Quit Your Job: How to Know When it’s Time

Quit Your Job How to Know When it's Time - picture of man running with files under one arm looking at watch

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If you’ve been working steadily at both a 9-5 and a side hustle, you’re probably beginning to fantasize about the day you can quit your job.  And if your day job is soul-sucking, like mine was, you’re probably ready to throw in the towel.  I certainly was.

Now, don’t get me wrong.  I actually loved my old job, enjoyed it, and thrived there.  However, I was working full-time AND writing 20-30 hours per week.  I was a workaholic who stressed out all day and cried all night.  I was burnt out, freaking out, and completely overwhelmed.  So, one day I called up my employers, made a visit to their house, and put in my two weeks notice on the spot.

Well, that’s not exactly how it happened.  There was actually a whole lot of thought and planning that transpired ahead of time.  And, to be truthful, it was really difficult to know when to finally pull the plug.  Honestly, it was really scary.  So, how did I decide that it was finally time to quit?  Here’s how:

Replace Your Income

Once I consistently replaced the income from my day job with writing jobs and side hustles, I started feeling more secure about making the leap into self-employment.  But, things were still a little tricky.  Freelance writing jobs and blog income can be somewhat unpredictable, and I didn’t want to quit my job on a whim.  At a certain point, I had enough consistent writing jobs that my guaranteed income replaced the money I was making at my 9-5. If you want to know how to start a blog and get freelance writing jobs, follow the links at the end of this post!

Fund Your Emergency Fund

Before you quit your job, it’s important to have a fully-funded emergency fund.  For me, that was fairly simple to accomplish; my husband works, and we generally live on about half of our income.  Our emergency fund fluctuates, but I tend to keep it a little on the hefty side since we own three houses.  Each person’s situation is different, and we all have to determine our own comfort level.  What you save is up to you.  Just make sure that it’s enough.

Have a Plan B

If you’re the main breadwinner in your household, it’s important to have a Plan B. After all, what if your freelance career doesn’t end up working out?  Or, what if you find that you seriously hate being self-employed?  Unfortunately, you’re not psychic and you may not find out until after the fact.  As we all know, the grass isn’t always greener, and sometimes things can turn out differently than you think they will.  So ask yourself, “If it doesn’t work out, what will you do?”

Most freelancers dream of the day they can quit their job.  However, it usually takes a lot of hard work, some serious savings, and some patience.  I quit my 9-5 job in April 2013 and haven’t looked back.  And I hope that I’ll never have to.

For more thoughts on work and life, check out these sweet posts!


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  1. For me it would be a last resort, I’d have to be pushed into it. I love my job and enjoy the security, and I’m really blessed to be able to write about interesting stuff all day! If I freelanced fulltime I know I would be a lot more stressed and I’d have to write about some stuff that didn’t interest me to some degree (money is money) … lord knows I’ve written about some deathly dull stuff for clients as well as fun stuff and educational stuff.

    1. Haha!

      Yeah, I write all kinds of boring things. To me, it’s still better than my 9-5.

  2. I have a lot of benefits including company car, paid cell and internet. I get to keep all my travel rewards when I travel for work. My perks equal to almost 50% of my compensation which I factor in.

    1. Nice. That’s pretty sweet. We got some free travel at work as well until the last year we were there. It was certainly a nice perk.

  3. Working on it now! I think having savings is really the biggest part of the whole thing, as well as having an actual plan. But you can’t jump out of your job if you are going to need immediate income or be out on the street. You need a cushion to get you through the transition period and allow yourself to make mistakes, which everyone will make.

    1. Yep, exactly. Being a 2-income family helps as well since you have another money source to count on.

  4. Justin @ Decisive Dollar says:

    I echo Matt’s position, above. It’s a work in-progress for me but in the very early stages. I agree that planning will make or break when and whether or not it’s possible.

    I’m curious as to whether or not most folks who make the transition actually wait until they are able to replace their current income from their day job. Also, it’s important to consider one’s “loaded salary” at their employed job, which includes any benefits, health insurance, disability, 401K match, stock discounts, stock options, discounts, travel points, phone plans, etc. like Charles mentioned as well.

    I guess it’s a very personal choice in deciding when is the right time to make the jump!

    1. I didn’t make a lot at my old job, about 36K, so it was fairly easy to replace my income. But, I wanted to also replace some of my perks like my 401K match and cell phone. So, when I left my job, I wanted to make 4K per month to add a little buffer.

  5. I’ve definitely thought about leaving my job to run a small business. I think the biggest thing is replacing your income. Actually, having an emergency fund is pretty huge too. Even if I created a second full-time income, I’m pretty sure I would keep working indefinitely until my finances were rock solid and the small biz I planned on working full-time was what I wanted to do long-term.

    1. I probably would’ve done both too if we didn’t have kids. When you have kids, you just have so much less time to do anything.

  6. Freelance, no, but consultant, yes. One of the big hurdles for us is eliminating some of our monthly expenses, like our mortgage. Once that’s off the books it will make our income needs drastically lower!

  7. I have a post coming up that talks about this same topic. The key is that you need to have a plan. Without a plan, your odds for success are limited only because you will spend a lot of your time trying to figure things out instead of actually earning an income.

  8. As Matt said – working on it now! Ideally, I’d love to manage my day job and my side hustles for as long as possible and stuff all my extra income from freelance work into investments. We already save 40% of our income from our 9-to-5 jobs, so my plan is to boost that savings rate via side hustles for as long as possible before I make the switch. I think rapidly increasing our net worth, along with a good emergency fund, will make me feel more secure if/when I do get to become self-employed.

    1. Yep! That’s how you get there. I just got to the point where I couldn’t do it all anymore.

  9. Good post Holly! My wife wrote on this, well in regards to me quitting, several months ago and I could not agree more Holly. I had thought about it for years and allowed fear/uncertainty to hold me back. Having a solid EF was huge and having a plan is nearly as vital. No job is worth being absolutely miserable in, life is just way too short. If freelancing isn’t for you, then by all means look for something else. 🙂

  10. Wow, it’s almost been a year! I think it’s good to point out that you don’t have to hate what you do to want to change it. 9-5 with two week’s vacation doesn’t allow for much other than come home, rush around, and go to bed. It’s really hard to fit side hustles in there without something breaking. I also used to love/hate hoping for a government holiday so I could have an extra day off so you don’t have to spend your weekend cleaning and doing housework. I’m so happy for you and how your time is your own now.

    1. I agree. A regular 9-5 job doesn’t leave time for a “real life,” even if you have ample vacation time. When I worked full-time, and sometimes 50 hours or more, I barely had time to do laundry or run errands. It basically sucked.

  11. Definitely working on it… We need to get out of debt first though (hubby still has $43K in student loans to pay off).

  12. I’ve been dreaming about either my wife and me quitting our job. It’s getting tough getting up early dropping off the baby to my parents (where I get discounted daycare) and picking him up after work…most of the day is gone. Not only are we tired, but we don’t get to spend as much quality time with him. However, my job has great benefits and a pension. Obviously if we could get to a point where we could replace one of our incomes, it would work for us.

    1. Yep, that’s exactly where we were in our lives. Having one spouse work from home helps so much. My kids still go to daycare but I’m able to do housework and run errands during the day so that all of our free time is “ours.”

  13. I’ve given it some thought, and I will be embarking on a side business this year. But I like the reliability of the paycheck too much to completely step away at this point. The ceiling on income is limited, but I sure like having a floor to stand on. You know?

    1. I hear ya. It helps to have a spouse with a reliable income. I would hate it if we were both freelancers!

  14. I enjoyed this post as I am coming up on my one year anniversary. It is important to have some plan in place even though reality will be very different.

    Btw I love the pic. Started singing that song (in my head) when I saw it!

    1. Ha! Yeah, haven’t heard that one in a while! =)

  15. I am actually not working on it. I really enjoy my current job. It allows me to think outside the box each day and grow my knowledge. I have also been self-employed and that was just not that great for me. I worked more and barely saw my family. That is not what I want right now.

    1. I hear ya. There are definitely pros and cons, Grayson! Do what’s right for you!

  16. Jennifer @ Budgeting in Baby says:

    I would love to quit my day job and work as a freelancer one day, however, I need to finish my bachelor’s degree (part of my back up plan). Between my two part time jobs, school, and taking care of Emmett there just isn’t enough time in the day to devote to becoming a freelancer yet. I could give up sleep however, then I would be sick all the time and not able to accomplish anything so that wouldn’t be any good.
    One day it would be nice to be a freelancer. So I will plan for the one day while I continue to work on my goals.

  17. I guess I’m not the norm. I quit before my business was making any money. I figured that if I was going to do it, I might as well go all in. It forced me to work harder since I didn’t have a back up plan. I love working for myself and could never go back to a 9-5 job.

  18. Thanks for the advice and inspiration. We’re attempting this same transition now. Although we feel like this is the right move for us, it’s still scary. Overall, though, we’re happier and excited about the future. For us, it’s about attaining the quality of life that we want and that doesn’t include working for someone else.

  19. This is great advice Holly! I also tell people who want to make a career shift to potentially earning less or at least initially, to live as though they are making less until they make that choice. While living for less, the money saved will help build their emergency fund. If they can’t live for less, then they know they can’t leave their current job.

  20. Great post! I am so happy that I left my job. Like you, I was extremely stressed out because I was working so much.

  21. I’d always planned to go back into private practice but it happened a bit sooner than I expected. I was fortunate that we a fully funded emergency fun and my husband’s income so I could take advantage of a great opportunity. There are always pros and cons to both sides, but I figure as long you are in financial position to try self-employment, you’ll learn fairly quickly where you belong. 🙂 I’m glad freelancing is working out so well for you!

  22. I think I was living your life for sure. I was so freaking exhausted blogging/writing 25 hours a week in addition to my day job. I was up so late every night, and it was just nuts. I’m so, so happy to be self employed now. It’s a little scary but so much better for my sanity!

  23. I completely agree with everything you said. Preparation is SO key! I was totally thrown into the fire as I started off my freelance career by being laid off…so it was not planned at all. It was trial by fire and I got burned…A LOT! But if I can survive that and live in an expensive city doing it, anyone can!

  24. While I haven’t done this, I can appreciate that you’re advocating thinking it through and really being prepared. There are plenty of success stories of people who put themselves in a position to do this and never looked back. I suspect those people were truly prepared, or at least most of them.

  25. Picking up some extra money by freelancing is something I’ve been thinking about giving a shot for a while. I’ll have to check out those posts and actually get started 🙂

  26. I may be a minority here, but I don’t fantasize about quitting my job to pursue my side hustles. I dream of switching my careers entirely. I really love my freelance gigs and my blog is a wonderful creative outlet — but I’m looking more long term and figuring out how to switch from my current day job into a completely different field. Either way, the two weeks notice will be a sweet, sweet moment.

  27. I think it’s inspiring to see people go after their dreams and go for it, even if it is risky. I can only imagine how scary it must feel to leave a stable 9-5 job behind but it seems like things are working out well for you!

  28. I can’t wait to leave my job-after I fully fund my emergency fund, pay down debt, and learn how to budget like a money ninja.

  29. I would say replacing your income for a long period of time so you can gauge sustainability is important. I’m not a job quitter, because I really enjoy the double incomes and I am suspicious of my online income (the internet is a bit too volatile for me and I can be a bit risk adverse when it comes to my livelihood), but I understand when some people need to.

  30. Being honest here, I totally don’t get how you can make much being a freelancer?? Most gigs seem to pay $25-$50 an article, I’d have to write all day and night to make any money! I put a lot of time and research into my writing and I think I’d be making $5.50 an hour, lol. What am I missing? How do you find jobs that pay anything? Very impressed that you make it work Holly!

  31. Tara @ Streets Ahead Living says:

    I do actually prefer the structure and paycheck security of an office environment but I know that’s not common. I do get frustrated when I face roadblocks from less enthusiastic coworkers who won’t do things “because it’s not in their job description” but I know that’s more of an issue with my current job as opposed to all jobs in field.

    People leave jobs generally because the job sucks to some degree, so if you’re filling an empty space that someone left, there’s probably a good reason why that previous employee left the job and you soon find out…lol. I wish my current job had a bit more structure but then the loosey-goosey atmosphere does make it easy on days I’m unmotivated.

    After three jobs in 3.5 years (I quit after getting job offer and try to leave on good terms), I’ve learned that they all kind of suck but they all have their perks to some degree. And since I do better in jobs with structure, I don’t foresee any freelance career in my future.

  32. It’s always crazy to me that people will quit a job without really having anything mapped out, or even a plan B in case what they’ve planned on happening doesn’t quite work. I look forward to being able to walk away from the 9-5 one day, but I need to have a lot more saved and a lot more generated from my side hustles.

  33. I actually decided to go full time freelancing after giving birth to my 3rd kid. I just can’t leave all three of them with someone taking care of them. It is still different when I am the one who looks after them. Anyway, my husband works for a company so we are still secured.

  34. I would love to get there one day, Holly.. But I need a lot of my big plans to work out perfectly to ever get there. My need for security is far too high to ever make the jump without some serious understanding that I had all my bases covered.

  35. I was basically pushed into it with losing my job and it’s taking me a while to catch up to the reality of the situation. Luckily I had paid off debt and built up a little emergency fund so it wasn’t super frightening. I still haven’t fully replaced my old income but I know that I will eventually. It will just take some more work! 🙂

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