I recently got another flood of stories submitted to Both&’s site (THANK YOU!), and I’ve spent the last week reading through and uploading them. And today, I wanted to talk about a common theme I see across so many of these career pivots — the simple notion of: “I wish I had done this sooner.”
Now, I want to preface that there’s some caveats with that little statement. These people all recognize that everything always feels obvious in retrospect, and many genuinely believe things “worked out the way they were supposed to”. And yet, alongside that acceptance, there’s also an acknowledgment that they missed out on time — that they carried unnecessary stress or workload for months (or years) longer than they needed to. And that maybe, if they’re being honest with themselves, they would have been just fine if they’d taken the leap earlier.
And I think two things can be true. You can look back on your life and feel no regret about the path you took, while also offering advice to others that there were things you wish you’d done sooner.
Those two truths are exactly why Both& exists. I built this site to share these stories — to show the path someone took and how it worked out, not as a perfect blueprint, but as lived perspective. To allow you to use someone else’s hindsight to your advantage. To see a career or job that looks a lot like yours through the lens of someone five, ten, or even fifteen years ahead of you, and maybe make a small adjustment in your own life sooner than you would have otherwise.
And all these stories do exactly that.
One woman recently wrote about landing what she thought was her dream job while she was eight months pregnant — completing the interview assignment while she was literally in labor. She loved that job. She planned to stay forever. And then motherhood arrived in full force: a newborn, a toddler, postpartum depression, and a pandemic. Six weeks after returning from leave, she quit.
She described the anger that followed. Like, right from the start, she had failed at being a working mom. But rather than wallow in it, she did what so many of us do when we think we are the problem: she researched harder. Podcasts. Books. TED Talks. And in that process, she realized she hadn’t failed. The system had failed her.
Almost by accident, she also learned she had missed out on three months of paid leave simply because she just didn’t know she had to apply. That moment became a tipping point - and today, she runs a parental leave consulting agency (Hello Bundle) helping parents understand and maximize their benefits so they don’t lose time, money, or recovery the way she did.
She works more hours now than she did before — but she sets the schedule. And when her daughters came home from school recently, they went to the beach. And it felt good.
But she also told me she wished she’d known sooner that there were other ways to build a successful career beyond climbing the traditional ladder.
(You can read Linzay’s story here).
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Another woman wrote about being a teacher — a role that looks flexible on paper until you’re the one with young children who aren’t in school yet. You have doctors’ appointments piling up, and only ten days off a year to make it all work. She eventually moved into a remote role, and it changed everything. But… when that flexibility was taken away again, she resigned.
Now she’s piecing together part-time work while looking for something more stable, navigating inconsistent income and the loss of benefits — especially health insurance, which had always been her responsibility to carry. She admitted something I see often in written submissions (though more often than people publicly say out loud) about their chosen paths: “Truthfully… I wish I never went into” in her case - education.
To be clear, she wasn’t saying the work wasn’t meaningful. She was acknowledging that it’s one of the many professions that makes it incredibly hard to support a family — and even harder to transition out of once you’re in.
She didn’t wish she’d worked less. She just wished she’d understood sooner how much her early career choices would constrain her later ones.
(You can read Larissa’s story here).
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Several women talked about staying longer than they wanted to because things were “fine.” Not awful…. just - fine enough to tolerate. One described being objectively successful — leading large initiatives, managing teams, delivering results — but feeling a persistent sadness she couldn’t quite name.
And then there are the stories — so many stories — with harder twists and turns.
The woman who was let go after returning from maternity leave and now feels emotionally battered, searching for work that understands family commitments while trying to catch up financially.
The journalist stepping away from a career she loved because childcare costs eclipsed her salary.
The attorney who endured an eighteen-month ethical and emotional unraveling before resigning with no backup plan, only to later realize her teenagers needed her more than ever.
Some stayed. Some stepped away. Some are still very much in the middle.
Across all of them, though, I keep seeing the same truth: most parents don’t wish they’d worked harder or waited longer to honor what they felt. They wish they’d listened to their inner voice — and leaned into what they were being compelled to do — sooner.
So I want to leave you with one quick exercise, if you’re feeling any sort of tug, to help prepare you before a leap ever becomes necessary:
Create an Excel or Google Sheet of your key contacts. And by “key,” I don’t mean titles — I mean people who:
Championed you
Enjoyed working with you
Thought highly of your work
You respected and trusted
Include:
Name
Personal email (not just work)
Company / role at the time
Notes on how you worked together (projects, context, anything that will jog your memory)
If you ever consult, job hunt, or need references, these are your people. LinkedIn is not built to recreate this. You have to build it yourself.
And I mean everything — projects, initiatives, pilots, scrappy side work, results, lessons learned — with as much specificity as you can remember.
If I could go back in time, I would’ve had one running document and updated it monthly.
Why this matters:
AI makes searching and repurposing documents incredibly easy, so this can be long
This becomes your true resume
You can quickly pull language for resumes, proposals, and pitches
Future you will not remember the details. Write them down now.
Most people only network when they need something — a job, a reference, an intro.
The real work is maintaining relationships before you need them:
Coffee
Lunch
A quick “thinking of you” note
Checking in after a big moment
This matters at every stage of a career — but especially if you ever take a career break. These relationships are what keep your professional identity intact even when you’re not actively “in” the workforce.
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You don’t have to do all of this perfectly. But if you do any of it, do it before you walk out the door. Your future self will be very grateful — trust me.
Thanks for reading today. I hope you join us in discussion in the comments, because I don’t think this is a one-way conversation!
What’s one thing you wish you’d done sooner — and what’s one small thing you’re doing now because of it?
Here for you,
Kaleana
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