Why I Stopped Following the Rulebook and Started Writing My Own Story, especially in my 30s.

We were told there’s one way to do life: school, job, marriage, mortgage. But what if that’s not your version of happy?

Rebelling Against the “Shoulds”

School. University. Job. Relationship. Buy a house. Get married. Have children. That was the story we were told, and for years, I thought it was the only version of success that counted.

I can still picture it: a male friend of mine, pint in hand, listing those milestones like a moral checklist, wondering why I always seemed to be doing things out of order. To be fair, I was constantly rebelling against the “shoulds.” I did a ski season when I couldn’t ski. Moved to New Zealand at 22 when everyone else was starting “proper jobs.” I quit a well-paid role because it didn’t feel right - even when I didn’t have a clear plan for what came next.

“There isn’t one version of success, happiness, or adulthood. We can write our own path - and that path might still include the milestones we grew up expecting, just in a different order, or maybe not at all.”

I know how privileged I am to have had choices, but even when my finances didn’t match my ambitions, I always had this quiet belief that I’d figure it out. That doing things differently wasn’t failing,  it was just a different kind of brave.

Rewriting the Script in Your 30s and 40s

At some point, between the noise of deadlines and the weight of expectations, I realised how easy it is to lose yourself trying to live life in sequence. We chase the next job title, the next relationship milestone, the next sign we’re “on track.” But who’s setting the track, and why are we all racing toward the same finish line?

For me, the answer came far from home in Mexico with my co-founder Sophie, watching the sun set and talking about how alive we felt when we travelled.

That moment became the spark for It Started With A Trip.

It wasn’t about “finding ourselves” in a cliché way. It was about creating something for people in their 30s and 40s who’d ticked a few of life’s boxes and realised they wanted more. Not more things, but more feeling. The ones who had the career, the home, maybe even the relationship, but missed that sense of curiosity and connection they once had.

The Freedom to Choose Your Own Version

Our trips aren’t about escaping your life; they’re about pressing pause long enough to remember what you want from it. They’re designed for people in their 30s and 40s who still believe in saying yes to things that scare them a little, who want to meet new people, see new places, and feel something real again, outside the emails, mortgages, and expectations.

“It Started With a Trip isn’t just our name, it’s a reminder that sometimes the best stories don’t start with a plan. They start with curiosity.”

Because life doesn’t have to follow a checklist. You can build a career and take a risk. Be single and be fulfilled. Want stability and crave adventure. We don’t have to choose between the boxes, we just get to decide which ones matter. For me, it started with a trip. For you, it might be something else entirely. But either way, it’s yours to write.

Sam

Co-Founder, It Started With A Trip