The following is a guest post series from Guild member elhapo#8226 with some light edits. Check out more stories on #oe-journals on the Overemployed.com Discord.
Day 16, Monday – Death and Taxes
Again, an easy peasy day. My main worry today is taxes. Apparently, I’ve been filling out my W-4 tax withholdings wrong. You would think after owing the government a bunch of money at the end of the year would clue me. But who knows what goes on in this brain sometimes.
This year with the extra income, I do not want to be on bad terms with the taxman. The OE community on Discord starts talking about if you are off 10% in your taxes then you get a penalty. No thanks! They helpfully mention that I should tally up the overall taxable total and then subtract the individual summed taxable total to figure out what extra taxes I should be giving over. It is not a small amount – but mainly because I filled out my J1 withholdings wrong and have been underpaying all year.
A word from Isaac: if you’ve little to no knowledge about taxes, it’s time to hire a certified (human) public account because the IRS withholding calculator wasn’t built for the highly paid Overemployed. If you don’t understand the underlying logic behind the calculator and enter the wrong information, then it’s garbage out. For starters, read our Top Five Tax Surprises with Multiple Jobs.
I went to the IRS tax withholding estimator and there’s a spot right on here for 2 or even 3 or more jobs. The IRS loves me so much that they made this easy 🙄. Either way, I go through each paycheck and enter all the values that it’s looking for. I get roughly the same number but then the estimator also tells me what I need to do to catch up for the year. It’s about one paycheck a month! For the first time in maybe 10 years, I finally looked at how much I pay in taxes. Holy crap, it is time to find a good tax guy because that is a crazy amount, even just 1x’ing.
Either way, glad that’s settled at least. The IRS calculator also spits out new tax forms for me, how sweet. I read up on the 401k’s and other benefits on OE but I’m more or less doing that already except for the self 401k because I don’t have my own company. This is probably something I need to look into as well asap.
A potential J4 pops up. The recruiter is awesome and sells me what an awesome position with great people. Sounds similar to the prior J4 position that I would have replaced J1 immediately with. I temper any excitement I have with thoughts of what happened last time. I think the background check for this job is also more involved so that’s something in the back of my mind. An interview is set for later this week.
Day 17, Tuesday – Is Anyone Out There?
J2 seems to have forgotten about me. I got some small bits of work that took me all but three minutes to complete. Crazy! J3 is pretty much the same but with more meetings – not a good sign. I have got two overlapping meetings tomorrow (J3 alone) but I’m completely chill about it since the expectations and behaviors from J3 become predictable.
However, I have no idea how this is going to work if J2 comes swooping in and wants to take up the same meeting time. Things will probably get pretty nuts if that happens. I am going to hope for at least 1 more uneventful day from J2, I could really use it, but who knows. All jobs end and I end up staying after and working on one of my own projects for the first time in weeks.
While yesterday’s tax lesson was something good to go through, I am bummed that an entire paycheck is going to the man each month. Whatever happens next year, I need to use that calculator right away to figure out what the proper withholdings are. I do a quick calculation to see what would happen if I didn’t have the other jobs and it’s worse. This puts a bit of pressure on me to continue to have more jobs but when I rationalize it a bit more I’ve had to save every January anyway so there isn’t much of a difference. Live and learn.
A word from Isaac: The simplest and relatively conservative approach is to set all your W-4s (the tax form Elhapo is referring to) to single with zero claims or deductions. Basically, you assume you won’t qualify for any credits or deductions (a safe assumption if you make over $400K). Even though I filed married jointly, I still use the same approach Then, when each quarter’s estimated tax payment deadline approaches, re-visiting your gross income and calculate your expected federal and state marginal taxes. Compare it to what was withheld in your paystubs. Pay the difference, if any. Refer to Top Five Tax Surprises with Multiple Jobs when doing your own calculations. Your tax obligations are your tax obligations, whether you know it or claim ignorance. The IRS doesn’t take kindly to underpayers. Don’t be a penny-wise but a pound foolish, get a CPA if you’re lost. Or, you might have to waste your precious time dealing with a tax attorney and the IRS when you get audited.
Day 18, Wednesday – Meeting Conflicts Here, Meeting Conflicts There
Pretty much felt like a product manager is supposed to feel if they are dealing with a multi-tier project that spans many departments. I just came up with those terms to sound fancy, I don’t know what a high-level product manager does. But I imagine it’s like this, constant meetings and people talking. I am simply amazed at how much people want to talk and feel important about getting their viewpoint across, and then other people with the same attitudes do the same as well. Basically, nothing gets done. Just people wanting to hear themselves talk.
J1 was suffocating today. Big meeting with me as the focus and it didn’t go well. I mean, it went well for me, but there was a big U-turn for the project. Probably could have been a Q turn because executives started suggesting the dumbest stuff I’ve ever heard.
Never had this happened before and I was a bit crushed. I immediately hit the job boards and start searching for J1 replacement. I vow to spend less time caring here and putting more time into other Js. For whatever reason, J2 has left me alone for the entire day again. I am super thankful, I was ready to nuke the entire thing if I got so much as a random phone call from them. I did get a few menial tasks which J2 gave me three weeks to finish. I just completed it today. Man, I am cool.
J3 meetings are succinct. They are mostly worthless but at least they start on time and end on time. The only thing is that all of them are very redundant. Any interaction I have in them is exactly the same, status updates to and from different people. Everyone here is overly nice, but there’s a reason this job is in the third position so I just keep that in mind.
After work is over I think about how much more exhausting meetings are than the actual work. It’s hard for me to talk to a large group of people. It’s hard to sort of pay attention to what people are talking about when it has zero relevance to what’s going on with your own work bubble. Multiply that by the entire day and I’m spent. Glad this one is in the books.
Day 19, Thursday – Run For The Hills
J2 comes after me like a hurricane first thing in the morning. No check that – they’ve wanted to know some statuses since last night. Crap, defusing mode activated! J3 is hitting me with some small stuff, and I do have a single task to get done for them today. J2 though looks like they need to make up for the lost time. I get some training and setup done, and then it’s time to do some introductory meetings and get flying.
The people at J2 seem happy, which has me curious as I’m wondering how people work like this. Small laptops, no cool equipment. Guess I’ll find out more tomorrow as I’ve been added to another daily standup, ugh. This one overlaps with another daily. I freak out a bit and then just settle into don’t care mode. I was told a different time by a coworker and was super relieved at first, and then I saw they actually overlap. I think I can handle this, and if not then…guess I’ll figure that out when it happens.
The anxiety is gone, the constant threat of “they are going to find out” has settled into a “if they find out then meh.” Meeting conflicts and various tasks are tiring but doable. At one point during the day, I just feel like nuking everything and going back to my lazy ways of working a few hours a day in one job. I’m a new person though. Forging forward.
A paycheck hits the bank. I obviously have been anticipating these but everything still seems so surreal. The magnitude of my bank account staring me in the face hits me. I have enough savings to have two months of living expenses if I got fired from all jobs at once. I’ll be ok one way or another. I’ve never had this before. The most I’ve had was probably 2 weeks of emergency fund saved up if I’m being generous. I feel very fortunate and lucky, especially because I feel like I’ve spent too much money in the past week. I do a quick calculation in my head and figure this would have taken me a good two years to save. It still doesn’t feel real.
Oh yeah, J1 is still pawing at me after yesterday’s fiasco. I get it done towards the end of the day and move on. I am trying to move towards the “stop caring so much” mode but it’s just hard. A J1 replacement calls me. We talked for a good half hour. I have no idea if this is the one for me due to my current JXing but it does lift my spirits.
That’s it for today. The only thing about tomorrow is the new meeting conflicts. Crossing fingers. 🤞
Day 20, Friday – Multi-Dimensional Brain Development
I need a strategy to deal with the meeting conflicts. Just ignore one? Drop a connection? Grow another brain? J2 meeting starts first, and I’m fine. No anxiety, nada. Having fun introducing myself and talking with the new group. Thankfully I stop talking and they get to everyone else. I tune that one out and then I hear my name called in the other meeting. I attend that one and finish. Then I just passively listen to them both – oh there’s me in J2 again. Talkity, talk, talk. J3 meeting ends on time in J3 style. while J2 we keep BS-ing about some other things and then hang up.
I did it. I have no idea how I snuck in talking to each meeting but everything concluded and it went just fine. Phew! The rest of J2 is just getting my environment set up. J3 I feel like everyone took a day off. J1 is J1.
I attend my interview with PJ4 (J1R – J1 replacement). I crushed the interview. I really like these people. We have the same sense of humor and they all seem super fun. If I don’t get an offer it’ll be just like the other PJ4 before – stunned. The issue with this one is:
- They seem to work a lot, or at least work a lot of hours, including weekends – yuck!
- Background check seems to be very involved. They want to see my bank accounts and I don’t think I’ll be ok with that.
- Some of the working conditions are not optimal for what I do. I’ve done it before and it isn’t an awesome experience.
I just wonder if Pj4 is going to be worth the extensive background check. Am I doing this for some sort of validation? I’ve talked with people who have had multiple jobs over the years and no one seems to care. Does this stigma really exist? I know it does but does it really? I might be fooling myself.
The day takes forever to end. Counting down the hours at the end of the day is a thing now. I am done, I stand up and walk away and look forward to the weekend.