When Having It All Really Means Not Having it All, And Why I'm Okay With That
- Casey Gentry

- 26 minutes ago
- 5 min read
I’m ambitious. Way more ambitious than I realized or was comfortable admitting until recently. Maybe it has to do with my kids growing and becoming more independent, but nowadays I find myself forward-thinking, regularly contemplating my next big 'move'. Sometimes, the result is simply me actively seeking something new to try (like my decision this year to enroll in commercial acting classes...more to come on that later). Often, though, I am picturing my professional self five years from now and working backwards to outline the steps that get me from here to there.
A little over 10 years ago, in February 2016, I was blessed with a remote job offer. It was for a company in my field (data science), working from home full time with limited, monthly travel. At the time, I had no idea that it would be the launching pad for my career. I had been in the workforce since 2005, primarily as a junior level contributor at local companies in Kansas City. During that time, I got married and had 3 children. Life at home was demanding and busy enough, leaving me little spare time or energy to pour into career advancement.
When that offer came through, my oldest was in kindergarten and my daughter was 6 months. And now, instead of taking breaks by the literal water cooler, I could use the time of respite to throw a load of laundry in the washer or set out dinner to thaw. I was hands on keyboard the same amount of time as before (in many cases more), but because I could be at home, I could more easily manage the little responsibilities in a way that allowed me to be present for the big ones. We adjusted our life around my new work situation. I was able to take the kids to school and meet them at the bus stop when they arrived home. As they got older, they would sometimes pull up a chair next to my desk and get out their homework, looking for whatever help I could provide (which became less and less over time). But even now that they walk themselves home from the bus, and no longer need my help with homework, they always come in the door and spend their first 5 minutes telling me about their day. (Unless I'm on a call for work, in which case they wait patiently until I am finished.)
While I was thriving at home, I was killing it at work. From the time I started working remotely, I advanced 4 levels in 7 years, moving from an Expert Analyst to a Senior Director (my current title). I finally felt like I was making up some of the ground I lost during my childbearing years, when I watched my counterparts (often men) continue their career progression while mine stalled. For most of the last 10 years, I’ve truly felt like I could be the mom my kids need (available, accessible), and I could do it while excelling in my chosen profession. I have, for the most part, felt like I had it all - a career and a family, without having to make sacrifices for either. That changed last week. For the first time in ten years, I found myself in the position where I had to make a choice between the two.
I was contacted by a recruiter in Kansas City, who was searching to fill a Vice President of Data position at a local company. An amazing opportunity to build on everything I have achieved to date. And if I could write the job description for my ideal next role, this would be a 90% match. It was a stretch opportunity - pushing me outside of my comfort zone - but one where I believe I would excel. And it was significantly more money than what I currently make (which, let's be honest, is a consideration for anyone when making a potential change). The only catch? It required being in an office 4 days a week. Goodbye to the remote working lifestyle I have experienced for so long.
I’m under no illusion about company expectations for executive level roles. They are high, and demanding, and often require a degree of leadership that benefits from in person collaboration. And for the first time in all my years of being remote, I felt a gravitation towards something different than the status quo. I found myself playing through the different scenarios of what my life - scratch that, our lives - would look like if I took a job where I was no longer at home before and after school. I went over various impacts and played through them in my mind:
Would the extra money be enough to compensate for spending more time in a car and away from my family?
Would I still be able to drop my kids off at school or would they have to ride the bus twice a day instead of just once?
How would the company react if one of my kids called me because they forgot something at home, or they didn’t feel well?
How would I ensure that everyone got to their evening activities with their stomachs full if I’m in transit during that time?
When my son's high school soccer season starts, how will the company feel if I leave early on game days to make it in time?
Last (but certainly not least), could I perform this job at the level it would require for success, knowing the adjustments I'd have to make?
For a job at this level, delivering against expectations is imperative, so it was critical for me to be confident in my assessment. Ultimately, I decided I could do two, maybe three days in-office and still maintain our lifestyle while successfully juggling my professional duties. But for the company, four days onsite was non-negotiable, which meant I was at an impasse. And I understand the business needs as stated. I really, really do. Yet I couldn’t help but feel a twinge of sadness: I was choosing to pass on an amazing work opportunity in order to maintain a lifestyle that sometimes I’m not sure my kids fully appreciate, because they have never known anything else.
It reminded me of something I heard several years ago at a conference I attended - and it has stuck with me to this day: You can have it all, but maybe not at the same time.
I am very good at what I do, so I know there will be other amazing opportunities to come my way. And this particular opportunity? Well, to be honest (and perhaps less humble than women are told we should be), I believe I would have killed it. I had the knowledge and the experience to come in and make a difference immediately. And my persistence lends well to learning new things, so I would have quickly filled in any existing gaps. But I only have 8 more years with my kids at home, and my once upon a time kindergartener will graduate high school in two years. I don’t want to look back in another 10 years and wonder if I made the right decision when I know that time is a commodity, and time with them is irreplaceable.
The truth is, whether we admit it or not, someone is making sacrifices, personal and/or professional, to keep a household running. In my network, it tends to be the moms, but I recognize that isn't always the case. I'm extremely grateful to have been in the position where I can continue advancing my career while also being present for my kids in a way that many working moms find difficult. And while this particular opportunity didn't work out, I will continue to be ready for when the knock comes again.
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