Learning to Live the Dream: What Surprised Me About Success

Dreaming of the future I’m living.

Yesterday, I had coffee with a very successful woman. She assumed control of her father’s company and has grown it to record profits. I’d only known her tangentially, and this was the first time we had an extended conversation. She was easy to talk to, and I was happy to discover how much we had in common (well, except for the multimillion-dollar company and the team of 160 people).

The only reason I know about her record year is because I mentioned a strange phenomenon I’ve been experiencing lately: adjusting to the absence of struggle.

After years as a single mother, putting kids through college, returning to school myself, and eventually launching my own business, I now find myself blessed with the security of marital bliss, a supportive husband, and a welcoming community with lots of opportunity.

Tough problem to have, huh?

If you had asked me at any point over the past 20 years what I wanted most, it would be exactly this. But what I didn’t anticipate was how this new happiness would require me to re-examine my sense of self.

Who am I without the struggle?

Decades ago, I had a dear friend who was a traveling artist. His van was always breaking down. I remember him once saying to his wife, “Why is it that I can always scrape together $500 to fix this thing, but I can never make enough to buy a van that doesn’t require me scraping together $500?”

He eventually became a successful filmmaker, traveling the world a dozen times over to perform. And yet, I’d wager he’s still had moments when he’s had to remind himself that he no longer needs to scrape.

I empathized when my coffee date admitted she wasn’t sure how to give up the anxiety that had somehow become synonymous with the drive that made her successful. Her husband has to remind her to pause, to celebrate, to even acknowledge her team. And as soon as she could, she went right back to the grind.

Lately, I’ve been wrestling with the question: Who do we become when we’ve aligned ourselves so closely with our struggle that we can’t imagine living without it?

Actually — that’s bullsh*t.

I already know the answer. We sabotage ourselves.

What I’m really wrestling with is not doing exactly that. I’m wrestling with old stories and fears that whisper I need to stay vigilant to be worthy. That happiness, security, and ease are somehow temporary — unless I earn them again and again.

So, I’ve decided to do something about it. Something simple, intentional, and, it turns out, really effective.

Here it is:

I thought about all the people I’ve met over the past few years — people in this new community who are seemingly successful and making meaningful contributions. Some I’ve met briefly, others I’ve admired from afar, like my coffee date. And I’ve invited them into conversation — over coffee, over lunch — and introduced myself as I am now.

I’ve asked about their lives, listened to their stories, and discovered where we connect.

It’s simple. But big ideas thrive in small ways.

And maybe, just maybe, that’s what living without the struggle looks like — showing up with curiosity, presence, and the courage to let ease in.