Life as a 20-something: “Looking back, it’s much easier to connect the dots”

Life as a 20-something: “Looking back, it’s much easier to connect the dots”

This is the first interview with a 20-something who is doing Really Cool Shit. Look out for new ones each Friday @ 


Lilly Rafson is the most level-headed 23 year-old that I know. And, she has already accomplished every young person’s dream: Quitting her job at a start up in NYC, traveling the world, and founding a really (really) successful travel company called Pack Up + Go.

Yes — you read correctly — all by the age of 23.

But, what is it actually like to quit your job and start a company? We all talk about it like it’s Euphoria or something, but do we really know what it entails?

Let’s find out.

“It has been the craziest learning experience — I’m not only a travel agent, but I’m also a social media expert, and a payroll specialist. I’m wearing every hat.”


Just Do

If you think that having a start up will be all rainbows and beach selfies in Tulum, then you’re wrong. Totally wrong.

While of course, I could hear the excitement overflowing in Lilly’s voice as she described Pack Up + Go’s impact so far (like helping to plan a wedding proposal!) — it was also clear that this job is just as confusing as any other. Maybe even more so, because there is no road map to starting your own business.

You just need to figure It out.

“As a 23 year-old, I have to figure out what advice to take. I want to be receptive to all the advice, because you know, I’ve never run my own business before. But where do I draw the line?” she pondered — like so many of us confused 20-somethings.

When do you stop taking advice, and start just doing?

Well, we could all learn something from Lilly, because it’s not like that confusion has stopped her. Only four months after launch, Pack Up + Go was already being featured by big-time names like Business Insider, and Thrillist.

We have Time

Yet, during our conversation Lilly was as humble and collected as she’s always been. I wanted to capture her cool, but wise insights and keep them as reminders for my most shitty days.

When we got on the topic of competition — because why wouldn’t someone like AirBnB take hold of this awesome idea — she reminded me that, “We’re only 23. The stakes are really low. We’re not going to take over the world yet, and that’s okay.”

It’s such refreshing advice, especially from someone who actually has the potential to do so.

But, with a self-effacing laugh, Lilly told me, “It’s insane how much other people’s vacation’s cause me stress. Owning your own business is the most stressful thing of all time. It’s crazy. It sounds more glamorous than it actually is.”

…It does sound so cool, right?

Being the founder of a company has this mystery to it, and sense of adventure that no corporate job could offer. You are your Own Boss. You create your own hours, and your own dress code. And, in this day & age — founders are almost as cool as celebrities.

“But, it does get lonely,” Lilly quipped. As a one-woman team, she often celebrates little wins (or big ones — like getting almost 100% approval ratings for each trip) by reminding herself that she is actually making people’s lives more fun.

Even if it if does keep her up at night.

Connect the dots

The most interesting part of our conversation was about finding your Thing, your Passion.

I had asked Lilly if she ever imagined that she would own a travel company when she was younger. “No,” she answered, almost immediately. “I wanted to be an actress — I went to a performing arts school since I was 11.”

As we started to dig a little bit deeper into her past jobs and interests, we uncovered that her utmost motivation was the experience of selling a product — tangible or not — that could make someone a little happier.

“It’s so easy to connect the dots looking backwards,” Lilly mentioned at one point, almost in awe of the distinct thread in her past jobs. “Whether it’s physical or consumer products, I love making things personal for people on the other end. The product that I’m selling doesn’t matter — it’s the experience.”

It looks like we may have a budding Steve Jobs on our hands!

But, in all seriousness — we could take Lilly’s advice and think critically about what skills or moments drive us; what get’s us excited?

And then maybe, we’ll be lucky enough to Connect the Dots, and find our Thing.

Thanks, Lilly.

‘Till next time.

If you enjoyed this — check out my blog, On Adulting, for more observations about this weird time as a 20-something. 

What’s your thing? How did you connect the dots? Share and share!


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