Why We Work....and Why We Feel Guilty When We Don’t

Everyone’s kids are officially back to school as of this week (I think), and I get really sentimental looking at how quickly all my friends’ kids are growing up. Reflecting on school in general is sentimental for me. All my friends will tease me about this but I LOVED school. Academically.

It’s crazy to think how much of my life was spent in school — I went for 19 years. Grade school, college, graduate school. Almost two decades in classrooms (which is wild to realize, as I’m slowly approaching two decades being a halfway mark in my life !!!!).

I learned SO much. I felt so prepared to enter the “working world” with all my academic experience. And yet, in all that time, the courses I now realize I never had — and wish I did — were the ones asking the deeper questions about work itself:

• Why do we work the way we do?

• How much work is enough work?

• What is capitalism and why does it shape everything about our families?

• Why do we feel guilty if we don’t work as hard as others?

• Why does rest feel lazy?

• Why is childcare inside the home treated as “less than” a career outside of it?

I have always been fascinated by thought processes and mental behavior. I studied psychology in undergrad, and then organizational psychology in graduate school. I loved (still love) analyzing people’s choices and thought this path would be the best way to help me give people meaning within the context of a society that spends most of our waking hours “working.”

With org psych, a lot of my research was really on what companies could do to help retain people within the context of their “culture”. How to keep people engaged. How to make companies more profitable, employees more efficient. And the underlying tone — or at least how I interpreted it — was that if you did all that, people would also be happy and fulfilled.

And for a long time, I believed it was that simple. I built my whole career around it. I spent nearly a decade at Sequoia (a benefits consulting firm) helping tech companies design better benefits — mental health programs, onsite healthcare, fertility coverage - you name it. This was the late 2010s, and with (seemingly) unlimited VC budgets at companies like Uber, Airbnb, and Dropbox, it was an incredible time to be advising on employee wellbeing. As an advisor, the world was my oyster! And we really did make an impact on people’s lives. I believe it.

But as a parent now, I look back on all these companies and programs that had (truly) the most amazing benefit programs - and I still see a piece missing from my general guidance. I’ve learned that the most meaningful benefit you can give a parent, that unfortunately never really comes from the employer side (for obvious reasons) — is simply the permission to adjust their role or opt out. An unspoken rule within the culture that says - if and when family becomes demanding — in a good way — it’s okay to slow down. And that when caregiving becomes essential — in a hard but honorable way — it’s also okay to stop.

A lot of people will read that and say the obvious: sounds nice but people need to work, people need money to live.

And yes, of course. But that’s exactly why I work so hard to highlight the in-between. The redefinition of work. The remote options, the alternate roles, the consulting projects, the part-time opportunities. The things employers often overlook because they go against policy, haven’t been done before, or seem “too complex.” But that change the lives of employees forever - and also instill the fullest amount of gratitude possible to that employer.

In org psych, we had terms like work–family conflict and role strain — academic ways of describing exactly what parents live every day. The impossible tug between being a “good worker” and a “good parent.” What we didn’t talk about was the philosophy or economics underneath: why we’ve built a system where these roles are constantly in conflict, or why guilt creeps in the moment you step out of the ideal worker norm.

• “It’s good for him to be with other caregivers.”

• “He needs to socialize at six months old.”

• “I’m really good at my job — they need me.”

• “I’ve built too much to just give it up now.”

Looking back, I realize a lot of this was caused by the fact that — through my schooling and readings — I had only consumed one kind of story before motherhood: ambitious stories. The kind where women powered through. Where babies didn’t slow them down. Where workplaces were being thoughtful of their employees, so why wouldn’t you stay?

And so when I went back to work, every choice I made was paired with justification. And every justification was paired with judgment — of myself, of other moms, of a system that didn’t actually fit anyone.

This is what org psych would call a broken psychological contract — that unspoken agreement between employee and employer about loyalty, effort, and fulfillment. When you step back, you feel like you’re breaking it, even though the contract itself was never built with caregiving in mind. It keeps a LOT of people stuck when they don’t want to be.

By the time I was pregnant with my second in 2023, though, my personal experience as a first-time mom and my new learnings about the working world had caused the narrative to shift.

So when it came close to being time to return from leave — I quit. I told my company: I will never get this time back. Which is the most simple, truthful way to put it. You don’t get the time back.

But there’s a larger reality to this choice: every parenting decision costs something. You don’t get the time with your kids back. At the same time, you also don’t get the momentum you lose in your career back. Every choice takes something.

At least - that’s what you’re told when the choices are black and white: full-time work or full-time SAHM.

The good news is — what I’ve come to find is that it’s not so much ambition or family as a clear battle. There’s also a messy middle. Not fully corporate. Not fully stay-at-home. Something in between.

And (to just use more pysch terms because I’m having fun with it) here’s where self-determination theory comes in — the idea that we’re most motivated when we have autonomy, competence, and relatedness. The middle paths parents are carving out — consulting, freelancing, portfolio careers — restore exactly those things. That’s what I’m doing and what I am LOVING.

And so it all comes back to the work we’re doing here. Three simple categories.
Stay. Shift. Step Away.
That’s the framework. And I’ll repeat it every week.
You may be in one of these buckets happily. You may be considering one of these buckets as your next step. Or you may be totally, completely stuck. But here they are:

• Stay — make your current role more sustainable.

• Shift — explore freelancing, consulting, entrepreneurship.

• Step Away — honor the caregiving seasons that call you.

What I didn’t learn in 19 years of school — the classes that asked why we work, how much we need to work, and what work is worth — are the ones I’m trying to write now, with Both&.

So if you find yourself judging another parent this week, pause. Ask yourself: What am I really trying to justify?

Maybe it’s the choice you made to keep working. Maybe it’s the choice you made to pause. Maybe it’s the choice you haven’t made yet but feel tugging at you.

But I hope you lean into whatever conflict you’re feeling. If you’re making a choice related to your job or kids and deep down you feel far from confident in that statement — you deserve more. And I’m here to help you explore it, one day at a time.

What I’m Reading
Hunt, Gather, Parent by Michaeleen Doucleff — Our first Both& Book Club pick! Reminder: we’ll gather in October to share reflections. If you want to join, just reply here and I’ll add you.

What I’m Watching
TikTok’s Momfluencers Are Giving New Moms Anxiety and Envy (USA Today) — A sharp look at how online portrayals fuel the guilt/judgment loop I wrote about above.

What I’m Researching
Personal Health insurance. How many of us have not quit a job because of it? Same here. This week I’m digging into alternatives: ICHRAs, marketplace plans, and stories from people who’ve navigated benefits outside of an employer. If you’ve done it — or have a product you’ve used — I’d love to hear about it.

Until next week!

Kaleana