The Multi-Hyphenated Millennial Killed the Traditional Holiday (and We Don’t Mind)

The Multi-Hyphenated Millennial Killed the Traditional Holiday (and We Don’t Mind)

Work and holiday – two words that needn’t be contradictory. Speaking to a new generation of multi-hyphenates, slashies and side-hustlers, we find that bringing the day job along for your trip may actually enhance your experience…

I write this, I’m sat on the deck of a hotel, on the southern
coast of Turkey.
It’s November. I’m wearing shorts. There is gentle chatter in the
background and, when my writing is done, I’ll be paying the
equivalent of £3 for shakshuka and heading to the pool for a couple
of hours. The three-hour time difference from the UK
means I get to have a sneaky break while people respond to the
emails which would have seemingly been sent to them at 6am.

Work and holiday. Two words usually considered contradictory,
but with the rise in popularity of side-hustlers, and liberation
provided by fast WiFi and Zoom, they’re no longer living apart. We
all have spaces where we feel most alive – whether that be a
certain city, perhaps a farm or an island. When we visit, it’s not
uncommon for many of us to think: “I might have to do some work
when I’m out there.” But there’s another way to consider things. A
way which makes your craft part of your travelling experience.

Alexandra Shulman, former Editor-in-Chief of British Vogue joked
in her Desert Island Discs interview that when she was growing up,
people with side-projects were mockingly referred to as “the
projecters”. It used to be uncommon. Why spend your free time
working? In 2020 however, it’s almost as common to have multiple
professions, as it is to just have one. Whether you’re a
multi-hyphenate, slashie or side-hustler, having multiple strings
to your bow has become the norm. So when you spend much of your
“free time” working, what does that mean for holidays?

As someone who runs a digital publication and podcast alongside a
full-time job in marketing, I’m all too familiar with the
challenges and opportunities this lifestyle presents. I was
interviewing DJ Laani recently for my podcast Hot Girls.
She’s a radio presenter on Worldwide FM and also works behind the
scenes at Brownswood Recordings. I asked her to describe her dream
day and this is the answer she gave:

“Me, on a boat, with beautiful sea – blue and gorgeous – sat on
the deck with my computer, working away quite happily and the sun
is shining. If I could be there in five years time… ahh.”

Is she on holiday or is she working?

When I was growing up, the commentary around work was generally
negative. It was something that limited you from doing the things
you wanted (socialise, travel), rather than something that enabled
you to do those things. For me, work has always felt quite
grounding. There’s a certain something about the feeling that comes
when you’re moving a project forwards – and it’s this relationship
to work that has changed the way I feel about travel. Rather than
looking for escapism, I look for inspiration. Rather than somewhere
to switch off, I look for somewhere to creatively invigorate

I put the question to my Twitter
: “Creatives or musical people. When you go on
holiday, do you like to work from there? Does your dream day
involve working in a hotel?” And the answer was a resounding “yes”.
and even Ibiza came back
as places people liked to go with a task in hand.

For many musicians working today, their instrument is their
laptop. Orchid, a singer and music producer, said: “I’m obsessed
with my work so I would always prefer to be away with a purpose and
see some amazing things at the same time.” Music PR George Service
opted for a trip to Stockholm as a remote working base, while
author Nate Holder said: “I spent 10 days in Rio.
My productivity was off the charts!” Jewellery designer Lucille
Whiting commented that her suitcases often included beads, ribbons
and polishing equipment.

It appears that, for creative professionals, the stimulation of
a different place can alleviate some of the stresses of work and
reconnect us to the joy of it. It’s an experience which can then
enhance your trip, rather than disrupt it. Rather than being a
chore, the work becomes an integrated part of your trip. You
discover new cafés and workspaces. Enjoy a change of scene without
falling behind or losing grip of the things which ground you.

That’s what makes the working holiday a special kind of travel
for me. You’re moving through the world while also moving forward
in your career.

Discover More
Working from a Hotel is the New WFH: Eight of the Best Workation Destinations