Michael Newborn on Second Acts, Fear of Failure, and Why You Should Just Go Do the Thing
Michael Newborn spent 18 years in tech — four different companies, barely a weekend between them. By the end of it, he described what he felt as simply: difficult to find the motivation to keep going.
So instead of pushing through, he took what he called a creative side road. He started a podcast about reinvention. Called it The Second Act. And in talking to ordinary people doing extraordinary things in their second chapters, he found his own.
Michael came on No More Mondays and we had such a good pre-show conversation that I almost forgot to hit record. Here’s what stuck with me from the conversation that actually made it to tape.
The Second Act Isn’t a Strict Definition
Michael is careful about this: a second act isn’t necessarily a dramatic career pivot or a full reinvention. It’s more of an idea — trying to do something new. It’s available to anyone willing to contemplate it. And as he put it, it opens up doors and things you never would imagine.
What’s changed is that we actually have the agency to do it now. The old model — go to college, pick one thing, maybe change jobs once, wait until you’re 62 and a half to have fun — is breaking down. We’re living longer, we have more options, and the idea of one career and one identity for an entire life is starting to feel as outdated as it actually is.
Be a Figure Outer
One of the things Michael said that I want to put on a poster somewhere: his team has a word they’ve made up that they embrace fully. They call themselves figure outers.
That’s the mindset. You’re not supposed to know how to do the thing before you do it. You’re going to suck at it at the beginning — Michael admits he wasn’t comfortable putting his voice out in public when he started the podcast. He did it anyway. And the podcasting world, as he notes, is forgiving. You get more reps, you get more comfortable, you start asking better questions. You find your voice.
The key thing he said: if you’re willing to go back to the starting line and suck at something, you find out more about yourself than you ever expected — and you become a more complete human in the process.
What’s Actually Holding You Back
I asked Michael what stops most people from taking this kind of leap. His answer: fear of the unknown, full stop.
We’re conditioned from early on to memorize, execute, achieve, and be perfect. So when something new feels messy and uncertain — and it will — the brain reads that as failure. But as Michael put it: failure, loosely translated, is a learning experience. Nobody gets a promotion, changes careers, or builds something new without trying something they won’t be perfect at and don’t yet know how to do.
The other trap is looking at reinvention as one giant, overwhelming thing rather than a series of small moves. Michael’s version of that was simply: I’m going to start a podcast and see where it takes me. One step, then figure out the next one.
The Compound Effect of 1%
The hardest part of his own transition, Michael said, was this: we tend to overestimate what we can do in the short term and underestimate what we can do in the long term.
His coach early on gave him a reframe that stuck: just focus on getting 1% better each day. You don’t even have to define what the 1% is. Just ask yourself — is there something I did today I can assign to the 1%? The compound effect of that over months and years is orders of magnitude greater than any single breakthrough moment.
It’s an endurance game. Not a sprint.
What Surprised Him Most
I asked Michael what he didn’t expect when he made this shift. His answer was immediate: how many doors just magically appear and open.
When you start trying something new, it attracts different people. Those people attract other people. And suddenly you’re connected to and working with humans you never would have crossed paths with otherwise — and the level of unsolicited support that shows up is, in his words, mind blowing.
We are, as he said, really amazing and supportive of each other — if we allow it.
Michael also co-founded Try Sam AI, a platform that connects people with coaches, which feels like the natural extension of everything he’s learned — keeping the human element front and center even as tech changes everything around us.
If you’re feeling stuck, or telling yourself it’s too late, or waiting until you have it all figured out before you start — this episode is for you.
