How I Learned to Stop Worrying About Money and Quit My Job

[As part of our new weekly column by Mr. 1500 of]


I left my job about 4 months ago and haven’t regretted it a bit.

My career didn’t even last 20 years. I started my first real job in January of 1998 and my last day was April 13th of 2017. Leaving wasn’t an easy decision.

I have money security issues and suffered from an acute case of One More Dollar Syndrome (the first cousin of One More Year Syndrome). When I started my journey to financial freedom way back on January 1st of 2013, I figured I would need about a million to quit ($40,000 per year per the 4% Rule). When I left, I had almost $1,400,000 saved up. And this didn’t include $400,000 in home equity.

Despite the big nest egg, picking up the phone to tell my boss the bad news was one of the most difficult calls I’ve ever made. Over four months later, I’m still adjusting, but life is pretty great.

How I Learned to Stop Worrying about Money and Quit my Job

The numbers part of retirement is easy. Figure out your annual spending and sock away enough to last a lifetime. The emotional part; not so easy.

Here is how I learned to stop worrying and quit my job:

#1. I’m frugal and flexible

I planned my retirement money needs according to the 4% Rule which has no shortage of detractors. It isn’t 100% safe, but nothing is. My advice is to stay frugal and flexible:

  • Frugality: If you can live on $40,000 per year, it doesn’t take much income to move the needle. Just generating an extra $10,000 turns the 4% Rule into the 3% Rule, drastically improving your odds of never running out of money. You can make $10,000 by renting a room, driving for Uber or getting a part-time gig.
  • Flexibility: Being able to react to the curve balls life pitches isn’t just a good strategy for early retirement, it’s a good strategy for life. Don’t get set in your ways. Be mindful of the world and be ready to pivot in the unlikely event that your net worth craters by 50% the day after you quit.

#2. I considered the worst case scenarios, and created backup plans for my backup plans)

Some of my worst case scenarios include:

  • Massive stock market drop early in retirement
  • Lack of meaning in my life

And one my biggest:

  • Boredom

The worst case scenarios are not that bad once you start thinking about them. If the market tanked, I’d step up my side-hustles or go back to full-time work for a year. If I was bored, I’d hire a life coach.

Perhaps my ultimate worst case scenario is this:

I die regretting all of the things I didn’t get around to doing!

I’ve helped eliminate that one by leaving my job. But, I still needed to come up with backup plans for financial disasters. My worrying brain constantly barrages me with what-ifs:

  • What if the stock market drops by 50%?
  • What if health insurance costs $3,000/month?
  • What if my wife or I come down with a major illness?

Here are my backup plans, in order of mild (stock market drops 50%) to terror (in a temporary bout of insanity, I “invest” all of my money in an MLM and lose it all):

  • Pick up a side-hustle
  • Go back to full-time work
  • Sell my home to get the equity ($400,000) out
  • Move to a foreign country for cheap living and health care
  • Create my own MLM!

Hmmmm, maybe I should implement that last one today… Brace yourselves readers. Today I’d like to introduce you to my new business: Mr. Money Marshmallow!

How would you like to be a downline distributor? Get in on the ground floor today! (And don’t tell Mr. Money Mustache…)

Just kidding. As much as I enjoy marshmallows, I really, really dislike MLM schemes. And now I’m all distracted. Pull yourself together man!

I don’t think that I’ll have to do any of those things, but knowing that I’ve thought through my worst case scenarios gives me peace.

#3. I realized that risk is OK (or even great!)

Quitting work at 43 isn’t the safe route. If I wanted that, I’d work until I’m 62 and continue to stockpile money. I’d have good insurance the whole time, a decent car, and maybe even… Oh wait, I feel something coming on:


To hell with that. A normal life of safety sounds pretty damn boring. I want to live on my own terms and follow my own ambition. Besides, no one ever did anything great taking orders from Mr. Bossman in a cube, right?

#4. I know that the work I love is my best work

I learned an important lesson on my journey to early retirement:

You can’t retire to nothing.

Retiring just for the sake of retiring is a horrible idea. Any well adjusted human needs meaningful activity to be happy. Many of us get it from work, and if that’s you, you better have something lined up when you leave. TV won’t cut it.

I have my writing. Without it, I probably wouldn’t have left my job. Financially, I would have been better off sticking with my career as a programmer. However, money only funds a certain amount of happiness. At some point, you max out that happiness account and need to move on.

This is exactly what I had to do. I realized that more money wasn’t going to make me happier, but working on my blog, a book, and related projects would.

I Should have Done it Sooner

Everyone says it. And here I am saying it too: I should have left my job sooner.

Chances are, you’ll say the same when it’s time.

Humans have a tendency to let their fears stand in the way of their dreams. We cling to worst case scenarios to justify the chains that bind us. And to make it more difficult, leaving work before you’re old and grey is still an unconventional concept! Humans are followers, and not many members of the herd leave their jobs early.

But I can’t tell you how much I’m enjoying my life now. Every day is different. This is how one played out earlier this week:

  • Woke up at 5am (life is too good to spend it sleeping)
  • Biked 20 miles up into the mountains (life is too good to not be in optimum health)
  • Ate breakfast with my girls
  • Worked on three different blog posts for two hours
  • Biked with the girls to the library
  • Went home for lunch
  • Spent the afternoon at the pool with the girls
  • Polished up a chapter on a book I’m working on
  • Dinner
  • Family walk
  • Played Ticket to Ride with the family

I left my job about 4 months ago and haven’t regretted it a bit. I encourage others who’ve already reached FIRE to strongly consider it too.

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  1. Nineandahalffingers August 16, 2017 at 6:12 AM

    I love this post. Anything that inspires change in me really hits the mark. Thank you.

  2. PaulM August 16, 2017 at 7:17 AM

    I always gain something from reading these posts and this one gives me one more reason to be ok with my decision to leave work within the year, if just to have time to play Ticket to Ride. I love all things about trains and cannot wait to have the time to play this one with my family. Toot, toot!

    1. Mr. 1500 August 16, 2017 at 10:50 AM

      Ticket to Ride is one of our family favorites!

  3. Ember @ An Intentional Lifestyle August 16, 2017 at 7:38 AM

    We were just talking about how hard it will be for my husband to quit his job when we get to FI. He loves who he works with, just not the job itself so much.
    I do agree about finding something to keep you busy and fulfilled after retirement. I have my writing, but Hubs doesn’t enjoy that. I think we will make sure to have rentals or something else he enjoys planned and ready when the time comes.
    Love the post!! Very encouraging!

  4. Apathy Ends August 16, 2017 at 7:48 AM

    I think we will suffer from 1 more dollar symptom as we get closer (we are a long ways away now however) – I can see how walking away from a sure thing is tough when weighed against the fear of the unknown. Thankfully there are a ton of FIRE people paving the path ahead of us.

  5. Ms. Frugal Asian Finance August 16, 2017 at 7:56 AM

    Your net worth is impressive! I’m glad you made the decision to retire early and have been happy with it so far.

    My biggest fear about early retirement is unexpected life events. There is no telling when a medical condition or family members in need of financial support (I.e. parents) will happen. I will try to stash away lots of cash and investment before I take the plunge.

  6. Lance @ My Strategic Dollar August 16, 2017 at 7:56 AM

    Love this post! I wonder what will happen as I get closer to retirement. Will I become a victim of one more dollar/year syndrome? I’m not sure. I hope the work I’m doing today positions me to be comfortable and understand the impacts of the scenarios you described. You can always go back to work…

    1. Mr. 1500 August 16, 2017 at 10:53 AM

      One More Dollar syndrome is hard to overcome. I’m still not over it, but my happiness more than makes up for any more dollars.

  7. The Savvy Couple August 16, 2017 at 8:00 AM

    I walked away from my job to run our site full time in May. It’s been an incredible journey so far. Having your finances in line before making the jump is HUGE. It allows you to invest in your business and not have to worry if food will be on the table.

    Great article as always. Thanks for sharing!

  8. ESI Money August 16, 2017 at 8:02 AM

    Sounds like we have the same life! (up early and exercising) We’re going to have to climb a mountain together some day.

    Love the MMM idea! ;)

    1. Mr. 1500 August 16, 2017 at 11:20 AM

      What 14er do you want to tackle? I’m game!

  9. Leo T. Ly August 16, 2017 at 8:03 AM

    Having something to retire to and having projects that you enjoy to work on is a great start to your early retirement. I am also on my way towards FIRE and I have a few hobbies/side hustles that I enjoy working on. If I make some money from these hobbies, then it’s great. If not, I am still keeping myself active, but will not break the bank.

    Also, keeping your body and mind healthy is crucial. Your wealth won’t matter if you don’t have your health.

    1. Mr. 1500 August 16, 2017 at 11:20 AM

      “Yourr wealth won’t matter if you don’t have your health.”

      Health is absolutely everything.

  10. Team CF August 16, 2017 at 8:09 AM

    Any advise for those who want to get out too soon? Been tempted by it for a while, but there is that (big) risk of running out of money……perhaps a part-time gig is not all that bad?

    1. Mr. 1500 August 16, 2017 at 11:22 AM

      I think you hit the nail on the head with the part-time gig suggestion. There are so many side hustles and if you live frugal, the part-time work may fund your whole life while you let the rest grow.

  11. Mrs. Groovy August 16, 2017 at 8:14 AM

    Coping with risk and having a backup plan (or creating one when needed) are the game-changers for me. It’s pretty easy to determine how much money we need to live on and what projects, hobbies, etc. will be fulfilling in retirement. But it’s the unknown negative ‘what-ifs’ about money that hold us back emotionally, even when intellectually we know we have enough.

    I’m happy to hear how much joy life is bringing you now. Thanks for sharing.

  12. The Grounded Engineer August 16, 2017 at 8:44 AM

    Your typical day you described is motivation for me to keep working hard. I want to increase my income so i can stock more money away into investments. Then, someday soon I too can play with my little daughter during the day instead of heading off to work.

  13. Franklin Bach August 16, 2017 at 8:46 AM

    hmm, I’m starting to get the idea that a programmer’s career cycle is about 7 years in a cube farm before one begins to peer over the wall. It does not seem like a long term career unless one moves into a Leadership position to coach and guide the next gen.
    You took that step toward leadership on a different tack with your blogging & a book project to make the life change to work on your terms which I appreciate to the full extent.
    So here’s my question. If you had job that was interesting, engaging,fun and helped employees, customers, patients, etc increase the quality of their lives, would you still pull the plug the FIRE pin?
    The retire to nothing statement you made continues to stop me in my tracks.

    1. Mr. 1500 August 16, 2017 at 11:25 AM

      If you love your job, you should stay there. Well, almost. If I were in those shoes, I’d push fora 3 month sabbatical. If you love the time off, retire early. If not, go back to work. The sabbatical will help you figure it out.

  14. Dads Dollars Debts August 16, 2017 at 9:09 AM

    For some reasons I want to roast some marshmallows now. Sounds like you are doing just fine. It is interesting how our fears can restrict our progress. I completely agree that you do not end up retiring to nothing. Most FIRE types, the ones that work hard and save hard, are motivated individuals. This does not stop with retirement. It just morphs into activities they dictate as opposed to the “man” dictating it for them.

  15. Mrs. Picky Pincher August 16, 2017 at 9:11 AM

    Ahhhh. You never have to convince me that FIRE is worth it. ;) My only regret is that we didn’t try to avoid debt in the first place–it would have saved us so much time! Ah well, the good part is that we’re on this journey. :)

  16. Vicki@MakeSmarterDecisions August 16, 2017 at 9:17 AM

    “We cling to worst case scenarios to justify the chains that bind us.” I was SO guilty of this too. It wasn’t until we defined our “enough” that I solved my OMY crisis… and going to one more funeral of a peer. That cemented it. Agree with your points about MLM – they make me crazy. Love that you are working on a book! I plan to do that too. Hope we can chat in a few weeks when we’re in Longmont!

    1. Mr. 1500 August 16, 2017 at 11:26 AM

      Funerals have a way of putting it all in perspective, don’t they!

      And yeah, I’ll be in PopUp too. Maybe we can have a BBQ of something. We’ll toast Mr. Money Marshmallows after!

  17. Joe August 16, 2017 at 9:37 AM

    Interesting to hear that you think you should have quit earlier. It sounds like you’re having an awesome early retirement. Congrats!
    Personally, I thought I should have waited 6 more months. I probably could have got a severance package if I waited a bit. Oh well, it turned out good so I can’t complain.
    Good luck with your book!

  18. Darren August 16, 2017 at 9:46 AM

    For me, my biggest fear about leaving early would be right before a market downturn. Not saying that’s going to happen but we are at highs…

    I’m sure you’re probably in a position where you aren’t drawing much if anything from your retirement accounts anyway, I assume? Congrats on getting FIRE’d.

    1. Mr. 1500 August 16, 2017 at 11:29 AM

      Yep, I’m lucky that I don’t have to draw anything (thanks wife’s job and blog $$$). However, I didn’t plan it that way. I never expected the blog to be monetarily successful and my wife’s dream job fell into her lap.

      If you’re worried about a downturn, accumulate a couple years of spending in cash. If the downturn happens, live off of that so you don’t have to withdraw from investments.

  19. Mrs. Adventure Rich August 16, 2017 at 9:53 AM

    I think the flexibility and considering the worst case scenario will be key for Mr. Adventure Rich and I. I tend to be very aggressive generally, but I think actually cutting ties with a paycheck will be a scary thing for me. Luckily, Mr. AR is great with reminding me that “if all else fails, we can always…” (fill in the worst case scenario solution) and that helps me to keep my head on :)

  20. New Father Finance August 16, 2017 at 9:58 AM

    It is articles like this that have inspired me to live a full, but low-cost life. I’m just starting out on my FIRE journey, but I hope to be able to quit when I hit my net worth targets. I definitely suffer from fear of the unknown, particularly around health insurance and costs like that (my father died pretty young) but I hope to not be paralyzed by those fears when the time comes.

  21. Physician on FIRE August 16, 2017 at 1:20 PM

    I look forward to the day where I look back and wonder why I stuck around as long as I did. I know you gave part-time work a whirl, and it wasn’t all that or a bag of chips, but I am excited to see how life improves when I make that switch.

    At the moment, the most likely scenario is that I’m done in one or two more years, and which ends up making the most sense will probably have more to do with external factors (i.e. who is hired to replace me and when they’re available) than my own wishes. Of course, I control my own destiny, but I’d like my exit to be a smooth transition for everyone.


  22. Sylvia @Professional Girl on the Go August 16, 2017 at 1:43 PM

    I love this post! And #4 is the reason why I feel so torn because I want to retire early (and be able to wake up everyday and do what I love in my PJs) but I actually do something I love now working at my job. So even though I am actively working on retiring early.. I don’t know if I will. I might develop the One More Year Syndrome when it’s time to push the go button.

    1. Mr. 1500 August 16, 2017 at 2:23 PM

      Sylvia, loving your job is a wonderful problem to have! :) I’d tell you to continue saving like you will retire early. Options are what makes life great, even if you choose the option to stay at your job!

  23. Candy Clouston August 16, 2017 at 3:41 PM

    I think it’s real cute that you think living on $40K/year is frugal. Do you have any idea how that sounds to people living on less than $25K/year with no hope of employment?

  24. Mr. Tako August 16, 2017 at 4:03 PM

    Glad you finally decided to join the ranks of the jobless! ;)

    Very cool btw, I didn’t know you were working on a book!

  25. EL August 16, 2017 at 5:44 PM

    Good post and its vital to find a plan for activities after reaching FI. WE all say we will never be bored, but many creative people have that fear. You can also volunteer time away once per week, as I will consistently do 1 day.

  26. The 76K Project August 16, 2017 at 5:50 PM

    Ticket to Ride! That’s a good one!

    I’ve spent the last few days daydreaming about all the stuff I’d do if I weren’t in a 9-5 job. I don’t think I’d be bored, either. Although I’m nowhere near being able to stop working, I’m trying to find a compromise between that and the kind of gig I currently have. Do I appreciate that I have a job? Yes. Do I like being in a cubicle all day? NO. Thanks for the inspiration and motivation!

  27. Jeff @ Maximum Cents August 16, 2017 at 6:02 PM

    Thanks for sharing your perspectives on early retirement. Would there have been any scenario where you would have wanted to stay at a job or did you just hate the one you had? You also mentioned that people could work on side hustles but those may not fill enough of the time gap in retirement. It seems that you really need to have hobbies that are meaningful as well.

    1. Mr. 1500 August 16, 2017 at 6:58 PM

      If they would have given me 6 months off with the possibility of going back, I would have taken that. With the nature of my contract, it was all or nothing. And I didn’t hate it. I just reached a point where I needed time more than money.

      “It seems that you really need to have hobbies that are meaningful as well.”

      Yeah! You need a rich life outside of work to have a rich retirement. I never had enough time and still don’t…

  28. steveark August 16, 2017 at 6:49 PM

    I was older than you are and had a larger nest egg and had no trouble walking away when it stopped being fun. I’ve never looked back but one thing that is beginning to bug me is a year and a half later I’m getting job offers for large amounts to go back to full time work. It kind of goes against my frugal gene to tell people to buzz off when they are offering me so much. I was a high earner in my career but these offers are ludicrously high. It is a different kind of worrying about money, I have more than plenty under the worst case scenario now. This is a weird kind of FOMO, fear of missing out on the chance to have a massive salary. It is nothing but a pure greed attack and I won’t give in to it but it bothers me that it bothers me.

    1. Mr. 1500 August 16, 2017 at 6:56 PM

      Well, that is a good problem to have!

      I was in IT and am barraged daily by recruiters. I look at it as my backup plan should I ever want to go back. As the days go by, I become more and more convinced that will never happen.

  29. George@20somethinglawyer August 16, 2017 at 7:50 PM

    Looking forward to my early retirement as well. Glad to see there’s light at the end of the tunnel!

  30. Jason Butler August 16, 2017 at 8:25 PM

    Loving this post. I can’t wait until I can quit my job and do my own thing. Until then, the grind continues.

  31. BMG August 17, 2017 at 5:58 AM

    Great article Mr. 1500.

    “If you can live on $40,000 per year, it doesn’t take much income to move the needle. Just generating an extra $10,000 turns the 4% Rule into the 3% Rule, drastically improving your odds of never running out of money. You can make $10,000 by renting a room, driving for Uber or getting a part-time gig.”

    This is some great financial awareness on your part – although I don’t think you are going to need to “get a part-time gig” or “drive for Uber”. You are where we all want to be, and I love that you show us what is possible.

    Thank you!

  32. Brian @ Millennial Money Guide August 17, 2017 at 12:39 PM

    I quit my high paying salaried position in order to pursue some projects. I thought if I didn’t do it then, then I never would. My savings took a hit during this period of time but I knew I always had my experience and quality resume to fall back on. But like you, I wasn’t worried about money. I had savings and knew something would work out. It always does. After I had my much needed time off, I’m now back in the work force and making even more money than I did at my previous gig. Life’s short, I wasn’t afraid to take that risk. I should note that I also am a millennial, don’t have any kids, and have a lot of flexibility.

    1. J. Money August 17, 2017 at 3:58 PM

      nice! did you knock out all the projects before returning back to work force? feels good to get them out into the real world and off your brain regardless of whether they take off or not :)

  33. Dave @ Married with Money August 18, 2017 at 9:17 AM

    There’s nothing wrong with retiring and deciding that doing nothing is just not for you. Some folks are just wired like that, where they need something to do. For my dad, that was actually going back to work part-time, because he loves what he does. For others it might be a side project. Keeping busy sounds like the biggest struggle especially for early retirees, but it sounds like you’ve got that part figured out.

  34. Mao August 20, 2017 at 11:17 AM

    This is great Mr.1500.

    Personally I have been contemplating on leaving my 9 to 5 already. Even though I am no where close to FI, I do have a fair amount of cushion saved up that generates some income already. The thing is I am increasingly cherishing my time as I really don’t feel like working at a job that I am not super passionate about for another 10 years just to reach FI.

    I will probably pick up on some side hustle and focusing on other passions of my, which could potentially generate income for me down the road.

    Does anyone think this is too crazy?

    1. Mr. 1500 August 20, 2017 at 4:06 PM

      Not crazy. If you can mostly get by with side hustles, go for it!

  35. Krystal @ Simple Finance Mom August 20, 2017 at 2:08 PM

    I love reading your posts. Always so inspiring! I do have a question for you. Assuming we can live off of $40,000 you say about a million is a safe number to save. Are you taking into account inflation and longevity of retirement years since you retired so early? I think $1M is doable for us, but my ever-worrying mind always wonders about taxes, inflation, insurance, etc.

    1. Mr. 1500 August 20, 2017 at 4:05 PM

      Yep! If the money ever starts to run low, I’ll just go out and get a job. Or, maybe move to a country where living expenses are super low. There is risk to retiring early, but there is also risk as staying at your job for an extra 10 years…

  36. Myfinancekits August 20, 2017 at 3:17 PM

    Everyone will need to quit his job at one point or the other. However, it takes courage for you to quit at your own instance. But it is better in anyway

  37. ZJ Thorne August 20, 2017 at 7:19 PM

    Having the flexibility and a few backup plans overcomes a great deal of worry. And Ticket to Ride is an excellent game. Looking forward to your book.

    1. Mr. 1500 August 21, 2017 at 6:46 PM

      Yep, flexibility is EVERYTHING.

  38. Dividend Growth Investor August 30, 2017 at 10:29 AM

    I love this post MF! ( mister fifteenhundred) Because it essentially resonates with my situation so much.

    I operate under the backup to the backup plan scenario..Which is somewhat ridiculous.. But most likely those were the genes passed from generation to generation that survived and made it into me ;-)

    I look forward to seeing where your journey takes you (and that book you are writing)