Category Archives: Career Change

Life update and what’s ahead for 2025

My youngest cousin just posted that she was promoted to VP and while I am, of course, happy for her, I can’t help but feel a tinge of jealousy mixed with some serious sadness about my own non-existent career at 41. She’s in a different field, but she’s 30 and sprinting ahead towards what I’m sure will be even more success and I’m… I’m not sure what I’m doing. I’m not even crawling in my career right now. It’s more like I’m stuck in quicksand.

Do I have a job right now? No. Managed to grow the net worth through 2024 thanks to the markets moving up and up some more, but that isn’t going to be forever. Money is important but at this point I just want to feel proud of what I’ve done and I don’t. I can’t get a job. I can’t get a good job and I can’t even get a not-so-great one. I thought maybe grad school, but then I realized that doesn’t make any sense… why throw money at my problem when I need that money to keep growing, and I’m the problem.

So… what do I do? I ended up having my disability extended for depression, which has been helpful given it softens the bleeding for a bit, but that’s ending in three months. I may be eligible for $1800 a month in unemployment for a while, but that doesn’t exactly pay the bills. Part of me wants to just wait until my daughter is one, and then, it’s basically summer and that same part wants to wait until the end of summer to get a job… the other part of me is freaking out thinking I should get something NOW.

Weird convo today with my now-aware-of-things 6 year old in the car, where I mentioned I was getting a new job in 2025, and he asked about the job I already had, which I had to inform him is no longer a job I have without saying “mom got fired.” Why am I not working there? I didn’t agree with what they wanted me to do. Well, that’s part of it. “Mom saved a lot of money in her 20s so you don’t have to worry we will be fine, I just want a new job so we can go on nicer trips and get better presents.” Sort of the truth. Sort of.

Right now I just want a career path. I want a promotion. I’ve never really had a promotion. I want to do a good job and go from IC to manager to director to VP. I’ve been “director” level for 15 years in most roles and only once had direct reports. I don’t know if I care about having a team, but I do just want to be good at what I do. Good enough that someone says “promote that woman.” Now, I know that person saying “promote that woman” will be 10+ years younger than I am and the longer it takes, the worse that will get. Not that I think younger people are not worthy of being my manager and my manager’s manager and so on… I just feel… old… and like such a massive failure.

I have been applying to jobs here and there. I’ve been through a few interview rounds, even make it to the final rounds with two companies. One, well, the hiring manager was fired about a week after I didn’t get the job. The other was weird and I’m glad I didn’t get it, I would have failed there. They were all over the place, basically asking me when I could start then… ghosting me. The hiring manager there didn’t think I’d be able to handle startup life as a mom with a young baby which… was not cool for him to say… but also, given I know what startup life is… is probably true.

Bullets dodged?

I’ve never aspired to… do anything in my career, really. It just happened. I just kept doing things. Whatever I was asked to do. Sometimes logical things. Sometimes things that made me roll my eyes or question the meaning of life. But things happened. When I had the energy. When I wasn’t 41 years old with 3 young kids, two of whom are on the spectrum, and all of whom need my attention 24/7.

I’ve felt better the last month or so because I decided to stop thinking about work entirely. Outside of a small side project I have that gives me a little needed reminder that I’m capable of working, even in small amounts. Maybe I can get a job. But what kind of job? Will it be a dead-end, will-never-ever-ever-get-promoted job? Does that even matter?

VP. I’ll never be a VP. I don’t care. I guess. I just want to do something… good… for once. I’m scared and sad and what’s new, but hey, my net worth is $3.6M, so that’s something.

Trying to learn to be a normal, functioning human being

“Your net worth is $3M — how can you not be a functioning human being?”

If anyone knows what is in my bank account, especially that the majority of it is from my personal savings and investments (even though I now track net worth collectively with my husband), the response to my explaining that I’m a barely-functioning adult human is this.

But it’s the honest-to-god truth. I’ve spent my life struggling. Not in the whoa-is-me sense, but just in my reality. It’s some combination of early childhood trauma (growing up in a domestic violence household), genetics, and whatever else makes me up. I’ve lost so many jobs over the years, from my earliest firing when I left a purse out at at train station at a little jewelry and accessories kiosk I briefly attempted to work at, to my most recent axe at the startup where I was on the executive team and failed to live up to expectations (I lasted a whopping four months).

I’ve long been embarrassed by my recurrent job loss. I look in the mirror and ask myself why. Everyone gets fired or laid off on occasion, but I’ve made it a habit. If we’re being honest here, I’ll let you in on a little secret — I’ve been fired nine times. Only ONE of those was what I’d consider a lay off. The rest were due to performance.

The good news? When I get the axe one more time, I’ll have a nifty clean ebook title “How I’ve been fired 10 times in 2 decades and have saved $3M.” Or something more punchy than that. I do like clean numbers.

No one understand how I’ve done this (outside of my husband’s $500k or so contribution to that). I don’t either. How — somehow — through luck, tenacity, fear, masochism, or some other force, I’ve managed to pick myself up again and again and push forward in the most positive and lucrative way possible. Loose a $190k job for being too socially awkward and unproductive to be an executive? Three months later, get another job that pays $250k a year through another contact that liked my from a prior position.

I kept jumping from one thing to the next. For the last 20 years, give or take. And every morning I’d wake up not knowing WHAT to do. My best days were the days I was working on a project where the task was clear and I could use creativity and my superpower of listening to a whole bunch of mildly sociopathic people who think THEY ARE RIGHT at all times and make them ALL happy (thanks childhood trauma and ability to walk delicately on eggshells!) This is not to say those sociopath-lites were untalented or wrong (some of the time), but…

I’m worn down and burnt out by trying so hard to make everyone else happy. It seems I can’t do it anymore. The asks may be impossible, or I may just be incapable, or both. I’m tired. I’m depressed. If it weren’t for my adorable sweet little kiddos, and certainly if I hadn’t somehow built this substantial cushion to see me through the dark times, I might be more serious about making an escape plan from this life.

But that doesn’t change that I’m 40 and don’t know what to do. I finally agreed to take antidepressants and am finagling doses with my psychiatrist to see if anything will help (but can’t take ADHD meds since I’m nursing). I’ve tried ADHD meds before and they just made me a bit manic, but I’ve never worked with someone to adjust and monitor until maybe I could fake myself out for being a real life functioning human being TM.

Every single path I consider is terrifying to me…

Stay the course — somehow get a job in what I’ve been doing and just do better next time. I’ve applied to 150 jobs in what I’ve been doing and haven’t had any luck. The market sucks at the moment so it’s not just me not getting work, but every job post I read makes me die a little inside… just knowing even if someone out there buys that I can do the job, the reality is I can’t. I don’t think that way. I don’t know if there are any classes that can teach me to be good in the career.

It feels like I have to start over anyway… so if I’m starting over, why not do something new…

But then I go down the path of what a mess it will be to invest in myself for any new careers. What if I spend $10k, $50k, or more, and I’m back where I started? That seems like a waste. Is it better to just try to live as frugally as possible (which I’m also bad at but getting better at — it’s just my $7k mortgage makes it impossible to cut down enough to cover our COL even without summer camp and vacations and dinners out) and get a low-paid routine job? The answer to that is no — as I’m pretty horrible at low-paid routine jobs. I do better in roles that require strategic thought, that keep me on my toes, that give me a little dopamine rush on a project that needs to get done and will have some sort of stage to show for it.

I also like helping people. I’m scared to put myself in a position where I am responsible for another person, and I don’t actually see how I can help others, but I do find my greatest satisfaction comes from actually helping other people — shockingly, since I’m a narcissist of some sort probably.

So — I don’t know what to do. The other options:

MBA > TBD: I’d focus on quant and finance, an area I have -0% experience in. I was in advanced math in 10th grade and then in 11th grade they kicked me out and I had to take the “easy 9th grade math” to graduate high school since I couldn’t focus enough to mange through FST. I bought a bunch of calculus books on a whim a few years ago. They are sitting in my garage.

CFP: I like the IDEA of being a CFP. I like helping people with their money. But I don’t like the idea that being a CFP is really being a sales person. I couldn’t work for a company that sold anything I didn’t believe in. And I don’t have it in me to build a business that requires contacting people, making them clients and keeping them happy. I’m also interested in helping people make and manage budgets, but not sure there’s much money in that.

UX/HCI: designing user experiences is interesting to me. This one is a recurring theme. However, I’m so far behind in learning this area and don’t have the technical or research skills for a job like this. I could go back to school but the market is flooded with bootcamp grads and to get a grad degree from any reputable institution requires a solid portfolio. It will take years to even get there. Feels impossible. And I’m not sure I’d be any good at it.

UX content strategiest: an interesting option with no clear path to obtainment. All the UX content strategy roles I’ve seen require experience and a portfolio in this. Which I do not have. So, next…

Therapist: if helping people is my goal, this could be a good career change. But who am I to help others when I’m this much of a mess? I can’t exactly miss appointments with my clients. What if I say something and they get mad at me? I’m bad in tense situations.

Coder: per my other post, this could be interesting. I really want to feel like I have a skillset that is valuable where I can actually DO something because I know how to do it and deliver quality work that — works. Not work in a field where success is subjective. But I’m scared of this path for so many reasons. Per the above, my quant abilities are what abilities would be if they were divided by 0. I like patterns and solving problems, but am I smart enough to do this?

Or… I don’t know. I don’t want to be a stay at home mom forever. I’m enjoying it now and wouldn’t mind it for the next few years. I just need to figure out something I can do and do well. Something where I can wake up in the morning and not dread the day. Is that possible? Am I hopeless? I don’t know. I know I’m not doing well. I haven’t been for a long time.  I need hope. A change. A dream. Something.

Should I become a software engineer at 40?

Like many people out there, I turned 40 and wondered — what am I doing with my life? For better or worse the tech job market has imploded. That, paired with my depression-fueled repeat firings and inability to do a job that requires a certain part of my brain to function, has led me to deciding that I need a major change. Given I can’t get a job and I’m moderately to majorly unemployable, this is not even an option.

So I wondered — should I become a software engineer at 40?

What’s funny is that everyone has recommended I talk to people in various roles I’m interested in to decide if they are good options for me. I’ve considered everything from UX to chief of staff to jobs outside of tech altogether. But it happens I know a lot of software engineers. Not only do I KNOW engineers — they are always my favorite people in the companies I work for.,. because they are often brilliant, socially awkward, and way more fun to talk to than anyone else on my (the business) side of the office.

But am I smart enough to be a software engineer?

My developer friends think so. Maybe they are just being nice… or thinking I have enough of a brain to manage an entry-level programming role. I have no support from my husband who only wants me to have a career that enables me to support the family. He has no idea what I should do but isn’t opposed to this. I don’t blame him that he doesn’t gung ho support me in anything. After all, he has dealt with my recurrent job losses and mental health cluster of a life. It’s no fun being married to me.

I want to prove to him… and to me… that I can do this. I want a job where I wake up in the morning and get to work. Where I don’t feel like I’m going to fail before I even start. I don’t know what that’s like. I don’t know what it’s like to wake up and not dread going to work. Not know that I could only fake it for so long until I imploded.

Last Feb, my boss, who hired me 4 months earlier, who happened to be CEO of the startup, slacked me and told me to cancel my flight to a conference I had scheduled the next day. I shouldn’t have responded to him on a Sunday but I did. He said to join him on a call first thing Monday morning. I knew what that meant. He was firing exec team members left and right and I knew I failed to live up to his expectations. Maybe I could have done a  better job if I didn’t let my anxiety get to me… but at the end of the day the role… was wrong for me. My whole career is.

Will becoming a software engineer at 40 help? Can I actually do this?

It all feels impossible right now. I don’t feel intelligent enough. I struggle with ADHD and anxiety and depression and am using most of my energy to keep 3 kids alive. How can I become a software engineer? It seems more like a joke to me than a possibility. But maybe it could be real. After all, I’m the girl who in high school was hacking together geocities sites for fun. Sure, it was just HTML (and a lot of scary bad frame design), but it was… me. Something. Something I could have pursued more. But I didn’t. Because as of first or second grade, despite testing as “gifted,” I accepted I was dumb. My father told me I wasn’t trying hard enough. So I didn’t. I stopped because it was too hard for me to focus. I gave up. I was seven years old, and I gave up.

Now I’m 40. I’m tired of giving up. I don’t have much life left. I want to show my kids they can do anything if they put their mind to it. I want to work for a company and cause that is meaningful. Maybe coding would be where I fit, I don’t know. But I’m so so so tired of not firing, tired of the constant suicidal ideation, the inner monologue that tells me I’m a failure and can’t do anything right. I’m just tired. I need a do over. Maybe this is it. Not for anyone else. For me.

 

Struggling and Scared. What’s New?

I have 70 days until I will feel good about leaving my current job. But that still leaves the big question – what job should I go to next?

Reading job postings is the most depressing thing ever. I don’t have any skills that would land me a new job. And the jobs I’m qualified for, well, they aren’t even clear fits, and they would pay A LOT less. My only hope for making the same income is to take a VP level role, which is possible since I think I can probably convince some company no one wants to work at to hire me to run a department… I’ve done it before… but that means I actually can’t suck at this time. And while I think I’d be better than I was in my early 30s, I don’t see myself really being able to do the job well.

I keep having this sinking feeling that I’m stuck. That isn’t worst case, of course. That means I continue to do a good enough job where I don’t get fired. For however long I need to do that. I’m just not getting any more relevant experience for leaving and the longer I stay the more stuck I become. Until I get so depressed that I can’t function and end up losing my job anyway.

But I feel like I need to dig into something meaningful as my next step. I’m scared because part of me likes not giving a shit about my job beyond just doing a good enough job. If I am doing something that actually betters the world then I will be extra angry at myself when I slip up. It feels good to not care, I guess, but then I can’t motivate myself to do good work, so I think I need to care overall.

I wonder if I took some time off would I have the energy to get back to things. But I’m still convinced I don’t have the ability to learn enough skills to be employable in any job that a sane person would want to have. My number one skill is managing to make crazy sociopaths happy by doing what they want even though I disagree with it entirely. It’s not the best life though, at least for the past few years, it has paid well. But this year it’s leaning into being asked to do things that I’m not ethically ok with plus I don’t believe in and I just hate it all.

I’m curious what I’ll get for my bonus and raise (if any) this year. If I don’t get a raise again that’s going to hurt because inflation is bonkers. But I’m, well, not putting any money on a potential raise. I know even 5% is going to be pretty standard this year and anything below that is just a kick in the face and a clear sign to GTFO. But where do I go? I really don’t know. I’m just so worn down. I’m taking it week by week. 10 weeks left. Just 10 weeks. I can at least get through the 10 weeks right?

Some Kind of Life Plan

Welp, here it is…

I think this is fairly conservative plan if I’m going to leave work in August and then seek to pick up a small amount of freelance work in January either building to a full time freelance business or going back to work full time when I start IVF to make sure I have good health insurance when having a baby (probably that.)

This model assumes my investments grow at 3% annually, that the only net new contributions are expected RSU/ESPP vesting and retirement maxing for both myself and my husband, and our monthly expense are $13k plus amount to max retirement.

Who knows what the stock market will do or my stocks that need to be better diversified will do but this seems like a somewhat realistic plan from now until Jan 2024 without work. I can certainly focus on cutting expenses but even of the $100k “lost” during this time in the model below, that’s all going to retirement savings so it’s not really lost at all.

This model seems realistic, right? As long as I can make it until July. Maybe I stay until September and do an extended vacation in August… I get some more stock and such in September so could be worth it. Depends what type of projects I’m working on. It’s generally best to leave in July I think. So that’s what I might do. Scared but excited!

Month NW RETIRE STOCK 529 H.E. AGE INCOME (HIM) INCOME (HER) TOTAL INCOME AFT TAX AFT EXPENSE
Oct 2021 $2,334 $752 $986 $284 $312 $8,333 $12,376 $20,709 $12,426 -$7,574
Nov 2021 $2,379 $754 $988 $285 $315 38 $8,333 $12,376 $20,709 $12,426 -$7,574
Dec 2021 $2,369 $775 $991 $285 $317 $8,333 $141,256 $149,589 $89,754 $69,754
Jan 2022 $2,376 $777 $993 $286 $320 $8,333 $54,136 $62,469 $37,482 $17,482
Feb 2022 $2,384 $779 $996 $287 $322 $8,333 $16,376 $24,709 $14,826 -$5,174
Mar 2022 $2,445 $800 $1,033 $288 $325 $8,333 $45,876 $54,209 $32,526 $12,526
Apr 2022 $2,453 $802 $1,036 $288 $327 $8,333 $12,376 $20,709 $12,426 -$7,574
May 2022 $2,461 $804 $1,038 $289 $330 $8,333 $12,376 $20,709 $12,426 -$7,574
Jun 2022 $2,473 $810 $1,041 $290 $332 $8,333 $31,876 $40,209 $24,126 $4,126
Jul 2022 $2,481 $812 $1,044 $290 $335 $8,333 $12,376 $20,709 $12,426 -$7,574
Aug 2022 $2,489 $814 $1,046 $291 $337 $8,333 $0 $8,333 $5,000 -$15,000
Sep 2022 $2,497 $817 $1,049 $292 $340 $8,333 $0 $8,333 $5,000 -$15,000
Oct 2022 $2,505 $819 $1,052 $293 $342 $8,333 $0 $8,333 $5,000 -$15,000
Nov 2022 $2,552 $821 $1,054 $293 $345 39 $8,333 $0 $8,333 $5,000 -$15,000
Dec 2022 $2,521 $823 $1,057 $294 $347 $8,333 $0 $8,333 $5,000 -$15,000
Jan 2023 $2,478 $825 $1,009 $295 $350 $8,333 $1,000 $9,333 $5,600 -$7,400
Feb 2023 $2,486 $827 $1,012 $296 $352 $8,333 $1,000 $9,333 $5,600 -$7,400
Mar 2023 $2,494 $829 $1,014 $296 $355 $8,333 $1,000 $9,333 $5,600 -$7,400
Apr 2023 $2,502 $831 $1,017 $297 $357 $8,333 $1,000 $9,333 $5,600 -$7,400
May 2023 $2,510 $833 $1,020 $298 $360 $8,333 $1,000 $9,333 $5,600 -$7,400
Jun 2023 $2,518 $835 $1,022 $299 $362 $8,333 $1,000 $9,333 $5,600 -$7,400
Jul 2023 $2,526 $837 $1,025 $299 $365 $8,333 $1,000 $9,333 $5,600 -$7,400
Aug 2023 $2,534 $839 $1,027 $300 $367 $8,333 $1,000 $9,333 $5,600 -$7,400
Sep 2023 $2,541 $841 $1,030 $301 $370 $8,333 $1,000 $9,333 $5,600 -$7,400
Oct 2023 $2,549 $843 $1,032 $302 $372 $8,333 $1,000 $9,333 $5,600 -$7,400
Nov 2023 $2,597 $846 $1,035 $302 $375 40 $8,333 $1,000 $9,333 $5,600 -$7,400
Dec 2023 $2,567 $849 $1,038 $303 $377 $8,333 $1,000 $9,333 $5,600 -$7,400
Jan 2024 $2,575 $851 $1,040 $304 $380 $8,333 $1,000 $9,333 $5,600 -$7,400
-$110,360

How Long Can I (Should I) Keep This Job If They’ll Keep Me?

Four years ago, I joined a much smaller company in a role that didn’t have a job description. The total expected compensation was more than I had ever made and I threw myself head first into the excitement of the new opportunity. The energy at the company was great then. Some people were clearly not top performers, but everyone joked a lot together and got along. It wasn’t a well-oiled machine yet in my department, but it was getting there.

A few months later a number of those fun, joking people were shown the door and others who joked in the corporate-appropriate way were let in to take their seats. I managed to come in with the new wave, despite not fitting with the rest of the group, and I flailed through the following years putting out a few good projects and being pregnant, twice (my best projects of all), enabling me to somehow still be gainfully employed to this day, despite plenty of reasons for me not to be.

Covid turned everything upside down and I also owe my current employment to the pandemic. Being able to work remote, heads down, and hide my awkwardness much more efficiently helped a lot. So here I am. Just months away from achieving my initial goal of surviving through my first vesting cycle. It’s a huge win. My net worth growth in the past 4 years has been strong due both to my existing investments and my stock in this company that has proven itself a rocketship.

So now the question is — when do I leave? If I have that choice, anyway. My ego is tore up all sides of Sunday (is that a saying? If it’s not it should be) but maybe that’s fine. I’m not getting any raises or stock refreshes or promotions — EVER — at this company — but does that matter? So what if they’re showing me the door. I can say “see the door, not going to go through it yet, you’re going to have to shove me through it.” And maybe they won’t shove me. Maybe they don’t care enough to do so, especially if I’m getting my basic work done and not causing anyone harm.

Looking ahead to next year, assuming I manage to last at least through April 1, when I plan to likely be heading out that door… I can stick around another year and it would be pretty darn lucrative and probably a decent situation for me as long as I don’t have to go back to the office. Going back to the office is likely a requirement if I want to have any sort of career growth in this company but as I’ve already covered that’s not really possible anyway so the best I can do is focus on getting my projects done, communicating effectively, and hiding as much as possible.

What I don’t want to do is get fired. And it’s hard to not get fired when I’m this bitter. When I see where I thought I’d be and where I feel I have things to contribute being handed to my peer (who happens to be a friend now but still.) A peer who was supposed to report to me when I went out on maternity leave, who was hired to fill in for me when I was having a baby, then who went on to surpass me in so many ways. These things happen but it still hurts. It hurts that he is the go-to trusted ear for my former boss, who I respect a lot, and she prefers to have nothing to do with me these days. I get it, I understand it, but it sucks nonetheless.

My new-ish boss, well things are awkward with him. I’m sure they got more awkward the second he saw how much I’m making. It was weird going from peer to report knowing he likely was making – a lot – less and then having him see how much I was taking home just – well it didn’t really set up our new relationship for success. He hasn’t been an asshole about it but I’m sure he would fire me in heartbeat if I slip up. Luckily I have a few high visibility projects no one else wants that I’ve historically managed well so I keep doing that and maybe… I’m ok? As long as I want to be.

I’m committed to. seriously applying come February. If I can get a better job that pays >$250k with base >$200 I think I need to leave. But it’s all sorts of questionable if I can do that. I’ve had 5 quick rejections from roles I applied to last month, so it’s surely going to be an uphill battle to find anything that is a fit. I might be stuck anyway. So perhaps I ought to try to focus on liking this job and doing my best and all that.

I just wish this job had any legs. Where do I really go from here? Any comparable role requires technical skills I do not have, nor can I gain these technical skills without going back to school and spending a lot of time becoming an expert to be competitive at my level. I’ve been specifically kept out of the projects that actually make sense in the broader industry and am allowed to work on projects that are pretty company specific with no results other than surviving them. So it’s a challenge in building up a story for what’s next, without an opportunity to do anything worthwhile.

Maybe for even $260k that doesn’t matter. Or does it? I have no career. I have no future. All I have is the next two years. It’s not enough to retire on. I still need to figure out what’s next… and how I get there.

Trying to Find a New Life as the Fall Air Breaks Me Down

Fall. It’s the season I struggle most with. I seem to either slip into depression or mania around this time, depending on the year and life circumstance. There’s something about the air. It’s hollow and scratchy. Each breath in on inhale feels icy and empty and yet not filling enough so I open up my lungs to take more in, only to have it attack me subtly from the inside.

But this time, which definitely feels more like the end of one year and beginning of the next (Rosh Hashanah got it right) is one that brings about reflection. And in this self reflection I feel how another year has passed and part of me feels like I haven’t taken any steps closer to whatever satisfaction is and yet the reality is I’ve produced an entirely new person AND increased my net worth substantially since last September. So time feels short but it was certainly filled with a lot of existence and growth.

I want to get to this point financially where I can stop worrying about money so I can pursue something I would love to do. The trade off is always time, because I want time with my kids, and I’m afraid even if I had all the money in the world to go back to school and try something different. I certainly don’t trust my anxious ADHD mind to get through coursework in a way that would make the investment worthwhile. And yet – doing something I love where I have purpose is the feeling burning in my lungs today. It’s no longer a nice to have. It’s a must. Money also is, but what if — what if I could live a life where my income could pay the bills but where I no longer had to aggressively save? What if instead of spending money on things to make me happy I actually found what makes me happy is the work I do. Because Amazon Prime purchases, however much dopamine they fill me with when I punch open a new box that arrives in under 48 hours, are not really making me any happier than I was prior to purchasing them. They’re just adding to my misery, also known as the pile of toys and crap on my floor.

So.

I’m still not sure what the math is. But it seems at the end of this year it’s realistic for our net worth to be about $2M if calculated without 529 and home equity which I should probably start doing since that offers a realistic picture of how much income we can one day have when we start to spend it down.

Now, I may have to dip into this savings a bit to find my way in the right direction. School is not cheap. If that’s the route I need to go. But also I know myself and I’m not going to stop working for an extended period of time. I just want to be able do work that is fulfilling. And luckily the kind of work I want to do pays reasonably well enough that after a few years I could probably get back into earning enough to pay the bills. I’m not sure how much I’d have to cut into my savings, or if I could stomach that, but let’s say somehow I manage to not cut into it too much, or at all…

$2M in 30 years at 5% average gains is $8.4M. And while $8.4M in 30 years won’t equal what it equals today, it’s still a sizable amount for a retired couple of 67. With 3% inflation rate that money will equal about $3.4M in today’s dollars, still a sizable sum to retire with at 67. The NerdWallet inflation calculator says that it’s actually worth $4M today (guessing their inflation rate is a bit lower than 3%.) So, if we never invest another dime, we will have $3.4M-$4M if we retire at 67, as well as most of our children’s educations paid for (with $300k saved this year for 2 kids)

Yes, we still need to afford $10k-$14k a month in expenses for the next 30 years, which means earning at least $200k-$250k per year  (together) total to “Coast.” And we’ll probably still save a bit because once my kids graduate high school and go to college our expenses will drop within that 30 year period. If I change careers to something I love perhaps in those 30 years I can move up again and make decent money as well.

There are so many unknowns it’s hard to plan for the future or be willing to take any sort of risk, especially with how little I trust myself to follow through on things. But I also know I’m miserable now because I don’t feel a greater sense of purpose in life.

I’m also feeling a pull to freelance work and the flexibility it provides. I have no idea how to get enough (or any) freelance work to start with, but if I could actually pick up a handful of stable clients who pay me reasonably then – heck – I could go to school and maybe not lose too much money and pivot and figure out life.

So I’m trying really fucking hard to be optimistic. I’ve got to work on a few things, the work that has purpose, building a small network of friends because let’s be real this introvert is capable of socialization like once a month (and then realizes how much she likes it and is sad when it’s over), having more time to spend with my kids and be there for them as they grow up, maybe having one more kid (yea yea I’m crazy) and… I mean, I do, deep down, think things will all work out. Having the money there really helps with that inner sense of – you know what, thinks are actually going to be ok. And as much as this job grates at my weak ego, it has given me the greatest gift in life — the freedom to know things will probably be ok. Things will probably be more than ok. Even if my kids decide to join some crazy extracurricular that costs $10,000 a year. Or god forbid someone gets sick. Or my husband, who refused to get life insurance and now probably can’t get it, ends up god forbid dying before the mortgage is paid off and our kids are out of college. We have the cushion we need where as much as I worry, I don’t have to worry. Not about running out of money, anyway. I mean, I may have to sell the house and move to a LCOL area. But we would be fine.

I have to keep reminding myself that. And while it makes sense to hold on for the next few months in this job to ride out the year, hit $2M in non home equity/529 net worth, and start planning for what’s next, it isn’t worth staying in this job — or even this field — when I know I have so much more to offer. At the end of the day I know I feel good and proud when I’m part of creating something that adds value to other people’s lives. That can be pretty much anything — I’m not so particular. It has to be something new or improved that makes lives better. I want to build things. Fix things. And so, that’s where my heart is. Yea, I’m a mom. But I want to work too. I just want to do something that isn’t so soul draining. Where we all kind of roll our eyes at our work because none of us really believe in it anymore, we just do it to make it to the next vest and the one after that. I’m tired of the golden handcuffs. And ready to call the shots in my life. I just need to find the courage. And the focus.

I Should Update My Blog: What Day Is It Again?

August 14. Also known, in my head, as 170 days before I can leave my current job and move onto the next one without making a major financial mistake. Or 24 weeks, give or take. That’s achievable. I think. I’m doing work, albeit overwhelmed by the work I’m doing. Nothing I’m doing is revolutionary or will get me a good performance review or pay raise this year, but that doesn’t matter since I’m leaving.

But where to? I’m just tired of being in the same situation again and again. Beyond exhausted. I have no experience. Have been working for over 15 years and yet no relevant experience to apply to other roles. I feel really sick about it. I know that I can take classes and such but that’s not really going to get me prepared for an actual position that requires 5+ years of specific experience. So while it’s nice to think I’m finally getting to the time when I can leave, it’s very not so nice to think about having nowhere to go.

Net worth wise I guess things are going ok. The stock market and particular stocks I’m invested in came down, so family-wise we’re hovering around 2.1M when I was hoping to be closer to 3M this year. It’s still possible we’ll get to 2.5M, for what that’s worth. I’d like to be at 2.5M before leaving this job. If stocks rebound it’s possible. Or I can be under 2M again. Oh well.

Just went on a family trip and spent too much money on hotels that were average or less than average and eating out too much. Now I’m focusing on eating healthy food and trying not to waste anything. Basic stuff, but things I’m bad at so if I can actually use all the food I buy that will be a major win (and good for the environment too.) I’m not that hungry today though…

I’m not sure when I should start applying for the new role. I was thinking I would go all in starting December. Bonus payout and 401k match happen the end of January, and if I start applying in December that means that it’s unlikely I’ll get a job offer and start my new role before Feb 1. I’m working on a few projects through April but by Feb 1 things should be in a decent place so I can leave. It’s not the best time to leave but also they clearly don’t want me to stay so why should I care about what is best for the company right now?

I’m trying to figure out how little I can make and still be able to afford life. Since I’ve earned at least $165k since 2016, it would be hard to earn less than that now (esp since lately I’ve been earning $300k+ with bonus and stock.) But I’m looking at the next few years as a transition period. Can I find a job that pays $150k that is lower level where I can get some experience and have a boss who can help me get relevant experience in a specific field, so I can move up appropriately? If I make $150k and have good benefits then I think that would be acceptable. I just don’t want to be underpaid for my work and experience level either. I don’t know. One company may see $150k as a lot of money and another may see it as the compensation for a relatively junior position. I do think $120k is probably more standard for the roles w/ 2-3 years of experience, which maybe is what I should be aiming for… though I don’t even really have relevant experience for those roles. And most won’t even interview me because they’ll think I want more money (I do) or that I won’t stay long if I can get a position that pays more (maybe true.)

So the big question is do I focus on getting a job that pays $150k (which is already $25k lower than my current base not even including bonus and stock) OR do I use my current experience to try to get a leadership role with comp closer to $250k. Will the $150k role actually be a better fit than the $250k role? Will the company see me as a junior/mid-level employee with potential vs a senior employee who sucks at leading? Maybe one day I can work up to leading but I don’t want to go there now. I think. I can’t focus on being a good mom and household manager and a leader right now. I’m bad enough at leadership as it is. So. $150k seems to be the number. I’d love to make $150k at a large company with good benefits and some kind of stock grant to make up for the difference a little bit. I don’t know if I can go under the $150k though, which limits my options a bit. I wonder if I should just delete half of my LinkedIn so people don’t know how old I am and make it look like I’m younger. People say I look young. But then can I really remove the year I graduated on my resume?

Eh.

I’m doing what I wanted to do. Surviving. But then what?

When To Move On From This Job — If By Choice, It’s a Numbers Game

Due to stock vesting, the income for this job goes from high to something I could replace fairly easily within a year. I am still unclear if I received a reduction in pay this year (or any sort of cost of living raise) as such changes were supposed to take effect this pay period and I didn’t see a change in my base pay. Since I’m on maternity leave, it’s possible the change doesn’t go into effect until after I return either way (no one has told me if there will be any changes to my pay yet, so it would be strange for them to change it either way without notifying me — however, last year even when I was placed on a PIP I got a small cost of living raise — so not even getting that is pretty telling… I need to start packing my bags.)

While I’m tempted to pack my bags today and never look back (I’ve had a few recruiter calls that are promising, but I’ve opted to not take them any further.) I’m either going to stay in my field and be really strategic and picky in my job search OR I’m going to change careers (same industry, different department.) The career change, based on some preliminary research, will be a major income cut, no matter how you slice it. I’m torn on this because on one hand, my heart is in that field and I think I might actually be excited to go to work when I wake up in the morning.) But this field — it sounds like — will pay entry-level around 70k-125k. While 70k is a non starter, if I could make 125k… I don’t know… it might be worth it for a year or two as I build up my experience in the field. The bigger issue is the ceiling of income in that field seems lower than where I am now. But I’m not exactly thriving where I am now. So there’s the value of perhaps being in a job where I’m not worried about getting fired all the time (and then getting fired all the time.) Trade offs.

In order to determine when I should leave my current job (and for how much $ I should consider leaving for if I’m staying in my current field) I’ve calculated my estimated income for the next 12 month period at 5 different times throughout the year.  This showcases both how ridiculously strong my earning power is at the moment and how quickly it goes down to still-good but “recoupable” l levels if I were to move to a new company. The challenge are retaining employment through the high income earning periods and then find a job to replace it that provides high income earning potential (a new sizable stock grant) or make the leap to the new field and take the massive paycut and trust it will work out (if anyone will even hire me for that field… I’m starting an online certificate program in it and will see how that goes.)

Income potential 12 month period starting following dates:

At current stock value:

  • April 1: $702k
  • July 1: $599k
  • Oct 1: $425k
  • Jan 1: $299k
  • April 1: $251k

At optimistic (highest analyst estimate) stock value:

  • April 1: $937k
  • July 1: $759k
  • Oct 1: $511k
  • Jan 1: $345k
  • April 1: $287k

At pessimistic (lowest analyst estimate) stock value:

  • April 1: $428k
  • July 1: $411k
  • Oct 1: $325k
  • Jan 1: $246k
  • April 1: $208k

The above tells me I would be a fool to leave prior to Jan 1 in all but the absolute worst company performance scenarios (and even then it’s unlikely I’ll replace my potential 12 month income prior to that date.) I think the actual income will be closer to the current stock value as it’s unlikely it will go up fast enough to hit the analyst target within my actual earning period, but I also think it won’t drop all the way down to the lowest analyst estimates.

But the absolute best my 12-month income will be worth as of April 1, 2022 (assuming I am not getting any stock refreshes or raises, which I assume to be true) is ~$287,000. Which is still a very good income(!) but it is definitely in a range where at least looking for a new role makes sense. It’s an extremely high 12 month income for the role I’m in now at work (after my demotion) so I’m not complaining about it by any means, it’s just completely unrealistic to think I will ever be able to replace my previous income in this very limited role that is unfortunately not respected in my industry. I’m lucky in that my company likely won’t go out of their way right now to reduce my pay after I just had a baby — but they also won’t ever go out of their way to increase my pay. My days are numbered at worst and my income potential has a sharp ceiling at best. The absolute most I can earn in 2023 would be $248k (no raises or refreshes) and in 2024, it would be $213k — whereas if I go into a new role in a public company I’ll get a new larger grant that can possibly increase in value. My company is doing a favor by not giving me any raises or refreshes at this point… it helps the math tell me what to do.

That said, this year has a lot of good 12-month earning periods. My expected quarterly income is as follows for the next 5 quarters:

  • Q2 – $191k ( 103k-265k)
  • Q3 – $219k ( 131k-293k)
  • Q4 – $191k ( 103k-265k)
  • Q1 – $101k ( 88k-113k)
  • Q2 – $51.4k ( 38k-62k)

This also helps me figure out if I can potentially obtain a signing bonus to make up for any lost income, where it would make sense to move to a new role.

The above also shows that if I can move into a new field, it may not look like such a horrible comparison if I base this off next year’s Q2 income (as it will take me another year to have the potential to earn a bonus anyway and my stock is not increasing.)

The big question is — how do I stay employed for the rest of the year? I’m going to try to focus on taking it one quarter at a time, and celebrating earning the quarterly income. I have to remind myself that my husband earns $100k a year and I very well may earn $200k in 3 months if I can manage to retain employment for those 3 months. Even if I were to get fired at that point, I will have made over  $450k this year, give or take, as of July 1. This alone should support my leaving my company and taking 6 months to gain experience in a. new field and figure out my life. But then the tradeoff would be losing out on another $300k or so, which also seems like a really dumb thing to do. At what point in the future of time will I ever have the opportunity to earn this much in such as short period of time?

I just assume my new boss is earning less than I am overall, and that’s not going to set anyone up for success here. He may be earning more but it’s unlikely given he came in at a later date. He may have gotten substantial stock refreshes since he’s a company star but even then I bet we’re around a similar income this year. Maybe he will realize my income will be dropping substantially soon and won’t hold that against me, but he may just look at everything I do in the lens of what I’m earning now (due to stock appreciation) and in that case I would agree I’m not worth what I’m earning.

…I don’t know how the company looks at that because it’s not my fault the stock has appreciated so much… but on my annual performance review they note my expected annual compensation and that’s based on the stock value at the end of last year. That’s a big number (even bigger than what it actually is now because all tech stocks dropped a lot since then.) In any case, I just want to get myself out of all of this and get a job where I can add value. Which means I should probably change fields. It’s tough when recruiters are calling me left and right for senior-level roles in my field, all that pay in the $250k range (and maybe I could negotiate more.) Do I really set myself back years and take a job that pays $100k-$125k to try something new at 38? And why does my husband get to earn $100k yet I can’t do this… even if it will make me happy? I guess he doesn’t believe anything can make me happy… and that might be true. But I have high hopes for this new field. I think it will at least work the right part of my brain vs the one that makes me constantly frustrated and unsure how to do good work. Hmph.

Serious Career Transition. It’s Time. Almost Time.

I had a heart-to-heart with myself this week. Self: it’s not them, it’s you. You hate your career. You hate your career because for the past 15 years your job has been to promote what someone else has built, instead of building it yourself. Plus, you suck at promoting. You like to come up with ideas and build them or manage the building of them (more managing the building of them.)

I want to wake up most every morning and be excited about MAKING each day. I want to work alongside people who are builders. I get along with these people better. Generalization, but I’ve found I enjoy spending time with engineers. Why? I like logic. People on the business side of the house are not so logical, even if they think they are. Business side is all about making the impossible possible. That drains you. You are under resourced and expected to deliver nonetheless. There is no “finished.” Not that there is “finished” in most tech these days given everything is software with constant upgrades and bugs and whatever, but a least you can put something out that people use and probably feel some sense of completion and that you built something or were part of building something.

You know what’s not rewarding? Taking a product that someone else built and then making people feel something about your brand so they buy your product. I want to make the product. I want to fix the product. I want to make the product great. Period.

If I get fired, I’m going to dig into my savings and go to some sort of coding bootcamp and try it out. If I don’t get fired, then I have a little more time to learn something. I have no fucking patience so I’ve never managed to teach myself how to code beyond HTML. I think maybe if I start drinking a shit ton of coffee a day that will act as over-the-counter Adderall and I can learn something. I want to build a more accurate rent-vs-buy calculator than others online (although I’ve seen a few good ones but it’s not super easy to adjust all the variables) so that’s project #1 I think. An idea. But maybe I’ll do it. One never knows with me.