Category Archives: ADHD

Career Revamp: How to Accept Lost Income and Savings?

I am trying to make it through my job, but at this point I’m acknowledging that my career is just not a fit. I’m very (incredibly) fortunate to be in a position where I’ve been paid a lot, which has allowed me to purchase a home and superfund my children’s college savings accounts. Compared to most of the world I’m in a really good place. It doesn’t feel that way, but I constantly I have to remind myself that I’m doing pretty great.

But it’s still hard to look at the future ahead of me and think about what to do next. I could pretty easily (with the right antidepressant anyway) stay in my current role and continue to earn $200k-$300k per year. If I knew 100% there was something else out there that would be a better fit I would be willing to give that up for lower compensation, but the reality is I don’t actually have any idea if another job would be any better. I could leave this role, take a position for $80k, have to dip into savings for years, and still be completely unhappy — maybe more so.

There are things about my career that aren’t a good fit for me. Some of these things are part of any job but maybe lesser so in another field. Having to influence people is really challenging for me. I am not a good communicator. I’m not great at being organized, but also I’m worse at it when I have a job that requires so much context switching and doesn’t have clear measures of success or completion. I worry that a job with clear measures of success and completion would bore me–when I’m bored I don’t do good work either.

I’m really seeking a career where I can be in “flow” more often than not. Maybe that’s unrealistic. I know I like working on projects where I’m collaborating with a team and building something and being part of that trajectory to create something from nothing and then get it out to the world. I think this is pretty consistent in the few moments in my career and life when I’ve felt in the right place. But this concept is not a career. This concept does not pay the mortgage.

I wish I could just figure out a way to do this job and not feel so horrible about it. But when it comes to creative work I find I’m either all in and doing really good work or I can’t engage at all. I can’t half engage. I can’t just get it done and not care and spend the rest of my day doing other things. It haunts me from the moment I wake up in the morning to the instant I fall asleep, and often even finds it way into my dreams and/or nightmares.

Really all I want is to feel good at something and like I’m actually contributing value. I don’t think I am now. Often I’m told that I must be or else I would’t be paid what I’m paid. Well, someone at the top believes in me despite my being a total mess, but not to the point where he cares to help my career make any sense. My job is to get random things done that are high-stress projects with no clear definition of success other than a bunch of people decide they are ok and then they are done.

The work I have is not impossible time-wise. It’s just impossible in the sense that I cannot do it. Or, I do manage to do it, at the last minute, after a whole lot of stress. Maybe that’s why I get paid so much. Because no one else really wants to do the jobs I do.

I’m just tired. Tired of not knowing what my career is. Tired of feeling like everything could fall out from under me at any moment. I realize I’ll never be perfect at my job, but I would love to have a real career where I start at a lower level and have regular promotions every few years because I’ve actually done a good job. Is it possible for me to do a consistently good job at anything? If I could do ANYTHING what would that be?

I think fundamentally I need to revisit if I’m really a creative person. I’m constantly pushed into creative type roles but I don’t think I’m creative at all. In fact, maybe I’m at the point in my life where I prefer to be quantitative in my work. Not that I know how to be, but maybe that’s an area to explore. I just can’t imagine myself in a job interview where I can hold my own where I’m asked questions about data. I process too slowly. No one would hire me.

And I like to do things my own way, which isn’t how the world works. People want you to know what you’re doing and follow the established path with minor deviations.

Part of me wants a job where I interact with people more. Again, going back to the drawing board — being some kind of counselor… or even a nutritionist? But then I realize that I’m just not mentally well enough to have a job that requires being stable enough to see clients regularly. So that crosses off a lot of jobs out there. I don’t know. Maybe my current job is the best job I’ll ever have. It pays well. It’s not that hard, it’s more like managing a puzzle that constantly has new pieces showing up and you just have to figure out how to put it all together well enough that people don’t realize you’re missing pieces and then you move on to the next puzzle. Nothing ever feels done or good. And that makes me feel sick.

I’m trying hard to start building a life outside of work. To at least focus on my health with exercise and eating well. If my entire career is going to go to shit then the least I can do is make sure I’m as healthy as I can be physically. I have to try to believe that there is an answer out there for me somewhere. I need to find it and I need to drive the change. I need to start believing in myself. I’m embarrassed of how I present myself to people. I’m going to be 40 soon. I need to get my shit together.  On so many levels. I should go to the psychiatrist and get meds and I will soon. I’m not sure how that really helps but maybe it does. I’m willing to try anything right now. To help me stop being this–whoever it is that I am. I need to grow up, grow a pair, and just get on with it. Life isn’t waiting for me and I’m too impatient to wait for it.

Two Roads To Nowhere and Everywhere: Stay at Home Mom vs Working Mom

I’m sure people reading my blog think I’m crazy with now over $2M in net worth not feeling comfortable leaving work for a while… a few months… a year or two… to spend with my young children. Maybe I am crazy. I’ll tell you what I feel. I feel no different than I did five years ago when my net worth was $500k or 10 years ago when it was $150k.

I am struggling with the concept of time and the time of time. 10 years passes in a blink and yet was it all that fast? I don’t know. 10 years ago with $150k net worth I was just starting my first job in this series of jobs after another series of jobs. I was making $100k. At the time that was such a huge salary I thought I would never earn more. Who would pay me more than $100k for anything?

10 years ago I was 27 going on 28. Approaching my 30s. A far different mindset than approaching one’s 40s. Pre children. Pre marriage. Living with roommates and dating my now husband and struggling with enough depression and self-hatred to push myself to keep going to prove that I could survive. Don’t believe me? It’s all here in this blog. All the years that have sprinted by. The failures. The successes. Three firings later. Day after day of waking up feeling not good enough. Not knowing what I’m doing. Trying to make it work. Trying to fit in. Having good moments. And many bad ones. Ten years later.

What will my life be 10 years from now? I’ll be 47 going on 48. What then? Will this decade feel over in a blink as well? How can I slow it down and make sure it lasts as long as possible – savor every second of it? I don’t know if one can at this age. Time just speeds up. And so there’s time and there’s money. It’s the race of both. You can spend less money. You can’t actually stop time. But to afford to leave the workforce you need a lot of money– and even then the system is rigged against you. That money in the stock market. Sure it will likely keep going up over time. That’s what they tell you. It has in the past. But the past is no indication of what will happen in the future. Though the only way to actually afford the future is to take what you’ve earned and bet on something that likely will go up but really who knows.

I’m too heavy in equities. Too heavy in individual stocks, although mostly in index funds. If the whole market crashes, how much does it matter? Does this mystical, mythical $2M disappear overnight? It doesn’t feel real if it’s not spent and if it’s spent then it isn’t real anymore at all. So it sits there, notated in an overly complex google spreadsheet that I look at each morning to see what it all looks like on that day. I open my computer and start trying to do work for my job that is fulfilling only in when I can help other people do their jobs that I’m uncertain if they find fulfilling or just acceptable in order to earn their own mystical, mythical money. I don’t know. I sit in meetings with senior executives who go off on some rant about something that at best doesn’t matter in the grand scheme of the betterment of the world and at worst are stained with sociopathy and that sly smile in passive aggressive attack that only someone with way more money in the bank can slide across their face so damn effortlessly. Everyone is trying to prove to everyone else that they are needed for those ahead of them to win and so even with the best of intentions it becomes this sick game that I’m not cut out to play.

10 years. My father was still alive. Still diagnosed with cancer. Still dying. But alive. Still yelling at my mother. An artist of arrogance. We were all so much younger then. I try to tell myself. 10 years is a long time. 10 years from now my oldest will be 13. Thirteen. My youngest, either 11 or 9 depending if I have another. I’ll hopefully be alive, but 10 years is also a long time for one’s body to attack itself, for health to slowly… or rapidly fail. For my husband to be here or to be ill or not here at all. For my mother to make it to 78 or pass away in her 70s, at an age that no longer inspires those who hear of passing to gasp noting “she was so young” in their condolences. It seems at 70 or maybe 75 it becomes acceptable to die. In ones 80s no one would feel pity over an early death. And 90 is when one feels pity that the person is still living. How fast the years go. Especially if you don’t make the greatest effort to slow them down.

And how can you slow them down? How can I? Well, I feel like there is a choice here. A fork in the road. Like in Squid Game — everyone chooses to play, even after they see what is at stake. Here I am and I see ahead of me 10 years of my children aging from babies to teens and I wonder how much of those 10 years is worth trading for days of panic attacks and feeling horrible at my job and to tired to be much of a mother.

Quit now and move somewhere affordable seems both like an impossible movie plot and an actual life story that could be mine. If only I wanted it enough. And then my husband agreed to it as well. Which would be quite difficult, but if I really knew in my heart it was the right decision — I don’t know — maybe I could convince him we need to leave this place. In a year sell our house. Get away from the rat race. The rat jungle. The rat infestation and bro culture and imposter syndrome and open office spaces and egos and people do don’t have time to connect or build community or they want you to pay a lot to buy in to a community you’ll never be a part of anyway.

If I quit here and stayed here I’d surely eat into my savings quickly. I’d want to do things during the day and going for walks to local parks would get boring after a while, wouldn’t it? There is much to sign up for if you’re a stay at home mom but then you need the money to fund it. Writing is free, at least. But what about my kid’s activities? How do I make sure I have enough to support their lives? I feel that I owe them the upper middle class life I was raised into. I didn’t know how to provide that but somehow through luck and determination here I am. Upper middle class. I guess. It doesn’t feel it. Not like my parent’s generation. One working parent and a nice house with decently nice everything. I’m certainly well off now in most of the world. I certainly don’t feel it.

But I do feel I owe my kids a life at least as good as the one I had growing up. My sister, who makes $14 an hour, refuses to have children because she says she can’t afford them. Yet many people have kids with low incomes — it’s just we were raised into a certain style of childhood and life and we feel our kids deserve at least that. I don’t want my kids to be spoiled. I don’t think I was either. Not horribly so. A little. But not enough to sit on my ass and do nothing. My sister has an incredible work ethic but no belief in herself or her ability to do better. I have random spurts of energy and a character flaw that is my need above all else to prove that I can survive and fit in and thrive in a world that may not be worth surviving.

What if — one year from now — I’m sitting somewhere, some nondescript down maybe — watching waves of a lake-ocean-river-sea crash to shore. Maybe it’s thundering. Or drizzling. Or pouring.  And I’m soaked and running in puddles with my children who are still children. And they don’t remember mom everyday at her laptop working or avoiding working and looking at social media only to be working later when she shouldn’t be because she can’t focus or get anything done. They wouldn’t remember the mess of a house or limited meals but instead clean floors and nutritious fresh food. We’d go on playdates and maybe get to know some people. Really get to know them as friends and build a community, though that’s wishful thinking as being a stay-at-home mom doesn’t suddenly turn me into Miss Popular. But still. What kind of life would that be? One where I am watching my account balances shrink each month instead of grow. I’d be terrified.

That fear is what drives me. But I don’t want to get to 2031 and look back on the last 10 years and say I traded moments for money. I let myself fall into the trap of worrying every single fucking day and waking up each morning feeling sick to my stomach because I know I’ll never do a consistently good enough job at work. Because I’m always on the verge of losing my job and having to admit failure yet again. To pick myself up again. And spend months trying to prove myself. A few victories here and there but nothing enough to stick. And so on. 10 years of that. I don’t know if I can take 10 more years of that.

See, 10 years ago seems like a long time ago. But 4 years ago seems like practically no time at all. Sure, in that time I’ve had two kids and both have grown quite a bit, but that time is all a blur and it doesn’t feel like 4 years it feels like 3 months. Though there is so much of it that I don’t remember. That skips time. And I’m afraid the next 10 years will be that but even faster. So I desperately want to slow the time down. To be present with my family. To take time to be a mom, not a mom who is thinking about the 10 meetings she has the next week while assisting her sons onto an amusement park ride.

I should be grateful that I have the money I do have. It does provide some options. It’s enough to tease me with those options but not enough for the options to be all that real. It’s enough, earned fast enough, to throw in my face that if I leave the workforce I’m not only going to be digging into my savings, but I’m also giving up the opportunity to really get to a place of financial independence for a lifestyle I want to have for my family. Why not a few more months? A few more years? Why not just keep holding my breath until my bank account ticks up to the next hundred thousand? I’m thinking $2.5M before leaving this job, but why not stick around until $3? Why not find another job to take me to $4 or $5M? $5M is the ultimate goal, $200k a year of income from the growth. Maybe then. Maybe then I’ll feel like I can slow down. But when will then be? Will my mind be complete mush by then? It’s hard to say. I just know I’m tired. I’m so tired. I’m tired mentally and physically and I need to sleep. So I’ll sleep now and wonder more about how people make decisions and how I can make decisions and if I’m even allowed to since now I’m a mom and a breadwinner and a home owner and I don’t get to just pick up and change things if they get too hard. This is real adulting. And it better be because I’m fucking old now.

When is There Time for Enjoying Life?

Another Saturday. Another October. Another fall. Wasn’t it just two years ago when I was going absolutely batshit in the middle of an undiagnosed mania, which was enjoyable only during a week in London when I wandered around and manically documented fall leaves against cobblestone on Insta? And mostly un-enjoyable when I was thrust into this alter-ego self who isn’t particularly acceptable by any standards of normal socialization. And now, back into fall, two years later, a world later, a pandemic still pandemic-ing later, an infant to toddler to pre-k’er and a new baby who is about to be a toddler later, $1.5M in net worth later, a house purchase and a health scare and a clean MRI later, here I am,  new place, same place, trying to be grateful for everything because I know nothing lasts forever, and failing miserably at embracing gratitude over guilt and grievances. So, same old, or same new.

Fall is a monster of melancholy. Autumn air exhausts exhaustion. I could easily lie in my bed for the following months and not notice how long I’ve been in hibernation despite how mild west coast’s seasonal changes are.

The truth is I’m incredibly overwhelmed, behind, and unable to figure out how to get any of my Iife in order. Having ADHD with a heaping of perfectionism makes it extra hard. My house is chaos. I’m trying, despite not sleeping much last night, to muster up the energy to clean it. Organize it. Ok, so it won’t be a home as in a home that I want to live in, without a private bedroom and instead a living situation I should have never agreed to but let my frugal house-hacking hat take charge in a decision I can’t go back on. It’s not the worst case. It’s a house. We own it. I don’t like being a home owner. I knew I’d be bad at it given I wasn’t the best at maintaining a one bedroom apartment. But there’s still something good about owning. Not financially good. It just feels like a real accomplishment. I haven’t had any accomplishments. None that felt worthy of being called an accomplishment, anyway. I guess graduating college is an accomplishment. Getting a job is an accomplishment. But they never really felt like much of anything to be proud of. Everything was barely completed. A failure in the making. Maybe home ownership is too. But I feel really good about buying a home for my kid’s to live in. I don’t think it makes any sense but it feels good to own a house. I know plenty of parents don’t own and it’s fine to raise kids in apartments but for me that would be rough to accept. I blame growing up with a mother who frequently mentioned the kids in “the apartments” as being poor and thus bad somehow. Not that I believe that now. But still part of me felt like buying a house made it ok for me to have kids. Saving enough to afford them, whatever that means.

But now I have a house. And savings. Nonetheless, I feel incredibly behind. And every moment I feel like I might be getting ahead life plays a joke on me. Like just now. I put my wash up and was just admiring how nice my laundry room floor looks like without the huge pile of clothes on it. And then a big “bang” shakes the ground and my eyes question what they just saw as a giant container of Woolite my husband placed on top of the washer apparently leapt to its death, with the lid flailing off of it and spilling soap all over the remaining pile of clothes and the chord to the Swiffer. Nothing unmanageable as one thing, but life feels like a big pile up of a cluster where you take 2 steps ahead and 3 steps back.

I wanted to be a full time mom on the weekends, with the in-laws NOT taking care of my children, and yet here I am again, 11am, in-laws watching the kids as I attempt to clean up. I’m always cleaning up but never getting anything clean. I also am so tired. I stayed up late catching up on work because the only time I can focus on work is when my son is asleep on me from 9-1am. Which is when I should also be sleeping. I’m still far behind on work. Luckily my actual work requires about 20 hours a week to manage at this point, it’s just the issue of finding uninterrupted time.  I’d give anything for 6 hours straight with no distractions. But that’s impossible since I either have to feed my son or pump. And yes, I can stop breastfeeding at any time but I’m not willing to sacrifice that for work. There are some things I won’t sacrifice and that’s one of them.

(loud thud on cue. Another bottle leaps from the top of my washing machine. This one seems to at least have its cover on tight and no spillage is observed.)

I keep thinking if only I can just get my life together. Just get my house in order. Get caught up at work. Make lists of everything I have to do. Go through the list. At some point. At some point I’ll be able to breathe this breath of fresh air and spend time with my kids in a way that feels relaxing. I will be able to make the case that my in-laws (especially my FIL who lives with us) should stay in his apartment/room on the weekends so I can be a g-d darn mom. That doesn’t mean spending every second with my kids, they should have some boring down time too. I had plenty of that as a kid. I really don’t like that grandpa is with my son from 9-4:30 straight every day.. I’m glad my son started preschool but that’s only 2.5 hours 2 days a week. And I feel like a failure not being a mom right now. Yes I’m writing this blog post. As a break from cleaning. And now a break from cleaning up the spill of soap on the laundry room floor. Before I need to feed my baby around noon, probably, then breastfeed at 1 and put him down for his nap (he’ll only sleep on me or dad and dad is working today so that means I’m stuck in bed from 1-3 or grandma takes him and he doesn’t sleep.)

There is this overwhelming feeling/acceptance at this point that I’ll never actually be able to live the life I want so why the fuck try anymore. That is what led to this idea to quit work in August. I know I’d be ok for a few months without an income but I’m really scared I won’t be able to find something else or if I do that the job will require even more work and less time with my kids. For all the things I don’t like about my current job it really is super flexible while I can work from home (not sure when I have to go back but eventually) and I shouldn’t given this up, even if my income goes down year after year because I’ve been demoted without a pay decrease but I won’t actually get any stock refreshes so there is no way my income will keep up unless I go to a new company. I don’t have the energy to go to a new company. I can barely keep my eyes open.

I wonder if there’s a way to get my life anywhere near where I want it to be. I ponder hiring a cleaning service for the house, then find out cleaning services will cost $350 to come for a one time cleaning and $200+ a month and it seems like I should just learn how to clean my home.

(Another bottle flails off the top of the washer with a loud clunk. Not joking.)

I just want a kitchen table. A non plastic-folding kitchen table. A bedroom with a door. Grout in the kitchen that isn’t brown when it’s supposed to be beige. A refrigerator that holds more food. Sheets that aren’t navy with an olive green comforter my husband bought years ago for camping. A backyard that doesn’t have an accidental tree growing against the wall of my home and breaking the foundation. And trees that aren’t in various stages of dying that need to get looked at for another few thousand dollars.

It’s funny because the more money I have the more I get anxious about it. In investments it doesn’t feel real. But I just know that I need it there as a safety net. I mean, if I were to have $10M I could never work again because it’s impossible for me to spend more than $400k per year if I knew that was something I’d have forever. Not that I need $10M before FIRE, but just saying where I’m at now is not FIRE for me.

A friend I met on a social site for moms in the technology world told me she got hired at a company and will be making 500k a year, and her husband is promoted to a job making 400k a year. They will be making 900k+ a year for the rest of their careers and probably much more as they continue to get promoted. How do I compete with that? I don’t have to compete with THAT but that’s what people are earning here in the Bay Area. Or one-worker families with engineers making like $600k or more. In my current company had I not fucked up I could have been on the high-earner trajectory. I even magically experienced it for a few years (I’ll be making about $600k this year with my stock earnings.) But that’s not forever. That’s not even next year. So just quitting doesn’t seem to be the right answer either. Do I try to convince a FAANG to hire me (they won’t) or do I go back to school or do I give up and convince my husband to move to anywhere else we can buy a house and not have a mortgage so high and where I can actually be awake to see my children on occasion. I don’t know.

I feel really sad is all I know. I should keep cleaning and I probably will. I need to get that soap off the floor. My husband is busy with a project he took on to earn $5k extra a year. That’s good for him. I always complain that he doesn’t take on any extra clients so I should be incredibly supportive. But then I wonder in the extra $5k worth it… $2.5k after tax. For all the work he puts into this project. Especially three days when he needs to be available full time and works into the night. I don’t know. Money is so weird. I know we have more than most people in the country but I’m in this weird bubble of Silicon Valley where money doesn’t make sense.

And I’m just. So. Tired.

 

Looking Ahead to What’s Next and Getting Through the What’s Now

I really, really, really want to stay in my job until at least the end of this year. I know it won’t be the end of the world if I don’t make it that far (even a few months into the year and I’ll have earned more than every single prior year of my life with the exception of 2020) — but, BUT… I really want to do this. I want to somehow, in the middle of a pandemic, in the first year as a mom to my second child, while trying to ignore the gnawing sensation of my ego being constantly ripped apart by a boss who has banished me from any semblance of leadership and telling me, flat out, that I will never, ever be a leader, hold on and get through it without any more wounds along the way.

But I’m also–exhausted. Sad. Upset with myself but also at the system that’s just… against working parents and especially new moms. I’ve got too many issues, I guess. If my mental health alone wasn’t enough to destroy my hopes of job stability, then we add in my having children. I don’t regret having children. But it does make it harder. Having to wake up every few hours to feed my child with my own body, well, that makes it harder. And I wish I could have stood up for myself more–but I’m not sure how that would have helped. Does anyone care why I’ve struggled? That’s just more reason to say I’ll never be a leader. So what if I tend to babble more on my worst days? I babble enough on my best ones. I’m not a leader. Not this type of a leader. Maybe not any type. I don’t have that kind of energy. I’m not consistent. I’m a ball of energy that can come in and explode and then need time to pick up the pieces and inflate again.

Maybe there could have been a little more support? I don’t know. On one hand, I’m completely to blame. I don’t expect anyone to hand hold here. On the other, some companies went out of their way to support working parents. To cancel performance reviews for the year. To provide time off and flexible hours. Others, like mine, expected us to just keep up. When I failed to meet a deadline there was no discussion of how I’m doing the best I can in a global pandemic while parenting a toddler and dealing with the exhaustion of pregnancy. I mean, who cares, right? I missed the fucking deadline. That I set. So, that’s on me. All of it’s on me. I shouldn’t have set an unrealistic deadline. And any deadline would have been unrealistic because my anxiety made it impossible to get the work done until I already was late and had failed. I can only do good work when failure is not only imminent, but it’s a sure thing. I can’t blame anyone but myself for that.

I don’t think the work was good anyway. But I guess it wasn’t bad. It seems some people thought it was ok. It doesn’t matter. I’m a never leader. And I cry about this every fucking day. Because she’s right. Because I can’t hold it together.

But my problem isn’t that I’m a never leader. Well, it’s that. But it’s more I can’t be relied on to do anything when anyone else is relying on me. That’s not a leadership issue, that’s an ability to keep a job issue. That’s an issue that has plagued me since I was fired from my first job as an admin assistant to every single job where I found myself too panicked to get work done. Why? I didn’t know what I was doing. I didn’t feel confident in the quality of my work. It wasn’t perfectionism, it was being embarrassed by how bad I was at my job because I didn’t know what I was doing. Sometimes I put out good work but in the grande scheme of things I never know what the fuck I’m doing. I don’t have the confidence or ability to fake confidence so people lose trust in me. They move on. They aren’t on my side, they’re against it. They say shit about me behind my back. They wonder why I’m still employed. Until I’m not.

This is a problem.

I could have been good at this job, too. I mean, I’m a never leader but at the very least I had some decent ideas, if anyone cared to listen. I had my hands tied. I tried to be collaborative, as I was told I was working in a silo and this was bad. Then I was told I was too collaborative, which is not leadership either.

It’s hard enough trying to navigate all this not as a tired pregnant mom in the middle of a pandemic, you know?

Is this an excuse or reality or a little bit of both? How much harder could I have worked? There was too much spinning and I was spun out. Off to “lead” a function that no one wants to fund properly and I must wait to be told what to do. And even in this role I managed to already mess up in a meeting where my former boss basically was on the verge of firing me at the end of it because I was a babbling mess.

I don’t think it’s this job. I think it’s my inability to do well in any job. So I need to fix that. But how? I have no fucking idea.

Junior level jobs still require you to be good at communication. Get shit done on time. The basic things I am bad at. What I’m good at is strategy and planning. But you don’t get to do a lot of that at the junior level. I just wish I knew what the fuck I was doing. Will I ever? Not when I’m this tired.

I go back to work in 2 months. That’s a world away but then it will be here in the blink of an eye. It all goes so fast. If I’m as tired then as I am now then I don’t know how I will make it. If I’m WFH that’s a good thing as I don’t have to drive half asleep commuting to the office but I do have to keep my eyes open on long zoom calls and try to appear alive when I’m clearly not. At least I’ll be too tired to physically appear jealous or sad or whatever when my work friend who is now in my former job is saying shit in a way that shows just how good someone can be at sounding like a leader as a reminder how I’ll never ever ever be that.

She’s right.

I don’t know what I’m good at. If anything. I just know I’m tired. Tired of constantly walking smack into walls. Tired of living on little sleep. Tired of being tired. Tired of reading articles about how working moms are not supported in society and feeling all righteous and angry for every other working mom out there but then when I turn to myself I feel guilty for absorbing any of that anger against “The Man” for me because I don’t deserve any of that pity or sympathy or empathy or whatever support should come with it, right? Other moms, they deserve to be provided something to get them through this but me? I’m failing for some other reason. My own reason. My own messed up issues that aren’t going away even when the pandemic is long gone and my kids are grown. I can’t ask for help because I don’t know what would help anyway other than maybe a personal cheer squad that tells me my work isn’t shit so I can just get onto the next thing and the next. Is it shit? I don’t know.

And I was on a performance plan a year ago and my boss clearly did that as a safe way to get me out and then I briefly was doing ok and that saved me for a short while and she was all excited that I managed to turn things around until I turned into a pile of shit sandwich on the floor. I feel and about it. I wanted to prove her wrong. Instead, I proved her right.

So I’m sad. And tired. And what’s new?

When You Do Good Work But It Doesn’t Matter.

I struggled through a new process at work that was ill-defined and required leadership where I did not serve the role as leader effectively for a number of reasons. In the past–less than two months–I went (briefly) from a top performer to bottom of the pack. This time, I really tried. But I didn’t get everyone to move fast enough. I didn’t get myself to move fast enough. I committed to dates that in hindsight were unrealistic, but I also didn’t know enough about what I was doing to fully scope the project and understand WHAT I was committing to, which was the biggest problem.

In the end, I lost my leadership role and was transferred to another position. Which is fine in that I don’t know if I would do THAT much better should I be offered another chance. I don’t think I’m creative enough for the position, or able to produce the best work required by the position. The guy who is taking over (who happens to be my friend) is way more confident, has a clear vision, and is a leader. He’ll do well. He believes in himself and his ideas. I wish I believed in myself but it’s hard when I don’t know what I’m doing.

I’m a bit sad this week because the project was actually launched on time, despite my initial delays that led to me losing my role. There is a lot more to it, but basically my failure to force everything through a new process and timing that I agreed to led to my hitting a wall. In fact, had I not been pregnant, I think I may have lost my job a few weeks ago. I’m not sure. In any case, I am conflicted because I’m proud of the work that I was able to put out and feel like I collaborated fairly effectively with the team, and yet in the end it doesn’t matter because I messed up when it came to certain delivery dates that really had no meaning outside of my setting them.

Talk about self sabotage.

It didn’t help that a project manager came in and threw me under the bus multiple times. That was not a good situation. Again, I take the blame for the dates pushing. She had convinced me that moving the dates for delivery of this one part of the project out a few weeks wouldn’t hurt, and that it was better to be realistic in whatever date I set if I was changing the delivery date. I had a planned vacation in there as well, so the date that was reset to seemed quite far out. I knew it wouldn’t impact the semi-planned launch date (I couldn’t get everyone to agree to a launch date or what launch meant to begin with, which was part of the problem) so against my better judgement (of which I have little) I agreed to the delayed delivery date. I knew this date still gave the team plenty of time to hit the semi-agreed on launch date by end of month for all of the other work that needed to be done once I delivered my part of the project.

Oh, it also happened that the week I was on vacation there was a meeting where my boss joined and the project manager said I decided to move the dates and acted like this was not her idea and she didn’t know why I decided to move the dates or why I was delivering the project so late.

Well, all of this set off a ripple effect of shit sandwich. Everything was hooked up in our project management system so suddenly dates for all the next steps tied to a launch date we never committed to moved out, and everyone freaked out. My boss was unhappy to say the least. I tried to explain that this shift wouldn’t actually move the project launch timeline we committed to (by end of month.) But that didn’t matter. I missed a deadline, which has been an issue of mine that I had to not do again this year, and so, I’m out. Kaput. Well, transferred.

The new role is fine. It’s an opportunity to focus on one area and build processes there and if I can just get shit done on time (and really pad everything even if I get pushback up front on how long the timeline looks) then maybe I can survive the next year and become a better project manager and people will trust me again.

I just wish I was judged for the quality of work and how it will help the business in addition to any pushed deadlines. I should have just said hell with quality and minimized scope. That’s what a true leader would have done. Or any person in their right mind who doesn’t want to lose their job. But I saw the opportunity to do good work and I didn’t want to skimp on anything. This took time and reviews and feedback from a lot of people. I don’t actually love the end result (it’s not even my vision, I took everyone else’s ideas and executed on them generally) but I think it’s solid. I think it will be good for the business. I think it deserves some kind of “not getting fired” recognition for being pretty ok.

What I’m most sad about is I get it now. I could take what I’ve learned and do it so much better next time. But I’ll never have the chance. Not here, anyway. Maybe that’s ok. I can take what I’ve learned and one day apply it elsewhere, even if the processes and people will be different.

On top of this project, I’ve spent the last year building a foundation for a lot of the general processes in my respective area. I’ve done a lot of work that my boss unfortunately doesn’t care about (which is dumb on my part) but I still know it will help the business and maybe, eventually, one day, someone will notice. Or not. But I feel good about that too.

In short, I’ve learned a lot this year and I think I’ve done pretty good work. That is meaningless because I missed deadlines that set and also suck at communication, apparently. Some parts of the communication were easier due to everyone WFH and others were harder. A few slack and email conversations were incorrectly interpreted. There were a lot of cooks in the kitchen and I was just trying to make dinner on time for our guests, but the cooks were all mad at me for delaying parts of the process. Dinner was served on time.

So I’m just frustrated at this point. And unsure if I’d be happier had I met deadlines and kept my role going forward. It would still have been hard, and I still would have struggled to drive alignment and get everyone moving in the same direction. I am sad because my friend (who is very good at his job) was given the role–not because he was given the role–but because of why. Because of all the things he is that I’m not. I’m not jealous or angry or resentful. Just sad. I process things too slowly. I don’t use big words or sound smart and confident when I talk. I don’t have that gusto that is needed where everyone just trusts you and your vision. Nor do I have it in me to put out work that I’m not proud of just to hit deadlines, which seems to be a key skill in leadership. To me, everything needs to make sense. If we’re doing something, we’re doing something that isn’t just to check the box and move on to the next thing. I actually want to put out work that adds value.

I just need to do that faster.

And it’s too late. I have a few weeks left at this point before maternity leave, and I’m already transitioning to my new role. When I come back, I’ll have to build processes from the ground up again. I enjoy doing that, but it puts me at risk for the same issues in a way–because I’m learning how long each part of the process takes and trying to sort that out with a whole other batch of cooks that are slightly different but equally opinionated. I don’t feel good about that. I want to be able to take what I’ve done and learn from it and do better next time, versus start over.

But it doesn’t matter. I don’t get that choice. And to be fair, my boss has given me a lot of runway through the last years, through my mental health issues, through having a baby, through getting a performance plan and then six months later being recognized as a top performer (not by my boss, but still) and then another two months later of letting everything get to me, falling apart, and giving me the opportunity to move to a new role that has less visibility, so I don’t make her look bad. I get it. I’m not upset at that.

I’m sad because I wonder had I just hit those dates, would I still have this job? I know there were other issues with communication and such. I felt like maybe the work I was producing wasn’t good for a while. The more exciting parts of the project requiring more work from others were cut due to reprioritization. I stepped in and filled in the holes versus just accepting that we were cutting a crucial part of the project.

What my colleagues get that I clearly don’t is that you just have to protect yourself. It’s all a game at the end of the day. Good work matters, but we’re already doing good work–that’s why we were hired. What matters is that everyone else sees you as someone they can rely on to deliver. I get that. I don’t know how to do that and also stick to my principles of always delivering high-quality and meaningful work.

In the end, the project was delivered on time, and I’m on-time being delivered to a new position.

I did not get a formal demotion or reduction in pay (likely because of the whole being pregnant thing.) I have no idea what my new title is because things are always so disorganized that no one has brought this up yet. No one has actually even informed me that my coworker is taking over for my role officially. It seems either they are too busy to do this or they are purposefully waiting until I’m on maternity leave to make the transition. However, it’s a whole bunch of awkward given that people keep asking me who will be doing my role and I have to answer them I don’t know. They seemed to want to set this whole thing up to make it look like it was my choice to move into this new role, but they really aren’t giving me a lot to work with to support that story. Meanwhile, if coworker friend takes my title, wtf is my title?

And should I even care? I don’t know what I should care about. My ego is trampled on yet at the end of the day, I still have my paycheck. I am so grateful for that. If I can step back and just look at this whole situation from a purely financial perspective, I’m over-the-moon fortunate, especially given the current state of the world. While there is no guarantee I will still have a job at this time next year, it seems odds are increasingly in my favor. So I should just shut up, stop complaining, and focus on doing a good job in my new role. There is absolutely no reason I cannot, in approximately 18 months, look for a position similar to my original role at another company and try this again, if it makes sense to try this again. I’m not sure yet if that’s what I want to do–but with the experience I do have I can actually go in and make a good first impression versus scrambling to figure out what I’m doing.

I think that will be a good thing.

Happy New Year: Embracing Myself as Myself

 

Quite randomly I ended up taking a neuropsychological screening this week. Well, it wasn’t entirely random. I was attempting to find a therapist (psychologist, psychiatrist, MFT, social worker, what have you) that accepted my insurance plan since theoretically I am supposed to be able to have $20-per-session visits for outpatient mental healthcare. Searching my insurance provider’s website however returned the names of hundreds of doctors who are no longer practicing or specialists for something that, despite being rather special myself, I’m not special enough for (i.e. serves youth or geriatric patients only.) I admit I didn’t call the entire list, but after about 20 google searches, emails and contacts I felt like giving up. Then, I found someone who responded to my email and said he was covered by my insurance (sort of) and could help.

This doctor didn’t do talk therapy. Instead, he is a neuropsychologist who does neuropsychological screenings. What on earth is that? Yesterday I found out. The screening itself is $1700. Insurance may cover that BUT they only decide after you get evaluated. Also, I believe it goes to my deductible anyway, so I’m basically paying for it out of pocket, or at least out of FSA. So much for the $20 per session mental healthcare. Continue reading Happy New Year: Embracing Myself as Myself

When It All Adds Up: Am I Autistic?

In the course of my mental health history, I’ve been diagnosed with, in no particular order, major depression, bipolar II, generalized anxiety, social anxiety, ADHD and, as I aged out of hyperactivity, Adult ADD. Yet my current therapist first to allude to the suspicion that I may be “on the spectrum,” so to speak. At first, I thought she was nuts. Well, I generally think she’s nuts because unlike my other therapists who have been more traditional talk therapists who don’t give direct advice, she’s more of a crossover psychologist and coach. And, maybe she actually sees something that others have missed. Or maybe she’s just crazy. Continue reading When It All Adds Up: Am I Autistic?

The Vicious Cycle of My Adult Professional Life

One of my longtime readers Taylor Lee left a comment that said what most people in my life tell me over and over again —

Not to be harsh, but I feel like you cycle through the same issues over and over again regarding work, depression, family anxiety, etc.

My advice is to break the cycle by choosing the path you haven’t taken before:
(1) Get a job at a bigger company. I think this will help solve a LOT of the problems you’ve been having with start-up life. Preferably some place near to where you live so your awful commute gets shortened.
(2) Figure out what triggers your anxiety/depression and what you can do to mitigate it. Whether it’s diet, exercise, more sleep, medication, therapy (I think you might benefit from CBT), your #1 goal should be getting your mental health on track.

I want to address both of these suggestions as they are good ones, but also aren’t necessarily solutions to the problem.

  1. Get a job at a bigger company. Is startup life the problem? Maybe. In my 10 or so years in the workforce, only six months were spent in a company larger than 100 employees. In the six months I spent in that larger company I witnessed so much inefficiency and bad middle management getting away with practically murder, I promised myself I would never go back to a large company. In between then and now I have applied for roles at larger companies – knowing that one poorly run large company does not make them all bad – but my experience in startups means my job prospects in larger companies are moot. Larger companies tend to look for someone with very specific experience in one area, whereas startups value that I’m a bit of a jill of all trades.
    I just honestly haven’t had any luck with even getting interviews at larger companies – whereas startups see me as the perfect fit (at least on paper.) I did get one job offer from a 300 person startup – which maybe would have been better – but in this case I did not feel I had the experience needed to lead the team I was going to be given and the stress would have been even worse. I also received a job offer for a poor-performing smaller public company that made business software which reminded me why I disliked larger companies in the first place – people pretended to be passionate about their products but you could tell they were just completely burnt out because they didn’t care. I checked a few months later and most of the people I interviewed had left the company (given its poor performing stock it may not have been by choice.)

    This would likely be different at a consumer-focused public company, but I’m far too unqualified for these roles to land so much as an interview. Believe me, I’ve tried. I can keep trying and maybe eventually something will stick. It isn’t even the money anymore (big companies would pay significantly less since I’d be in lower level roles with less responsibility) – it’s just the reality that no one will hire me at a larger company – at least one I’d actually want to work at.

  2. Figure out what triggers my anxiety/depression. Well, I’ve figured this out, and there’s a lot of things…
    1. Doing a job where I’m supposed to know what I’m doing on day one and there is no room to be developed or to get better at what I’m doing before I’m judged and thrown to the curb (ok, this is a startup thing.)
    2. Being responsible for too many things at once without clear definitions of what those things are (i.e. unlimited number of things I can do, and not knowing whether to focus on the few things I know how to do well, or spend time on the things that I know will add a lot of value that I don’t know how to  do well, so I spend too much time on them and get extremely anxious over them versus being product)
    3. Having to be social on a daily basis with the same people. This pretty much will be an issue in any office environment. As I’ve noted before I’m an ENFP with massive social anxiety, so over time a “work from home” job would also be draining… I need human contact. But having to be the person who makes that contact on a regular is anxiety causing. I often think it would be much better to be an engineer because it’s a given that you’ll be socially awkward and that makes it easier.
    4. Work hours. I am not a morning person. My ideal situation would be working 11am to 7pm. Well, now I work about 8am to 7pm. If I work for a bigger company it’s unlikely my hours would get any better – right now I theoretically take an 8:30 train and get in at 10. If I worked at a big company job closer to home I likely would have to be in at 9, so the commute would be shorter but the time to wake up would be the same. I might get home earlier, which would be nice, but doesn’t help matters as I want to be able to sleep in and work later if possible. I guess if I get to leave at 5 everyday, if that exists in big companies, then maybe getting to work at 9 would be fine. But even bigger companies require long hours.
    5. Work location. If I could work two days from home that would be hugely helpful. That way I could get a few days of social interaction but also have time to just focus on getting my work done. I think this would be the ideal situation.
    6. Money. Whether I’m paid too much or too little when working for a business I’m always anxious about money. I’m anxious about it for many reasons. One, it’s ridiculously expensive to live where I live and my soon-to-be husband does not make enough to cover what we need to live a comfortable life here. I estimate that to afford a comfortable family life in the Bay Area you need to make at least $300k as a couple and even that is tight. So if I make $200k and he makes somewhere close to $100k, we might be ok. He’s at more like $60k right now and I’m a bit under $200, but we’re getting closer. I’ve saved a lot right now which is great but I’m now at the age where I’m about to have kids (if my body allows me to) and the numbers don’t add up if I take a lower paying job. Can we live on less money? Of course we can. A two bedroom apartment here will set us back $36k a year. Beyond that we can cut costs on food and clothes and entertainment. Lots of people survive on less. But I don’t want to. I want to have a comfortable middle class life. I want to buy a house or at least have an apartment in a safe area that feels like a home and not a temporary residence. I could go and make $140k and that’s still a great salary — and maybe that’s fine. Together we’d make $200k and we should be able to live on that. But will a $140k job really be that much less stressful than a $200k job? It might be. But then if I want to actually get back to $200k+ salary I’ll just have to move into more stressful positions and I’ll end up back where I started, only at that point I’ll be so deeply handcuffed to the lifestyle and supporting a family that I won’t be able to just pick up and leave or check myself into a mental institution.
    7. Lack of completion. I really like jobs which are projects that have a beginning, middle and end to them. Without a sense of completion, I am extremely stressed out. And those projects must be substantial enough that my boss and peers see that there was significant effort put forth to do this thing and it was done and we all agree it was done well. I need that in my life to feel ok.
    8. Not being trusted/respected to do what I was hired to do. I guess this is a double-edged sword… either the person who hires me doesn’t trust me and then I am constantly feeling judged or the person trusts me a lot and then I eventually cannot do the things they trust me to do and then they get very upset at me… but they were delusional in the first place to think I’d be able to solve all of these problems. But not being trusted is worse. But then I don’t exactly earn trust given that I tend to over commit to things and deserve that lack of trust. It’s just when I start out not being trusted, it’s a deep hole to dig out of… and so much of the trust stems from the ability to pretend like you have your shit together and everything is fine. And I’m the exact opposite of that where I am just too honest and will tell you when something is an issue and explain why. And this is going to be a problem in bigger companies even more than it is in smaller ones. In bigger companies it’s less about 1:1 relationships and more about politics, which is a game I can’t and don’t play.

What can I do to improve my mental health? Sleep? Diet? Exercise? Therapy?

All of the above.

I know when I sleep I feel better and less depressed/anxious. But I don’t sleep enough. I go to sleep at 1am and wake up at 6am and still end up late for work because I’m too anxious to move despite doing work in bed.

Eating healthy helps a lot. As does exercise. But when I exercise at 6am I lose out on sleep so I think it kind of offsets its productivity.

Therapy… I have a love-hate relationship with therapy. I’ve been to so many therapists I know that it’s a huge time and money suck with no successful outcome. It’s sanity maintenance which has value in and of itself, but not for how much it costs. Yes, I make a lot of money and yes, I can afford to spend it on therapy ($700-$1000 a month for 4 sessions) but then I end up anxious over the value of those sessions. It’s so expensive and this year I decided to put my money into personal training ($600/month) – my physical vs my mental health – because I’ve spent so much on therapy to date and where has it gotten me?

I’m not on any antidepressants and maybe I should be, but I know that sleep and diet and exercise all can help me be a lot less stressed and sad all the time. Drugs don’t change my work situation.

So… do I need to address these issues and make a significant change to my life soon? Yes. How? I don’t know. I’m spending all my money on my wedding right now – which is stupid but it is what it is – and then I’ll have time to figure out what to do with my life.

An old boss of mine from my journalism days offered to review a freelance pitch from me if I had any ideas – so I just sent one off and I haven’t felt this engaged and motivated about a potential paid project in a long time. I have no idea if they’ll accept my pitch but I’d love to get back into non-business journalism where I’m writing about issues that actually help people and represent those who do not have a loud enough voice to be heard. But I can’t make a living doing that, so it’s only a fun side project for now – but pitching the story this morning was rewarding in and of itself.

It’s a Man’s World

Isn’t it ironic that as I sit here at a city Starbucks pondering my gender than  the context of my recurring professional setbacks I noticed that “It’s a Man’s World” was playing on the speaker system? Well, it is. Here I am, for the thousand billionth time, at a point of failure. I’ve done a lot of good work, but it’s never enough. I’ve also made a lot of mistakes. But it still feels like there is something more than just making mistakes that gets me where I seem to always end up.

My office has public calendars and I wasn’t calendar stalking but happened upon an interview occurring with someone who clearly is in the running for either my new boss or my replacement (I can’t figure out which.) That someone is an old dude. Maybe he’s great. His resume certainly is impressive. Maybe he is what the company needs. But I also see an unfortunate trend in my life – I accept roles where no one can succeed and then when it finally is possible for someone to come and be successful (and the role is more desirable) I get replaced with someone who is a lot more charismatic and better at faking being good at things or maybe is actually good at things – I am not sure if it matters. What matters is I can’t fake it. I’m honest to a fault and then some. It doesn’t fly in business. Well, it flies me out of every single job I have.

I’m learning a lot. I’m the kind of person who likes to really understand what I’m doing before I do it. I enjoy systems thinking and understanding the architecture of a broader infrastructure and envisioning ways to fix what isn’t working. I’m not so good at actually getting things done – which is enough of a reason for a company to kick me out – though when I am being productive I’m probably much more productive than most other people might be. I’m a poster child for ADHD though now a woman and no one in real life has the patience to put up with my occasional bouts of extreme productivity paired with stilted outputs due to anxiety, depression and distractedness, in no particular order.

I’ve been writing a lot about gender biases and I do wonder if bits and pieces of my situation happen to be caused by my being female versus male. It’s a catch 22 and all – am I doing bad work because I’m anxious caused by the way I’m treated due to my gender or am I treated the way I am because I’m anxious and doing bad work in a way that’s embarrassingly and stereotypically “female,” whatever that means. The ADHD is real and it doesn’t help. At best I’m seen as a creative savant who is hopeless when it comes to maintaining usefulness in business. At worst I’m characterized as a hot mess that can’t even motivate herself to be lukewarm.

What’s even harder is being in management. I really do enjoy managing employees from the sense of coaching them and helping them grow however I can. It’s just the day-to-day smalltalk that is so draining. I think back to bosses who would always put on a smile and ask how things are going even if they didn’t really care because that’s just how they knew how to be great managers – and although some of them faked it better than others, it worked. I find myself struggling to so much as say hi and bye to my team each day. I know it’s so dumb – as I can envision myself with a big smile asking them about their weekend plans, but then whenever I try I end up feeling so drained just by the effort to come across personal without being too personal. Friendly, but not a friend. Boss-like, but also cool boss, but also someone who has her shit together, despite clearly not having her shit together.

The long and short of it is that I can keep doing this to myself over and over again… for, oh, I don’t know how long… or I need to find a completely different path. I know I’ve said this before a zillion times but now I actually believe it. I mean, I went from making $90k six years ago to nearly $200k today and that’s helpful in terms of my bank account but only feels like an accomplishment in deceit. A good friend of mine – now long-time colleague – has suggested that I take a job that doesn’t pay quite so much in order to provide a little less stress – and less having my bosses constantly calculating if my ROI is worth my cost and then being so passive aggressive about earlier negotiations.

I’ve been rather aggressive when it comes to negotiating because as a woman all we’re told is that we get paid less and we should ask for more. Ok, I did it… and I still have no idea if a man of my “level” would have asked for even more or less, but I felt good about pushing and I had two offers at this rate (actually the other one was for even more) which made me feel justified in accepting one of them. However, getting a salary offer and having that salary not haunt you for the entirety of your tenure with a company – especially if that company is a small business and your boss knows that every dollar spent limits his changes of success and wealth – is probably worth more than $10k or even $20k more a year after tax.

There are two paths here that are the easiest, and then many others which will be much harder and more scary. I stay on the path I’m on, and with my newly-gained experience try my best to stay in this role as long as possible and then when I need to (which may unfortunately be sooner than later) I interview like crazy and try to convince someone that I’m great and negotiate strongly again and walk away with a similar salary and another six months of attempting to do my best without that actually being anywhere near good enough. OR – I find a job that’s maybe lower level by a bit – maybe at a bigger company (though it’s really hard to get hired at a bigger company when you mostly have smaller company experience) and take a salary of anywhere from $120k-$140k (which isn’t bad by any means but it’s a massive pay cut) and then just see if I can maintain that job.

Or I just take another path entirely. Open my own small business. Go back to school for design. Return to my earlier profession as a journalist. Write a novel. Or a yawn-inducing memoir. Learn about shooting film. Move to the middle of nowhere and take college art classes until I’m credentialed to teach. Make a living selling crafts on Etsy. “Come out” as the author of this blog and make a name for myself as this depressed, anxious 30-something who is so remarkably spoiled that despite her disability the only response she gets from the universe is a series of eye rolls and “woe is you’s.”

It’s just at this point where I am at my wit’s end. I can’t even talk to my fiancé about this anymore because he doesn’t like hearing about how I’m failing over and over again. I don’t blame him. He also doesn’t work in business, so he can’t really relate. And he knows a lot of it is my depression and a lot of it is me being lazy but I swear that due to this constant ridiculous anxiety that just builds and builds and builds.

And it’s all fine and well to fall over on my face as many times as necessary to get through life / build a nest egg … but not if I have kids (which I want to do and have to do soon if I want my own.) And so I feel like I’m running straight for a brick wall that someone told me is made of styrofoam but we all know damn well it’s just made out of actual very fucking hard brick. I know I can’t keep running straight ahead, but the older I get, the faster my momentum, and the harder to slow down, the more impossible to stop and turn away from the inevitable outcome of shattering into a million pieces.

The Reality of My Professional Apptitude

As I review my next steps, I have many, many, many variables to consider. Above all, I want to take on a role where I can be successful *long term,* not just for a few “burn myself out” projects — OR, take on a role where “burn yourself out” projects are the norm. I’d be much better off in a creative industry working on television shows or movies, but it’s a bit too late for that, especially given my massive fear of change. I’m trying to work with what I’ve got here. And, at the least, I have options. And good ones at that.

Ten years ago at about this time, I was getting fired from a marketing internship at a non-profit. It was my first year out of college and I didn’t know what on earth the future held or what I wanted to do. I applied for hundreds if not thousands of jobs and rejection emails gave me a warm, fuzzy feeling that someone or something out there reviewed my experience, or lack thereof, and decided to personally not give me a chance. Since the full-time job thing wasn’t working, I applied to a pretty-much unpaid reporting internship and, when I found a place to live, found a part-time admin job which was never a good fit for my ADHD self. I survived the entirety of the internship, but the part-time admin gig was, well, a predictable disaster.

Although I moved on and continued to apply for job after job after job, I didn’t know what I wanted in life. I had no friends in the area, very little family, and the only reason to live was to try to make money… to save a little bit… to build something when everything around me was crumbling. I somehow impressed a magazine that I was a worthwhile hire for an editorial assistant role and I stayed for a year, writing articles and attempting to become a better reporter. But my social anxiety really got in the way of that. I did the blogger thing for a short while, which was even worse, because bloggers need to be super aggressive and not let anxiety get in the way of getting a scoop. My journalism career practically ended before it started.

Without rehashing my C.V. for the thousandth time, the point is that I haven’t really massively succeeded in any one role. There have been pieces of roles where people have seen my strengths, and there have been times in the past 10 years where I’ve really poured my heart and soul into projects, and they’ve been considered significant successes. But nothing has ever been sustainable – you can say I just need to suck it up and work, but when you have ADHD and bipolar disorder, it’s not that easy. My mind doesn’t work that way. I have the potential to do great things, or not so great things, but very rarely anything in the middle. I seem to be failing at acceptable.

When it comes to my two or three job opportunities that are getting closer to being real, I consider all of the elements of the role and companies. A few of you long-time readers have warned me that it would be absolutely idiotic to take on a role at a smaller company again. But – there are reasons I failed at those companies that #1, are unique to the companies (not due to their size) and #2, there are similar issues that would happen at a company of any size. If anything, I am more suited for smaller companies because I need to move fast and get things done, or else I get bored and demotivated, and that’s when I do my worst work. If I’m just a cog in a corporate machine, I might keep my job longer just due to HR policies, but I certainly won’t be helping myself or my firm.

The smaller company job is exciting to me right now because I can see many things I can do in a very short amount of time to make a huge difference. I want to compare this opportunity to my past failures at smaller firms to try to hash out the difference, and realistically explore why a smaller company is or isn’t a good idea…

My past two companies, which have ranged in size from 20 to about 100 employees, had significant challenges unique to each opportunity.

Upon leaving a smaller firm where I stayed four years without getting fired(!), I took on an opportunity I knew I wasn’t the right fit for. The head of the company was an expert in my field, and while it’s his fault for hiring me without asking some basic questions to establish if I actually knew what I was doing or what he expected me to do, I also had a boss who had a very set way of how he expected me to get my job done. I really didn’t know what I was doing and it became clear pretty quickly that I wasn’t the right fit. If I were to take on that job now I’d actually do  much better at it. I still wouldn’t be the right person for the position, but I now know enough that I could have lasted longer. I was just clueless and five months in when I was let go, it was the right decision for the business. Given the industry the company was in, I couldn’t even do the things I do best there because of the industry. It was just a very bad fit from the start.

My next job, where I stayed a year (which is respectable in startup time), I picked a company in an industry that I care about. Yet again I found a CEO who was starry eyed about me and recruited me so aggressively I had no time to discuss my strengths and weaknesses. I was thrown into the fire, but at least was given a reasonable budget to work with. But everyone at this company would agree – there are some serious management issues teetering on schizophrenic. Another trend – the head of the company had a background in something similar to my role, so he had a lot of strong opinions on how to do the job, and would basically force me to do a whole bunch of things that didn’t make sense at the expense of time to do the things that had to get done. I did fail to hire a team for a number of reasons, some of which were out of my control – the biggest problem was that the company had a lot of fundamental issues and it still does (lots of people have quit by choice over the last few months and the trend seems to be continuing.) Beyond the basic issues of the core business, the head of the company’s behavior teeters on sexual harassment (anyone working at the firm would agree) and everyone working there is so stressed and upset that they end up taking it out on each other.

Despite the challenges at the company, and it being the right time to leave by choice or by force, I learned a ton in the last year. I worked with an outside agency who taught me a lot about how to do my job. I learned how to not waste money through a bunch of trial and error and how to do things faster. I also discovered a bit about the types of people I like to manage and the types of people who I cannot manage. I learned how important recruiting is and how challenging it is at any company but – it’s actually easier at a hot young company than a big corporation or a startup that has been around for years and is on the verge of falling apart. If you can’t attract the right candidates to your firm, you’re pretty much fucked (or you’re spending a whole lot of time on recruiting that you should be spending on getting your job done.)

Ok, so why even think about going to a smaller company again? Haven’t I learned my lesson!?! Well, as you can see, a lot of the issues had at these companies were company-specific, or addressable by the fact that now I have about two more years of experience and I much better understand the bigger picture. I understand how much things should cost so I’m not freaking out every minute about budget and wasting too much money or not spending enough. I’m not saying I’ll be perfect at my next job, no matter where I go – but I do know I do my best work when I care about the product my company is making and respect the people who are making it.

The smaller company I am considering is SMALL, don’t get me wrong — there will be challenges for sure. But the founders are a bit younger – closer to my age (I think the head of the firm is maybe 2-3 years older than I am) – and this makes a huge difference in team chemistry and respect. I’ve always worked for teams where the execs are in their 40s/50s, and much older than I am. I’m fine being the only woman in a senior leadership role, but it helps with the others aren’t all dudes who are going through their personal mid-life crisis while making the younger women of the company feel uncomfortable.

What’s great about the small company is that I believe in them. I see that their product is already getting a lot of traction, and I see a lot of ways I can quickly help – and I’m super excited to jump in and do just that. I know I have some hiring to do – but I also have the momentum of the company and it’s early stage to help source the right talent. There are really two types of employees in Silicon Valley – the ones that like early stage startups and want to be part of growing something — and then the ones that want to work for a very late-stage startups or public companies that are big and somewhat stable and come with that fancy brand name and cult-like culture. It’s really hard to hire for the middle ground… the companies that are not hot, sexy startups but that haven’t made it… the ones that are dying a slow and painful death, who often have second or third CEOs who are brought in to “save” the company which had about a .00000001% chance of actually saving.

So, in short, not all small firms are created the same AND my experience today is vastly difference than my experience from a year ago. I have a fairly strong opinion on what to do and who to hire, and I won’t be floundering quite as much for the first six months on the job. I’ll certainly hire a detail-oriented person to be on my team, who balances out my big-picture strategy style. And I just think I can knock this one out of the park. If I didn’t, I’d never even consider it. But something tells me this is a really good opportunity. But I could be delusional. I could be lying to myself because it’s the most exciting opportunity, but not actually the best fit. I’m trying to sort that out.

The larger private firm is also a really good option. What I can’t figure out is how much is broken right now and how much is working. It’s not a stable public company and it’s not a small, early-stage company with the fun moments of cherishing each win and feeling part of that with the whole team (I really love that about smaller companies.) My role would be very vital to fixing some of the pieces that aren’t working right now… and I can see what those are and have some ideas how to get things in order… but once I get the basic stuff functioning, I’m not sure where I’d go from there. The role seems a bit more limiting. The company’s product, while useful and needed, is not something I can get super excited about. Maybe that’s a good thing? But I’m an INFP and I really need to feel morally connected to my work. I told myself I’d never work for a company selling to marketers again, and, quite frankly, the two larger opportunities I have are selling to marketers. I’m not sure that’s the right fit for me either. Yes, it may be more stable and it may be closer to home and the salaries may be higher (don’t know that yet) but… if I’m not feeling passionate about the product I’m just going to crash and burn pretty quickly.

There are other jobs out there — but so much of the business technology lacks the human side. I like to have that human piece to spin stories and generate buzz. The smaller firm has so much going for it around the stories I can tell, and that’s what I do best, with the right company and right stories. I think I could help all three companies but I see my value being most at the smaller firm. I think what they’re looking for and what they value is a lot more in line with what I do best — they very much appreciate that I can do all the other stuff, but I do feel like they’re hiring me for the skills I actually have, and will value my ideas and contributions in those areas vs constantly debate me and tell me I’m wrong.

So… I am most enthusiastic about the smaller opportunity, but I’m also not 100% on it. I think that the feedback from my readers warning me to not go to a small company again has merit. I hope the above explanation shows why I’m not just jumping into any smaller firm, and that this one specifically excites me for a lot of good reasons. It will be hard and a lot of work… but I want to feel inspired and work hard. I want to go to work everyday thinking that I feel good about building something great with people who deserve to be winners. Good people who aren’t sociopaths or narcissistic or delusional or suffering from borderline personality disorder. Just people who want to build something great. That’s where I want to be, and that’s why I’m excited about this opportunity, history be damned.