1. Hey, can you please introduce yourself?
Hi! I’m Steph. 3.5 years ago, I left my cozy consulting job and 2+ hours commute to redesign my life. Now, I’m lucky enough to work remotely as a growth marketer, writer, and indie maker.
I spent 3 years at Toptal, first as a Growth Lead and most recently leading their Publications team. As of this fall, I continue to work remotely at The Hustle as a Senior Analyst, focusing on their new product, Trends.
I’m a big advocate for remote work, as I know how instrumental it can be in helping people change their lives for the better. I often write about the topic over at my blog, alongside other topics like continuous improvement, women in tech, and learning to code. Since inception in 2019, I’ve been lucky enough to have over 300k people read my thoughts.
Along the way, I’ve been lucky to explore 52 countries and have captured some of my life here.
2. What motivated you to choose remote working?
There were multiple factors that drove me towards remote work, but at a high-level, they all fell under one bucket: having control over my life.
In 2015, I started a job that led me down a very clear and likely “successful” path. However, to continue following that path meant that I would need to continue working 60+ hour weeks. It meant that I would need to spend 2 hours commuting daily. And perhaps, most notably, it would mean that I would need to live in a city that I didn’t love.
Many people make these sacrifices for good reason, but in my unique circumstance (i.e.: no one depending on me), I knew that if I tried hard enough that I could find a better path forward for me. I didn’t know much about the space, other than that it existed and seemed to remove some of the more prominent problems in my life. I’m very happy to say that transitioning to a remote role has not only given me the freedom that I was looking for, but has over-delivered in ways that I hadn’t initially considered, including the ability to improve my work ethic and getting to work with incredibly talented people.
3. What were your initial months like? Did it live up to your expectations?
The first few months were surprisingly difficult. I went from a job with very clear expectations, instructions, and hours to something considerably more ambiguous.
I distinctly remember during my first couple weeks this sense of confusion. Was this a real job? Do I really not have to tell my boss about my dentist appointment at 2pm on Wednesday? Is he really okay with me moving to Europe or is he just saying that?
It took me a while to really get my head around the concept of remote work, since every experience prior had taught me that this was not the way the world worked. I had never been given this level of trust and autonomy. It was a beautiful thing.
But the next few months were tough for that very reason. With no one there to set boundaries, I was left to do that myself. And for a long time, I didn’t. I worked far too hard and far too long. To be fair, it was an exhilarating time and it was probably the best team that I’ve ever experienced.
It took me somewhere between 6 months to a year to really design a work environment that was optimal. This time period will be different for each individual, but it’s important for people entering remote work to be cognizant that there will be an inevitable adjustment period.
4. How did you find remote working roles?
I started searching in 2015, when there was far less infrastructure to do this. These days, people are much better served, with dozens of remote job boards and platforms out there. There are also more types of jobs that can be done remotely. If you’re looking for a non-technical remote job, I wrote an article about that here.
Regardless, I still think there are a lot of parallels in my journey to someone searching today.
I spent the greater part of a year (~10 months) searching for the right remote role. I started looking in fall of 2015 and started at Toptal in August of 2016. I think the reason it took me so long comes down to two things:
- I didn’t have the typical digital skills that many remote roles were tailored to (ie: development, digital design, etc.)
- I didn’t want to trade away my career. In other words, I didn’t want to trade my potential for the opportunity to work remotely. I didn’t see those as mutually exclusive and was determined to find a solution that would enable both.
At the beginning, it was difficult to find anything. I quickly learned that many companies hiring remotely wanted to see that you had already experience working remotely. Since I didn’t have that experience, I decided to open up my prospects and apply to almost everything. I had no ego in this process and although I don’t necessarily recommend this to everyone, it’s what worked for me.
Throughout that year, I built up a short resume of 4-5 jobs that I worked alongside my full-time role in consulting. I did some SEO work for a search engine, despite having almost no experience in it. I did social media work for a menstrual cup company. I even did some customer service for a media company.
One of those companies offered me a full-time role, but I knew that wasn’t the direction I wanted to take my career. So I just kept at it. I kept iterating and applying, until I found a role that I could see a real future with and that was the role at Toptal that I took.
If I were to give someone searching in 2020 tips, I would encourage them to do the following things (which I wrote about in more depth here):
- Learn basic digital skills. They will get you far, regardless of your background.
- Search for the right roles and the right company; hiring is not a one-way street. Please do not give up your dreams to work remotely! You can have them both.
- Drop your ego and prove you can learn.
One final tip for prospective remote workers that I would give, is to just ask your current employer, so long as you’re doing work that makes you happy. Even back in 2016 when I gave my notice, I was shocked to find that my prior employer — despite being in a traditional industry with basically no remote workers — offered me a remote role to stay on board.
I ended up still moving on, but it goes to show that companies are willing to be more flexible for people they know and trust. Four years later, it’s even more natural to let employees “go remote” and there is a wealth of new types of jobs that can operate remotely, that previously could not.
5. What have been the best, good and worst aspects of remote working for you?
I started working remotely with the anticipation that I’d remove my commute, move somewhere warmer, and live happily ever after. However, I’ve been pleasantly surprised to learn that remote work is much more complex in nature.
I should first say that remote work is not glamorous! Please don’t fall for the image of a nomad working on the beach. No one does that. In fact, I almost certainly spend more time on my computer than most of the world.
But remote work can be a beautiful thing, for certain people.
I’ve found myself benefiting greatly from the additional autonomy, but it has taken a while to readjust to this freedom and learn how to maximize it. I would also add that this freedom fits well within my personal work preference in that I’ve always avoided strict routine. For some others, the lack of rigidity can be daunting.
The other underrated aspect of working remotely for me has been the people I’ve gotten to work with. There’s a level of self-selection that I believe exists (at least today this still seems to be true), in which many of the people who opt to work remotely are looking to in some way improve their lives. This assessment is in no way scientific, but I find so many remote workers that I encounter to be more ambitious, creative, and self-regulating. They often also share common values, like trust over micro-managing.
The biggest downside that I’ve experienced is something that I believe is still not fully solved for in the remote space: social structure. The beauty of going into an office and getting to experience hundreds of micro-interactions is lost when you work remotely. Communication is normally centered only around the task at hand (i.e.: it’s more transactional) and I do think that a lot more effort needs to be put in to create cohesive teams. Even then, I think it’s hard to compare to an in-person environment.
As people assess whether remote work is for them, I think it’s important not to compare in silos. In other words, acknowledge the pitfalls of remote work alongside the “perks”, but don’t dwell on either individually.
If you find this topic interesting, I’ve written about the bright and dark sides of remote work here.
6. What tools do you swear by while working remotely?
Budget-aside, the tools that I would recommend to any company with remote workers includes Zoom, Slack, and the Google Suite. Outside of that, there are tons of tools to help you organize your life effectively, but everyone has their own unique preferences.
7. Your most exciting/ hilarious experience since you started working remotely.
There are so many!
One of my favourite memories of working remotely actually happened during my first month or so on the job. I was on a video call with my team, which wasn’t that big. We probably had 7-8 or so of us in total. But we were so distributed. We had a team member in every single continent (minus Antarctica, of course!).
I was in Europe. My boss was in Africa. Someone else was in Australia. Another person was in Asia somewhere. One guy was hanging out in Colombia. And there were a few across the US.
I just remember thinking, wow. We’re in hypergrowth as a company and the people making this happen are literally all over the world.
8. What is your golden advice to a new remote worker?
I think the most important thing for any remote worker to recognize is that remote work is not an “end goal”.
Many people see the glamorized version of remote work and hope that it will solve their problems. But remote work is just an enabler. It gives you more autonomy to design your life, but that still means that you need to actively do that. And it certainly will not bring you happiness on its own. You still need to work on your skills, relationships, and goals because they will not develop without effort.
So if you choose to work remotely, expect challenges and roadblocks, because they’re a part of life, remote or otherwise. And as you embark on this journey, remember to have fun, but also not to sacrifice your integrity or personal goals to get to where you want to be.
9. How do you see your career shaping up and your goals?
When I first started working remotely, I was fearful that my career would flatline. I think a lot of people feel that way.
While I can’t guarantee that this will happen for everyone, my career ended up skyrocketing in a remote environment and undoubtedly faster than if I had stayed in consulting.
I got lucky enough to join a company that was willing to bet on people, despite their age or prior experience. However, I think this is more common at remote companies — people are willing to think outside the box.
But regardless of the company that you join as a remote worker, the advice I would give is to grow past your role. Take the initiative to learn things when people aren’t looking (both inside and outside of work). Ask questions because you’re curious. And make the effort to identify opportunities. I did this during my three years at Toptal and ended up leading a 20-person team at 24 years old. If you’re curious to learn more about my philosophy on this, I wrote about it more deeply when I recently switched wrote.
10. How do you expect remote working to evolve in the future?
The future is remote. What I think many people miss is that people often choose to work remotely not because they’re lazy or entitled, but because it’s a more optimal solution.
The reason that we developed infrastructure to work in-person was that the online tools for the last few decades did not exist or were not at scale. Now, we have the capabilities and we’re waiting for perception to catch up.
There are many parallels that I can dream up, but I like this one in particular.
Imagine you’re living during the era prior to cars. You use a horse-drawn carriage as your mode of transportation. One day cars become available. Some people don’t understand them or their benefit, while others are strongly skeptical. Nothing will ever replace the horse. They’re just for lazy people, anyway. But for those who are open to change, they have a new device that allows them to get further, more quickly, and for less.
Ask yourself the question: Had the technology that we currently have existed in the decades when the modern-day workforce was being shaped, what would our workplaces have looked like today?
The reason that there’s so much resistance is simply because people tend to be inherently resistant to change. But I do believe, as we have with every new innovation, change will happen.