Category Archives: Career Change

What Does it Take To Be Successful in this Business?

Removing myself from the equation, I ponder what persona would be successful in a role like my own. I seem to care far too much personally about everything I do, which renders my work occasionally high quality but too often belated.  The quality, the “artistic merit” of the work is not valued – only its completion, it’s project management of other people playing their parts and getting their projects done faster and more effectively than anyone else, or at least making it seem that way while in reality surviving on little sleep to make sure everything gets done and no one has to ask twice regarding the whereabouts of a deliverable.

It’s the alienating daily experience of being an “NFP” in a strictly “NTJ” world… welcome to Silicon Valley, oh sensitive artistic one.

Everyone appears to be satisfied with this world, stressed, maybe, but focused, determined, and given those drawn to this industry are the types who always got A’s on their exams and submitted every last ounce of extra credit assignments possible, I feel like a complete outsider. I’ve never actually fit in anywhere, so the outsider role is at least my status quo. As I observe those in the world around me and age in the industry where I’m no longer the youngest in the room (now, far from it), I feel even further removed from the center of gravity here. I’m off kilter, wobbling about and hoping no one notices I’m slipping sideways, that is, until the inevitable face plant. Continue reading

When You Come Home from Work Shaking With Anxiety…

There are plenty of signs that my current job is on its last legs, and soon it will be time to move on. Although I can potentially obtain another role with the same or even a higher salary, at this point there is the logical side of me that says “stay just another month” as each month is coming to an end, just to save up for my future, just to get to a point in life where I won’t need to be stressed so much about finances, where I can focus on living instead of worrying every day.

My objective in life is to be in my 50s and to be able to take my children and friends out to dinner and get the check, without worrying if I can pay my rent. I imagine I need $2M by my 50s in order to afford this lifestyle. That seems rather impossible, but with my current savings if I can earn 10% YoY for the next 17 years, I’d have over $2M. The 10% annual growth is unlikely, though, so bringing it down to a much more likely 5%, that only gets me to $1M at 50. This doesn’t include any additional contributions between now and then, so it’s still possible… I need to save about $40k annually for the next 17 years in order to hit my goal.

Today, with my current lifestyle and savings, I’m able to save ~$6k a month or more. To be conservative, I would easily save $72k a year at the moment. If I can sustain that for the next 17 years, I will clearly hit my goal (unless all hell breaks loose in the economy, of course.) However, I know I cannot maintain this career for 17 more years. I also don’t want to — I don’t want to get to 50 and look back on my life and see that I didn’t create anything significant or impact the world in a positive way. Yes, I can “start” my life at 50… assuming I have kids soon, they’ll be in high school then, and I can go back to school or change careers at that point with $2M in the bank as a safety net, but that seems sad to me… I cannot imagine spending my children’s entire childhoods and adolescence working a job that requires me to rarely be home… missing out on important life events and just being there for my kids. I really don’t want that.

Of course, if I can’t have kids, this is a moot point… if I end up not able to have children, then two things happen – I can stay employed in this type of role for longer, saving more money, and I don’t have kids, so clearly I would be not spending as much either. Regardless, I still want children, and I’m still going to try to have them.

If I do get pregnant and have kids, I know my life has to change, as does my expectations for the future. I don’t think I’ll be able to continuously save $40k+ a year – some years, I’ll be lucky if I can max out my 401k. If I want to change my career, I’ll likely need to go back to school and invest in that and start at a lower wage for many years. I’m not going to do that until I know for sure what I want to be when I grow up… which may never happen. But this career isn’t right. This career is going to cause me to have a heart attack before I even make it to 50.

There is other $ variables at play, that I don’t consider when planning my future, as they’re all “extras” and “nice to haves” but cannot be counted on. My husband makes a living as well, and although his salary is much lower than mine, he still is able to save something each year, and eventually he can earn more as well. Then we have our parents who may pass down something to us one day, but planning for a life with a potential inheritance seems both futile and deeply morbid. Neither of our parents are well off, but there’s a chance we’ll get a few hundred thousand dollars or more one day down the line. That alone could pay for our retirements. So, the reality is I’m in a good place… the $500k mark in my networth will be a sigh of a relief, a moment to celebrate maybe a glimmer of financial freedom… the opportunity to take a few more risks… to start to find out what really matters to me in this very short life, versus just working for works sake.

I have a new boss. New boss is great in the sense that new boss is really good at her job. New boss is everything someone in a senior leadership role in this career should be. New boss is, in many ways, the opposite of me. New Boss (I’ll call boss “B” for the sake of simplicity) is a tiger. B doesn’t take shit from anyone and knows what she wants and she gets it done. B knows what to do and how to navigate the political waters of the workplace with ease. B is on the ball, all the time, and doesn’t let emotions get in the way of decisions.  B is not someone I can aspire to be like — my entire being cannot be that person. I can’t fake it. I can’t just wake up every morning and put my “B” cap on and suddenly be this great senior executive. B will never be me.

In the meantime, if I want to stay, I have to impress B. I am already starting from far behind as B was clearly told things about me in the interview process that were far from flattering, and B has visibility into my salary and knows that it’s high for my current role (it was high but fair for my prior role where I was running the department, not so much for my smaller and smaller role, which is shrinking by the day.) At some point the numbers just won’t work. At some point either they would give me a pay cut or let me go.

B is very strategic. B knows there is a large amount of change required and will make those changes in an organized manner, getting the most value out of me as possible before I am removed from the organization. If I continue to provide value, I don’t think I’ll be fired immediately. I could be wrong, but the organization seems to have a policy around being fair, and if I’m doing the job requested of me and fulfilling the role, I do not see being tossed out as long as the company is doing well and isn’t going through any formal layoffs. In the case of formal layoff it is clear I’d be one of the first to go. But as long as we’re doing well and I’m doing my job and getting things done on time and at a quality expected of me, I should get to stay.

Yet I’m not sure I’m capable of getting the things done that are required of me on time and at the level of quality expected. I’m determine to try – focusing on doing my very best and giving it my all for ~3 months is not a bad objective, even if my future tenure is limited. That’s 90 days, $18k+ in savings, and ideally a good reference to walk with based on the fact that I really did try my best and, as the song goes, I guess my best wasn’t good enough.

According to my latest networthIQ entry, my networth today is $468k. With that $18k additional, that gets me to about $486k, within an arm’s reach from my $500k goal.

Or, I get another job that pays less, and is more sustainable, and I get to $500k sometime later this year — which is the goal anyway and theoretically I could work through the end of May, get to $486k, take my PTO dollars and some of my savings, take 3 months off and travel the world, come back with $475k in the bank, get a job that pays less than my current one (say $7k take home per month after tax vs $10k), save $4k a month, save $16k for the rest of the year, get to around $491k by the end of the year (and that’s WITH taking 3 months off and taking a job that pays much less when I get back.) So even if I take a ~$3k paycut and take 3 months off, I should still be within striking distance of my goals.

OR, I just suck it up, work in this role through the rest of the year by giving it my all and somehow being “not firable” … save $70k more, get to around $538k, get pregnant sometime this summer, stay at work for the 9 months of my pregnancy, say 5 more months in 2018, save another $35k, get to ~$575k then freelance for a few years earning a lot less, but living off the money I was able to save fighting through this job for … 15 more months. That seems like a very long time and between now and then we could easily have a mass layoff which I’d be caught up in anyway, but logically staying 15 more months gives me +2 years in my current job (good for the resume), and the amount I’d save is almost worth it. With interest, I could have $600k saved up when I leave work for a more flexible lifestyle for a few years when my kids are young. My objective, then, would be to not tap that $600k… to make enough money to pay rent/mortgage/taxes, for food and any vacations/entertainment travel with whatever I earn (and what my husband earns.)

In that reality, with $600k untouched for 10 years growing at 5-6% YoY I get to $900k-$1M by 44. That’s not the $2M by 50, but it’s still rather exciting that this seems possible — better if I stay in my current role for 15 months (or obtain another role that pays the same or more that I can successfully stay in for 15 months!) … or I just say fuck it, stick this out for 3 more months, take a few months off, then come back and get a lower paying job that I can sustain throughout being pregnant and the early years of parenting.

At least, thanks to savings a substantial amount in my 20s, I have options.

 

 

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

The Good, the Bad, the Ugly: A Contract with 2017

2017 – how did you get here so quickly? Time continues to fly by, and  although my bank account is looking healthier than it did a few years ago, I am still the same old person. 2017 already looks a bit shaky given our political climate (how on earth did Trump get elected president? So #unpresidented). Anyway, 2017, here are some things I want to accomplish in you — which sounds awkward but you are a year and therefore I’m not doing anything obscene by entering your cavernous orifices via January 1. Continue reading

And So Life Begins… Thoughts on Turning 33

In five days, I will be turning 33 years old. I was just reminiscing the time of my life when I thought 33 was quite old, and I realized I still think it’s substantially ancient. Sure, I have a lot of years ahead of me, but 33 is no longer my “early 30s” which could pass off as an accidental overage of my 20s. Thirty-three is serious adult business.

I honestly never pictured myself at 33 because I couldn’t imagine it. I’m not sure how many people see themselves as working professionals or mothers or whatever else it is 33 is supposed to be when they’re younger, but I didn’t have any sort of vision of who I’d be at this age. If a six-figure salary and wedding ring on my finger = success then I guess I’ve made it. But I feel ridiculously behind and lost, which is much scarier at this age than it was my 20s. Continue reading

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The High Cost of Mental Illness

Mental Illness is a touchy subject –  unlike, say, cancer or diabetes, it isn’t something that can be diagnosed via blood tests or biopsies. And everyone suffers some amount of anxiety and depression at different times in their lives. I’ve struggled with my own mental illness for years, both being tortured by its overwhelming nature, and, often in the same day, telling myself that I’m overreacting and totally fine.

Mental health conditions cost employers more than $100 billion and 217 million lost workdays each year. When I’m lost in a web of anxiety, I know I’m not being a good employee. This reminder of my failure as an employee spins me into a deep cycle of depression and worthlessness which quickly spirals out of control. I get so mad at myself because I simultaneously feel like the greatest impostor of all time and know I can do a better job that what I do right now, but the sadness of being an obvious fraud gets in the way of productivity. Eventually, my boss catches on, and I move on. I put so much of my personal worth on my job, I really don’t have much else in my life outside of my job and my husband. My career is everything. Maybe that’s the problem. Continue reading

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.

When You Made It and You Haven’t Gotten Anywhere

This week, I’ve been reading a slew of posts about how women make less money than men, and why.  Mostly, the argument against this being an issue goes, that women tend to work less than men one they have kids, and they also and generally less competitive so of course they don’t make as much money. In every single job negotiation I feel the weight of this on my shoulder, and try my best to negotiate. I have no idea what a man would do in the same situation with my experience, but since my first couple of jobs when I took the starting salary with no negotiation at all, I’ve tried to ask for a little more, and I’ve gotten more ballsy over time. It helps now that I now have competition offers, and I seem to be fairly good at interviewing these days.

On paper, I sound qualified for a very particular type of role and particular type of company. I’m not sure at all how life has sculpted itself to this specific career path, but it has, and I’m locked and loaded into it, full speed ahead until retirement to gain more responsibility, earn more wages, and look back on a very successful professional career. It hit me this week that I’m nearly making $200k (which, even for one of the highest cost of living areas, is one of those numbers that I thought would never be possible — ten years ago I was making $20k.)

Yet as I look ahead to potentially having children / starting a family, I realize that if I have an opportunity to leave this profession and move into something that is more flexible and personally fulfilling, I would. As much as I like money, and as much as I’ve been driven by this random “$500k in networth before I have kids” goal for the entirety of my 20s and early 30s, I just can’t see myself, 10 years from now, in this same type of role. I don’t want to be a vice president or C-level executive. Even though the pay would be great, I have no desire to be that person. I could potentially figure out how to fake who I am enough to get there… given my success getting this far, I have to believe that someone out there would want to offer me such an opportunity one day.  And I feel very guilty, that as a woman — as a woman who has an actual chance of getting to the top – I don’t want it.

As I sprint full speed ahead towards my mid 30s and the next phase of my life, I wonder what to do about it. I’m so busy these days with just trying to do my job and do it well and planning my wedding that I don’t have a ton of time to ponder what’s next (which is probably a good thing.) But, as my rent has increased this year by $2040 for the year, and the cost of living in this area shows no signs of refraining its hockey-stick growth, I know that at some point soon, I either need to commit to this career or come up with an exit strategy. I’m leaning towards the exit.

I don’t want to “not work.” I LOVE working. I love collaborating with a team to create new products. I wish I could be a ux designer or product lead. I’ve said that now for 12 years. I’ve failed to make any progress in that direction. I tried to study for the GRE and even booked a test slot and then didn’t go because I hadn’t studied enough. I couldn’t focus. I gave up. I got a better job. I made more money. It became less fiscally responsible to go back to school anyway. I got older. I passed that age when people go to grad school into the age when some people do but they’re much older their classmates. I entered the age where you take online classes or executive programs but only in rare cases do you go back to school for an entirely new career. Sure, people do it, and I may eventually as well, but I’m really getting older now — not old, per se, but old in the sense of I have a career. I have a good career. I manage a department, small as it is, I’m still in a high-level role, and there is so much good in my life that I kick myself every time I want to start over.

At this point, I’m committed to another year or two in my current job. If I do get pregnant then that will certainly be an opportunity to think through what’s next. Of course, if I get pregnant, it will be even harder to change careers. If I opt to apply to grad school for 2017 I’ll be 33 when I start, and I may want to put having kids on hold, which means I likely won’t have kids, which is, at this point, out of the question unless nature says I can’t (also a possibility.) In any case, there has to be some major changes in the next 2-3 years of my life, which will likely include moving to another state, or at the least, finding another career path and opting for lower pay and a lower quality of life here. I know this isn’t something I can maintain. It will be hard to say goodbye to the near-$200k salary, but I know if I figure out how to do something I’m really passionate about, maybe I can get back there over time. Or maybe I can just make less money and live somewhere more affordable. Either way, there are options, and I’ll always feel guilty as a woman for throwing away a successful career, but I have to. I have to rethink my entire life, my goals, and the directed outcomes. I do finally feel ready for a change.

Do I Choose to be Stressed?

A friend of mine, a stay-at-home mother who is married to an engineer who is likely earning over $200k a year, has told me to stop making choices that make me so stressed. I should go to a mindfulness class, she says, as this helped her resolve the majority of her own anxieties. They aren’t rich by any means for this area, but they do have a small condo that the husband’s parents purchased and they are renting the unit from them. I agree with her that I put myself in stressful situations and even when I don’t I have a tendency to stress about every little thing, but it’s hard to have a conversation with her about the stress I feel about money and the ability to live a comfortable life. I hear my mother’s voice, someone who doesn’t really want to understand money or retirement savings, but who just assumes it will all work out. And maybe it will for her. And maybe it will for me. But maybe not.

In the case of my life, I just don’t see it all magically working out. I have to make it work. And,  yes, that is stressful. I am literally making the choice between jobs that will pay over $150k and jobs that would pay $60k — and the crazy thing is it’s easier to get hired in the former right now. Those well-paid jobs come with a heaping dose of responsibility and the corresponding stress.

Here I am, one month from turning 32, and — this is the year I’ll get married and when I want to try to have children. I know having children will be challenging due to my health issues, and I also know that stress can contribute to infertility and miscarriages. I need to focus on being healthy and stress-free right now, but that’s hard to do when I am staring down these startup jobs that I’ll always feel under-qualified for and incapable of any sustained success. And just logistically these companies don’t have paid leave for maternity or anything, so I’d basically have to quit when I have a kid, if I have a kid. Which really sucks since I’m currently the breadwinner (well, at least prior to getting the axe!) I don’t know how I can make this work. It works FINE now – living in a one bedroom apartment and being ok with having to move if our rent goes up too much… but I can’t do this with kids. I mean, people DO do this with kids. But if I’m stressed now… then I can’t imagine how I’d feel then. And I don’t want to be a stressed out mother around my future children.

Today, I’m trying to decide whether to do COBRA for health insurance or to purchase it on my own. Neither option is great. For $550 a month I can have a $1500 deductible plan… or I can buy my own and do something like $350 a month for a $5000 deductible. In either case, it’s just a catastrophic plan and any other health needs… like… pregnancy stuff… wouldn’t be covered (well, it would go towards that impossibly high deductible or not at all.) My fiance doesn’t have insurance through work so it’s not like I’ll be better off when married. We’ll just be paying more in tax (if we’re both working) as our big reward for tying the knot.

I know I’m fortunate to even have these problems… but the next few years of my life are legitimately terrifying. These are the years when I either become a mother OR become a woman who never has kids. Either is a major, major life-defining situation. I want kids, even though I’ll never feel ready. I don’t want to watch my 30s go by and have just let work become the only thing that matters in life. And I’m the type of person that is all or nothing — it’s so hard for me to be just enough, but not too much, especially when in the startup world the general unspoken agreement is that you should work 14 hours a day, 7 days a week (give or take.)

Becoming a contractor would be ideal – for the flexibility – but then I’ll really have to deal with the health insurance situation… I mean, after rent, health insurance, and car insurance … that’s about $1800 a month right now. I just don’t think I can – for the long term – do the consultant thing. I think, even though the stability kills my drive, I need it. I just don’t know WHAT to do. It’s not like I can bring up the whole “hey… so I may get pregnant in the next year or two… and also, I may need to take crazy hormones and take time off of work in order to get pregnant because my body doesn’t work so can I negotiate some of flexibility into this contract or you know what just go hire some woman who doesn’t want kids or who already has them at least or just someone who probably won’t have substantial medical issues trying to get pregnant.”

My friend would tell me that I shouldn’t be stressing over this. But, I guess, I would want to ask her if she’d be stressed if she didn’t have a stable place to live and a husband with such a well-paid, high-stress career. She says she doesn’t care about money but I know she likes nice things — she has good taste — and I know she says she doesn’t really care about money because that would be too stressful, but that’s because at this point, perhaps, she doesn’t have to care, or she chooses not to think about it or be involved in her financial future.

There really isn’t anyone I know who is in a similar situation either — my friends here (the female ones) are either married and stay-at-home mothers or part-time self-employed types with husbands who have high-paid tech jobs, or they’re in a situation where they’re making about the same as their significant others and will probably leave the area since their careers don’t provide the salaries needed to last here. I don’t relate to (or have any friends to people who are) powerful women who have high-paid jobs. I mean, I’m not that type, I’m just faking it… for now. I really want to just tell these companies I’m interviewing for all the reasons they shouldn’t hire me… because I’m so tired of being a good interviewer but then feeling like I just don’t know what to do or how to do it when I start – or especially after I get through the few things I know how to do… and am left with a whole bunch of “figure it out” that never goes so well when I’m in charge.

 

 

 

 

 

 

 

 

As I sat on the baggage claim floor…

Some people hit rock bottom when they’ve found their addiction to drugs or sex or alcohol has pushed them to a point where there are only two options left — just about cold turkey or their own demise.  I sat on the baggage claim floor yesterday I found it impossibly hard to move. I had just returned from a two-week conference circuit, unfortunately one which was less successful than I’d hoped and the details far too imperfect. I sat and read my work email – one thing after another of items that I failed to do correctly or questions on problems I thought I had solved. And as I felt the hard, barely-carpeted cement floor grace the soft cushion of my over-padded bottom, and as I sat there unable to move for a good three hours, I thought – gee, I’ve hit rock bottom.

I also thought that I ought to shut up – my current situation is no where near as bad as so many have it in the world. I read the Humans of NY Series discussing Syrian refugees who barely made it out of Syria alive and now have nothing and no one. I have so much. I have a savings account and an apartment and parents who want to foot a ridiculously high bill for my 2016 wedding. How is this rock bottom?

In just three weeks or less, I’ll be out of a job. I have, for all intents and purposes, caused the rapid demise of my own employment. This was an inevitable end to my current reality, but it didn’t have to happen so fast. I let my anxiety get to me, I let myself stare at a computer screen for hours on end unable to function. I let myself fail to listen to my alarm in the morning because I couldn’t bear the thought of a two-hour commute only to feel hopeless and frozen and humiliated. I couldn’t muster up the energy to fake it. And so here I am, rock bottom. I’ve been here before. It’s a familiar place. Almost comforting. It is the calm before the storm. The eerie quiet before the big bang. And thus, this is the moment when everything feels futile, yet a new life is about to begin.

The challenge now is fighting the instinct to jump into whatever it is that comes along next. In the case of now, that would be two really solid opportunities which I’m currently in the running for — both jobs in startups that are similar to the one I have now, though, of course with different people and in different markets. My job right now is to figure out what it is I want to do. I’m turning 32 in a month. My 20s were fabulous for the experience and the wealth building. I’ll likely exit this year with $350,000 to my name – short of the $400k which was my stretch goal but certainly enough where I feel the entirety of this year has not been for naught.

To shine a light on the past year, I’ve learned a ton, had the opportunity to work closely with a good friend who I respect and admire, and even can step away from this knowing I at while I fucked up over and over again, I now know how not to make so many fuck ups in my next rodeo. I jumped in and for quite some time gave it my all. I burnt out fast when I realized my all would never be enough. And then, I just fizzled. And here I am.

I’ve been reading a lot about INFPs and how we such at employment. Our idealist personality type doesn’t really like to manage others or be managed, which is generally speaking the majority of roles in the workforce. What’s more, we need a position which maps to our values — map to our values and we’ll go above and beyond. Go against our values (i.e. the cut-throat manipulative world of business) and we’ll peace out. Thus, I’m about to “peace.”

Where I started a good 11 years ago, in 2005, was a place about an hour from where I ended up here in an internship at a non-profit. I was fired from that because I was absolutely depressed at the time. I wanted to be involved in the creative side of the house but I wasn’t competitive for that, so I became a marketer. I never wanted to be a marketer, it just seemed the most natural use of my ability to write decently and a mind that was born out of learning how to convince my parents not to fight all the time (I guess I got some value out of that.) The internship, which was supposed to go for a year, lasted a whopping three months. I don’t even remember what my job tasks were beyond organizing giant file cabinets and mailing postcards. I was most upset over not knowing where I was going in life — I didn’t want to be a marketer.

I didn’t actually know what marketing was at the time, at least not the breadth which the field covers. But I didn’t jump into a marketing role immediately after that. I enjoyed journalism so I found myself an internship at a newspaper. But my anxiety got to me again. Going out into the world and interviewing strangers nearly gave me a heart attack. I lasted about two years as a journalist, moving up to entry-level roles at magazines and blogs, falling into the world of technology, and being grateful for it. At least technology was connected to the world at large. I was writing about technologies that would completely adjust the world as we know it. I liked being part of something that big. I liked knowing about these things first.

Yet journalism as a field required constant anxiety – between needing to continue to talk to strangers day in and day out, and being judged on getting the story first, which I never did. Assign me a feature article which required more research and time, and I’d fare much better than rushing to get a story to the wire, or sussing out said story in the first place. I left journalism within two years because my writing was atrocious (I can write a lot and somewhat poetically but my grammar and organization is not suited for professional publishing) and I couldn’t handle the stress. I got myself laid off at my third publication and decided that journalism was not for me. But what was?

Given I needed to find myself a job I applied for any position which required writing that wasn’t in journalism. I must have applied for nearly a thousand jobs at the time when I finally got a hit. A startup was looking for a junior-level writer for a contract role. The company had an online social site and it sounded up my alley. I went there and ended up jumping in wherever needed, responding to user issues by email, creating copy for the entire product, and they eventually made an offer for me to join full time. That was the most successful moment of my life. While they laid me off three years later when they needed to trim down their already tiny team to be acquired, I knew I had taken the most important professional step in my 20s. I went from having really no experience to having – some experience. And I still was so cheap compared to my peers, that I could maybe get a job.

At that point, I still had trouble finding employment, but I managed to obtain a contract role at a big public company doing social media through a connection at a last opportunity. That role actually, in quite an unexpected way, brought me closest to the entertainment industry – as I was able to work on a project with a Hollywood producer that involved the company’s technology. While I felt rather useless in my contributions, it was a big company that had money to spend, and I was sent to Europe for a month to help drive awareness of the project. I felt completely out of my element and yet it was one of those really cool things that I had the opportunity to do in my career, and I’m grateful for it. Nonetheless, that job ended after my six month contract was up.

At the same time, I also took on a freelance opportunity with a very small startup to do some writing work. That freelance role really took my career in an entirely new and unpredicted direction. It was my first B2B (business to business) startup, and while it had a consumer bent to it I quickly became versed in the world of companies that sell to other companies. The only reason I managed to remain intrigued by the product was that it ultimately would be used by end consumers (they call that B2B2C) and in some use cases was used to improve the world. I thought it was pretty cool technology so I managed to get hired there full time and stay for a whopping four years, which in startup years is a very long time.

While I learned a lot in that role I hardly learned enough to make myself valuable to other companies. On paper I looked great but in reality I failed to pick up many of the actual skills needed to succeed in a more senior-level position in marketing. Theoretically I could just read the internet and teach myself a lot of this crap, but I didn’t have hands-on, live experience doing much of anything that would be applicable to another business. I thought I’d just have to fake it until I made it… if anyone would hire me, I’d give it my best shot.

So that happened. Twice. I got hired for one startup and within five months they figured out I didn’t have the skills to do what they wanted. I fault them for not figuring this out in the interview process. I also fault myself for not having those skills, and not being able to fake it. My second opportunity, another where I was clearly hired in a fit of delusion by the CEO, I pushed myself so hard to make it work. I took what I learned at my last failure and tried to apply it. I hired a rockstar consultant to help me in the areas I knew I was weakest. But there were just too many weaknesses on my part. Really, though, I just was never senior enough for the role. I neither was senior enough to effectively manage teams and convince my superiors of resources needed, or senior enough to be so strong in one area that the success in that area shone above the rest (which I actually was at the startup where I stayed for four years, but I found the strategy I used there for this particular need wasn’t working in this opportunity.)

In short, I’m back where I was 11 years ago, only with a lot more experience – on paper – and the new challenge of being a senior-level employee who would probably do best in a more mid-level or even junior-level role. While I might be open to take the pay cut (and it would be a significant, life altering pay cut) for a more junior position, no one would hire me. The sad truth is that even these junior level roles –  or at least the mid-level ones – want some specialty, some area where you bring something that no one else has on the team – some area where you an execute flawlessly without needing any outside help. Well, I’m not so sure I have one of those areas.

Even beyond that, I return to my INFP impulses, my failure to succeed in environments where I feel the company/organization does not align to my value set. I’m only hirable in B2B environments right now, and only a limited set of those companies. I’m interviewing for a few opportunities and all I can think is that I’m really just continuing on the wrong path. Maybe I could do better this time around — I have some learnings from the last year that are applicable. But I’m not looking at a long-term thing. I’m looking at a few months of working my ass off followed by a return to this very same place. It’s time for a change.

I’ve considered graduate school and theoretically am taking the GREs this month… which I’ve studied for a bit but not enough to merit a score that will get me into any worthwhile program. There are other schools which don’t require the GREs so I’m looking into them. I have about one year left or less until I want to be pregnant with my first child so that throws a whopping wrench into the equation. And ultimately I’ve realized I just need a job that aligns to my moral compass, one which I feel I’m doing something for the greater good of the world. Working in a B2B startup, or worse, huge company, won’t ever give me that.

I’m about to spend the weekend sending my resumes out to non-profits and “for good for profit” companies. These roles either pay very little and/or are highly competitive, but it’s worth a shot. I also think as soon as I’m laid off (likely first week of November) I’ll focus on my graduate school applications. The most anxiety-driven part of those is asking people for recommendations – that on its own is enough to keep me from applying to grad school!

At least I have some awareness of myself and what I don’t want to do. It’s taken eleven years to get to this point in my career. What’s crazy is thinking about how in 11 more years I’ll be about to turn 43. Where will my life and career take me? Who knows.