Travel YouTuber & Head of Partnerships at a YC Startup
Megan is from Ottawa, Canada & heads B2B partnerships at SafetyWing, a YC startup. She also run a popular YouTube channel for travel tips & remote jobs.
1. Hey, can you please introduce yourself?
Hi, my name is Megan and I am from Ottawa, Canada. I’ve been location independent working with leaders in the remote space for 5+ years as a consultant. Most recently, I’m excited to have taken on a larger role with SafetyWing as their Head of B2B Partnerships. SafetyWing provides health care plans for those that traditionally do not receive coverage, like remote workers, nomads, freelancers, and entrepreneurs. It’s great to be part of a team solving such a real problem we face today.
Outside of SafetyWing, I use my experience from working with remote companies to help people find and land remote work. As a remote career coach, I offer courses/coaching to help career-driven professionals find and land epic remote jobs so they can work from anywhere, save time and structure their day their way. Nothing makes me more excited than the lightbulb moment clients have when they realize they really can have it all - the benefits, the salary, the time freedom - without having to sacrifice their career goals.
2. What motivated you to choose remote working?
I actually didn’t choose remote work or seek it out in any way. I was actually under the impression that work from home jobs were scams and only available to those in the tech industry! I ended up graduating university with a business degree and landing my first ‘career job’ with a large US company I had admired for years. My main motivation for applying to the job was that it kicked off with a dream internship that sent three applicants on a fully paid trip around the world visiting major players in the tourism industry, such as Emirates Airlines in Abu Dhabi.
After several months of travel, the position shifted to full-time remote work. Taking a remote position was something I never realized would change the course of my life so drastically. It’s funny to think I initially considered it to be the one drawback to working for this company.
3. What were your initial months like? Did it live up to your expectations?
I’m not going to lie… the first few months were rough. Thankfully I did not have expectations as it would have been quite discouraging. The transition from the stimulation of a university environment and worldwide travel to suddenly working in isolation is not an easy adjustment.
I enjoyed the work I was doing, but knew that I needed to make a change or leave the company all together. I was isolated, lonely, and stressed working way more hours than I should have. I felt like I needed to prove how hard I was working with consistent measurable results, honestly putting way more pressure on myself than my managers or coworkers ever did.
Friends and family also expected me to be available anytime of day since working from home obviously meant I had a ton of free time. My Grandpa, still to this day, will ask me when I will stop fooling around and join the workforce. It was hard to take pride in the work that you do when those close to you treat it as a joke. Several months in I was job hunting for in-office work, desperate for a job title beyond ‘remote worker’ in the eyes of my peers.
I soon realized remote work wasn’t the problem, but the way I was approaching remote work was. Boy am I happy I stuck with it!
4. How did you find remote working roles?
Networking, networking, networking! I have found remote roles through various sources, none of which have been remote job boards. When it comes to finding work, both remote and in office, who you know is critical. Having a personal recommendation from someone who already works for the company is by far the most effective way to get you foot in the door. Attend events, reach out to people on Linkedin and make your career goals known. People will keep you in mind for a position that is available.
Having a personal brand online is also a great way to have offers come to you or to help you land a job once the application process has started. It can be a blog, an instagram, a youtube page, a killer LinkedIn profile… anything you can commit to building that tells someone what you are all about. It’s a way to show your career goals are rooted in the things you feel strongly about, or your passions.
The job market is competitive and it can sometimes feel like everyone has a degree, experience, certifications and multiple languages on their resume. You need to get creative to stand out. Imagine two equally qualified candidates for a pet company with the only differentiator being that one also commits to weekly blogging on all things pet care. Showing the employer that passion sets you apart. Another way to stand out is to take initiative on a value add project by identifying a gap/problem/opportunity and do the work to resolve it. Get the company a result before they hire you.
5. What have been the best, good and worst aspects of remote working for you?
As an introvert, my biggest challenge has been overcoming the temptation to isolate myself.
Studies show that the number one determinant of human happiness is how often, and how deeply, we connect with others. While I know this in theory, it’s still tempting to want to recharge alone after a long day or week. When you work remotely you miss out on daily social interactions, like coffee room chat, that would be taken for granted in an office environment.
I have to put in extra effort to get out of the house and be around other people. Joining coworking spaces and scheduling weekly calls was a good start, but it wasn’t enough for me. Signing up for activities like group fitness and joining sports teams was a total game-changer. Building these activities into my schedule and committing to getting out is easy when you know people are expecting (and counting on you!) to show up.
The daily flexibility, not having to commute, and the ability to structure my day around my most productive hours without being stuck in an office from 9-5.
The freedom to do extraordinary things without sacrificing career goals, I’ve been working from a laptop and slow traveling for the majority of the past 5 years. Renting an apartment and spending several months in a location gives me the time to get my work done while checking off my bucket list on evenings and weekends. Escaping Canadian winter is also up there as an incredible perk!
6. What tools do you swear by while working remotely?
A laptop stand. Word of warning: once you use one you will never again be able to work with your laptop on a flat surface. It’s a game changer for your back to have your laptop at eye level.
As for the tech, I love the free app F.lux that tints your laptop screen in the evenings/overnight to block the blue light that suppresses your body's ability to produce melatonin (the hormone that makes you feel sleepy). This is perfect for late evening work sessions so you can get stuff done without later disrupting your sleep.
Tools and apps honestly run my life and my business. I have a full list of everything I use to work and travel here.
7. Your most exciting/ hilarious experience since you started working remotely.
I’m at my best when I have the tools to work effectively, like quiet space and strong Wifi, while also feeling inspired by my surroundings. One experience that really stood out was closing a major deal while standing on top of a pagoda at sunrise in Myanmar. It felt like something out of a movie.
8. What is your golden advice to a new remote worker?
You probably saw this coming, but video calls really are king for remote teams. Outside of video calls, take some extra time to add emotion to written communication with emojis, GIFS and memes. Try to over-communicate in order to compensate for the fact that online tone can be significantly colder than in-person tone.
Additionally make an effort to reach out via IM or Slack with more than just questions and colleague requests. Frequent fun, non-work related conversations (like sending a cool article or a funny meme) lighten the mood, making work-related requests seem less robotic.
This might be overkill…. But 2 other key things to try include:
1. Building a dedicated workspace
Designating an area in your home where you do nothing but work is probably the best thing you can do for your productivity and sanity. Not all of us have the luxury of a home office, but try to find a spot where you are away from your family, the fridge, the TV and other distractions. Set a rule for yourself that the only thing you will do while at your workspace is work. No eating, no social media, no listening to the news. If you have trouble staying on track, consider using a tool, like SelfControl, that will lock you out of distracting websites.
2. Set working hours and stick to them!
Set working hours for yourself, and communicate them to your family and your colleagues. This includes a set start and end time for your workday. You need to do this, and you need to be vigilant with yourself. If you don’t respect your time, you can’t expect anyone else to.
Be clear with your colleagues about when you are done for the day, and reinforce the cut off by not opening or responding to emails after hours. Consider the timezones of your colleagues and make a point to schedule emails so they are sent during their working hours as well. Clearly communicating these boundaries removes the expectation that you will respond 24/7, and allows you to avoid work FOMO while on your off time.
9. How do you see your career shaping up and your goals?
I definitely see myself continuing to grow with SafetyWing. I love startup culture and it’s a great work environment given my coworkers are very entrepreneurial. It’s inspiring to work with people that are always launching new projects and doing interesting things while off the clock. I’m also very passionate about SafetyWing’s mission to build a global safety net for remote workers worldwide. There are a lot of exciting things in the pipeline like pension plans and access to remote doctors that I am so proud to be a part of.
I also love sharing content on remote work, travel and lifestyle design over on youtube. Working 1-1 with coaching clients is very fulfilling, but the beauty of youtube is that you can leverage your time to reach many people with a single video. I definitely want to continue to explore more ways to impact more people, such as taking on more keynote or panel positions. My long term goal is to continue inspiring people to challenge the way we have traditionally lived and worked. I want to spread the idea of remote work being a vehicle for lifestyle design, while also delivering the strategies and tools to make the shift to remote as seamless as possible.
10. How do you expect remote working to evolve in the future?
2020 marks a massive turning point for remote work with COVID widely considered to have forced the world’s largest remote work experiment. I anticipate the move to go office-less will be a more permanent change with remote work becoming so common that it just becomes ‘work’.
Increased awareness of both the benefits and the drawbacks of remote work may also lead to a better work experience for remote workers in the long term. Working remotely has often been seen as a perk in itself, thus putting little pressure for employers to offer additional benefits like health insurance or a competitive salary. I think this will change as so much of the workforce is at least temporarily remote. Employers will need to do more than simply offer a work-from-home option if they want to attract top candidates in a world where remote work is normalized. I am optimistic that conditions for remote workers will significantly improve over the next decade.
On the flip side, I imagine employees and employers will continue to face challenges with this new normal in the short term. Many employees that were quickly forced to go remote are getting an unrealistically poor picture of remote work. Employees are not likely reaping the benefits of working remotely while doing so from their kitchen tables alongside their family. Activities outside of work are halted, cafes/coworking spaces are closed and anxiety is high with unprecedented global uncertainty. We are trying to maintain productivity at a time where work-life balance is nearly impossible.
Furthermore, both employees and employers may not invest the necessary time and money to build systems that support their newly remote status, especially if they see this shift as being temporary. I imagine those that can manage the transition and embrace remote work as the future of work will come out on top.
11. Where can we follow you on?
I am definitely most active on Youtube with new videos every week. I’d love for you to join me there for all-things remote work, travel and lifestyle design. I try to give very actionable advice on topics like apartment hunting, cost of living comparisons, remote work tips and fun stuff like little-known travel hacks.