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Remote Career Development: Rhiannon Payne On How To Advance and Enhance Your Career When You Are Working Remotely

An Interview With David Liu

A lot of noise happening in this space right now is around how young people should work in an office before working remotely, otherwise their career opportunities will be limited, they won’t learn as much, they will struggle to get noticed and grow, etc. This is only true in circumstances where an organization or manager is not properly equipped for remote work.

Career development is the ongoing process of choosing, improving, developing, and advancing your career. This involves learning, making decisions, collaboration with others and knowing yourself well enough to be able to continually assess your strengths and weaknesses. This can be challenging enough when you work in an office, but what if you work remotely? How does remote work affect your career development? How do you nurture and advance your career when you are working from home and away from other colleagues? How can you help your employees do this? To address these questions, we started an interview series called “How To Advance and Enhance Your Career When You Are Working Remotely”. As a part of this interview series, I had the pleasure of interviewing Rhiannon Payne.

Rhiannon Payne, based in San Francisco, is the Author of The Remote Work Era: The Guide For Women to Go Remote & Thrive (remoteworkera.com). She is also a product marketing leader at Remote (remote.com) and runs Sea Foam Media & Technology, a consultancy working with global startups. When she’s not writing or working (and sometimes while she’s writing and working), Rhiannon is often traveling, speaking at events, and hanging out with her cats.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

My career path has been an unconventional one. I dropped out of high school at 17 due to mental health challenges (which I learned 13 years later was yet undiagnosed ADHD) and moved across the country by myself from Florida to California. I had a few connections in California and some limited support from my parents during that time, and over the next few years I would work a variety of retail jobs and make an unsuccessful attempt at community college before deciding that I was never going to find success on a traditional path — as someone who is neurodivergent, I am literally not wired that way!

Inspired by my friends in Los Angeles who were digital content creators, I decided I was going to make my own “thing” and prove that I had marketable digital skills. So at 20, I started an online magazine publishing original content by and for women, bringing together a team of volunteer writers and editors all over the world. This was my first experience with remote work and distributed team leadership, although to me, working with collaborators all over the world was something that felt quite natural, even in 2011.

I launched and grew the site successfully, and even though I was less successful at monetizing it, I had a lot of fun in the process and was able to prove to myself and others that I was capable of more than what people had previously expected of me. I also made some incredible connections with other writers who I still work with to this day!

After this experience, I got my first entry-level office job in the tech sector, working as a marketing assistant. From there I worked my way up with annual promotions for several years until I decided I wanted more from life. I had always dreamed of a life full of travel since I was a kid growing up with my grandma, who told me stories of her adventures living in many countries all over the world. Now that I was making enough money to live more comfortably and even buy an international plane ticket or two, I felt like I was stuck in a catch-22 where the desk job that was enabling my improved lifestyle was also limiting my possibilities.

Even though I recognized this predicament, at the time I didn’t realize that I could actually make a sustainable living while working 100% remotely. It was 2015 then and I thought that remote work was something only an elite few tech workers or influencers were able to manage. But that changed when I was suddenly offered a new job opportunity, which happened to be mostly remote (with some travel to the main office in Vegas). I realized I could maintain my lifestyle and afford travel without making any sacrifices in my career — so I accepted the offer (earning almost twice as much as I was at my previous job) and booked a trip to Greece leaving just two days later!

After a year of working remotely, with trips to Greece, Japan, and Canada, I decided I was done working for someone else. My eyes were open not only to the possibilities of remote work but also entrepreneurship, and I was ready to start my own thing once again. This time I partnered with business leaders who I connected with while visiting Japan and helped them co-found a SaaS business with clients including the Ritz-Carlton and Grand Hyatt hotels in Tokyo. I was even able to briefly live in Tokyo, and launching a product to such incredible clients was nothing short of a dream. Although the relationship with the company wasn’t long-term due to conflicting expectations across the group of co-founders (most of them were independently wealthy while a few of us had rent and bills that needed to be paid while waiting for outside investment), I took this experience and decided to start my own digital consultancy, Sea Foam Media & Technology (seafoam.media).

In my work at Sea Foam, I brought together a team of 20+ contractors across the globe to deliver product design, development, branding, and content creation work to early-stage startups. During this time, I was asked to speak at the European Women in Technology conference in Amsterdam (2018). While I thought they might want me to speak about the specific types of technology my team was working on, they actually wanted to know all about how I was successfully leading a team of people around the world! Something that felt so natural and normal to me was actually something that a lot of people were interested in. I had so much fun preparing and delivering my talk that I decided to expand on the content and turn it into a book — which became The Remote Work Era (2020) (remoteworkera.com).

In The Remote Work Era, I interviewed 50+ women remote workers around the world, from the CEOs of brands that are household names (such as Wikipedia) to those thriving in their roles as virtual assistants. I compiled all of these insights along with my own story to help other women discover their remote path and gain the freedom in their lives that I was lucky to achieve when going remote.

Throughout the book writing process, I interviewed Elisa Rossi, the VP of Growth at a startup called Remote (remote.com). When I decided to step back from consulting and do something new, I messaged her about opportunities at the company and it ended up being a perfect fit! Today I work on their product marketing team leading the benefits and country knowledge vertical, and Remote is now a billion-dollar unicorn tech company with a team of 800+ employees across dozens of countries — all fully remote, of course!

Can you share the most interesting story that happened to you since you started your career?

You can use any of the specific anecdotes above or ask me to expand on one!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The “funniest” mistake I made was probably not realizing sooner how easy it is to make money and start a business remotely. In my experience, it’s actually harder to find a great remote job than it is to start your own thing and market your skills or a product to others online. There is such a high demand for great talent across technical and creative fields, you just have to put yourself out there, follow some role models or get mentorship from others who are already doing it, and be prepared for a wild ride. Honestly, I sometimes wish I had started earlier, but everything I have done in my career has led me to where I am today so I am grateful for each experience — including my draining office job.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Unsure

What advice would you give to other business leaders to help their employees thrive and avoid burnout?

The number one thing you have to do if you’re running a remote business is to embrace asynchronous communication. This is absolutely crucial for the wellbeing of your employees AND the success of your business. It’s impractical to ask employees to all be online at certain times of day and constantly invite them to meetings. I see so many companies making this mistake — meetings after meetings after meetings, and their folks don’t have time to get their core work done. You have to create a culture of written documentation, autonomy, and trust. Otherwise, burnout and attrition is inevitable, and you can’t afford that in this competitive talent market.

Ok, let’s jump to the core of our interview. Working remotely can be very different than working with a team that is in front of you. This provides great opportunities but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits and opportunities of working remotely?

The benefits of remote work are being able to expand your talent pool far outside your local market. If you’re a small business owner in Boise, Idaho (like one of my former clients), you’ll find it challenging to find the right folks to bring your vision to life. Embracing remote work is vital. Even in big cities like San Francisco, where I live, it can be hard to find the right people. But when you open yourself up to talent across the world, your business can soar to new heights. You also gain a rich diversity in perspectives which is so valuable if you’re trying to build world-changing products. It’s impossible to build great products if you’re only working with the same type of person with similar lived experiences, there will inevitably be things that you miss.

Can you articulate for our readers what the five main challenges are regarding working remotely?

The primary challenges of working remotely, from what I have witnessed with previous clients, are trying to create a cohesive workplace culture; navigating cultural differences with a globally distributed team; conflicts that arise when leadership is unwilling to embrace asynchronous work and instead tries to replicate what they used to do in the office; and providing great mentorship to employees.

Based on your experience, what can one do to address or redress each of those challenges? Can you give a story or example for each?

There’s a lot of talk lately about offering mentorship to early-career folks who are working remotely (or those transitioning to a new career), so I’m going to focus in on that piece.

A lot of noise happening in this space right now is around how young people should work in an office before working remotely, otherwise their career opportunities will be limited, they won’t learn as much, they will struggle to get noticed and grow, etc. This is only true in circumstances where an organization or manager is not properly equipped for remote work.

To combat this, you have to make sure managers are trained on the best ways to communicate with their direct reports. Encourage asynchronous communication (don’t mandate daily standup meeting — that’s never helped anyone!) but also make sure the manager and report are getting some face-to-face time. Once a week or every two weeks might be a good cadence for a call depending on what the employee’s needs are. These calls should be treated like informal coffee chats to take the pressure off and give the employee a safe space to actually share and feel heard and understood.

It’s vital for managers to use these chats as an opportunity to ask explicitly about the employee’s career goals, what they want to do at the company, and what they want to do later in their career too. Then give them opportunities to take on new projects and challenges internally that are aligned with their goals and interests. Also open up opportunities for colleagues to connect internally to learn from each other — encourage knowledge sharing and create a culture of informal coffee chats, which again is a great way to do this, and is something we do at Remote.

As the employer, you can also offer a professional development stipend as an employee benefit so they can take courses or attend workshops and events.

Let’s talk about Career Development. Can you share a few ideas about how you can nurture and advance your career when you are working from home and away from other colleagues?

As an employee, don’t be afraid to be loud in your virtual workspace. Make sure you’re super visible and always providing written updates in Slack, Notion, or whatever other tools you use. Also keep a running list of your output and major accomplishments. Having this list handy will make your performance reviews a breeze, because we all need a reminder of the great stuff we’ve done.

And make an effort to reach out to your colleagues across departments to learn from them and build relationships — they may be your allies in your future promotion and can give you insight into the organization that will help you do more impactful work.

Can you share a few ideas about how employers or managers can help their team with career development?

See two answers above.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Helping women and other historically marginalized workers take advantage of all these new opportunities in the remote work era! Also refugees who are displaced from their homes — this is something we are doing at Remote through our Remote For Refugees program and is especially important right now.

How can our readers further follow your work online?

remoteworkera.com, @rhiannon_io on Twitter

Thank you for these great insights! We wish you continued success

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David Liu

David Liu

David is the founder and CEO of Deltapath, a unified communications company that liberates organizations from the barriers of effective communication