Is it Time to Quit Your Job?

Is it Time to Quit Your Job?

In the bookย Born for This by Chris Guillebeau, he recommends setting a date to resign from your job each year. On that date, you commit to resigning if your job is not the best fit. This exercise forces you to re-evaluate every year with an ultimatum. Are you miserable? This is quitting day! Things going great? Reset the calendar reminder for next year and carry on.

What if?

Many advocate that if you prepare for the absolute worst case scenario, you’ll get over your fear. So, what if you lost your job tomorrow? What is the worst that could happen? Your family goes hungry. You lose your house. Jobs are scarce. Keep the thought experiment going. What would you actually do?

I’m lucky to have a family support system (I realize many do not). My parents have provided us housing during a stretch of unemployment in the past. If we both lost our jobs tomorrow, both of our families would ensure that we and our children would not be homeless. If our home was paid off, we would only have to come up with $800/month to pay for our housing expenses (including utilities such as gas, electric, trash, and water), but since we’re talking about tomorrow, our mortgage would not be not paid off. We have savings, so we wouldn’t be destitute immediately. We also have a large amount of salmon in the freezer that could carry us until next dipnetting season (at which point, we would ensure we actually caught our household limit of 65 salmon which could feed us for 4 days a week all year!). Obviously, we’d cancel our cell phones ($75/month) and stop paying for travel. As I’ve said, we’ve been through this before (we only had one kid at the time). We’ve proven we can win the unemployment game. We would get to work. Since we were able to survive in nearly the exact same scenario (with way less savings and confidence!), I’m not that afraid of a job loss tomorrow (also, since we each bring in income, the chances of us losing ALL income overnight is very low… the power of income diversification!).

What are your biggest fears associated with a job loss tomorrow? How would you survive? Have you gone through the whole thought experiment?

What Next?

The difference between the “worst case scenario” job loss situation and the annual job resignation is that instead of asking “What if?” you’re forcing yourself to ask “What Next?”

If you had 5 days to spend in a hotel room alone, what would you choose to do? (Not going to lie… Catching up on sleep and binge-watching Britcoms would cover my first day, but that would get old quickly!) You couldn’t see the sights. You couldn’t leave the room. You could, however, bring tools with you (ie: computer, books, wood, paint, actual tools, etc.). How would you spend 5 days?

For me, this is a much more difficult thought experiment than the first one. My days would definitely involve some reading, writing, and researching. What exactly those days would look like is hard for me to pin down.

The point of this exercise is to identify your work passions. If your answers in this thought experiment have nothing in common with what you do for work, Guillebeau would argue it’s time to quit your job.ย 

What If and What Next in Finances

When you create a financial plan, both questions need to be asked. You shouldn’t cater entirely to your fears of What If? but you also shouldn’t ignore those real fears. (I’m sure our previous unemployment period has something to do with our desire to pay off the mortgage early!) And if your What Next is just retirement, it’s time to think about how you actually want to spend your days (even if you manage to reach financial independence!).

Based on the What Next? thought experiment, would you be resigning from your job tomorrow? How do you plan for both the What If and the What Next in your finances?


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  1. We are kind of living the what if? and What next? right now. =) Mr. Mt had originally tried to go part time with his job about 9 months before he quite, but they said no. Then we found out we were expecting a baby, and I knew it was time for a change. Today I am set to publish our “what’s next” post. I try to get these things out early, but today will be a late one. There will be edits and additions. “What’s Next” is proving to be a much harder question for us than “What if?”

  2. ChooseBetterLife

    Being trapped in a hotel room sounds like a nightmare! We stayed in a hotel for a few months when our house was being repaired, and it was okay… until the hotel treadmill broke. I need to move!
    But I also love to read. At home, I walk slowly on the treadmill while I read a good book. Can you help me figure out how to combine these in a lucrative career?

    • MaggieBanks

      ha ha ha! Like I said, I’m terrible at coming up with awesome business ideas based around passions. But I think there’s major potential here! ๐Ÿ™‚

  3. TJ

    In contrast to Julie, I think I’d be just fine in a hotel room. And up until a few months ago, I wouldn’t have even cared that there isn’t a kitchen because I basically never cooked. I guess you can bring a camping stove to the hotel room. ๐Ÿ˜€

    I tend to spend my free time goofing around on the internet, being physically active, and consuming various forms of entertainment. The realization that I can do all of these things anywhere. I don’t have to stay in a super expensive region just because that’where I’m from and it’s where my family lives. There’s a whole country where I can mostly have the same routines going on. And, to some extent, a whole world.

    And um yeah, I’m firmly quitting my job by the end of February. It’s getting closer!

    • MaggieBanks

      I was picturing a suite… so you could definitely cook. ๐Ÿ™‚ And I’m super excited to follow your awesome experiment next year!

  4. I think I’ve been living this experiment for about 4 months now! Surprisingly, my days fly by. I usually have some type of writing or blog-related project to work on and sometimes people even pay me to do these things!

    I’m fortunate to not have to worry about the money side of the equation since we’re in a good place financially. Regardless, I’m hoping to build this freelancing gig up to something pretty decent. I’ll be sharing my experiences along the way to let others know possible to do well without a traditional job.

    • MaggieBanks

      Your experiment is great! I suppose you could say I’ve been living this experiment my entire life as a stay at home mom.. except I still have a kid home with me, so there are definitely distractions… and I have a part-time job and a blog I spend the rest of the time doing. ๐Ÿ™‚

  5. Matt @ Optimize Your Life

    I just finished reading Born For This last night! I really like Chris Guillebeau. The concept of setting a quitting date each year seemed like a great way to avoid status quo bias and make sure you don’t get stuck in a rut out of habit.

    I would love to be trapped in a hotel room for 5 days right now! I have not been able to dedicate nearly as much time as I would like to sleeping, reading, writing, and podcast listening lately. I would love to have the unstructured time to get deep on subjects that interest me and explore my own thoughts on some issues.

    • MaggieBanks

      I LOVE Chris Guillebeau! I agree with you. I enjoy an occasional retreat to figure out where I’m at on things.

  6. I actually do think of this from time to time. I feel like we have a good plan in place to get us to FI, but what if I were to lose my job? That would be a game changer and I noticed I try to squash the notion any time it pops into my head, so I’m actually not really sure what I would do.


    As far as the hotel scenario goes, I would love it!! I feel like I could get so much stuff done – especially all the changes I want to do on my blog! So… how who do I talk to in order to get this scheduled? ๐Ÿ˜‰

    — Jim

    • MaggieBanks

      Oh Jim… I feel you. If I could get that scheduled for all of us, it would be great. Just think if the entire PF community took a 5 day hiatus to work on passion projects… we would all emerge to greatness! ๐Ÿ™‚

  7. Honestly financially I’m at the stage in life where it wouldn’t be a concern, 10 yrs ago it would have been a bigger deal. The problem for me would be the same as your second question if I lost my job suddenly. Now what. I’m financially secure enough to last a long time, but no where near where I want to be at retirement. I tend to be planned 6 steps ahead. So if something surprising like losing my job happened I’d really have to consider what next and I’d be stressed with actually deciding (move to new job, take a gap year, try to start a business, physically move and take a new job, etc. ). I’m really not sure. Having that feeling that I don’t have to plan for that eventuality in detail though is nice.

    • MaggieBanks

      Agreed. I like to get as far as: “We’d make it work” – but asking “what next” is tricky!

  8. Maggie, I like the concept, but it misses something. In my case (and many others), we may be within striking distance of the “FIRE Line” if we hang on for one more year. While we may not particularly enjoy what we’re doing, the longer term financial benefits (pension growth, in my case, lucky me!!) outweigh the short term costs.

    I realize that argument could just become a convenient excuse to NOT jump, but in many cases that may well be the best long term decision.

    Good food for thought, and an interesting concept. I think I’ll stick around for 18 more months, and then leave for good! 5th Wheel Dream is getting close enough I can almost taste it!!

    • MaggieBanks

      I agree with you Fritz. Always following your “passion” isn’t the right answer for everyone (clearly we don’t adhere strictly to this rule because Mr. T still has his job!). For now, we’re following your path, but if life gets too miserable at Mr. T’s work or if a passion project presents itself, we reserve the right to change paths! ๐Ÿ™‚

  9. I used to do a similar reassessment of my work happiness with each anniversary of my start date. If I wasn’t happy with how things were going, I’d give myself a couple months to fix it — or to leave. I think that’s a great personal policy to avoid getting stuck in work we don’t enjoy.

    The hotel room question is an interesting one that speaks to the usual “follow your passion” advice. I’m not quite sold on that one. Would I spend a bunch of my free time reading about [bland corporate thing I did for work]? Maybe a little bit — but like Fritz said above, it was interesting work that got me to my financial goals, even if it wasn’t my “life’s passion.”

    • MaggieBanks

      agreed. I think there’s definitely two paths people take – get in and get out or strive for “passion” throughout the journey and try to intertwine money in there with it. I don’t think there’s a “right” answer either way.

  10. That type of reassessment is what led me to quit my last job and find a new one – so far it’s been a great decision. ๐Ÿ™‚ With the last 2 yrs how they’ve been in my industry, I’ve played the what next game a lot. Mainly because another similar job would be near impossible to find. We wouldn’t be totally hosed, but I’d need to find about $3k/month to not dip into savings. Not too difficult, but I bet it would involve working a lot harder and longer than I do now to find that. I have my ideas and plans in place should the “what if” become a “what next”.

    5 days in a hotel room sounds fabulous! I’d bring a banjo, my dobro, a computer, and a drawing pad and pencils. Beyond sleeping the first day, I’d just have fun playing music and practicing drawing. Maybe I’d write some too, but that’s about it. ๐Ÿ™‚

  11. This is a timely post, because I just found out unexpectedly this Monday that it is my last week of work! I was hired on at my new job this summer, and it had a little-known cap on the amount of hours I can work. Well, just found out that that limit will be reached on 12/5.

    I’m not worried, however. I’ve got more than enough freelance work waiting for me and I can essentially step off full-time the next day into freelance/blog work until I’m able to get another position back. Hopefully this will be soon, since they’re opening a new, more permanent position up any day now and I plan on applying, but even then it’ll be s-l-o-w because I work for the fed gov’t. And, with Trump coming into office and talking about a hiring freeze, I’m not even sure I’ll be processed through in time even if I do get the job.

    Interesting time. I’ve never been more grateful for my fallbacks though!

    • MaggieBanks

      You’ve set yourself up nicely! Sorry about the unexpected twist of events, but good look on moving forward!

  12. I really and truly hope that if I ever feel like I need to quit my job, I will. I think it’s true for many professions, and I can’t help but feel it is especially important for teachers who feel burned out to leave. It’s a constant worry. I love what I do, and I always want to give my all.

    • MaggieBanks

      agreed. And with teaching, it’s even more dire. It’s like a doctor hating his work and still doing. You don’t want that doctor! ๐Ÿ™‚ Mr. T’s answer to the question is probably 85% “time to quit” but he hasn’t been able to answer the “what next” question for himself, so for now, he’s sticking it out (at least until it gets uncomfortable!)

  13. Unemployment tomorrow would simultaneously piss me off (BUT MY SAVINGS GOALS AND PLANS), worry me a bit (not saving? What is life?), tickle me a bit (I’m totally leaving JB in daycare for another month and sleeping during the day for at least four days. I’d have to anyway, they require a month or two notice to pull a kid). I have unreasonable cash savings because I was unemployed for nearly a year during the recession and because I too completely suck at launching big ideas, I was job hunting the entire time.

    I’m always evaluating our expenses to cut them further but I’m not convinced I have an easy bare bones plan ready anymore. For example a major cost is daycare and an obvious one to cut except if i wanted to take this as an opportunity to build something, I couldn’t do that while also chasing a toddler 40-50 hours a week. I work primarily on the internet and that’s where I’d ideally continue working so cutting that isn’t happening. It would fall to discretionary expenses like food and charity because I already don’t shop for clothes, shoes, accessories etc.

    In a weird way, I pursued my passion as my career and I can’t say I recommend it. The money did come eventually but mainly because I pushed and advocated for myself and kicked major butt for ten years. If I had picked a profession where I cared a bit less about the work but it paid much more, I suspect I’d have come out ahead on the total money plus happiness calculation. Mine isn’t true passion work like Penny’s but it’s related to a thing I care about.

    I’ve been giving myself arbitrary deadlines to leave my job and do something I care about but working 14 hour days has me a bit deflated and perhaps a bit sour on the idea of working for myself. I’m tired and I don’t even own the company. Then again, at least I’m not doing our marketing. I hate marketing.

    Huh. I need to stop talking at you. This has turned into a post of its own.

    • MaggieBanks

      I love this post! I like your perspective on working on a passion that has turned sourish. I think it’s possible to have happen, but I also think it’s rare. People (like Guillebeau) that have figured it out think it’s SO EASY because they’ve done it, why can’t we? Also… I hate marketing too. I’m a terrible salesman. You don’t want it? You hate it? Oh, um. Have a good day?

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