Remote Work ↗


It’s no secret that both the size and scope of remote work has increased significantly over the past decade. With companies like Buffer, Basecamp, Automattic, Toptal, and Mozilla living as proof that success isn’t defined by the number of hours you clock in, we’re seeing many people at least consider the transition.

While this trend hasn’t and may never reach “hockey-stick” growth, it possesses a surprising seasonal element, where people are considering this new life as they look to redefine their own each new year.

The search volume for "remote work" over time.

As you envision a new life, whether in January or any ordinary day, I wrote this guide to help shed some honesty and more grounded views on the remote work experience. It often gets a bad name from people essentially sustaining this lifestyle off of selling it to others. That is not what I’m here to do. In reality, it takes only the click of a button to book a flight somewhere to start working remotely (and another if to return if you don’t like it).

Instead, this guide focuses on my experience working remotely for the past 3 years and is likely more helpful to those looking to transition or those at the beginning of their journey. Feel free to jump to the sections that are most useful for you, including some practical tips at the end.

  • Remote Work != End Goal
  • Can I Even Go Remote?
  • The Good and Bad of Location Independence
  • My Personal Experience
  • Practical Tips

Who Am I?

To preface, who am I and why am I talking about remote work? I’m Steph and I’ve been working remotely for the last three years. Most of this time was spent at Toptal, starting as a growth lead and more recently joining their executive team and leading a Publications team of ~20. I’ve also done remote work spanning SEO, social, and web development.

Throughout the years, I’ve seen Toptal grow as a leader in the remote space and also have traveled to ~50 countries meeting other remote workers spanning from the more traditional to the obscure. I should clarify that these views are my own and don’t necessarily represent the views of Toptal.

Remote Work != End Goal

I think this is the section missing from almost every remote work guide that I’ve come across.  Even though I’m a huge advocate for remote work, this needs to be said:

Remote Work is not an end goal.

What do I mean by this? Well, one of your goals in 2019 may be to transition to remote work and that’s great. However, you should have multiple other goals and this goal should not trump essential goals or more importantly, your happiness or integrity.

Let me explain:

Working remotely operates on your life the way that an adjective operates on a noun. It’s a descriptor, but there can be many descriptors in your life. Working remotely allows you to design your life in different ways, but ultimately will not bring you happiness on its own. So, as you look for remote work, keep in mind your true “why”. For example, "working remotely allows you to":

  • Spend more time at home and be a better dad
  • Move to a new city to be with your partner
  • Learn to code on the side so that you can eventually start your own business

I want to make it clear that getting a remote job will not solve all of your problems, but it gives you space to operate and make your other objectives true. Even if you work remotely, you still need to work on your skills, relationships, and goals because they will not develop without effort.

Above all, do not sacrifice your integrity to work remotely. This may seem obvious, but your happiness will stem from what you are actually doing day in and day out, not where you are physically working. Removing a commute or degrading office is certainly positive, but keep in mind that in the below diagram the top left is still better than the bottom right.

As remote work becomes more ubiquitous, new opportunities are emerging everyday. With these dynamics, there is just no reason for you to need to sacrifice your personal or professional goals to “go remote”; you can have your cake and eat it too (you can find remote work and a job that you love).

Can I even go remote?

There are usually two currently limiting factors to remote work jobs which are represented in the following equation:

Remote workforce = workforce * % of A * % of B

A = jobs that can be done remotely
B = companies or individuals open to remote work

Both of the A and B multipliers are growing due to recent psychological and technological shifts, resulting in a larger remote workforce.

A: Jobs That Can Be Done Remotely

If what you do is already 50%+ online, you can skip A and move straight to B. That’s any developers, designers, e-commerce peeps, SEO experts, and social media managers, but also product managers, marketers, business consultants, writers, and more.

If you don’t think that your current role can transition to remote work, my advice is to at least do the research. Many people stop immediately and limit their options if they don’t see their job as one of the most accessible and obvious options. Meanwhile, although not as common, I’ve met remote doctors/nurses, architects, teachers, psychologists, and more. The key here is to remove barriers; rethink elements of your role and not the role as a bulk entity.

For example, if you’re a nurse, you likely can’t continue to work remotely while hopping around to different hospitals executing as you are today, but there are likely many elements of your job or new elements you can add that can be done online. Although it seems elementary, create a chart of things that you currently do and things you can do within your role, and mark off whether they can be done on a computer.

If you still don’t believe your current skill-set lends to remote work yet want to make the switch, refer to the Practical Tips sections to get you on the right track.

Think Bigger

It’s also important to note that the workforce is constantly changing and technology is creating new remote-friendly roles everyday. For example, I saw firsthand at TechCrunch Disrupt (2017) multiple companies developing AR/VR technology that would allow people to train and work offsite in industries ranging from construction to the laboratory. As always, remember that the workforce is transitory and what does or doesn’t exist now may not be true in 1, 5, or 30 years. As we move forward, a greater proportion of these new jobs will overlap with remote work.

As the job market changes, the introduction of future jobs will have a higher proportion of remote jobs.

B: Just Ask

If you are lucky to already have the skills to work remotely and want to continue with your current job, then my advice is simple: just ask. You may be the only limiting step in enabling this element of your life.

From my own experience and many that have ended up quitting to take on a remote role, companies normally offer you the same thing upon your departure if that was the reason for your leaving.

It’s always better to come up with a plan as to how you and your company can make the transition together. If you’re planning on embarking on a remote work program like Remote Year, some offer basic templates or guides for how to approach this situation, but ultimately don’t overthink it. If the company or your boss is not mentally prepared to let you transition, this opens you up to other opportunities (see Practical Tips section) and you should move on.

The Good and Bad of Location Independence

I’m not the first to say that working remotely comes with its own set of opportunities and challenges, many of which depend on how each individual operates.

Autonomy and Productivity

If there’s a single word that I feel encapsulates remote work, it’s autonomy. Working remotely gives you the freedom to design your life, both inside and outside of work. That’s partially because working remotely naturally blurs those lines.

Is responding to a Slack message on your phone at dinner “working”?  

Even if you have a boss while working remotely, your number one accountability partner is yourself. I believe this is what allows some people to naturally thrive, but just as importantly, others struggle in a remote environment. If you’re considering remote work, consider whether your tendencies align with this lifestyle.
Although certainly not scientific, I would encourage people to take the Four Tendencies quiz and also to listen to the Audiobook. If you fall into either of the categories that resist inner expectations, that does not mean that you can’t work remotely effectively, but may be an indicator that you need to work on a few habits at the outset.

The Four Tendencies by Gretchen Rubin

The lack of imposed structure in remote work means it’s even more important for you to develop your own structure and expectations outside of work. If you don’t, you’ll often find that your personal aspirations are the ones to slip to the wayside. Make sure you select personal goals (ex: learning X), allocate time to them, and specific KPIs to each.

Within your scope of work, learn to identify different types of activities and how you respond to them. This is a personal exercise so be honest and objectively label the things you struggle with. For example, I know that I can spend 8 hours straight in a spreadsheet, but find it exhausting to write for more than 1 hour straight. I recognize this and actively take breaks or shift when needed.

With that being said, task-switching is a major energy depleter, so make sure that you’re blocking off large segments of time to focus on specific tasks (especially of a similar function).

For many people:
1x4h of work >> 2x2h of work >> 4x1h of work >> 8x30min of work >>>> 16x15min of work

Why? There's a transition period where you calibrate to the task at hand that is inevitable. Optimizing for more flow and less calibration results in more being done. I would encourage anyone to better understand the concept of context switching from a technical point of view, by listening to Algorithms to Live By.

Let me be clear that autonomy does not mean doing less; it means the freedom of doing things in a better, more optimized way. One thing that I have learned from observation time and time again, is that despite working miles away from one another, it is incredibly easy to tell who is working hard and who is not. If you plan to transition to remote work so that you can relax and do nothing, you won’t be fooling anyone.

Self Selection

Speaking to autonomy, one of the best parts of working remotely is the people you interact with. I’ve developed a hypothesis for why this is: most people don’t fall into remote work - they actively seek it out.

In order to transition to remote work you normally recognize that there’s a better, but more unconventional way of living and pivot your life to match that. Coming from someone who took around 10 months to find the right remote work, it’s not always a straightforward or conventional path. With that said, I think that this leads to a form of self-selection within the remote work community and a development of specific traits and values. People tend to be more ambitious, creative, and self-regulating, and this is a great place to be to further those qualities within yourself.

Although there is certainly personal bias here as I am a “questioner”, it would not surprise me if there were more “questioners” and “rebels” in the remote community (referring to the 4 Tendencies again).

Speaking to values, remote workers tend to value efficiency > time spent and trust > micro-managing, so consider that this reality will be present with most people you work with, regardless of where they are in the organization. Even though there is a shift towards "flatter" organizations in many places, I find this to be especially true in the culture of remote organizations. It's unclear to me whether this is due to the forward thinking nature of these companies or due to them being typically newer and smaller. It'll be interesting to see how some of these scaling remote companies enter the age of Enterprise.

Basic Traits to Develop

I believe that traits are simply habits formed over time, and thus can be molded if you have enough motivation to do so. Below are the few key traits that I think you need to work remotely. The rest that people say you need are often some permutation of these or are not as necessary for "success" as one may think:

  • A bias for action
  • Clear communication (this takes work)
  • Preference for quality over quantity in everything. I would specifically recommend this for investing in good technology.

Especially if you’re working for a startup, adequacy is important across a broader base. I would encourage everyone to learn basic:

  • SEO
  • Analytics/Excel modelling (I once heard someone say, “If you don’t know what a pivot table is, what are you doing with your life?”)
  • Copy-writing
  • Design and UX theory
  • Development (basic HTML, CSS, scripting)

Those who work in technology are starting to recognize that in order to be most effective, you should have this awareness of the other disciplines that contribute to the entire "tech pie". Since working remotely intersects with technology significantly, this remains true.

Social Life

One of the least disputed pitfalls of working remotely is the social structure. With no more team lunch breaks or water cooler chats, remote work can be very lonely. The transition to this lifestyle requires calibration, but I would encourage you to set up both your digital and non-digital life to account for this:

  • Create your own water cooler - online. If you work for a fully remote company, have intentional calls that facilitate team bonding. Call them what you want: coworking, weekly catch-ups, etc., but the important part is to account for time that is meant to foster relationships. If you don’t work for a fully remote company, find others like you in places like NomadList or specific groups tailored to your interests.
  • If possible, start your remote life in one of the hubs. These are places where more digital nomads choose to stay for reasons like nice weather, low cost of living, and good internet, but are more importantly where you can more easily meet other nomads. You can get a sense of where they are on NomadList homepage, but my personal suggestions are Canggu, Chiang Mai, Lisbon, and Medellin.

I believe there is one other notable factor that remote workers should actively improve on: encouraging empathy. When you’re not physically working next to someone, whether intentional or not, there is less awareness of the person’s feelings or time. It takes active involvement to turn this equation around.

Moreover, working remotely is built on the idea that impact is king and in most cases, personal (not group) impact is what is measured. This can create a negative dynamic that I have seen multiple times over. In an office, you’ll see someone stay late to help their teammate but with remote work, most “giving” goes unnoticed except to those benefiting from the giving. Without active acknowledgement of giving and reciprocity, remote work can quickly become a zero sum game.

I would encourage everyone, but especially remote workers, to read Give and Take and to be mindful of this. Remember that not everyone chose to work remotely for the same reasons so accommodate if your coworker still needs to sign off by 5 or needs to go pick up their kids. This sounds self-explanatory, but isn’t always second nature.

Finally, don’t compare your remote lifestyle with an in-person lifestyle through silos. Although improving, I don’t think the social nature of remote work will ever be directly comparable to in-person interaction. However, working remotely offers so many other benefits, so acknowledge its pitfalls but don’t dwell on them individually.

I like to think of remote work as a new relationship that you're embarking on. It's a relationship that is not guaranteed to be better, but has the potential to be. Consider remote work a new lifestyle that spans both the positive and negative; so long as it’s a net positive, learn to accept and actively improve on certain facets.

Physical Health

As for physical health, once again, make sure you’re allocating thought to this. The theme here is that the additional autonomy requires you to put thought towards certain things that may happen naturally in a less fluid lifestyle.

Schedule time to take walks during the day and be mindful of the fact that you’ll be sitting at a computer for many hours! For those of you staying in one place, some of my fellow coworkers have bought $100 treadmills that they are often on during calls. For those on the move, I recommend apps like Teeny Breaks that focus on how to be more mindful.

Remote Work and Traveling

Many people opt to work remotely as it opens them up to travel the world. This was originally my intention, but once again isn’t an end-goal. Traveling the world forever won’t fulfill you unless it comes with other ambitions.

I wrote some tips in this recent thread for those traveling and working remotely, but to sum it up:

  • “Slowmad” so that you can focus on other goals.
  • Write down your thoughts and ideas as you travel. Moving around introduces you to new things and therefore, new ideas will develop more often.
  • Use travel time to learn by reading/listening to books/audiobooks (buy a Kindle).
  • Use your travels to challenge your beliefs. Not just culturally, but about the way you think, work, set goals, etc.
  • Once again, be empathetic and treat people well.

My Personal Experience

I’ve been lucky enough to call the road my workplace for years. In many ways, it’s all I can remember, but I do acknowledge that it took time for me to calibrate to my current state which is much more productive than last year and I hypothesize to be much less productive than the next.

That really captures my personal point of view of working remotely. Within an office, I was able to optimize within a small box and now I find myself to be maximizing a much larger box. Each quarter or year, I find new opportunities--not just externally, but internally.

Practically, this was my approximate timeline of habits and key learnings:

0-6 months: Lived in Edinburgh. This period was mostly spent getting accustomed to working remotely. I would encourage others to stay relatively put during this period and “optimize before scaling”.

  • The first ~3 months felt very weird. I was afraid of being away from the computer for more than 15 mins during “key work hours” and didn’t really understand how to internalize that hours did not matter and work was only impact-driven, even though this was communicated to me multiple times.
  • 3-6 months: I got better at optimizing my habits, but still spent way too much time working. I didn’t know how to differentiate between life and remote work.

6-18 months: I traveled a lot. It was a lot of fun, but ultimately this year wasn’t focused on any concrete personal growth. This year is the reason I can say with confidence that “working remotely and traveling” on its own is not an end goal.

18+ months: I slowed down my traveling and re-focused my life on impact, both inside and outside of work. I clearly identified goals of mine (like learning to code) and made them my “north star”. This helped me be even more effective in work, even while transitioning to lead 20 people, as I actively adopted the mentality that my life was agile and could be designed to maximize impact and eliminate waste.

I would estimate that I’m now somewhere between 2-5x more productive and impactful than I was when I first started working remotely due to the expanded box and choosing the right  goals. Naturally, I think many people will go through similar life-cycles as they begin to work remotely.

Practical Tips

If you’re still reading and interested in finding a remote job, here are my tips:

First, decide if you want to work for a remote company or freelance. Both are valid, but quite different in nature. If you’re a freelancer, you’re working more independently (often not part of a team), need to spend time on things like marketing yourself or attracting clients, but ultimately you can have more autonomy.

If you do decide to go the company route, I would encourage you to work for a company that is completely remote. Here are two lists of such companies from Buffer and RemoteOK.

They naturally set up social structures and systems to combat some of the pitfalls of working remotely. If you are one of the <10% of remote workers at an organization that is mostly in-person, there is no significant incentive for them to set these up. Not because they don’t care, but because most pitfalls of working remotely are subtle to onlookers but significant for the remote workers.

If you choose to seek work at a company, this is my advice:

Learn Basic Digital Skills

Regardless of the role you’re applying for, understanding basic marketing, SEO, design, and development skills will get you very far. With the democratization of learning omnipresent, you can pick up a course in any of these topics on Udemy. If you’re specifically interested in coding, I gave a talk on this recently.

As an example, when I was looking to work remotely in 2015, I knew that I didn’t have enough skills to land the right remote career. Luckily, I wasn’t willing to trade my career for the ability to work remotely; once again, I realized I could have my cake and eat it too. So, I ended up working 4 side jobs throughout the year across SEO, social media, email marketing, and online research that helped me build new skills and accelerate my learning so that I could find the role I was happy with (Growth Lead at Toptal).

Search in the Right Places

With 2018 being the year of job boards, there are dozens of places to search but that also means a lot of noise. When I was searching 2-3 years ago, I had the most luck with Flexjobs and RemoteOK and to my understanding, they are still leading the pack in terms of finding the best remote jobs (including full-time remote jobs) and in ensuring quality (which is what matters). I was able to find paid remote positions on both of these in 2016; 3 on FlexJobs and 1 on RemoteOK.

It’s worth noting that FlexJobs is a paid platform for $15/month or $50/year, but when you think about the cost savings of finding the right job, it’s one of the better investments I can think of.

Swiping Left to the Right Company

In 2019, anyone who operates fully remote companies is still an innovator. Less than 1% of companies work entirely remotely, so when you apply, remember who you’re talking to and speak to their values, which are hopefully aligned with your own.

Remember, there are many reasons why a company may choose to employ a remote workforce. Some of them include:

  • Access to the global talent pool
  • Saved costs
  • Employee retention
  • The belief in higher productivity
  • Etc.

You can normally get a sense of which reasons resonate with each company based on their public persona and their /culture page. Again, use this to gauge whether your values align with theirs since not all remote employment opportunities are a fit.

Remember that any job is a two-way transaction so even when you're looking for remote work, vet the employer and position.

Keep in mind that a rewarding job is normally a challenging one, so long as it challenges you in the right ways. For that reason, I normally suggest that people don’t go for remote jobs that promise you fairies and rainbows unless that’s truly what you’re looking for. Remote work will permeate into your life more than a desk job, so make sure you’re finding the right company offering remote work.

Drop the Ego

As you apply, keep in mind that those hiring for remote roles tend to have a different agenda compared to typical hiring managers. They care less about:

  • Prestigious degrees or sometimes any degree at all
  • How much money you currently make
  • Buzzwords

They care more about:

  • Proof of malleability
  • Proof of grit
  • Proof of ambition

Notice the word proof in the above segment. For example, telling a remote hiring manager that you “have ambition, grit, or are malleable” means next to nothing. However, if you learned to code on your own so that you could find a remote job, that act itself proves that you’re malleable to learn new skills, are ambitious enough to start, and have the grit to power through the process of learning.

I also found when I was applying in 2016 that each application got easier as I added remote work experience to my belt. This is partially due to me having more confidence, but also due to remote work being another piece of proof to hiring managers that I was accountable.  As I shared with my personal experience above, the first 3-6 months of working remotely is a learning curve, so if you’ve already gone through this phase, companies can trust your ability to work remotely effectively.

If you don’t have remote experience, use this as a chance to uplevel your skills. Even if you’re a “professional with 10 years of experience” in one industry, you can always keep learning. As mentioned previously, development, SEO, and marketing skills are all solid additions to any skill-set. This is especially true with remote jobs, particularly in operations/marketing, as they’re dynamic and require you to do more than one thing over time. Your ability to constantly learn is a major plus for you and the company.

As you’re interviewing, don’t be afraid to talk about the side projects you’ve built or the time you hacked something together. Proof of your ability to do remote work is hidden in the problems that you’ve already solved.

The Future of Work

There is no doubt that remote work will continue to become more ubiquitous as we move forward and I hope that every single one of you is part of that future.

I also hope that this guide gives a more realistic picture of location independence and some of the skills you may need to learn to maximize your impact. In the end, remote work is what you make of it and I believe that it can allow you to design a better life, with the right adjacent goals in mind. Happy living!

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