Most of us grow up mistaking obligation for love. I did too—until I finally saw what a healthy connection actually feels like.
Here's what nobody tells you about dysfunctional families: they don't feel dysfunctional from the inside.
The scariest part isn't the apparent toxicity you see in movies. It's how completely normal your patterns feel when they're all you've ever known.
I spent 49 years thinking I understood connection. I was wrong about everything.
Twenty-three years ago, I stood on a chair in front of a room full of creative professionals, asking, "Who's new?" I thought I was the guy who brought people together.
I had no idea I was about to meet the woman who would teach me that I didn't know the first thing about real connection.
The Performance
That night was September 19, 2002, and I was running SCAMP – the South Coast Alliance of Media Professionals. We'd built this community before social media existed, bringing together the freelancers and gig workers who lived in Santa Barbara but worked in tech and entertainment.
Every month, I'd get up on that chair and spotlight the newcomers, giving them a minute for "shameless self-promotion."
When Kymberlee introduced herself as the producer of Flash Forward and mentioned she'd just finished her second book on Flash, my ears perked up. I'd left Wavefront eight months earlier and was trying to push Flash into 3D territories it wasn't yet ready for.
Plus, she was beautiful.
So I did what I always did – I made my move. "Want to have lunch?"
That first lunch lasted three hours. We closed the restaurant, talking about Flash capabilities and creative possibilities. But here's what I realize now – we were both performing.
She'd walked in with an attitude to prove, having learned from her developer that I was "The Mark Sylvester!!!" and she wasn't about to be impressed. I was trying to live up to being "The Mark Sylvester."
Two résumés are having lunch, each playfully trying to out-credential the other.
However, here's the thing about performance-based connection: it's exhausting, and it's not actually a genuine connection at all.
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The Sunday Drives
The fundamental shift happened over the next few months. My friend Peter Goldie from Macromedia called with an opportunity – their CEO wanted to sponsor something at TED, and did we have any ideas?
Kymberlee and I had sketched out this back-of-napkin concept using new Flash capabilities, and suddenly we had eight weeks to build something for TED.
Every Sunday became sacred. We'd load up the car and head north on Highway 101, a six-hour drive to San Francisco, to work with Macromedia's top developers.
And here's what I discovered about those drives – they were pure freedom.
I love driving, and we both love talking. There's something about staring out at the open road that frees you up in ways sitting across a restaurant table never could. The negative space of all that open air between Santa Barbara and San Francisco – expansive vistas, rolling hills, with hardly any cities and hardly any traffic on Sundays – created this bubble where we could just... be.
We talked about everything. School, family, friends, hobbies, jobs, and dreams we'd never shared with anyone. I don't recall anything being off-limits.
And because we were between destinations – not yet at work, not having to respond to emails or handle business – we were freed entirely up from performance mode.
I found myself looking forward to those Sunday drives more than the actual work. The six hours up, diving deep into conversation. Six hours back, processing what we'd built together, what we'd discovered about each other.
Somewhere in those dozen hours of driving each week, without either of us planning it, we stopped trying to impress each other and started actually knowing each other.
And somewhere in that knowing, we fell in love. We got married four years later.
The Revelation
That's when I noticed something that changed everything.
During our non-work moments – rare as they were – Kymberlee would call her family. Her mom, her dad, her grandmother, her aunt. For no reason at all.
Seriously, no reason. To say hi, ask how their day is going, share a random thought.
I'd never heard of such a thing.
In my world, family calls happened on holidays, birthdays, when someone died, or when something was seriously wrong. You needed a reason. A purpose. An occasion.
But Kymberlee would just... call because she wanted to hear their voices.
Stuff You Should Know
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On Purpose with Jay Shetty
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