The Curveballs That Forced Me to Rethink Success
How illness, motherhood, and leadership revealed the cracks in my career plans.
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“Ouch.”
The nurse pierced the same vein for the fourth time.
I was 22 — just nine months out of college — and stuck in a chair for six hours of blood sugar testing.
I had ballooned 40 pounds in under a year.
High cholesterol. High triglycerides (that’s fat, by the way). No period.
I felt like the Stay Puft Marshmallow Man.
My body thought I was pregnant.
I wasn’t.
I was just very, very sick.
And none of this… was in the plan.
It wasn’t part of the plan.
I was 22 years old, having achieved everything I was supposed to, and deeply miserable.
It was the first of many life curveballs that challenged my notion of success.
What matters.
What doesn’t.
High achievers are taught to aim for clear goals.
Hit one milestone, climb to the next. Repeat.
But here’s the part no one prepares us for:
Your body doesn’t follow your plan.
Your family doesn’t.
Life doesn’t.
And when things go sideways — really sideways — that’s when the most successful people get thrown.
Not just distracted. Shaken. Unsteady.
Why?
Because you’re used to being in control, setting the pace, and hitting your marks. I know I was.
Getting sick at 22 was one of the best things that could have happened to me.
Here’s why.
(Re)learning how to prioritize what actually matters.
I thought landing one of the most coveted jobs in a competitive industry meant I’d “arrived.”
It didn’t.
It was the end result of a decade of playing it safe.
Following paths carved by people I didn’t know.
Not trusting myself.
When you choose a direction that isn’t right for you, there is only one result: Stress.
Even if your head can’t admit it — your body will always tell the truth.
Mine did. Loudly.
Here’s what it said:
High, constant stress → I was scared I’d get fired every day
Severe lack of sleep → I was working 18–20 hours a day, 6 days a week
Poor diet → 3,000–4,000 calories a day just to self-soothe
Mild depression → I felt trapped in the “dream” I had worked so hard to build
No one was mistreating me.
No toxic boss. No hostile environment.
It just wasn’t the right fit.
And still — it took me months to admit it.
I didn’t take action until my bloodwork screamed at me.
It took leaving that job, moving home, and 2 years of a completely different lifestyle to regain my health.
It was the beginning of learning to choose myself.
I stopped outsourcing my direction.
I started making career choices based on my compass.
It’s how I ended up traversing media, e-commerce, and social impact. Every change brought critique and baffled former colleagues.
That was OK.
I wasn’t making my decisions for them. I was making them for me.
I thought getting sick in my twenties was the hardest curveball I’d face.
It wasn’t.
That was just the warm-up.
Parenthood cracked me wide open.
Fertility treatments. Chronic nausea. All the “fun stuff” women rarely talk about in boardrooms.
But the real blow came after the babies arrived.
My kids have each suffered severe sleep anxiety that lasted for years: 5+ years for my son, and 2+ years for my daughter.
Eight years. Back to back.
Those years were hard.
I wasn’t just tired, I was frequently ill, emotionally drained, and mentally foggy.
All of this happened while I occupied executive posts with large, complex mandates.
People’s jobs were dependent upon my ability to lead.
I felt that responsibility daily.
And yet, I was breaking out in hives from the stress of holding it all together… barely.
Eventually, I took a step back, descoped my role, and took a salary cut, all with the hope of reducing my stress.
That was fall 2019.
And then… well, you know.
2020 arrived.
So much for good intentions.
Coupled with a global pandemic, 3 out of the 6 executives in my company took 4 months of parental leave — each.
I didn’t begrudge them their time and still don’t. But the reduction in work I had thoughtfully planned? It never materialized.
Emergency after emergency came up.
Every temporary coverage plan turned into another temporary plan. What was supposed to be a time of reprieve became a four-year stretch of treading water.
And yet, similar to my illness at the beginning of my career, I needed this to happen to realize what I truly wanted.
I thought start-up leadership was my forever lane.
I thought I’d stay until retirement.
But it took a crisis — one that wrecked my health, strained my marriage, and tested my sanity — to see the truth:
I was done.
When my role was eliminated in January 2024, I felt clear.
Not devastated. Not lost.
Ready.
I took a sabbatical.
Launched the coaching practice I’d dreamed of for nearly two decades.
Picked up my paintbrush — something I hadn’t done in 35 years.
None of that would’ve happened if I hadn’t been cracked open first.
The curveballs — the ones that wrecked my health and blurred my sense of self — gave me space to imagine a new chapter.
A chapter where I live in alignment.
Where I help other leaders do the same.
I don’t know what the third curveball will be. But I know it’s coming.
Life tends to deliver in threes.
I don’t wake up dreading it.
But I do expect it.
And when it arrives — like the ones before — it will bring hard-won gifts.
Painful, yes. But clarifying.
Because when we stop resisting the hard things, we start making decisions that are aligned with what actually matters.
If you’re navigating your own curveball and wondering what it might be here to teach you — I see you.
I coach senior leaders through these exact moments: where your body says “no,” your calendar says “more,” and your soul is quietly asking for a different kind of success.
And if you’re ready to talk about what’s next for you — I’d love to connect.
If you feel like sharing, drop a comment or email me privately. Sometimes just saying it lightens the load.
And if this story spoke to you…
Pass it along to someone who might need it today.
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I also host regular Substack LIVE sessions where we talk career evolution, leadership power moves, and finding clarity in chaos.
Today, November 4, 11am ET: Evolving Your Career Path to Fit Your Life with
of Still Wandering. (Link to join)Monday, November 10, 11am ET: Join me for a conversation with the former Commissioner of the NYC Fire Department, Laura Kavanaugh (link to come)
Tuesday, November 18, 10:30am ET: Join me for a conversation with
from Sense Labs (link to come)
Looking forward to seeing you there!
May you lead without limits,
This is a remarkable story.
I applaud and admire your grit and perseverance. 💪
Simply inspiring Kathy 💪