Risk Perception (aka “How to Make Decisions When You Prioritize Stupid Things and You Have No Optimism”) [Updated Again]

Two job offers in one week and strangely, I still feel like a failure.

Honestly, I still feel this way, two job offers later. Image by John Hain from Pixabay

I even negotiated the offers for the first time in my life, arguably successfully (as I then got two improved job offers in one week), and yet I still feel like a failure.

I can’t quite pinpoint exactly why. Because neither was quite what I was looking for re: salary? Because it feels like any other person would have been able to use two offers to get even more money and I feel like I’m compromising since I didn’t get quite what I was looking for? Rationally, I get this is a uniquely stupid reason to throw myself a pity party, and I am definitely happy to have these offers in hand so I know there is a way out of Current Job; I just can’t entirely shake the “feeling like a failure” feeling.

I suppose if I had been offered a lot more money, it would have been a sign that I am really underpaid, which also would have been disheartening. I suppose that means I am not underpaid (although other people make more), but it feels kind of like when you get a tax refund check for $2.83. Like thank you, this is better than not getting a check for $2.83, but what am I supposed to do with this? (True story: I received a state tax refund check for $2.83 once). Ok yes, both offers are a raise of more than $3, although the % change doesn’t feel as meaningful as I would have hoped. Cue tiny violin.

I imagine this stock photo violinist saying, “Seriously, this is whom I’m supposed to feel sorry for? Here is my best WTF face.” Photo by Trần Toàn on Unsplash

I have two other non-final job interviews for other jobs early next week – one I’m not going to get but it’s too late to cancel, and one that seemed promising, but it’s early in the process and I’m not sure I want to risk of waiting and losing the offers I already have. Husband and Therapist think I am being stupid about taking one of the non-perfect offers now, although Therapist was nicer about it.


That’s the thing about risk – everyone perceives the benefits and risks differently based on their own priorities and fears, none of which are fully rational. I’m self-aware enough to realize that some of my own priorities for a job are stupid and flawed, and yet, seemingly unable to stop thinking stupidly. For example, here is a list of what should be priorities in looking for a new job (not in order):

  • Good move for career
  • Growth opportunities
  • Good management
  • Work-Life Balance
  • Compensation appropriate for role
  • Commutable from a location you want to live in (or WFH)
  • Work you enjoy & want to do (Update: I managed to leave this off of both Normal Person Priorities list and JYP’s Stupid Priorities list, although it is actually quite important!)

Here is a list of my priorities (not in order):

  • Higher title so I look better on LinkedIn
  • More money than I think my peers/colleagues are making (although I have no real way of knowing this)
  • Not having a boss who is younger than me (because I am deeply ageist, insecure, self-judgmental)
  • Allows for a move to a place with a vibrant egalitarian synagogue community where the people my age don’t have children, and also isn’t expensive and isn’t a ridiculous commute (this place doesn’t actually exist)
  • Job that is not 100% WFH
  • Quitting current job on Monday so I can finish my my two week notice period before Shavuot (upcoming Jewish holiday)

I know some of this is dumb. Having to take a couple vacation days for Shavuot if I don’t quit on Monday is not a big deal. I once managed someone older than me and it was fine for both of us, but I hate the idea of being on the other side. I know titles vary wildly at different places (for example – one job offer has a higher title than the other, and yet the base salary is identical) and yet title is extremely important to me.

I can’t get everything on my stupid priorities list anyway. In this case, the job offering the higher title is also the job where my boss would be younger than me. Both of the jobs I’m interviewing for next week have both Higher Title and Older Boss, but I’m not willing to risk losing these offers and having to work longer at Current Job to find out if I even get one of those, especially because I might not even get one.


It comes down to short-term vs. long-term. One job offers more money in the short-term but less in the long-term. One job offers the line-management responsibilities I want now; one job potentially offers them later, but there are no guarantees. One job offers the title I want now; one job potentially offers it later, actually a better, more impressive title, but there are no guarantees. One job has the potential for me to make a lot of money in a few years, but it’s a high-risk, high-reward situation – do I really believe it will pan out?

One job requires a relocation and one job doesn’t necessitate a relocation – it’s hard to tell if relocating is the right move short-term or long-term, but I also feel that way about current community. I can barely research better places to live in any community because I can barely tell which factors really matter anymore. I can’t tell if I should be looking for somewhere to live assuming children are still a possibility in my future, or just accept that they are never going to happen.

Ultimately, the question is, which community is more likely to come back to pre-pandemic normal? I don’t feel especially optimistic about post-pandemic life anywhere, to be honest.

How do normal people with optimism make decisions? Image by Gerd Altmann from Pixabay

I just don’t feel any optimism what so ever, really about anything. Even when I got my first vaccine shot. I didn’t really feel anything. No side effects, but also, no hope or possibility or optimism that things were going to open and go back to normal. Getting the vaccine just felt like an ordinary task. Maybe it’s the second shot that feels all hopeful and transformative, but I kind of doubt it.


Side note: I realized that second vaccine appointment is during the work day during my would be two-week notice period. I tried to change the time to be considerate, an attempt to not screw over Current Job as much (because they will be extremely screwed once I leave), but the appointment scheduling system won’t let me. I wonder if the second shot side effects really are as bad as they say. I would feel a bit guilty needing to take sick days when I’ll be at that job for such a limited time. Maybe it will be fine and manageable. I am working from home, and I’ve gone to work completely hungover after 3 hours of sleep before – are the second shot side effects really that much worse?


I’ve mentioned before that I hate rich people even though by most definitions, I am one. Hence why this post reads like a tone-deaf rich person’s post (feel free to hate me for this post – honestly, if I wasn’t the one writing it, I’d hate the author too). The really successful rich people found ways to take advantage of the pandemic, like by moving to low tax states with great weather or getting even richer off of the pandemic. Less successful rich people just worked from home as their only hardship. We were in the latter category.

Husband was disappointed we weren’t in the first category of people who could invest. I didn’t really care. Not because I don’t care about money; I am materialistic, shallow, and I absolutely do care about money. I didn’t care because a) I found the idea of profiting off the pandemic distasteful and b) more importantly, investment requires optimism, which I truly did not have in any measure about anything. It’s really difficult to make investment decisions when you don’t think anything is going to go up.


At the end of the day, it’s a job. It isn’t going to be a ticket out of my shitty living situation (I mean it could, but it isn’t necessarily going to and could just as easily involve living somewhere less desirable if I am not careful). It isn’t going to change anything about myself as a person.


Update #1: Interview that I thought would go nowhere was actually super interested and willing to move pretty quickly. This job offered Higher Title, More Money, Job That Looks Good On Resume, and Boss Who Is Older Than Me. However, I had other reservations about whether I would enjoy working in this organization, a criterion that multiple people reminded me was important. And I was afraid the process would take longer than they claimed and I still didn’t know if I would get the job. So I graciously declined to continue. Interviewer/Would-be Boss was not pleased and tried to make me feel like an idiot. He was successful, as I do feel like an idiot.

Update #2: Interview that I thought could have gone somewhere probably would not hire me. I am a good candidate for that job, but not an amazing candidate for that job.

Update #3: I made a decision on which offer to take and I feel happy about my decision! I am looking forward to quitting my job tomorrow! YAY!!!!

Also, I no longer feel like a failure.


  1. I have these feelings too sometimes, so I relate. I think it’s okay to acknowledge we have less than perfect emotional reactions. As a side job, I format resumes… and people way younger than I am often have fancy managerial titles and make gobs of money. I can get down about it. I start beating myself up for not doing better etc. I get it. On the other side, the bureaucracy involved in a new hire can make for huge delays. Not giving advice here, but might it be okay to see what happens with that third possibility?

    Liked by 2 people

    • I’m 35 with a fancy managerial title and I beat myself up about the people younger than me with better, fancier managerial titles and more money (and they definitely exist – my industry is dominated with young ambitious people). Rationally, I know it is stupid and unproductive, but it is hard not to do.

      Liked by 1 person

  2. Mazal tov on the offers! Good luck making the decision; the options made me dizzy just thinking about them. I won’t give you advice because I’m the worst person to give careers advice.

    Liked by 2 people

  3. I’m glad you’ve got options, even if figuring out what to do isn’t necessarily easy.

    I wonder how far afield you’d have to go to corral enough people to bring that vibrant egalitarian synagogue community into existence.

    Liked by 1 person

    • It is definitely a good thing to have options. I started drafting this positive on Friday and now, I feel less negative, but I do still feel confused.
      There are vibrant egalitarian synagogue communities. The most vibrant ones are in high cost of living areas; the ones in lower cost of living areas don’t have the same density of people. Community building is a lot of work, but certainly something to think about.

      Liked by 1 person

  4. I too live in fear of having a boss who’s younger than me. I’m sure the day is coming, probably soon, since I’m not by any means an ambitious career person, and I’m honestly not sure how my fragile ego will handle it.

    Anyway, good luck with your decision! I too am a risk-averse pessimist by nature, and I’ve faced a few professional decisions where I had to weigh all kinds of, for me, impossible to balance factors like this. For what it’s worth, when I’ve taken the path of least resistance, aka the safest choice, I’ve often come to regret it. But then big risks can also lead to big regrets too. It’s a conundrum for sure.

    Liked by 1 person

    • I swore I would never take a job with a younger boss – I actually got an offer about a year ago that I turned down in part because of this, although I had other reservations about that job. I suspect that my largely non-existent self-esteem was not going to survive a younger boss. And yet here I am considering it because it comes with a higher title. But also, I recognize independently I would probably have to get over this because the nature of work is such that I will have a younger boss.

      I could be content picking the safer, risk-averse choice in this case. The challenge is that I don’t really know which one that is. Both have risks, albeit different kinds, and I can’t tell which one is really the lower-risk one.

      Liked by 1 person

      • I wasn’t very old before having a younger boss was pretty much the norm for me. I was only somewhat heartened to learn, a little after that, that the Gynormous Communications Company I worked for rather preferred its managers to be young and dumb. I think, however, I live(d) in a very different world than you.

        Liked by 1 person

        • I’m not sure if mid-thirties is “not very old” for a younger boss but here I am. Funny enough, I once managed someone older than me and it was fine. I keep telling myself that I’m getting something out of this job and I did get a better title, but sometimes, the age difference just hits me and I cringe.


  5. You have to prioritize what you feel is success, and I say feel, because there is a point where logic just won’t do it: I’ll go back to Covey, here -what do you want to be able to look back on, in your last moments of life, and be proud of? It won’t be money, I’ll bet. Most people think that I am either crazy or stupid because of my choices over the last 20 years, but I stand by them, because I know that when I die, the fact that I am now prioritizing my key values (“do not stand idly by while the blood of your neighbor is shed” )…

    Shalom, in the fullest sense of the word.

    Liked by 1 person

    • That is really important. One of the job offers on paper looks obviously better and not picking that one looks at face value to be a much stupider decision. I can hear my colleagues telling me I’m crazy if I don’t pick that one. And yet, I have reservations about it. Although I must admit my reservations are of the selfish shallow career-advancement variety, not the noble values-driven kind. I admire you.
      Thank you for your blessing of shalom. I really appreciate it.
      Safe air hugs! (if you want ’em)

      Liked by 1 person

  6. Lol, the way you’re presenting all this information kinda reminds me of myself, when I have things that are seemingly the same, yet I choose to overthink things.

    The upside is that you are overthinking legit things, like a job, that will inevitably affect your life. I have the same thought processes when it comes to picking damn inks for my fountain pens, lol. So I definitely feel you on this one. Thanks for this post!

    Liked by 1 person

    • Oh these offers are not similar at all (although I did a lousy job of separating out details, in part for anonymity), and yet I’m still struggling with the decision.

      I respect a person who takes fountain pen inks seriously! And also a person who uses fountain pens in the first place!


  7. Oh how I dread having a boss younger than I! Especially as my career is…. non-existent, so it’s easy to be above me. And I’m hitting an age now where it’s gonna happen sooner rather than later now.

    Liked by 1 person

    • I wound up taking the job offer with the younger than me boss because it offered a higher title and better compensation overall. And I have met her and respect her. If I hadn’t LinkedIn stalked the heck out of my soon-to-be boss, I would have no idea that she is younger than me. But oh, I cringe thinking about this!

      Liked by 1 person

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