Making The Decision To Leave

I’ve hinted in some other posts that I’m not feeling entirely fulfilled at my current job. But it wasn’t until this week that I decided it was time to move on.

The decision was a hard one to make. I’ve been at my employer for over five years. This was my first job out of college and the only offer I received at the time and since. I worry that once I quit this job, I won’t be able to find another. That, as has happened time and time again, I’ll put myself out there to be judged by hiring committees only to be rejected again and again and again. And with fiancé unemployed as well, the stakes feel even higher.

I don’t have an offer yet, but the reality is I can’t stay here. Staying means I only half-heartedly look for other positions. Staying means I keep coming home day after day feeling depressed, despondent, and useless. This Reddit thread comes as close to mirroring my feelings without actually being me. As much as my FI plans mean to me, and as much as quitting will put those plans on ice, I can’t use delayed satisfaction as an excuse to keep wishing years of my life away.

So, here’s the plan: annual bonuses in my company get distributed mid-March. After those are sent out, I will inform my manager of my intention to leave the company. I will stay at my company until June 1st unless I get another offer before then. That gives me four months to job search and squirrel away some cash. In the “worst case” scenario, I take the summer off in the city, which is the best time to be idle around these parts.

Over the next couple weeks, I’ll go into the financial preparations I’ll be taking for this potential self-funded sabbatical. Also, you’ll get to see me try to spin up some side hustles that will (hopefully) help tide me over should I remain unemployed for a while.

In any case, wish me luck.

Have you left a job without an offer lined up? Am I foolish to quit a stable, well-paid position? 


16 thoughts on “Making The Decision To Leave

  1. I think the math for not getting another job first is undeniable. The idea that you cant make a serious job hunt while employed is not supported by the millions who have done just that. Living an intentional life means you don’t run away from things you don’t like but you run toward what you love. I’d stay put while you look for that love. You are more attractive to that dream job employer if you are employed and you will appear more confident and less stressed in inteviews because you will not be money stressed.


  2. You aren’t foolish if you can afford to self-fund a sabbatical and it is worth it to you. It is a personal choice.

    I’ve never left a job without something else lined up, and I generally don’t think I would unless the situation was very dire. I’m pretty risk adverse and anxious and panicky, so it would be really really hard to make that leap – even though we are now in a financial position that it would be fine.


    1. I’m super risk averse too, which is partly why I’ve stayed as long as I have. Hopefully it all works out without a gap in employment, but it’s good to know I’ll survive even if it doesn’t.


  3. While I think it’s demonstrably easier to get a job when you already have one, senseless though that may be, if you can afford to job hunt full time instead of being miserable and barely motivated to do anything but exist, there’s value in that as well.

    I’ve left jobs, one by choice and the other not, without having a job lined up. It took a long time to find another one and it was incredibly stressful but that was at least half due to the fact that there was a recession on at the time. Before that, I had very little relevant experience in the industry and I was searching in an area where the type of job I wanted was scarce. It still worked out in the end.


    1. Yeah, I’m worried about it being tough if I’m not currently working. Luckily I seem to be getting a lot of recruiting calls, at least this past week, so I *think* I’ll be able to find something else before June.

      Good for you managing to switch industries during a recession! Further evidence of how epically boss you are. 🙂


  4. My husband left a job without having a new one lined up, but we were prepared for that and I was still working. It took a few months to get another job, though he likes the one he got which is really the only one he sent in an application for (step 1 was tapping his networks). #2 on our blog left a job and it took about a year to find another; most recently she found a new job (after a few months of searching) without having left the job she was working.

    Networking is really important.


    1. Supportive, working partner is key. Hopefully my fiance will be able to find a job before I quit. That’ll help assuage a lot of the anxiety.

      Good to note on networking. I am… pretty bad that. But necessity has a way of forcing us into these things.


      1. Networking for DH meant reaching out to people who had worked with him in the past (including at school) and letting them know he was available. #2 on the blog has a little more of a bizarre networking story for her last job. Her most recent story is more typical– basically do good work and talk to people and when they let you know they have an opportunity available, jump on it.


  5. Not sure my original comment went through, so posting again:
    Well, I’ve quit without something lined up twice–once because I started getting depressed at my job, and then again when I moved to NYC. Both times it took about 3 months to find a new full-time gig. To me, staying in a crap job wasn’t worth the stress. I’ve always been risk happy, and I have skills that can transfer to lots of industries. Plus, I was single with low expenses and money saved up. But I’m not going to lie–the first month of unemployment feels great, and then by the third you start to panic.

    In your case, it’s definitely more complicated that your fiance is unemployed as well. I would think about what it is about your job you dislike (is it the industry, the job itself, the people?), and what’s most important to you in a job. Finding a job in the same industry will of course be much easier than finding one in an entirely new one. Also, sometimes just changing companies does wonders. I work in advertising and my last job I hated, but the new company is like night and day in terms of culture and work-life balance.

    The other thing you could do is maybe do a backpacking trip, and sublet your apartment. It would probably cost less than living in the city. Then you can explain that easily to a potential employer.

    Also, ALWAYS take those recruiter calls!


    1. Great and thorough advice, thank you!

      I think if I end up unemployed for long enough, I’ll file for an LLC, code up some side projects, and call my respite “consulting.” There is also a lot of demand for start up developers/analysts in my area, so in a real pinch I could take a demotion. Obviously not the ideal outcome, but if I start to panic there will be off-ramps, I think.


  6. Agree with many of the others – I haven’t done it before although husband has with my support (and it was much harder and turned out to take much longer than expected).

    But if you can swing it financially and it really is taking a mental toll, then it’s certainly a viable choice.


    1. Fiancé is also doing the same thing and it’s taking longer than he expected to find another position. I’m hoping being in tech will help insulate me from a really long bout of unemployment, but we’ll see.


  7. Well it makes watching how it works out for you interesting, so will check back.

    1. We are Not in a recession
    2. You have 6 month emergency fund.
    3. You have a strong skill set

    1. Your fiance doesn’t yet have income from employment
    2. May put a kink in your FI forecast.
    3. Now that you gave notice to employer, possibly of being let go before you plan, if they get a good hire.
    4. Maybe very stressful being unemployed, looking for employment.
    5. May take a long time finding employment.

    You might luck out. Fingers crossed.

    Been there, done that. Was in IT, Took a long time to find a job, too stressful and never put myself thru that again. It was also my first job out of school. Had been there 4 years. After that experience I always lined up a job before quitting. In the end I did obtain FI and retired early. So good luck.


    1. Thanks for the well wishes. I’m feeling pretty good going into the break. Since this post, fiance has found a job and, even without his income, I should have enough cash savings by the time I leave to last 12-18 months. I’m also in the lucky scenario where my employer wants to contract my services, which is good for them to maintain continuity on projects and good for me to take a break from the politics of w2-hood. I’ll have further posts on the numbers and major events as they hit, so feel free to follow along.


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