Reinventing Yourself at 40: Motherhood, Sailing, and Choosing a Life That’s Yours

What does it really mean to reinvent yourself — in the middle of life, motherhood, and the public eye?

In this deeply personal episode of Go See the World, Aubrey O’Hare shares what it’s been like to become a mother again at 40 while living and sailing full-time, running a long-standing YouTube channel, and navigating life’s biggest decisions in public.

From the early days of sailing with doubt and imposter syndrome, to raising children at different stages of life, to stepping away from YouTube to reevaluate everything — this episode explores the cost and reward of choosing an unconventional life. Aubrey opens up about regret, growth, public judgment, and the quiet confidence that only comes with experience.

She reflects on:

Becoming a mother again at 40 — and why it feels profoundly different

Learning to trust herself after years of self-doubt

Sailing with a baby as a single mom and captain

Living and creating in the public eye — and the emotional toll it takes

Why reinvention isn’t failure, but a necessary part of staying alive and inspired

How slowing down has made her a better mother, leader, and human

At its heart, this episode is about forgiveness — forgiving yourself for past decisions, trusting that you will always find a way forward, and believing that if someone else has done it, you can too.

If you’ve ever felt called to start over, change direction, or live a life that feels more aligned — this conversation is for you.

In this episode of Go See the World, Aubrey O’Hare and co-host Jordan get real about the part of sailing nobody warns you about: crew dynamics. Living with people in 200 square feet means no privacy, no escape, and high consequences—so small habits (like what “clean” actually means on a boat) can turn into big tension fast.

We talk about how we choose crew, the red flags and green flags we look for, why expectations matter more than vibes, and how we’re building our “Houdini Bible”—a simple onboard guide to keep the boat running smoothly and the mood intact.

If you’re joining a boat, hosting crew, or living in close quarters with anyone, this one will save you a lot of resentment (and probably a few broken dishes).

Sailing down the Pacific coast of Mexico sounds romantic—until you’re in the rolliest anchorage of your life, your bilge pump won’t stop, your stuffing box is leaking, and you’re doing it all with three women and a baby onboard. In this episode, Aubrey and Jordan share a real-time update from the coast of Oaxaca as they make their way south toward Chiapas, Costa Rica, and eventually the Panama Canal.

They talk about living on a 1977 Formosa ketch, the constant maintenance of an old boat, why new boats aren’t always better, and what it’s like returning to this stretch of ocean after a difficult, fear-filled passage the last time—this time with better planning, a stronger crew, and a very different mindset.

They cover: Rolly anchorages and why sailors sometimes leave at 3 a.m. Stuffing boxes, engine alignment, and why some problems are above your pay grade Living with mold on boats—and the product that changed everything Sailing with a baby and the vigilance it requires Safety, intuition, and navigating Mexico as an all-female crew The emotional difference between survival sailing and confident sailing Editing burnout, storytelling, and why this podcast feels freeing again This is not a polished highlight reel—it’s the honest middle of a long journey, shared from the cockpit.

Go Sea the World Podcast is a sailing, travel, and lifestyle podcast about love, motherhood, relationships, and personal growth, hosted by sailor and world traveler Aubrey O’Hare.

In this episode of Go Sea the World, Aubrey O’Hare and Jordan share how they got started living an unconventional life at sea—and why taking the first step matters more than having a perfect plan.

Recording from a 51-foot sailboat in Mexico, they talk about choosing freedom over comfort, overcoming fear, and how discomfort often leads to growth and inspiration. From sailing for the first time to swimming with dolphins, navigating fear, and preparing for a passage toward Panama, this episode explores what it really takes to build a life outside the traditional path.

Topics include sailing around the world, personal growth, adventure travel, living aboard a sailboat, women in sailing, leadership, fear, and staying inspired while choosing an unconventional life.

In this episode of Go Sea the World, Aubrey O’Hare and Jordan share what it was really like sailing in Greece with Sailing Doodles—from collaborating as creators to navigating chemistry, expectations, and the reality of life on YouTube.

We talk candidly about creator burnout, work ethic, thumbnails and algorithms, and what happens when an online connection meets real life. From age gaps and dating myths to sailing YouTube growth and collaboration dynamics, this is an honest, behind-the-scenes conversation about building a life—and a career—at sea.

Filmed during our time sailing the Greek islands, this episode pulls back the curtain on what it’s actually like to collaborate with another major sailing channel while staying true to yourself and your story.

Topics covered:

Sailing Doodles collaboration in Greece

Life as a sailing YouTube creator

Chemistry vs commonality in relationships

Online dating vs real-world connection

YouTube thumbnails, algorithms & burnout

Sailing, travel, and life at sea

Subscribe to Go Sea the World for honest conversations about sailing, travel, relationships, motherhood, and choosing an unconventional life on your own terms.

We’re recording from a 51’ Formosa in Mexico with a squealing baby in the tub and a whole lot happening in a tiny space. In this episode, Aubrey and Jordan talk about what dating looks like when you live on the move—how relationships become pressure cookers at sea, why “normal” timelines don’t exist for travelers, and what it means to protect your peace while still wanting love.

Then the universe drops a full telenovela plotline in our laps: Aubrey accidentally meets Violet’s paternal grandfather in the street… which turns into a sudden, emotional introduction to Violet’s extended Mexican family—tears, laughter, healing, and a whole new perspective.

And just when we think the day couldn’t get wilder? A 3AM “surprise” arrival at the boat sparks a hard boundary conversation, a co-parenting reset, and a surprising moment of hope for what a healthier future could look like—maybe even tandem-sailing around the world.

In this episode:

Dating abroad vs dating on the move (and why it gets intense fast)

Protecting your peace without closing your heart

Meeting family you’ve never met—by total accident

Co-parenting while traveling

The dream of “together, but with separate boats/houses”

If you’ve ever loved unconventionally, lived nomadically, or tried to co-parent while building an extraordinary life—this one’s for you.

We didn’t set out to do this.

What started as a quiet morning at anchor in Zihuatanejo, Mexico turns into a reflection on how quickly life can change—and what happens when you say yes anyway. In this episode, Aubrey and Jordan sit down over coffee aboard a classic pirate ship to talk about the unexpected chain of events that led to three women and a baby preparing to sail the wrong way around the world.

There’s no master plan here. No polished answers. Just honest conversation about motherhood, risk, trust, and the strange clarity that comes when familiar paths fall away. From failed plans and near-misses at sea to the quiet confidence of choosing a different kind of crew, this episode sets the tone for a journey shaped more by instinct than expectation.

Along the way, Aubrey opens up about leadership, fear, and the weight of making decisions that affect everyone on board—while learning that there may not be a “right way” to do something as wild as circumnavigating the globe.

This isn’t a how-to.

And the story is just getting started.

Fan Mail! Jake reach out by email and asked us a few really great questions about purchasing a boat for the first time or trying ones hand at buying a boat and selling it for a profit, or what we have been calling a "boat flip". 

Hi, love following your YouTube channel. Your pretty much living the life I want.  My plan is in about 3 years to sell my business and live aboard a sailboat at least half the year. 

My question is how do you find the boats that you flip?  I’ve been casually looking for a boat for several years and I rarely come across a good deal.  Is it mostly knowing people and right place right time or are there websites that I don’t know about! 

I look at boat trader, eBay, Craigslist and even Facebook market place with very little success. 

My other question is how do you manage having multiple boats? 

My concern with buying something now (assuming I could find something) is I live in Montana and can’t be there to take care of most of the time.  Do you have any suggestions or recommendations for me?

A BIG thank you to Jake for his email! 

Hello, and welcome! This Podcast is geared towards some of my most frequently asked questions by those of you watching Sailing Miss Lone Star on Youtube! If you have any topics or discussions you would like to hear about, send me an email at [email protected]

• “Tell me more about your background” – perhaps when did you start sailing/how did you start sailing/what did you do before you started sailing.

In this podcast you will find out where to find your own dollar boat and NOT make the same mistakes that I did. I bought a boat for a buck and refit it myself. Find out what I wish I would have known back then.