healthcare after quitting job

Journal: First Try on J2 – Jobman#8738

The following is a guest post from Guild member jobman#8738 with some light edits. Check out more on this story on #oe-journals and #2x-fail-stories on the Discord.

The Night Before

My feelings about finally starting J2 have been fluctuating like crazy. I originally signed my offer for J2 months ago, but for personal reasons my start date wasn’t until now. I’ve been getting more and more excited for weeks. All the talk and the success stories on the Overemployed Discord are getting me really pumped. About a week ago I suddenly started feeling a wave of nerves. I know that it’s just nerves and I’ll absolutely be able to handle this. But I just want to get started and get into my routine. Tonight, with J2 finally starting tomorrow, my nerves are starting to clear. I’m just excited for what’s to come. Still a little nervous, but not any more than any other time I’ve started a new job. Looking forward to getting started.

On another note, I’ve got my home office all set up. The company laptop arrived the other day. I’ve got my KVM, USB switch, and everything else all ready to go.

Day 1

I’m currently on paid leave at J1, so I have a couple of weeks to get into a flow with my new J2. My first day was really chill and I’m more optimistic than ever that this is going to work out. 

First of all, I can now see my company and team’s calendars and the meeting schedule is really light. I have some orientations in the first few weeks, but once those taper off, my calendar will be very open. I even glanced at the calendars of some of the other engineers who have been on the team for a while and their calendars are mostly clear as well. And the best news: none of the meetings overlap with regularly scheduled meetings at J1! Seems like the companies have different preferences about times to meet, so I’ll easily be able to block off my calendar and avoid overlaps almost all the time. One of the senior engineers on the team seems really against meetings. I think I’ll get along with her 😂.

Secondly (and relatedly) there seems to be a lot of autonomy. I had a couple of onboarding sessions today, but not that much. Still, I only spent about 5 minutes talking to my manager and maybe 15 minutes talking to my “onboarding buddy.” I’m hoping it stays like this.

Day 2

I reconfigured my webcam, headset, keyboard, and mouse setup. The way I was before, everything had to move and be active on the same computer together, which wasn’t what I wanted. I want to be able to keep my headset and webcam connected to a meeting while switching the keyboard and mouse to work on something for the other job at the same time. I tested the new setup and it’s much better. 

I also have my first Jira ticket assigned to me. I think I’ll be able to knock it out pretty quick, but I don’t think anybody is expecting that of me. Will probably take my time with the dev environment set up before even really looking at the ticket.

Week 2

Haven’t been keeping up with this journal, but not a whole lot has happened. Just getting into the swing of things. Knocked out the first Jira ticket in a timeframe that was deemed “impressive” despite taking my sweet time with it. Now I have another one to work on. We’ll see how that one goes. But I feel like I’m picking it up pretty quickly and looking forward to getting back to my J1 after this leave and really getting going with this 2x thing.

On another note, early this morning I got my first 2x paycheck, complete with a $20k sign-on bonus from J2. That was $22k appearing all at once in my bank account. And that’s after-tax withholding and benefit deductions like 401(k), insurance, and ESPP. I know the bonus was a one-time thing, but even without that, a regular 10k combined deposit twice a month is going to feel really nice. I can definitely get used to this!

Tragedy Of A Bad On-Call Culture – Goodbye J2

A few weeks in, and I’m inserted into J2’s on-call rotation (for non-software engineers, this is exactly what it sounds like, being on-call in case things break, much like an ER doctor).

Ugh, J2 seems to have really bad pager hygiene. I just came on call for the first time (on the weekend, no less) and already appear to have four snoozed pages from other people on the team while they were on call and scheduled to re-trigger in the middle of the night or early in the morning.

I don’t mind having pager duty, but if people can’t be bothered to fix the alerts when they happen, that bothers me. You can’t keep passing the hot potatoes onto someone else. But what’s really dumb, and bothers me a lot, is how pager alerts are triggered – like getting woken up on every little exception or issue.

Perhaps I’m being a little harsh and comparing unfairly as my J1 does such a great job at paging/alerting on the right issues and not on the wrong issues. My hang-up is the paging noise from J2, getting bothered on the weekends and off-time unnecessarily. There’s a real cost to that. Too bad, I’m going to drop J2.

A Close Call On Healthcare After Quitting Job #2

Ok yikes, I’m afraid I messed up pretty bad on healthcare.

For 2021 I enrolled in insurance through J1. But J2 has better insurance so I switched to that during open enrollment for 2022. But now I’m quitting J2 and my last day is tomorrow. I’d really want to enroll in J1 insurance again for 2022 but I’m afraid I can’t. Since I never actually had insurance with J2, I don’t think quitting the job counts as a loss of coverage for a qualifying life event (QLE). Also for the same reason, I think I can’t get COBRA. I asked the Discord hivemind for advice and the consensus is to jump onto another J2 as quickly as possible – easy day. So I hit the interview circuit again…

But then, I got lucky. My health insurance issue actually resolved itself. I had enrolled in dental insurance at my old J2 for 2021. It’d appear losing that counts as a QLE so I’m able to enroll in J1’s health insurance once again.

Cautionary note from Isaac: When Overemployed, it’s better to not overoptimize health insurance. Get double insurance if you need to until you hit your stride, recognizing which job is the cash cow and which is the burner(s).


  1. Shocking they put in you in the rotation that quickly. We usually wait a couple of months at least for new folks to get their sea legs before putting them in the rotation.

  2. I know in US pager/Oncall doesn’t pay extra. I’m Canada companies can’t do that. We get paid minimum 3-hour minimum for every call, usually it’s a small issue that gets resolved in minutes. Team members in US did not get extra money for Oncall. I’m not sure if it is everywhere or in some state. US team members are in PA.

  3. Love these honest stories that capture the ups and downs. I’m thinking of taking the leap to get J2 but I also have a little one on the way and think it’s gonna be overkill. I’m definitely type A and obsess over details and want to over deliver. Any tips?

    1. Nothing like double parental leave! But only if your state does not do any parental leave entitlements or pay associated with them — not my area of expertise but you’ll have to research a bit.

      It also depends on when your little one is arriving, since some companies have minimum time employed for paid parental leave. IMO, you get parental leave once, twice, or three times in a lifetime so might as well max it legally if you can pull it off. But you’ve to weigh that against the stress and family priorities.

  4. I’m going to guess he’s Type A, like a lot of us, and he said it’s his first J2. Blowing off pager duty doesn’t feel good at first, so probably felt easier to come up with a reason to leave then to feel unreliable or under-par.

    1. Yeah, true. A year of double paychecks helped me get over that, too. I’ll be your dirtbag, baby!

  5. I’m a little taken aback by how quickly the author dropped J2. Would be interested to hear more about that. Why not push back on pager culture to get it fixed? Alternatively, why not play along and push the snow down the road like everyone else? Or just blow pager duty off completely until someone calls you out? Feels like a missed opportunity. Did you have to pay the signing bonus back? I figure every day I hang on to that extra job is $400 in the bank.

    This has the makings of a good stand-alone topic, too: “how long to slow-play the job before you drop it,” or, “when do you HAVE to quit?” (i.e., you don’t want to get fired, but does it matter if they put you on a performance improvement program / probation / warning / timeout chair / take your allowance?)

    Great cautionary tale on the health insurance, though. Ideal situation for the 2x’er is to have a working spouse and stay on their benefits. If the 2x’er carries the benefits and loses the job with benefits, they _could_ open a life event at the non-benefit job by claiming their spouse lost their position and was carrying benefits for the family. I’m generally against lying, but desperate times call for desperate measures…

    1. Can you think of any downside (other than cost) to just having benefits at both jobs? Not only do you get double benefits to help pay down any medical bills that come along, but you have no chance of losing benefits if you have to leave a job.

    2. Cost would be the only downside. Contrary to what others may say, having benefits at both places would NOT increase your chances of getting caught. Yes, the health benefits provider would have to coordinate benefits with the other plan, but that is something they do all the time, and they >can’t< tell your employer about your medical situation.

  6. I just realized today that my main job is my burner job, and currently interviewing at 7 companies to find a new main job. I am finally ready to take that leap as no 5% raise will ever equal 2X ing.

  7. Thanks for your story. Interesting takeaways from your experience. In hindsight, this will give me a good discussion about on-call culture in my hunt for J2

    1. Should have kept J2 until they put you on probation or acted like they were going to fire you, or you were about to do damage to your reputation with your non-performance. Why would you ever, ever quit if you don’t have to?

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