STUCK ON A SUNDAY — ISSUE NO. 2

I find December to be such a strange time to be a parent navigating career and family. It’s framed as “cozy” and magical and slow… and while there are many mini moments of that, in reality I think it’s hands down one of the craziest seasons of parenting and work all year.

School is barely open, childcare has a lot of hiccups as kids are getting sick more often, there are performances and parties (many during the work week and sometimes during the day???), family travel — and among all of this, somehow, work still expects the same output.

Finish strong. Set 2026 goals. Establish what’s next. Be ambitious and reflective and present at home all at once. That is the anthem!

While I’m now almost two years removed from “corporate life,” I still get anxious this time of year, thinking about all I’ve accomplished, all I haven’t, and all I want to do next year. And while I have really, really ambitious goals for Both&, my consulting, and general projects, I’m also working hard to take inventory of the ebbs and flows of this last year as it relates to the boys and childcare — to predict and anticipate when family needs will be higher. Holidays, school closures, travel, summer, classroom transitions, more holiday breaks, repeat. It’s one of the reasons I’m so grateful for the flexibility consulting has provided me — what scaling back with work and upscaling with childcare has given me — and how much growing a community of like-minded people redefining success has meant to me, especially at the end of the year and the beginning of the next.

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Speaking of like-minded new friends — I had to share a story today of a newer “consulting” friend I’ve met, who for the sake of this story and some shifting projects asked to be called “Natalie.” And December of last year just happened to be Natalie’s breaking point — and the beginning of her new, better path.

Her story is very familiar to many. When she became a mom, she had been working in tech for over 10 years and spent the first few years of motherhood becoming the person who made it all work. Then one year, December arrived… with one no-school day after another, a sick kid that wouldn’t bounce back, and a daytime Christmas performance she missed because she couldn’t step away from work. Looking back, she said it wasn’t just one moment that made her break — it was the cumulative weight of countless “I don’t have time for this” decisions that finally pushed her over the edge.

By January, she had quit her job and gave herself a timeline: three months off. Not because she had a master plan, but because she needed space to breathe and understand what she actually wanted. During that time, a local business reached out needing help with marketing. It wasn’t tech. It wasn’t the “impressive” brand name people recognized instantly. But the flexibility was there. The pay was still solid. And the stress level dropped dramatically.

She took the role part-time. That flexibility alone changed everything — especially this past summer when she realized she didn’t need to sign her kids up for every possible camp just to survive the days. She could actually be present for some of it.

When I asked her about her biggest learning, she said something that I think a lot of us deep down worry about: that it was the optics of her new job that felt harder than the reality of it.

There was no big stock upside, no “bragging rights” around friends that you worked for a company “taking off” to the moon. But there also wasn’t the constant pressure that came with that kind of potential payout. “It covers the bills I need covered and then some,” she told me. “And even if some of my online connections wouldn’t recognize the name, it’s a really cool local place where I can actually see the impact of my work.”

A story I love to see, and a friendship I’ve come to cherish — a fellow mom who’s totally re-aligned her definition of success.

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I have about 42 articles tabbed this week — but one article I read that I’ve been thinking about a lot was this one, “AI is reshaping work. It could also spark an entrepreneurial boom.” Instead of leading with fear about jobs disappearing, it talks about how AI could actually open the door to a new wave of everyday entrepreneurship — especially for people who already have real experience and real skills.

Yes, AI is automating parts of jobs that once felt untouchable. That part is real. But the author makes the case that big shifts like this don’t usually erase work altogether — they just change where human value lives. And right now, that value seems to be moving toward small, independent businesses. One-person consultancies. Niche services. Passion projects that actually make money.

With AI handling things like admin, content, marketing, customer support, and even accounting, the barrier to starting something on your own is dramatically lower than it used to be. What once required a team and a big budget can now, in many cases, be done by one person with the right tools and a monthly subscription.

This was one of the best highlights in the article: most U.S. businesses are already solo operators. AI could accelerate that trend even faster. But without real support — training, access, grants, community — this shift could also deepen inequality instead of shrinking it. The article argues that we need systems in place before people are pushed out of jobs, not after.

Essentially, the article reminds us that the barrier to entrepreneurship isn’t really a team or a budget anymore — it’s mindset and access. And honestly… that feels very aligned with what so many parents in this community are quietly experimenting with already.

I’d genuinely love to hear what your take is on this — are you feeling hopeful about where work is headed, or more skeptical?

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If you’re looking for something that ties directly into all of this, the AND / Both podcast (I know — kindred spirits with the name, we have bonded over this many times) recently did an episode with Brea from Lions & Tigers on the future of remote work. It’s one of the most exciting (I mean it!!) conversations I’ve heard on what flexibility actually looks like in practice — not in theory.

Takeaway: the future of work isn’t going to be one single model. It’s going to be many shapes at once — and the more honest we are about what different seasons require, the better chance we have of building work that actually lasts.

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If any part of this — Natalie’s story, the optics shift, the local versus tech question, the AI conversation, or just the general December pressure — stirred something for you, I’d love to hold that with you in Chat this week.

Here for your questions and commentary!
Kaleana