My Staged Plan For Unemployment

Six weeks and counting until I leave my job. Time flies by quick.

I’m waist-deep prepping for work deadlines that wrap up right before I leave so I’m in adrenaline rushed, get ‘er done mode. Even though the burnout part of my brain is ready to check out, I’m doing pretty well at making sure all the big things go smoothly. I want to make sure my teams are in a good place by the time I depart. I haven’t told most of my colleagues I’m leaving yet. We’re all in a crunch so I’m waiting to announce until things slow down around mid-May.

There was a period that I considered contracting for my company part-time. With Fiancé’s new job, I’d be able to make enough for us to live on pretty readily. I’d still be open to the possibility if it works out, and management seems to be on board, but the bureaucracy doesn’t seem to be able to get it together in time for us to have a contract in place by the time I leave. And I refuse to stick around in limbo all summer hoping that changes.

So I’m now outlining the plan assuming I won’t be contracting and I won’t find a new job before I leave. Originally I drew it up still relying on a separate finances model. (Honestly, I’ve been putting off combining my finances with fiancé because of my upcoming unemployment. I really hate the idea that right when we merge our financial lives, I’m no longer contributing to the family pot. He’s been very supportive about everything– pointing out that I’ve contributed the lion’s share while he’s been unemployed before and that I’ll probably be back to work again soon. Still, it feels weird and vulnerable and while I like that we can rely on each other, it’s very scary to loosen my grip and feel less in control.) But I’m coming around to basing things off our proposed joint budget.

Introducing a staged approach

Because this period of unemployment is going to include my first real summer in the six years since I graduated college, I really want to make the most of the time to decompress. But in order to make that happen, I want to set boundaries so that I feel free to really enjoy this time and not rush myself into hasty decisions going into my next job.

According to my monthly net worth projections (based on my monthly tracking), I’ve done pretty well enough adding to our cash position that even if I stuff most of my upcoming paychecks into my Mega Backdoor Roth 401k, we’ll be sitting on more cash than we would typically want or need in our emergency fund. How freaked out I plan to be will be based off of where we are in terms of that cash position: well above normal emergency fund, getting close, at or below, or in the red.

Here’s my unemployment in four potential stages:

Stage 1 – Guilt-free decompression

  • Primary goal: relax.
  • Spend money as I would normally.
  • Put together revised resume and LinkedIn. Otherwise, no obligation to search for jobs.
  • Only accept job offers from companies that align with my values as well as my professional and personal goals. No accepting low-balls or any position I don’t feel 95%+ about.
  • Duration: until 1/3 of “excess” cash position is spent, approximately two months (June 2018 – July 2018)

Stage 2 – Strategic workforce re-entry

  • Primary goal: get a good job.
  • Spend money according to joint budget.
  • Apply for jobs in product management. Use variety of avenues — recruiters, LinkedIn/Glassdoor/Indeed/AngelCo, Meetups, alumni networks, personal network
  • Accept job offers that align with professional and personal goals.
  • Duration: until remaining “excess” cash position is spent, approximately four months (August 2018 – November 2018)

Stage 3 – Aggressive workforce re-entry

  • Primary goal: get a job.
  • Spend money according to joint budget but cut personal allowances.
  • Apply for multiple types of tech or tech-adjacent roles- product management, software engineer, data analyst, QA, technical writing. Continue using variety of avenues. Use side hustles to supplement income while waiting for full-time work.
  • Accept job offers which meet minimum salary requirements, that I could deal working at for 1-2 years.
  • Duration: until half of emergency fund is spent, approximately nine months (December 2018 – August 2019)

Stage 4 – Drastic times call for drastic measures

  • Primary goal: stay afloat.
  • Revise joint budget and cut personal allowances.
  • Apply for work within and outside tech. Continue using a variety of avenues. Get in touch with temp agencies. Beg for my old job back? Use side hustles to supplement income while waiting for full-time work. Consider renting out second bedroom to roommate or on AirBnB. Investigate strategies for tax-effectively liquidating assets as needed (brokerage > half retirement > home > rest retirement).
  • Accept any non-illegal job that’ll keep household afloat.
  • Duration: ???

I refuse to write out a stage 5 plan. I’ll worry about it if we get there. Here’s hoping I stay in stages 1 and 2!

What would you do if you left your job? Would you start finding a new job immediately? At what point and by how much would you lower your standards during unemployment? What would you cut first?


8 thoughts on “My Staged Plan For Unemployment

  1. I have several thoughts on leaving a job. I am 58 years old, and have been in jobs that made me absolutely sick. I think I should have left one job, in particular, two years before I was forced to because of budget cuts. My boss was vile. It was also smack dab in the middle of the Recession, and I just about lost everything (house), due to pay cuts two years previously to the complete budget cut. If you are that unhappy in your job, then leave. No job is worth your health. I will say, four months later, I got a similar job with similar pay a couple of hours away from my old job, and I love this job. I also got another house. While losing that job caused me huge financial problems, I am overcoming them. The best case would be for you to have a job lined up to start a few weeks after this one ends. However, I also do understand your wanting your summer off, while you are young, and before kids/weddings etc. arrive. My thoughts are, you are only young once. Enjoy your summer, if you can financially swing it. Line up free lance work if you can. I also have another line of thought. I left a job in my late 20’s, that I wish I had never left. However, at the time it seemed like the right thing to do. You never know until you do it, if it is the right decision or not. There are so many variables that come into play such as health, family’s health, the economy, etc. Sometimes you just have to step off the cliff and go. Sometimes you need to stay on the cliff and hold on. It is hard to know what the right decision will be, and only time will tell. Best of luck to you, no matter what you decide. Life is an adventure.


    1. That’s true you can never know the future. I’d like to think I won’t regret losing this job. Even if I feel trepidation at times, I think leaving this job behind will ultimately be good. Worst case scenario I could freelance in this line of work and make pretty good money after my non-compete runs out in two years if that’s the direction I want to go (which I don’t, but it’s an option). Like you said, life is an adventure. I’m ready to start questing.


  2. I really like how structured you plan is. If I left a job without one lined up and wanted to take my time, I’d need something similar, otherwise I’d probably feel to anxious about it when there was likely no need to be. This is great.

    I most likely would only leave my job with another one lined up. I did take a structured approach for my job search when we were moving, and only applied to a handful of jobs that I really wanted (literally 3 jobs I think) before considering broadening the net. I did manage to arrange 3-4 weeks off in between due to the nature of the new job, which was great.

    I don’t know. We’d probably cut simple things because I’d have more time to pay attention to food budgets and I’d probably skip splurges/upgrades/big irregular purchases. We wouldn’t have to cut into savings unless we were both unemployed though.


    1. Thank you! I really like having structured plans, even I only kind of sort of follow them half the time.

      I’ve not gone through the exercise of seeing what it would take to live on Fiance’s salary alone. Like, I think we could do it, but if we kept the big stuff (condo, his car) it’d require to cut everything but the absolute essentials.


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