Do I go Solo? Yes or No?

I can still remember sitting at my computer with my finger hovering over the "Book Now" button. Go - or stay home?

It wasn't really about the cruise. It was about everything the cruise represented.

For years, I had travelled across British Columbia on my own teaching Emergency Support Services (ESS) courses. I flew into communities, checked into hotels, found somewhere to have dinner, taught all day, and then moved on to the next community.

Was I always comfortable? Not at all.

There were plenty of evenings when I walked into a restaurant by myself feeling a little awkward.

But I had to eat, so I did. Sometimes I'd hide behind a book, I kept telling myself people were wondering why I was alone. Eventually, I realized that most people were too busy enjoying their own meal to notice I was dining alone.

But work travel was different. I had a purpose. I knew why I was there. Every day was planned around teaching, meeting people, and helping communities prepare for disasters.

This cruise was different.

I had recently come out of a long-term relationship, and for the first time, I was choosing to travel simply because I wanted to.

• No workshop to teach.

• No classroom waiting.

• No work schedule.

Just me. That was both exciting... and terrifying.

As an emergency planner, planning is what I do.

Give me a challenge, and I'll have a Plan A, a Plan B, and probably a Plan C

before most people have packed their suitcase. Sometimes that's a blessing. Sometimes it's a curse.

I researched everything.

• The cruise ship.

• The ports.

• Hotels.

• Transportation.

• Restaurants.

• What to pack.

• What could go wrong.

I was as prepared as anyone could possibly be. But there was one thing I couldn't plan for. How I would feel. My mind was full of questions. What if everyone else was travelling with someone? What if I felt lonely? What if I hated eating alone? What if something went wrong? Then another question quietly appeared.

What if I don't go?

That question changed everything. Because deep down, I already knew the answer. If I stayed home because I was afraid, I would regret it far longer than I would ever regret feeling uncomfortable for a few days.

So I clicked Book Now.

Walking onto that cruise ship, I honestly wondered if I had made the biggest mistake of my life. The first dinner felt awkward. Watching couples together made me question my decision. There were moments when I wished someone was sitting beside me. And yes, there were evenings when I returned to my cabin, closed the door, and felt the quiet.

Solo travel isn't perfect. But then something unexpected happened. Because I was alone, I started talking to people. I met other solo travellers who completely understood what it felt like to take that leap. We shared meals, excursions, conversations, and more than a few laughs. Some of those friendships are ones I still treasure today.

There were incredible sunsets. Beautiful little towns. Long walks. Amazing theatre. And quiet mornings with a coffee where I realized something that completely surprised me. I was exactly where I wanted to be. And somewhere along the way, I discovered something even more important. I actually enjoy my own company.

People often ask me where I found the courage to travel alone. The truth is - I wasn't fearless. I simply decided that regret scared me more than travelling alone. So, if you're single and you've been sitting on the fence wondering whether you should book that trip, let me encourage you. You don't have to start with a month overseas. Take a weekend away. Explore a town you've always wanted to visit. Book a few nights somewhere different. Or try a short cruise.

Will there be lonely moments? Probably. Will there be awkward moments? Almost certainly. But there will also be freedom. Unexpected friendships. Moments of complete happiness.

And most importantly - memories that simply cannot happen if you stay home.

Sometimes the hardest part of the journey is clicking Book Now. Everything after that is simply living the life you've been dreaming about. For me, travelling solo didn't just change the way I travel. It changed the way I see myself. It reminded me that I am stronger than I thought. That I can create a life I love on my own. And that waiting for someone else to start living was never really the answer.

So if you're wondering whether you should go - My answer is simple. Go!!!

Your adventure—and perhaps a new version of yourself—is waiting on the other side of that Book Now button.

Jackie Doing Jackie

About Jackie

After more than 30 years helping communities through disasters, Jackie Kloosterboer is now focused on a different journey — her own. When a 15-year relationship unexpectedly ended, Jackie found herself rebuilding more than a future—she was rediscovering herself.

"Jackie Doing Jackie" is about solo travel, meaningful work, theatre, coffee shops, reinvention, and learning to fully live again. Because preparedness matters… but so does choosing yourself.