I’ve spent exactly a week in Lisbon, Portugal with Nomad House, a small group coworking and coliving community. We’re staying in a multi-story apartment with 20 people from around the world. 


The Nomad House community is a diverse group of entrepreneurs and specialized freelancers. Some are pursuing a remote or semi-nomadic life, and others are traveling through on a work-cation. There are developers, writers, startup founders, grad students, an investment fund manager working Tokyo hours, online business owners, a record label owner, and more.

Despite Lisbon’s attractive distractions, we’ve found a way to balance work and play. It’s been a productive, inspiring, and laughter-filled week. Most of us spend the day working from the house or Canopy coworking space, though we come and go as we please. At night, we cook community dinner, go out, or stay up talking on the patio. Last night, my friend hosted a mastermind talk on cryptocurrencies, and I presented on the art of investor relations and fundraising.

Last weekend, a few of us flew to Azores (a beautiful island off the coast of Portugal) for a quick getaway. We hiked through the clouds, soaked in the Atlantic ocean’s natural thermal baths, and ate all the seafood. And in between, we squeezed in some work (I’m guilty of sitting shotgun in the car, working on my laptop while attempting to navigate us.)

Nine of us spent Friday evening driving around the island in our van, chasing the sunset for the best views to fly drones. Rebecca and Matt shared their hobby with us, taking stunning aerial photos and videos with their drones. Between playful jokes and embarrassing stories, we talked about our side projects, life lessons, artificial intelligence, spirituality, and the cultures we come from.

Drone pilot and photographer: Matt Slater

Initial Reflections on Working Remotely


I’ve struggled with getting used to the time difference between Lisbon and San Francisco. When clients wake up in San Francisco, it’s evening my time. I found myself pressured to work around the clock and always be on, checking Slack for anything urgent.

I’m currently managing the fundraising process and investor relations for a startup raising their seed round in San Francisco. Fundraising mode requires tight communication cycles. Over the past three weeks, I’ve helped sharpen the pitch, booked 22 meetings in SF and NY over 2 weeks, crafted investor communications and follow ups, prepared diligence materials – all while acting as an emotional support and sounding board for the founder. In between, I’m taking calls with new potential clients, crafting proposals, and blogging. A whirlwind. 

Hostel living is TOUGH for remote working. I’m sure it depends on the hostel, but that was my experience as I stayed in hostels the first week of my trip. I met awesome people, but it was hard to stay productive. I was surrounded by short-term vacationers, backpackers, and college grads. There’s pressure to socialize. Even during the day in the common areas, I was often the only one with a laptop open. At Nomad House, I’ve found myself more productive and inspired, surrounded by people who are working on cool projects.

The competing priorities can be overwhelming. While traveling and working remotely, you’re juggling so many balls at once. And some are directly related to your survival and well-being. Travel, socializing with new friends, exploring the city, planning and booking your next flights and accommodations, logistics (like getting toothpaste or figuring out laundry), client work, new potential client outreach, exercise and “me” time, reading and reflection, tracking your spending and budget, and the list goes on. It’s not glamorous.

You encounter unexpected roadblocks in the simple things. I’ve had quite the adventure so far: wandering around Seville to buy the universal adaptor I forgot to bring, waiting for my laundry for 2 hours only to find I’ve burnt some of my clothes in the broken dryer, and accidentally locking myself out of my room one night. 

When I’m up past midnight responding to emails or Slack messages, I’ve questioned whether I can make this a sustainable lifestyle. During those times, I’ve asked myself : “Am I happy? Do I enjoy my work?” The answer is yes. Despite odd hours at times, most of my work can be done autonomously. I find myself more productive when my clients are sleeping, and I have everything ready for them when they wake up. My days are broken up and fit my natural cadence. As an early riser, I can get work done in the quiet hours of the morning, explore the town for lunch, then head to a coworking space. After dinner with friends, I hang out some more or hop online for a bit. Since I’m traveling slowly over the long-term, there’s no need to rush the sightseeing. Without meaningful work, I know I’d feel restless.

I don’t really know what I’m doing, but somehow I’m figuring it out. There are so many people on the same journey who are willing to lend a helping hand. I’ve found my community at Nomad House, and there are so many more waiting for me.

Remote Work and Travel Tips 


Don’t try to pressure yourself to do it all. It’s important to pick your top priorities for the day and cycle through. Know what you need to keep your mood stable and happy. Resist the FOMO and appreciate where you are in this moment.

  • If there’s a major time difference with your clients, send action items, updates, and questions before bed. Get your questions answered to remove blockers before your client signs off from their work day. Hand off items for review and be clearer in your asks so they can reply in line.
  • For tough conversations and exchanging feedback, schedule a video call. It’s always better to address issues over voice than text.
  • Travel slowly (ideally stay 1.5-3+ months in one place) so you can get situated and live like a local. Integrate routines and habits you enjoy from home (like running, meditating, or cooking eggs for breakfast).
  • Make sure you have your laptop, phone chargers, and a mobile WiFi pack with you. You never know when you’ll need to hop on. With that said, set your boundaries. In most industries, outside of very time-sensitive communications and projects, you don’t need to facilitate a culture where you’re expected to reply immediately. 
  • Don’t take on more clients than you can chew. I’ve had to turn down awesome clients because I want to focus on a few major clients at a time. In the future, I’d like to scale myself with productized consulting offerings.
  • It’s ok to skip a night (or more) of drinking with new friends. You really won’t miss out much. Choose the people you want to invest in, and don’t go out if you don’t feel a strong connection with the group.
  • If you can, alternate between coliving experiences and retreats, private rooms in Airbnbs for recharging and focus, and private or double rooms in hostels. Save the multi-bed hostels for shorter trips and getaways, unless you don’t get distracted easily and can sleep well.
  • Find coworking spaces that fit your vibe and introduce yourself to people. Offer to present a talk or host a workshop. This can help introduce you to new friends and potential clients. 
  • Set aside a small budget for fixing mishaps or changing your plans last-minute in favor of happiness, great people, and well-being. This is my spontaneity budget.

Tools I Like

  • Quickbooks Self Employed: Track your business expenses, manage quarterly estimated taxes, and create invoices. Automate categorizing your expenses and easily toggle between “personal,” “business,” and “split”. I’ve found it a breath of fresh air and so simple to use. You can get 50% off with my referral code here: http://fbuy.me/f1eIX
  • Air Wander: Search for flights with multi-day layovers in another destination and save money. You can select the number of layover days you want and scroll through destination options.
  • Rev Voice Recorder: This app is great for recording your calls so you can stay focused without taking notes. It helps me keep track of all the details and nuances in potential client calls, so I don’t miss anything when I create a proposal or scope of work. This is also great for interviewing people for your blog!
  • Polymail: Free email platform for managing multiple email accounts in 1 place (you can integrate your Gmail accounts without having to get kicked out when you switch between accounts). Here’s a code you can use for 1 month of Polymail Pro: QJX6PP
  • Google Translate App: Translate text in images by pointing your camera. A lifesaver when trying to buy a metro ticket in Lisbon, especially if there’s a long line of impatient locals behind you!

Start Creating

If you want to overcome your limiting beliefs and accelerate progress towards your dreams, check out the short thought experiment below.

6 Limiting Beliefs Keeping You From Your Dreams — And a Thought Experiment to Overcome Them:

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