines from my favorite movie, The Shawshank Redemption, some birds just weren’t meant to be caged. It’s time to get busy living, or get busy dying.

More about...Career, Retirement

Become A Money Boss And Join 15,000 Others

Subscribe to the GRS Insider (FREE) and we’ll give you a copy of the Money Boss Manifesto (also FREE)

Yes! Sign up and get your free gift
Become A Money Boss And Join 15,000 Others

There are 32 comments to "Should I stay or should I go? Wrestling with the decision to quit a career".

  1. El Nerdo says 09 October 2019 at 07:18

    It’s early for me, have busy morning ahead, and so I only skimmed; but if you’re an extrovert: why not just ask for the old job back, the one that paid well and you enjoyed, and just up your savings?

    Writing isn’t the most extroverted gig around. Hell, it’ s often recommended as “a career for misanthropists” (trust me, I’ve googled, lol). Not that you *have to* be a misanthropist, but.. a lot of quiet time in front of the empty page.

    Anyway—best wishes!

    • FoxTesla says 09 October 2019 at 10:11

      Hopefully the author will respond, but from my experience of working at large corporations, there are a number of obstacles to the “just go back” idea:

      Budgeting – the projected workhours are locked in (either at a lower level because he left, or a new person took his spot). Finding the funding to move him over, on top of the cost of replacing the new job he took makes this a non-starter.
      Poisoning future opportunities – by backing out of the job, he’ll carry (fairly or unfairly) in the eyes of any future hiring manager the stain of “someone who will cut bait and run” (or the old group, for that matter).
      Old group wants new blood – I’ve seen someone take on a new opportunity, the old group hire a young worker to try and train someone to be in the group for many years, and then have to say “sorry, we’d rather have the new go-getter, thanks”. Sometimes this overlaps with the previous two items listed.

      • El Nerdo says 09 October 2019 at 12:59

        Ok, sure, maybe his old company can’t demote him. But a job is not a career. He could have moved maybe to a position like his old position—elsewhere. Baby vs. bathwater problem.

        Ditch the ugly new job, keep the sweet well-paid career (in a nice, pleasant, abundant and rewarding plateau, helping people).

        No need to always be climbing up the ladder and hitting your head with Peter’s Principle, suffering from burnout.

        Sometimes staying put right where you are is the best move. Yes, it’s against the usual convention, but it can be done, especially if you have money saved and can work for pleasure at something you’re good at.

        I have this uncle who had a very successful small business. People always told him to grow grow grow. He would respond “nah, I love it just the way it is.” He customized his lifestyle to do something he loved, had a happy work life, and retired loaded.

        Anyway, it’s great if this is what the author really wants, but returning to a pleasant job was not an option examined here.

        • Mike in NH says 09 October 2019 at 15:44

          FoxTesla kinda hit the nail on the head. A few months after I took the new job I realized it wasn’t what it was supposed to be. I spoke up, and was given the option to go back to my old position, but it had already changed into something I wasn’t really interested in (along with the political cost of stepping back). Just not a great move in that culture. I chose to stick with the new position. At the end of the day, either/or, would not have made much difference. That job had been getting old anyway, which is what prompted the change in the first place. I’m not sure if it was burnout, a head start on a mid-life crisis, or just the twitch that seems to come the closer you get to “your number”. In terms of moving to a different company, my value in the field was mostly tied to my tenure at my specific company. I wasn’t interested in trying to move to another company and continue the career somewhere else. Regarding trying to write as an extrovert, that’s a great insight El Nerdo, I’ve been a remote employee for almost a decade so luckily I had already built a solid social foundation into my life. My current plan involves quite a bit of other stuff that gives me a chance to spend quality time with good people. Thank you both for the comments!

          • El Nerdo says 09 October 2019 at 19:24

            Ah, right right, I get the whole narrative now, thanks for clarifying. Congrats on your escape!

  2. Joe says 09 October 2019 at 07:25

    I was in a similar position when I was 38. I hated my job and I had to make a change. Luckily, I already talked with my wife and we worked on it together for 2 years by then. I quit and never looked back. After 7 years of early retirement, our lives are much better than when I was working full-time. My wife still works because she values security more. However, I’m trying to convince her to retire next year. We’ll see…

    • Mike in NH says 09 October 2019 at 15:47

      That’s a very similar arc, Joe. Let’s check back in 7 years and see if it still lines up 🙂

  3. dh says 09 October 2019 at 08:19
    • Mike in NH says 09 October 2019 at 16:02

      This is great, dh, thanks for sharing! I was feeling for a long time that I was meant to accomplish more with my life, so I guess challenge accepted.

  4. Angie says 09 October 2019 at 14:20

    I enjoyed this piece but I would’ve like additional insight into the discussions that he and his wife had prior to his resignation and more information about his intentions for his next steps.

    • Mike in NH says 09 October 2019 at 15:57

      I appreciate the feedback Angie! My intent was to write this piece as an introduction that might provide an opportunity for a follow-up or as a start of a series on what it feels like to pull the trigger somewhat on the fly. Also very hard to write about something near and dear to my heart in a certain number of words. A lot of our conversations focused on my plan for what I would do with my time, me offering to be her personal concierge, ensuring that I had exhausted the options before leaving my career, etc. We check in on this often, the last thing I would want to do is alienate her. My next steps/immediate goals were to find some reliable income with a flexible schedule, pursue my dream of getting paid to play in the mountains, and trying to get some of my writing published (thanks j.d.).

  5. Kevin says 09 October 2019 at 15:21

    This spoke to me. We need more reader stories J.D.

    • Mike in NH says 11 October 2019 at 03:47

      Thanks so much for the comment Kevin!

  6. Jordan Burnett says 10 October 2019 at 08:27

    I faced many of the same decisions this year and decided to pursue my post-FI “career” before reaching the financial goal. I, too, was going to be fully independent with only 5-8 more years of toughing it out, but in my opinion the juice wasn’t worth the squeeze.

    I traded in a $200K/yr guaranteed IT Consultant salary (with benefits) for a 100% commission position helping people achieve their fitness goals.

    The first few months of trainer commissions went like this:

    I’m on track to have all of my fixed monthly expenses paid in around 6-12 months. Given, I had a fairly substantial cash cushion to make this feasible, and I still do part-time IT consulting for my own S-Corp to “make up the difference” in the interim.

    However, I now only take on projects and clients that I want to work with and that I like working with. And I never have to attend an “All Hands Meeting” or Forced Happy Hour ever again.

    • Mike in NH says 11 October 2019 at 03:53

      The juice being worth the squeeze always reminds me of the movie the girl next door haha.

      That’s great steady progress on the income! I’m always a little envious of those in the IT world that have a skillset that travels. My value was mostly tied to my company and the time I spent there (I was the guy that could always help, or get you to the right place/person).

      Really pumped to not be spending my time listening to 2020 business plans this time of year.

      Best of luck Jordan, looks like everything is trending nicely for you.

  7. Candi says 10 October 2019 at 10:38

    What a great, open and honest article. I’d definitely love to hear the rest of the story as Mike’s mentioned above. I can relate to so many of the feelings you shared about work. Unfortunately,I can’t relate being financially ready to leave it yet. But I’m working on it (might need to kick it up a notch or three though).

    I usually skim long articles, but you kept me hooked on every word Mike. You definitely have talent as a writer.

    • Mike in NH says 11 October 2019 at 04:00

      Aww thanks so much Candi! Getting some positive feedback from the always to be feared “strangers on the interwebs” crowd feels pretty great. It’s one thing to have your friends and family say nice things, but taking the step of putting something out there was an important mental hurdle for me to get over.

      Keep grinding and doing the right things, adjust if needed, it’s all just math and time.

  8. Giovana says 10 October 2019 at 19:50

    I loved your story. And the part where you regretted having been introduced to FI kind of resonated with me. I’m thankful for it and for opening my eyes but it also makes me frustrated that I have at least 6-10 years to go before my husband and I can pull the trigger. Wishing it was sooner. Good on you for taking the chance and on your wife for supporting your decision. Funny that I also work for an insurance company… I guess it’s not the most thrilling field ever, huh? Good luck with your writing career, hope it’s all you wished for!

    • Mike in NH says 11 October 2019 at 04:12

      Giovana those feelings conspired against me towards the end, honestly. I didn’t grow up with much so there was a lot of guilt surrounding the decision of giving up a job a lot of people I know would be thrilled to have. It’s like a lot of things I guess, you can’t really understand unless you are in that person’s shoes.

      I don’t know if it’s insurance in particular or just the corporate world in general and the way our society is currently focused? I only worked for one company so I don’t have much else to compare it to. For me, the further I got from our actual customers, the easier my job got, but the less rewarding.

      Thank you for the kind words, I appreciate it!

  9. Educator FI says 11 October 2019 at 06:24

    This was a great read. I loved reading the thought process. That description of feeling ready, but still not yet totally financially secure is exactly where we are now.I have mornings like that, but so far we’ve always stayed on course for our plan. I yearn for a different life pattern, but don’t hate my job so that makes it bearable. I suspect it will be different in two years and am okay until then.

    As another commenter said – this spoke to me. Thanks for writing.

    • Mike in NH says 12 October 2019 at 11:11

      I’m not sure whether I should be thankful or not for that project which was the proverbial straw that broke the camel’s back, time will tell. I’ve always been a pretty meticulous planner, hopefully going off script will be a good life lesson for me.

      Best of luck on your home stretch and thanks for reading!

  10. DJ says 11 October 2019 at 14:33

    JD – thank you for this posting. Mike – thank you for sharing. I’m on the ledge so this really resonated for me. Thanks for your willingness to share this story. For me, it truly helps!

    JD – your new focus on your blog is recognized and in my opinion outstanding. Not to say your previous work wasn’t just to say I see the new focus. More like Mike and the 10 year recap from ERE!

    • J.D. says 12 October 2019 at 06:37

      Thanks, DJ. I appreciate the kind words. As you’ll see in my upcoming article on deep work, I’ve enjoyed the change in focus too. The pace will slow, but I hope the quality will improve. Plus, Tom and I are hoping to bring on another writer to add material during the lulls while I’m writing each new piece.

    • Mike in NH says 12 October 2019 at 11:12

      Thanks DJ! Plenty of room on the ledge, hope you are enjoying the view 😉

  11. ed says 12 October 2019 at 17:53

    I can relate to the push/pull this decision must have been. I retired at 56 ( not 100% my choice) and wasn’t quite ready so unretired at 57. Learned a lot about myself and realized how much my self worth and identity, friendships etc. was wrapped up in my career. I’ve made a concerted effort in the last two years to build interests and outside friendships. I now find myself wrestling again with “Is it time ?”, to leave an executive position to explore and really “live” the last third of my life.
    Read somewhere You’ll know ” when you have enough and have had enough!” Good luck !

    • Mike in NH says 13 October 2019 at 06:43

      Good luck to you too, sir!

      For me it was interesting, in my early 20s when I got the job, it honestly might have saved my life. I was really lost after college and felt like a failure. It was the job that propped me up through that rough transition period. Eventually I got my confidence back and found myself, which is when I really began to create an amazing life outside of work. After a solid decade of lifestyle design, the career was now what was holding me back from my goals vs. the thing helping me to achieve them.

      Part of that, my own fault, by not growing up with much I had probably set my career goals a little too low. I just wanted to have a decent job and not have to worry about money like we did growing up. I got that goal pretty quickly and then made conscious choices not to move around the country for opportunities that might have helped me work my way further up the ladder, but destroyed the precious work life balance.

  12. Sam says 13 October 2019 at 12:27

    I like the idea of a FFFday. It sets a time for questions and discussions to keep everyone on same agreed to path.

    • Mike in NH says 15 October 2019 at 05:50

      Corporate life taught me that we tend to do a better job of managing the things that we measure, I’ve found that to repeatedly be the case in anything that I do personally or professionally. Like J.D. is fond of saying your decisions shouldn’t always be about the money, but you should always be aware of the money choice you are making. FFFday helps us stay on track with our goals, remain in-tuned to each other, and be aware how our “family business” is performing.

      Lots of good content out on the Internet too if you Google money questions/life questions to discuss with your significant other. GRS has some as well:

  13. Treo says 15 October 2019 at 15:13

    Love this article, very much resonates with me.
    I am just about to turn 36, and while that’s pretty “young” by most standards, I probably only have another 10, maybe 15 years in me, particularly in my industry (high tech startups).
    I’ve gotten quite far, in a relatively short period of time, and enjoy that immensely, but I often find myself having to do things I don’t particularly agree with but that I realize are “required”.
    I don’t quite yet have F-U money, but at the rate things are going now, by the time I am 40, I’d have enough to probably last me 20+ years, if I wait until 45, I’d probably have enough for the rest of my days and my family would be taken care of as well. I safe / invest about 40% of my after-tax income and have no debts left. We do have a rental in a high cost of living area, but also a paid-for condo in a relatively modest area, the high cost of living area is a requirement of the job and field I am in, unfortunately.

    My biggest question / issue is what to do about health insurance. I love the idea of freelancing (I do some on the side already), but my wife needs high quality health insurance (which luckily is provided 100% by my employer right now). What have people done for this before they are eligible for Medicare/Medicaid? What does JD do for this?

  14. Susan says 16 October 2019 at 07:21

    Great article…I think I might have been writing parts of it. I recently had a work trip in Alaska and it totally turned my world upside down. What is it about Alaska? Anyway, now I’m running numbers on how to a) pay for a helicopter license and switch out of a 13-year career, or b) pay for a helicopter license and create a new path that uses my skill set that has been cultivated over the last 13-years. Both options seem impossibly far away.

    Thank you J.D. and all the readers for the great content. You have had an integral part in shaping my financial goals/mentality.

  15. Suzie says 21 October 2019 at 11:37

    Mike, great post, agree with those who said you are a talented writer. Despite the length, read the whole thing! Can’t wait to read what the future brings. Resonated with so much and I’m old enough to be your mother. There have been more times than there should have been when I said “f-u” and quit a job. I was “fortunate” in that I didn’t have time invested in a career but have pretty transferable skills. I can honestly say I look back now and can’t think of any regrets with a single one. It is really not that surprising how resourceful we can be when push comes to shove.

    • Huckleberry says 27 October 2019 at 10:24

      Thanks J.D. for Mike’s post (and all of yours – having trained counselors, I believe you would have been a good one unafraid of being vulnerable and self-disclosing).

      Re Mike’s, and many others facing a life-determining choice. It comes down to choosing between what you know (in Mike’s case what he knew so well he was bored with it) and what is unknown (again in Mike’s case he didn’t have a clue as to what he would do). Under such circumstances I’ve personally found it works out best if you take the chance – essentially betting on yourself. At worst, as Teddy Roosevelt said, you’ll fail by at least daring greatly. At best, as Churchill advised, “Play for more than you can afford to lose and you will learn the game.” Best to you both.

Leave a reply

Your email address will not be published. Required fields are marked*