Career growth roadmap for women is something I think about literally every damn day right now, sitting in my apartment outside Chicago with snow piling up on the fire escape again and my third cold brew of the morning going warm on the windowsill. Like… I’m not some perfect exec babe with a TED talk. I’m the one who still gets nervous before big meetings, who once literally hid in a supply closet for ten minutes after a presentation because I thought I sounded stupid, who has definitely cried in the car on the way home more times than I’ll admit on the internet. But somehow I’ve made it to a director-level role and people keep asking how, so here’s the messy, honest version of my career growth roadmap for women—no sugar, no corporate filter.
Where I Completely Screwed Up at the Beginning (aka the Real Start of Any Career Growth Roadmap for Women)
I thought “hard work = promotion.” Lol. Rookie mistake. I was 26, living in a shoebox in Brooklyn, pulling 70-hour weeks thinking that sheer volume would make someone notice. Instead I got burnout, resentment, and a really awkward convo where my boss said “you’re great at execution but not strategic enough.” Ouch. That stung for months. I basically lived on instant ramen and anxiety while I tried to figure out what “strategic” even meant.
Lesson that actually stuck: visibility matters more than hours logged. I had to learn to speak up in meetings, send summary emails after projects, literally force people to see my name attached to wins. Took me way too long. If you’re early in your career growth roadmap for women phase—start documenting your wins somewhere. Google doc, Notion page, napkin, whatever. Because memory is garbage and your manager’s memory is worse.
The Part Where I Finally Got a Decent Mentor (and Almost Ruined It)
Mentorship sounds bougie until you realize most senior people won’t randomly adopt you. Mine happened because I awkwardly slid into her DMs on LinkedIn after a panel she did. Sent probably the cringiest message ever (“Hi I loved your talk and I’m trying not to suck at my job”). She actually replied. We met for coffee. I was so nervous I spilled oat milk latte all over the table like thirty seconds in.
But that mess turned into the best professional relationship I’ve ever had. She taught me how to negotiate, how to say no without sounding difficult, how to spot when I was being pigeonholed into “the reliable one” instead of “the visionary one.” Key thing on the career growth roadmap for women: find someone who already sits where you want to go—and then actually listen when they tell you the ugly parts.
Shameless plug but also real: Lean In circles and Elpha have been gold for me. (https://leanin.org/circles) (https://elpha.com/)
The Stuff Nobody Warns You About on the Leadership Path for Women
- People will question your ambition like it’s a personality flaw
- You’ll get told you’re “too aggressive” for saying the exact same thing a man said five minutes earlier
- You’ll second-guess every outfit before important days (yes I still do this in 2026)
- Some days the imposter syndrome is so loud you can’t hear your own thoughts
I once got passed over for a VP role and the feedback was “you need more executive presence.” Translation: act more like a 55-year-old white dude. I was pissed. Cried in an Uber. Then I channeled it into getting a speaking gig at an industry conference six months later. Revenge arc energy.
Also read this if you haven’t: “The Memo” by Minda Harts (https://www.mindaharts.com/the-memo) — hit way too close to home.
Quick Hits That Actually Moved the Needle for Me
- Record one win every single Friday. Even tiny ones.
- Ask for stretch assignments before you feel 100% ready.
- Practice saying “I want to be considered for X role” out loud to yourself until it stops feeling weird.
- Build a personal board of advisors (not official, just people you trust to tell you the truth).
- Stop apologizing in emails unless you actually did something wrong. (I still catch myself doing “sorry for the delay” when it’s been 45 minutes.)
Where I Am Right Now (and Why the Career Growth Roadmap for Women Never Really Ends)
I’m a director. I have direct reports. I run a P&L. And I still feel like I’m winging it half the time. Last month I completely blanked on a number during an exec review and had to say “hold on let me pull that up” in front of twelve people. Cringe. But nobody died. Turns out humans forgive humanity.
So if you’re reading this and you want leadership roles—start where you stand. Map your next six months. Pick one scary thing. Do it badly at first. Get better. Repeat. And if you’re feeling stuck, lonely, or like everyone else has it figured out… you’re not alone. My DMs are open. Seriously. Drop a comment, send a message, whatever. We’re all making this career growth roadmap for women up as we go.
