Going Remote: An Intro Guide For Normal People, Part 1

Disclosure: this post is long, serious and pictureless. On the bright side, it might help to change your life… still, we should probably throw a few waterfall photos in here to keep you engaged. Also, we should make it a two-part post. Just thinkin’ out loud here.

Upon hearing that our travels have been powered by remote work, people’s minds inevitably wander as they imagine themselves in the same position. Often, it results in them offering up questions like, “do you think I could find a remote job? And once I get one, can I just start traveling?”

The answer, of course, is… it depends. But that’s not the most productive advice, so instead we’re going to offer up a bit of a blueprint here — with a few assumptions baked in:

  • That your best option is to make your current job remote (as classifieds are a bit limited)
  • That your current job is theoretically remote-friendly (e.g., not a cashier, bartender, etc.)
  • That you want to travel while working remotely (plenty of remote folks sit at home; you don’t need our help with that)

So you’re still with us, yes? Great. First an outline so you know what you’re getting into, as this is fairly long for a blog post (but pretty short for a guide):

  1. Evaluate Your Life
  2. Know Your Audience
  3. Create Transparency
  4. Say “No” Productively
  5. Rinse And Repeat

A bit of motivation — or maybe tough love — before we start. The foundation of this guide lies in taking back your time… but owning your time is an epiphany before it’s a strategy. A large amount of office activity is unproductive, and driven by fear. Declining unnecessary meetings, automating mundane tasks, setting realistic expectations for response times, and slowing down frantic behavior is imperative if you are to take back your time. If all that sounds fantastically unrealistic to you, it’s because you’ve been brainwashed into participating in these unproductive approaches.

Food for thought as you consider Step 1. Need a waterfall break?

Step 1. Evaluate Your Life

Surprise! The first step in any major life decision is introspection. Here are some of the key considerations.

Career Growth: there may come a day when face time doesn’t unfairly impact your odds of getting preferential treatment, but that day is not today. Expect a more difficult road to promotions and internal job opportunities once you start working remotely, simply because humans are primitive and tend to be more trusting of what they can see in front of them.

As a counterpoint, your experience telecommuting will put you ahead in the race for your next remote job… a useful claim to fame given that remote opportunities will be ever-increasing. And as a more socially conscious counterpoint, people who might otherwise find themselves struggling to get ahead because of their higher-ups’ biases and stereotypes may find that tucking their race or gender or age or body type behind a computer helps to level the playing field.

Economic Impact: ignoring long-term career discussions for the moment, your remote job will have a (mostly positive) impact on your finances. You’ll likely drive less (yes, even if you drive across the country), which means you’ll save on gas, parking, maintenance, etc. If you normally go out to lunch at work, you’d likely be saving money there as well. Of course, you could spend more, because you’ll have more time available to utilize your disposable income, but all in all telecommuting grants you more practical means to be a frugal Freddy. In one extreme example from Rogue Trip, our rent costs went from roughly $2,000/mo in NYC to less than $100/mo as van dwellers.

That said, your company will not experience the same immediate cost savings — and while your remote job will eventually be an economic benefit for them, you’re a few years too early for that. Consequently, you may end up in a position where you’re negotiating a lower salary to sweeten the pot for an employer. Mitch does this pretty religiously with remote-unfriendly employers, offering a 15-25% “discount” on his market rate in exchange for the freedom of full-time telecommuting. Should you have to employ the same tactic (or take a more junior position which pays less), you’ll want to estimate ahead of time how that will all play out as part of your financial situation.

Emotional Impact: being isolated from a social environment isn’t necessarily bad or good, but it’s certainly different. It also impacts what skills will naturally develop and atrophy, which may change how you interact with people. Lastly: numbers aside, you might have an emotional tie to your salary or your job title as a measure of your worth. As the aforementioned points imply that your career growth may stagnate, it’s a consideration you need to be honest with yourself about: which do you value more, the freedom or the status? Hailey took a less influential role as part of her negotiation to work remote; she went from being the CEO’s right hand to having a layer of management separating them, which obviously changed the way people saw her at the company. You may have to make similar adjustments if you’re looking to take back your personal time.

Skills Development: some people are not naturally prepared to work remotely, and it’s useful to know whether you’re one of them. Organization, prioritization and good written communication skills are vital. People often mistake “written communication skills” for “having a good grasp on spelling and grammar.” No. Good written communication is the ability to be clear and concise, minimizing the risk of misinterpretation. If you’ve ever worked with someone who clogs up email threads with off-topic questions or misleading jargon, you get the idea.

Once you do start working remotely, some skills will likely improve — like organization. But other skills will atrophy, such as verbal communication. We can personally attest to losing a fair bit of our natural vocabulary by being isolated from the rest of mankind. If you don’t work to keep your verbal and in-person skills sharp, it may negatively impact your career’s growth potential.

Family & Relationships: the most obvious issue Mitch has come across in his decade of working remotely and managing telecommuters is how remote employees balance their work and life. It takes experience and discipline to get the balance just right — most people, especially early on, will either overwork or underwork themselves.

In the case of the former (overworking), it’s often because they’re natural perfectionists, people-pleasers, or even poor managers of their time. If that sounds like you, make sure you’re prepared to challenge yourself with a “new year, new me” resolution-type thing. You will not do anyone any long-term favors by overworking yourself.

In the case of the latter (underworking), it’s usually because the person simply wants to do something else with their life, and they see remote work as a way out of a real job. Welp, that will only last ya so long, buddy. It’s not a good approach — there’s a huge difference between escaping the inefficiencies of the office and avoiding responsibility.

Now, you may wonder why that whole spiel was written under the heading of “Family & Relationships.” It’s because most ineffective telecommuters are sacrificing their personal life for their work, or vice versa. You may have envisioned the “underworker” as some lazy self-absorbed millennial, but in Mitch’s experience the prime examples are often parents of young children. And ironically, the “overworkers” are often parents of older children.

It is really, really hard to get work done and maintain a clear head with toddlers around, partly because de-prioritizing them is not an option. In contrast, once your kids are old enough to make their own food and get in other people’s cars, it becomes temptingly easy to ignore them and push your work far into evening hours at the expense of family time. If you’re in either of these positions, you’ll want to ask for reality checks from your loved ones and co-workers on a regular basis. Balance is vital.

Still with us? Awesome. One waterfall, comin’ your way champ!

Step 2. Know Your Audience

In all likelihood, there are two audiences you need to convince before you can take your job remote: 1) your boss, and 2) your company.

Each of these two targets has their own interests in mind, and you are selling them on an investment. It’s imperative, then, that you learn how to sell. Sounds fun, no? Think about it another way: selling is just empathizing and giving advice, with the caveat that your advice happens to point to the outcome you want. So start with the empathizing.

Your boss: how does it reflect on your manager to be supporting a remote employee? If their supervisor became concerned about your absence from the office, how would your boss be able to defend the decision? How concerned do you think your manager is with your job satisfaction? Is your boss under any real pressure to improve department efficiencies or lower operating costs? What does your boss stand to gain here? When preparing your argument, it’s best to assume the worst: that your boss is only interested in this for selfish reasons.

In Part 2, we’ll cover some of the useful ways in which to empower your boss and give them confidence in your being out of office. Beyond that, you know your supervisor relationship better than we do… obviously the more important and well-respected you are, the easier the conversation is going to be. That said, Part 2 will also show you how to tilt a not-so-flowery relationship in your favor.

Your company: for better or worse, convincing your company is going to be more of an economic discussion than a personal one. You need to show them how this is an investment, rather than merely a risk.

To that end, think about whether your company is keen on embracing new technologies and approaches, or whether it’s risk averse and traditional. Consider how much the executive team relies on data to make decisions versus politics or protocols. Does your request for remote work fly in the face of their efforts to create a “collaborative office environment”, or might it be exactly the kind of initiative they’re looking for in an overcrowded office?

We’ll talk about some of the ways you can tackle this in Part 2, where the next step is “creating transparency.” What does that even mean? Well, here’s an example:

The knee-jerk reaction for many executives is to fear remote work as a tool for employees to hide from their job. Hailey flipped that stereotype on its head by having a transparent discussion about her daily work routine, which involved two hours of underground subway commuting per day. Working remotely, then, could increase her availability by two hours every single day, and during the most important non-work hours, at that. This was a key benefit to her work, as someone whose tasks were often time-sensitive and unpredictable.

Using metrics that objectively mattered to the business, Hailey created transparency to challenge the taboo of remote work: her company would either have to acknowledge that getting back two hours of availability per day would be mutually beneficial, or admit that they’d rather waste that time each day just to be able to watch her sit in a chair. Obviously they chose the former because they trusted Hailey, and in the next post we’ll provide some guidance on how transparency establishes that kind of trust.

Ready for Steps 3, 4 and 5? We’re not. Check back soon for the thrilling conclusion! We promise, it gets more tactical and less motivational speaker-ish.

Thanks for reading… here’s your parting gift.