Nomad Stories: Lessons from Outsite Co.

Digital nomads (AKA remote workers) are resourceful people. You have to be when you travel from city to city or country to country while juggling visa runs and meeting interesting characters along the way. But when it comes to networking and making meaningful connections, some nomads hit a wall. 

One of the easiest ways to build up a network anywhere you go is by keeping an ear open for events and meetups that cater to your lifestyle and interests. During my first year as a remote worker, I rarely attended events or meetups outside of whatever coliving home I was staying in because I didn’t have to. So when I heard that Outsite Co. was hosting an event in San Francisco, I jumped at the opportunity to attend and meet fellow nomads who live or were passing through The Bay. 

Nomad Stories would introduce us to three CEOs who run successful remote companies and three digital nomads who are veterans to the lifestyle. The event was open to those already living a location independent life and also those who were aspiring to leave their desks to see the world. Fortunately for you, I took notes and am now here to pass on their infinite wisdom! So if you’re curious about how remote companies hire or are wondering if this lifestyle is for you, take heed: 

CEO Panel: Joel Andren (PressFriendly), Miriam Brafman (Packlane), and Fred Perrotta (Tortuga)

• Companies are looking to hire remotely because they can find more individuals that are passionate about their work and what they do.

• The possibility of finding someone in the world who will share and help you build your vision rather than someone just taking a job based off of their location/pay is better.

• You open yourself up to more and to people who are not burnt out.

• Companies are using their customer base to network and hire.

• As a leader, you should model the behaviors you want and not expect it from everyone else.

• Judge an employee based on their finished product, not the process they took to get there.

• Andren said that he was “less concerned about creating a culture for employees, but more on the supervisors. You should let the employees choose how they want to work and look at the results at the end of the day.”

• Because working remotely can be a challenge for any team, Brafman suggests “setting up a structure with helpful tools like Confluence, Jira, Slack. You need to document all the processes”.

• When the panel was asked how they thought a remote team could bond better, they unanimously agreed that company/team retreats were the thing to do (if you have the money for it).

Digital Nomads Panel

Digital Nomads Panel: Alexander-Derek Rein (Software Development Engineer at Amazon Prime Air), Sarah Beyahte Sandnes (co-founder/CTO of SafetyWing), and Grayson Smith (Product Manager)

• Each panelist expressed the same sentiment about why they chose to work remotely and it was either because they didn’t feel a strong connection to their current company and they preferred working independently or because working remotely would allow for them to “find themselves” through travel and confronting different obstacles and situations

• (Can’t say this without enough exclamation points:) Build your professional and personal networks!!

• When searching for a remote opportunity, look for something that would support your lifestyle.

• How to approach the question of working remotely at your current role if it is not something you already have the opportunity of doing: first, be a top performer, then ask your manager if you could try working from home for a few days/week and make sure that you “kill it” to prove it can be done.

I’ll leave you with one final, important piece of advice that I’ve heard echoed by other veteran nomads...

“You need to find YOUR balance”

Whether it be making time for an afternoon workout in the middle of your workday or choosing wisely which nights are for going out and having fun, it's vital that you strike a balance, otherwise it can feel like you’re on a constant vacation - which is not as great as it sounds when you also have to make a living. It may be a drawn out process of trial and error, but make the time to find what works best for you.