I had my first child five years ago today — and nothing has gone to plan since that day.

My son turned five today, and even though I feel like I’ve said this every single year since he was born, this one really got to me.

Five just feels… big. Maybe it’s how functional he is now. How much he talks. How you can take him out to a restaurant and it’s not completely chaotic. That this is the first year he made his birthday invite list and it’s not just our adult friends with kids coming over. How next year he moves from his part-time preschool to kindergarten and will be five days a week in a big kid school. How he helps my younger son get ready in the morning and says things like, “Hey, don’t be mean to him — that’s my brother!”

Our adorable, stubborn, thoughtful, cuddly, temperamental, wonderful boy.

I got pregnant at a really weird time — June of 2020 — a time when we were still hopeful that what was happening in the world would “all be over soon.” I imagined returning to the office, wearing maternity dresses, talking about baby things with coworkers who I had watched grow a baby, go on maternity leave for a couple of months, and return to the office in heels as if not missing a beat. I pictured mapping out daycare drop-offs on my commute and joining mom groups on weekends alongside baby music class.

But we never went back to the office. No one ever saw me pregnant. I had a baby shower on Zoom. I wore a mask while giving birth, and friends did drive-bys to meet our little guy as we held him up like Simba from our front porch.

In retrospect, I am of course incredibly grateful for how everything unfolded. Daycare closures led us to find an amazing nanny who came into our home after my son was born — allowing me to see him throughout the day, breastfeed easily, rarely deal with pumping (and never pack pumping gear), and experience a degree of flexibility working from home full time that I know millions of mothers only dream of.

But the image I had of myself powering through, returning to my normal job, and continuing to excel in my career didn’t happen the way I expected.

I did return. I did get promoted within my first year postpartum. I grew my team, my clients, and our product. But I didn’t love it the way I thought I would, no matter how hard I tried.

I didn’t love the newborn stage. I didn’t love my job the same way. It was like I had lost this “ambition” I had always prided myself on, and yet I was in this strange desert of not feeling great at being a mom while also not feeling great at my job.

The only thing that seemed to give me energy, though, was talking about exactly this. Sharing a POV online that felt almost like the antithesis of the “Lean In” movement I had once made my return-to-work bible. Bringing a “this is really hard — why are we all pretending we are loving this?” honesty to LinkedIn felt a little scary given I was still employed, but it resonated with so many people.

As I started to get my footing in parenthood — paired with the feeling that I was also a ticking fertility time bomb — I got pregnant again right before my first son turned two.

But by that point, something had seriously shifted. I was meeting more and more women who were giving me a different perspective on motherhood. Women validating that yes, motherhood is hard, but that motherhood is often made harder by the structures corporate careers create for us. That if I removed a lot of that stress, I might actually enjoy it more.

As I slowly started saying no to more things at work, building stronger boundaries, and turning down opportunities that weren’t truly priorities, I started to see the truth in that.

I saw how motherhood could actually be enjoyable.

Bedtime wasn’t inherently stressful — it was stressful because I was rushing to log back online. The after-preschool meltdown wasn’t actually that insane to deal with — it was just hard because I was already short-tempered after a long workday.

As I chipped away at my own work baggage, I started to see how enjoyable home life could be.

So when my second son was born, I made the call to quit my job.

I never — and I want to emphasize never — imagined myself being a stay-at-home mom. I always pictured myself with a big title at a big company, introducing myself by where I worked.

But there I was. “Scaling back.” “Taking a pause.” Setting up consulting work on the side to validate my existence beyond my role as mother.

And I can tell you this: as the months — and now almost two years — have passed since I left, life has gotten so much better.

Mornings are smoother because we’re not rushing. Sick days don’t create tension between my husband and me because I can handle them. Bedtime goes better because there’s no logging back on afterward. Consulting fills the slower seasons and scales back easily during holidays and summers.

Five years has flown by. I truly mean that. I can’t believe I not only have two children now, but that I’ve also completely flipped my career upside down, inside out — rebranding and reimagining it along the way.

I know so many parents who are exactly where I was five years ago, two years ago… and I feel for you deeply.

That’s why I started this newsletter.

And as we move forward, I want to both apologize for — and celebrate — the inconsistencies of it. I’ve aimed for so long to send this weekly, but we are also in a relentless pursuit of finding our groove over here.

Life has been very full lately.

Not busy in the way I used to say it — hectic, survival-mode busy.

Full in the sense that we are enjoying life.

We are partners in a new rhythm where my husband takes on more of the paid work outside the home while I contribute through consulting and the work inside it. Life has slowed down — in the best way — doing many of the same things I did when I was a “working mom,” just without having to multitask every waking moment.

We sit down for dinners instead of making lunches during them. I let my kids help make their lunches instead of getting frustrated that it takes longer. I linger longer at bedtime instead of doing twenty-five pop-ins because I need to finish something on my computer while they fall asleep.

Again, I never write these newsletters to criticize anyone else’s choices. They’re simply to paint a picture.

A picture where in one chapter I lived the working mom life full time, another where I both struggled and relished two very different maternity leaves, a chapter where I stayed home full time, a chapter where I consulted, and a chapter where I continue to build as life evolves.

Here to share the stories — and to hear yours. And I hope you stick around, because it’s about to get really good. I’ve gathered the stories. I’ve collected the data. I’ve learned what you all want.. and I’m going to share it in a variety of new ways, from an upcoming virtual Summit in May (more on this next week!!) to some in person events in San Francisco and other opportunities to connect in a meaningful and educational way as you navigate your own career journey.

But for now, happy birthday, my big guy. Thank you for unknowingly setting me on a path I never could have planned for — one that brought my attention back to what matters most, forced me to make the changes I needed to make, and reminded me every single day what love and importance really look like.

Kaleana