Reader Q&A: Style picks, travel tips, and the work behind the window seat
Answering questions like why I document every trip and my worst travel mistakes
Most of the time I’m writing about hotels or travel products, but every now and then, it feels right to turn the focus inward a bit. My first-ever Q&A seemed to be well received, so I might try to make this more of a regular occurrence. The aim is to help you learn more about both the seat by the window (my travel tips) and the person sitting in it (me)!
Read on to learn:
My worst travel mistake
How I manage work/leisure when traveling
The highlights on my portugal itinerary so far
How I grew my business before I went full-time
How you can make trip planning more manageable
Favorite brands to shop right now? —Ariane
If I could build a daily uniform from one brand right now, I’d probably choose Donni. They do button-downs and simple pants so well; that’s my favorite kind of outfit formula.
Other brands I love are St Agni, STAUD, and Still Here. For some reason, sport-inspired styles are really calling to me right now. I’m obsessed with these (not sure how tall-friendly they are though as I’m 5’11”), and I’m loving this St Agni pair too. Then there’s the sporty windbreaker-style jacket; I haven’t been able to stop thinking about STAUD's.
Any advice for someone who wants a great trip but doesn’t have the headspace to plan? —Emily
As I’ve mentioned in past letters, I’m a big proponent of using free tools that can make your life easier like Chat GPT. I’ve mentioned a lot of the things I use it for like building a budget and aggregating recommendations. This frees up headspace for me to focus on the more exciting aspects of trip planning.
I also find that making an itinerary can often be the most stressful part of trip planning. FOMO can be really powerful. So to that I say: pick a few things you’re REALLY excited to do or see. You might have a list of 30 restaurants, but I’m sure only a few really call out to you. Pick your top 5 of every category (cafe, bar, restaurant, etc) and then anchor your days around a couple of each. That way, you’re always seeing or doing something you’re excited about, and then you have plenty of whitespace left in the itinerary to happen upon something new—that’s half the fun of being in a new place anyway.
Best NYC restaurant you’ve been to recently? —Jessie
Cafe Zaffri was worth all the hype. We were sat in their super elegant back room and everything we ordered was delicious. But what I can’t stop thinking about is the coconut rose sorbet. I neeeeed to go back for it.
What’s the worst travel mistake you ever made? —Debbie
I think it was back in 2018. The night before I was set to fly out to see family for the Thanksgiving holiday, I realized I had never actually booked my flight. What!! VERY unlike me as someone who is very Type A. I had to pay a premium to get on the flight I needed to, but I made it.
Then, in Kyoto for my honeymoon, my husband and I decided to stay in a ryokan that looked super nice. We booked all the rest of our hotels on points; this one we paid cash. It was the splurge of our trip, so we had high hopes. Unfortunately what we walked into was not at all what we saw online, so we only stayed for one night out of the 4-night stay we booked. That really sucked. But it worked out in the end, because the hotel we absconded to was the Park Hyatt, which remains today as one of my top favorite hotel stays ever.
How long did you grow your business before quitting your full-time job? —Samantha
I’ve actually been doing freelance work for 10 years at this point. It started as selling digital portrait illustrations (a canon event, I fear), and grew into offering other small creative services.
But 2020 was the real turning point because that’s when I made it official with V1 Projects (EIN, QuickBooks, actual invoices instead of Venmo (lol)…the whole deal). Around the same time I launched a merch company called New York Old Friends, which was profitable and taught me so much about entrepreneurship, but I eventually shut it down because it just didn’t light me up anymore. (Side note: normalize ending things you don’t want to do anymore!)
So depending on how you frame it, I’ve been building my business for either 10 years (if you count the scrappy freelancing chapter) or 5 years (since I got serious about treating it like a real company).
How did you get your foot in creative strategy / brand strategy? And how did you become a pro at this? —Doyoufancy
I started my career in creative marketing: first in financial services, then in hospitality. I then went on to work at a digital marketing agency which, despite being a job I hated, gave me foundational skills for my future creative strategy roles. Those jobs can be quite fun given the range of brands you can work with and the creativity involved, but if you don’t understand the unsexy basics of CPMS and how ad campaigns work, no one will hire you.
Those roles comprised about the first five years of my career. From there, I went on to work at a super tiny media company where I was hired as a PM, but I was in my girlboss era so within six months I managed to convince them to create a new role for me and became their integrated marketing manager. This is where my creative strategy work really started in earnest, and where I realized that it was the kind of work I wanted to be doing as a career. But then the Pandemic came along, so it was short-lived.
Luckily, I landed at an e-commerce startup as a creative strategist, and I got to do a lot more of that kind of work at this job than I probably would have done at the previous one. But the volume of work was intense. I was creating about seven decks per week—by myself—for all kinds of brands across every vertical. I lasted about a year and a half before I burned out and came across an incredible opportunity to jump ship to: Snapchat.
It was another creative strategist role that—fun fact—I got via cold LinkedIn DM (shout out to Theo, one of my favorite managers). I worked there for almost three years honing my skills even more before the inevitable tech layoffs came for me. I was only gone two weeks when I got a call from an old colleague asking to come help out at Complex. A 3-month contract turned into a full-time role as Head of Strategy, which I did for about a year before leaving to pursue my own projects full-time.
What does a typical (if there’s one) work day look like for you? —Doyoufancy
Most days look like this: I work from home, so I wake up and get ready for the day. I usually have at least one meeting, but even if I didn’t, putting on an outfit and makeup just makes me feel better and I like having a routine. At this point I probably won’t ever be someone who has a slow, intentional morning routine because I’m just not a morning person and I’m tired of trying to force it.
Once I’m ready for the day I sit down at my desk and get to work. I catch up on emails, take my calls, and work on the design & strategy projects on my plate. In between, I’ll take breaks to write my newsletter and do any planning that’s needed for the next couple weeks on that front. I’m trying to be better about posting on TikTok, so my goal is to make a video every day so I have one ready to post the next morning.
I always have some kind of beverage, usually two, at my desk with me. If my husband isn’t also working from home that day, I might occasionally play music, but I’m more of a work-in-silence kind of person (is that weird of me? I think it might be weird of me). Other than that, I break up my weeks with reformer pilates twice a week and occasionally I have an in-person meeting or event to go to.
Do you travel to relax and unwind (no documenting) or is all travel for work/content? —Ellen
This is such a hard, but important, question.
The ideal version of me wants to say that I’ve struck a balance of both: some trips are purely work and others are purely leisure: no fumbling around to make sure to capture the moment on my phone in both photo and video formats and then my film camera and then my husband’s DSLR camera…
But realistically, if we’re characterizing “work” as documenting or making content, then I have to say all travel for me is work. But let me explain.
I don’t mean it purely in the capitalistic context in that I’m taking all of this content to try to make money somehow. Yes, if I’m pulling out 7 different cameras and retaking and restaging for the best shot then there’s no denying that. But otherwise, I’m documenting for me.
I’m documenting for past me: the person who had this hotel on her vision board for years, hoping she’d make it to this moment she’s standing in right now. The person who, at one point, had never flown overseas—to Europe, to Asia—and only ever dreamed of those far-flung places. The person standing at the base of the Eiffel Tower as it glitters in the moonlight, neck craned up in awe of something she’d only ever seen on TV before tonight.
And I’m also documenting for future me: someone who will look back someday and say, “remember when?” I’m a very sentimental person; I love reminiscing. I can light a candle, hear a song, or eat a particular food, and instantly be transported back to a time and place in another country on a vacation that, at one point, was all I ever wanted.
So if you see me in another country and my phone is out and I’m capturing it all, yes, some of it will probably be for work. But most of it will be for me.
Going to Portugal next month, can you share your itinerary? —Jaqueline
I’m not sure if you’re asking this because you know I’m also going to Portugal next month, but in any case—great timing! Maybe we will be there at the same time. :)
We’re going to see a dear friend get married in Braga, a small town outside of Porto. We’re flying from Amsterdam to Porto, driving straight to Braga where we will be for two days, then driving back to Porto for one day, then driving to Lisbon where we will spend two days.
In Lisbon, I’m most excited for a walking food tour I have planned with Devour Tours (I think this is such a great way to see the city and eat like a local). Other itinerary items include eating pasteis de nata at Manteigaria; dinner at Ponto Final; drinks at The Kissaten (I try to find a listening bar in every city I visit); and shopping for pajamas at Paris em Lisboa. Hopefully I’ll be able to hit the Feira da Ladra flea market in the morning before flying out. For accommodations, I’m very excited to be staying at the gorgeous Torel Palace in their Royal Suite.
My itinerary is less worked out for Porto. We only have a day, so right now my plan is to maybe go for a treatment at the spa at The Rebello hotel because it looks insane. I’m also staying at bucket list hotel I’ve shared here before, Villa Foz (we snagged one of their coveted Manor House rooms!), so I do plan to spend some time in the hotel as well.
If this sparks even more questions, you can always come hang out in the Window Seat chat where I and plenty of other travel lovers are swapping tips, recs, and answers daily.
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Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.
i love working to a bit of music but know a lot of people who also prefer silence. not weird in the slightest 🫶🫶
Aweee the documenting for you and future you. Saved that for my board