He built a dream life behind the lens — world-class travel photographer, founder of Jacob Media, millions of eyes on his every post. So… why didn’t it feel like enough?

In this episode, we crack open what it’s like to have insane reach, total freedom — and still wrestle with not feeling good enough. Jacob talks about going from shooting epic landscapes to proving he’s a “serious” business guy (ugh), the identity spiral that comes with being online 24/7, and what he’s learning as he preps for the biggest role yet: fatherhood.

We also ask some spicy questions:

Are you cool? Are you trying to be cool? Are you trying to prove you’re not who you used to be?

And why do so many men struggle to show up during pregnancy?

Spoiler: It’s less about the answers, more about what it means to stop performing and start showing up — for yourself, your partner, and your future kid.