Dear Ada,

I am a woman in my late 30’s working for a tech startup in the Midwest. For the most part I feel like our company does a good job fostering gender equality, and a positive work/life balance, and we’re certainly more progressive than anywhere else I have worked, but it was recently pointed out to me that the only people in our company who have children, are men. I know that doesn’t necessarily mean anything, but I can’t help but feel like it’s a red flag, especially as an ambitious mid-career professional, who hopes to one day have kids. Am I reading too much into this, or should I be concerned?


Working Wannabe Mama

Dear Mamabe,

That flag may not be fully red, but it’s certainly hot pink. 

Ever heard of the “Motherhood Penalty”? It’s a set of workplace disadvantages, in the form of lower starting salaries and higher expectations (because of-fucking-course) that pretty much universally affects women with children (see exhibit: Serena Williams). 

The shitty flipside to that already shitty coin, is that there is also something called the “Fatherhood Bonus” in which men with children actually are believed to benefit professionally when they have kids. Their perceived responsibility, reliability, and investment in their own family’s future, translates to higher earnings, more frequent promotions, and more leniency when family duties take them away from work. 


Since the age of Don Draper (yes I believe he was a real person, don’t @ me), companies have elevated the “family man” while dismissing working mothers, and it sounds like your company is no different. They may be progressive, but there are some subconscious biases that are too ingrained to just erase overnight (like my subconscious bias that even though I know Don Draper is a douche, I still totally want to bed him). 

The good news is, you caught it early. Because you don’t have kids yet, you now have a wonderful opportunity to enact change in your company, both culturally, and in terms of concrete workplace policy (or…if that doesn’t work…go find another job before you start making new humans). 

If I were you, (and I basically am, because I am in the exact same situation: wanna have babies, no other moms at my work) I would begin by examining the areas of your company’s hiring, compensation, and benefits policies that may directly or indirectly discriminate against women (or trans, non-binary, GNC, or non-cis people) with kids. What are their policies on medical leave? What about flexible work hours or working from home? Ask about the possibility of adding a “lactation lounge”, which, despite having the most cringe-worthy name of all time, is a real necessity for nursing humans who want to be productive, and not in excruciating boob pain. 

Diversifying a company’s workforce also means providing resources to those with varying degrees of privilege. Make sure that your company’s approach to family/work balance isn’t all talk, and that it’s backed up by policies that don’t assume that one parent (usually the mother) is staying home with the kids. Are childcare subsidies available? Does their caregiver’s policy assume a dual income household? All these are totally valid questions to be asking leadership and HR. 

Honestly, I could go on and on, but you don’t have time for that. You’re a woman in your late 30’s! You don’t have time for anything but making whatever babies your aged uterus can still cough out! 

Kidding kidding. All that shit’s a hoax. 

What I’m trying to say is, you are totally right to be alarmed, but it sounds like your company at least wants to do the right things. So, now’s your chance to start pushing them in the right direction, before you start pushing humans out your cooch. 

Much love,


Dear Ada,

Is following your dreams ridiculous? I have been working in a “secure” profession for about 10 years now, but I’ve always loved making art, and though I have financial security, and a stable life, I can’t help but feel like the little kid version of myself would be really disappointed if she saw where I ended up. I’m seriously considering saying “fuck it” and quitting my job to become an artist. Is that a completely bogus idea? Or the best thing I could possibly do? Help! I feel like I’m getting further and further from myself every day that I stay in this secure, but meaningless job!


Artless Artist

Dear Artist,

  1. Are you the primary financial support for another human being (child, parent, other dependent)?
  2. Are you in a relationship where a major career change should be discussed relative to your goals as a couple?  
  3. Do you have a soul-crushing amount of student/medical/personal debt?

If you answered ‘no’ to all of these questions, then you should absolutely quit your job and become and artist.

If you answered ‘yes’ to any of these questions, then you should think very hard about what is important to you, seek counsel from trusted advisors, crunch some serious numbers, and then probably quit your job and become an artist.

Life is short. The oceans are rising. Following your dreams is absolutely ridiculous, but then again so is everything else.



Dear Ada,

I’m in a new to a job that is, for the most part, too junior for my background. One of the elements of the job involves a lot of accounting and finance, which I have no experience in and was not trained on. I have messed up a few times in the past couple of weeks, all in different ways, but I am afraid I am about to be canned. What should I do?



Dear Canned,

According to SOME STUDY SOMEWHERE I’M SURE*, employees are A LARGE PERCENTAGE* more likely to slip up, make mistakes, or drop a bunch of balls at work when they don’t feel engaged in the work they are doing.

*Eh, I am sure there are stats to back this up, but I’m not trying to do a bunch of research to get those numbers.

I would venture that the reason you’re messing up and making mistakes has less to do with the fact that you have no experience or training in accounting and finance, and more to do with the fact that the job itself is too junior for your background. If you’re rolling into work every day knowing you could be spending that time doing something else, or, thinking “ugh, why am I fucking this up if I’m already too good for this job!?” then that’s not exactly priming your brain for kicking accounting-ass and taking finance-names.

However, to say you should just quit and go find a job that is more “on your level” would be a deeply privileged and shortsighted thing to say. So, I’m not gonna say that. Sometimes we (especially when ‘we’ are women, immigrants, people with disabilities, POC, or LQBTQIA+ people) have to take jobs that don’t match what we’re capable of. Sometimes we have to work for years, decades, lifetimes even, doing things that we know are way too junior for our backgrounds, and we have to figure out a way to be successful and satisfied in those positions.

So – and you very well may hate this advice – if you need to keep this job, then you need to figure out a way to be successful in this too-junior role. You will need to reframe your thinking so that you view the job as “on your level”. You could choose to view the job as an opportunity to gain accounting/finance skills, or you could even approach your boss about continuing education or professional development in those areas, to demonstrate self-awareness of your weaknesses, and a personal investment in the role.

If you don’t need to keep this job, or you think you could find something that isn’t “too junior”, then I say peace the fuck outta there and let someone else who needs the gig, have it. Invest your time and energy in something that engages you and feels like a challenge. You’ll do better work and you’ll open up an opportunity for someone else. 

You got this,


Dear Ada,

I want to date a coworker! Well…kinda. Mostly, I want to feel like I could ask out a co-worker if one came along who I wanted to date. I’m a single dude in my early 40’s and I hate hate hate the dating apps. They feel so shallow and directionless, and more and more it feels like work would be the place to meet the kind of woman I’m looking for (smart, hard-working, curious, ambitious, similar values).  

The problem with that is pretty obvious these days. I swear to god I’m not a creep. I’m not going to leer or stare or touch ANYONE without knowing they’re interested in me, but I also don’t want to feel like work is a totally off-limits place to meet a potential partner.

So, what do I do if I do want to (respectfully) ask someone out at work?


Not a Creep

Dear Creep,

You’re totally not a creep. You know how I know you’re not a creep? You TOLD me you’re not a creep! See? It’s so easy.

Except not so easy. The thing is, a creep seldom knows when they’re being a creep. Take it from someone who has definitely been a creep (of the lonely, sad, too many glasses of wine at work karaoke and suddenly I’m singing the full Bodyguard soundtrack at our graphic designer variety), if you want to bring romance into the workplace, you’re going to have to practice a super human level of self awareness. Times they have a-changed, and thank the damn stars that they have. 

So, what to do when the times have changed, and the basic human need for love, companionship, compatibility, and someone to doink doink, hasn’t? Well sir, this is when we tread…extremely…lightly. It sounds to me like there isn’t one particular person at work who you’re interested in, and more that you would like to feel like if someone came along at work, a place where many people are  “smart, hard-working, curious, ambitious” and have similar values to yours, that you would like to be able to give it a shot. Honestly? Be still my damn heart over a man looking for someone smart, hard-working, curious and ambitious. Is it too bold to say “c’est moi”? 

So, a beautifully ambitious (and funny/talented/smart/hard-working) Ada lookalike strolls on into your office on her first day at a new job. Here are a few post-me-too tips that I would like to offer before you pursue her. 

  1. Does she work for you? If the answer is yes, in any way…I’m sorry but you can’t go for it. A disparity in power dynamics is the #1 way to exploit someone, and anyone who’s professional trajectory is in any way linked to your approval is off limits. 
  1. Get to know her (but don’t ask creepy weirdo questions). Ask her about her work, what she’s excited about or interested in. Make stupid water cooler (or cold-brew tap if your office is hipster like mine) convo about light topics like climate change and gun control. Don’t ask about boyfriends/girlfriends and don’t compliment her appearance. I know, it sucks to not tell someone you find beautiful that you find them beautiful, but you gotta hold it.
  1. No touching. At all. Until you’ve established verbally that there is a MUTUAL interest in touching, then make sure it happens outside the office, and that you check in on (enthusiastic) consent often. Probs more often than seems right. Probs so often that it starts to feel weird. If you’re checking in on consent often enough that it becomes a funny joke between you, that is the right about of checking in on consent. You’re welcome. 
  1. This last rule I I cannot stress enough…back off if she seems turned off. Tune all your receivers to radio rejection, and if you get even the teensiest hint of a signal, move the fuck along.

I’ll close by telling you that finding love at the office, can actually totally work out, primarily because attachment and attraction grow most fruitfully with proximity and shared experience, and when you’re spending 40–60 hours of your week somewhere, that’s a lot of proximity and shared experience. Also, people are increasingly choosing professions, and companies that they feel really reflect their personality and values. This means they’re spending those 40–60 hrs surrounded by exactly the type of peeps they would want to spend the next 40–60 years with. 

I totally see why you would want to keep work open as an option for finding love, and I still think you can. You just have to make sure that at the end of the night, you’re not the dude in the karaoke booth with an empty wine glass screlting I Will Always Love You at someone you work with. 

Safe conquests, 


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