Category Archives: Career Change

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.