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.