You know how we all have that thing? The one we keep pushing off until some magical “perfect” moment?
For years, my son was my excuse. A really good one too – because who’s going to question a parent putting their kid first? “When he graduates,” I’d tell myself, tucking my dreams of adventure into that nebulous someday-space we all know too well.
Well, guess what? Someday showed up. And it’s terrifying.
Everyone talks about empty nest syndrome as either grief or excitement. The sadness of children leaving or the joy of newfound freedom. But nobody mentions the third option: the fear of stepping into a life that’s suddenly, completely yours again.
The Moment I Took the Leap
It happened in the most ordinary way possible. There I was, scrolling through email (probably procrastinating on something else), when a flight deal popped up. Iceland. Direct flight.
My brain did that thing where it starts spinning up reasons why not. But for once – just this once – I didn’t listen.
Click. Book. Done.
Just like that, I committed to driving Iceland’s Ring Road by myself. Chasing lighthouses. Hiking trails that look more like Mars than Earth. Alone. (Did I mention the alone part? Because wow, that’s a thing.)
After building a successful career and raising a son, I thought I’d be braver by now. Turns out, professional courage and personal courage exercise different muscles. I can lead teams, make tough business decisions, and navigate complex workplace dynamics. But book a solo trip to a foreign country? Apparently, that requires a completely different kind of fearlessness.
The Long Road Here
This wasn’t a sudden leap into the unknown. I’ve been deliberately challenging myself for years, starting back in 2017 when I embarked on a year of experiments – trying new things every month, from new music to food to wellness activities.
I have no issues going to restaurants, concerts, or anything else alone. I’ve developed a genuine taste for my own company and preferences over the years.
But for some reason, leaving the country felt like risking my life. It became the final frontier of my comfort zone – the one thing I kept circling back to but never actually doing.
I love hiking and have a passion for seeing lighthouses. Somewhere along the way, my lighthouse journeys became few and far between because I’ve seen most of the ones in the US. Iceland has popped up again and again. I will always regret not signing up for a half-marathon at midnight in Iceland when I was still able to run competitively.
The question haunting me: Who am I when I’m not actively mothering? When my primary identity shifts from “his mom” to just… me?
The Fears That Actually Keep Me Up
Here’s the weird thing nobody talks about – when you finally take that leap, the fears don’t disappear. If anything, they get louder.
I’m not worried about the logistics. I’m an excellent planner with backup plans for my backup plans. I’m not directionally challenged, I don’t worry about missing flights, and I’m completely comfortable navigating new places. These are skills I’ve honed in decades of business travel and professional problem-solving.
What terrifies me is falling off a cliff on a hike. Being run off a narrow road. Falling into hot mud pits. Some other terrifying death that is plausible but unlikely as long as I’m smart and careful.
The more I research, the more I panic. I’m afraid of dying alone far from my son and that it will not have been worth it. That somehow staying small and close makes me a better mother. That being bold, brave, and adventurous is the past me.
And I miss her. I miss being fearless and just doing the thing because it sounds amazing and like something I’d enjoy.
But here’s what I’m really afraid of: What if I’ve forgotten how to be her? What if years of putting everyone else first has eroded that part of me beyond recovery?
The Safety Trap
I’ve been doing the safe thing for so long, prioritizing my son’s (and others’) interests over my own. There’s nobility in that, sure (maybe). But there’s also a slow erosion of self that happens when you consistently put your dreams last.
My ADHD craves novelty and adventure, while my Autism wants safety and routine. For years, I’ve let the safety-seeking part win. Partly because it’s easier. Partly because it’s what mothers are “supposed” to do. Even my boldness at work is tempered by what a successful professional is “supposed to do” – minimize risk, plan for contingencies, stay in control.
But what if the best thing I could do for my son – and for every team I lead, every person I mentor – is show them that courage isn’t the absence of fear, but doing something despite being afraid? That leadership isn’t just about making others feel safe to take risks, but modeling what it looks like to take them yourself?
What if this isn’t just about a vacation, but about reclaiming the part of myself that takes bold action in every area of life?
The Permission Slip I Finally Wrote Myself
Seeing that discount ticket email was like waving a red flag in front of a bull. A sign that my excuses were just that – excuses.
My son will be fine – he’ll be with his dad for a few weeks. He has other support. I’ve just been using him as the perfect excuse because who questions a parent putting their child first?
But I had to finally write myself a permission slip that said:
- It’s okay to prioritize an adventure that’s just for you
- Being a good mother doesn’t mean sacrificing everything
- The version of you who was brave and adventurous is still there
- You can be a successful professional AND someone who takes personal risks
- Living courageously at home makes you more fearless at work
This isn’t just about midlife. This is about what happens when any major life transition gives you permission to step back into yourself. Empty nest. Retirement. Divorce. Career change. That moment when suddenly you can, but you’re terrified you’ve forgotten how.
No Guarantees
There are no guarantees in life – whether I stay home or travel the world. The fears may be realistic but are unlikely as long as I’m smart and do my research (now I hear that a volcanic eruption is imminent…seriously?!?!?).
I’m not sure how to get past the fear other than to just go. To trust that the planning part of me will keep the adventurous part of me safe. To believe that whatever happens, this act of reclaiming a piece of myself is worth it.
What I’ve learned through this process is that knowing your fear and naming it are the first steps to taming it. When I stopped saying “I’m afraid to travel alone” and started articulating exactly what scared me – leaving my son without a mother, forgetting how to be brave, losing the adventurous part of myself forever – the fear became something I could examine rather than something that controlled me.
The leadership skills I use every day – breaking down complex problems, naming what’s really at stake, making decisions with incomplete information – these work on personal fears too.
Your Turn (Because Yes, This is About You Too)
Maybe your “Iceland” isn’t actually Iceland. Maybe it’s starting that business. Writing that book. Having that conversation you’ve been avoiding. Taking that promotion that scares you. Dating again. Moving to a new city.
Whatever it is, I bet you know exactly what it is. That thing that makes your stomach flip when you think about it. The thing you’ve been putting off until the timing is perfect, the kids are settled, the work calms down, you feel more ready.
Here’s what I’m learning: The timing will never be perfect. You’ll never feel completely ready. And that’s okay.
Want to know the secret? As Mel Robbins teaches in her 5-Second Rule, count down from 5. That’s it. Five seconds to push past the excuses your brain is already cooking up.
5-4-3-2-1.
Then do one thing. One tiny thing that moves you forward. Book that class. Send that email. Buy that ticket. Schedule that difficult conversation.
Because here’s what I’m learning: Being scared doesn’t mean you’re doing the wrong thing. Sometimes it means you’re finally doing exactly what you need to do.
The courage you build in your personal life makes you more fearless in every other area. The risks you take for yourself teach you how to help others take theirs.
A Letter to My Future Self
As part of pushing myself past my fears, I wrote a letter to the me who will return from Iceland:
Dear Future Me,
I hope you took all the photos of those gorgeous orange lighthouses. That you talked to strangers even when it was uncomfortable. That you took a side quest, got lost, and found your way again. I hope you ate something weird and liked it.
But most of all, I hope you remember what it felt like to be bold, brave, and adventurous. To make “someday” today. To prove to yourself that the fearless version of you isn’t gone – she was just waiting for permission to come back out.
I hope you bring that version of yourself home and into every boardroom, every difficult conversation, every moment when someone else needs to see what courage looks like.
Because this is just the beginning.
Love, The You Who Finally Said Yes
What Happens Next
While you are reading this article, I’m actually IN Iceland doing the thing I said I’d do (I write and post ahead so I can take breaks like this…now it’s finally for something fun vs life happening).
Over the next few weeks, I’ll be sharing what it’s really like to do the thing that scares you – the fears that don’t go away even after you take the leap, the tools that actually work when you’re tempted to back out, and what’s waiting on the other side of terror.
Because this isn’t just about one trip. This is about what happens when you stop waiting for permission to live your own life.
I can’t wait to get back and read this again. To share how it felt to step back into the brave version of myself. To tell you whether the fear was worth it.
Spoiler alert: I have a feeling it will be.
Your Turn (For Real This Time)
What’s your “Iceland”? What’s that thing you keep pushing to someday – in your personal life, your career, your relationships? What are you waiting for permission to do?
Maybe it’s time to stop waiting and start planning. The courage is there. You just have to decide you’re worth the risk.
5-4-3-2-1… Go.
