Strategies for Finding Remote Work

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Disclaimer: This transcript is provided as a courtesy for accompanying the associated episode it represents. The content of the transcript may provide errors or incorrect statements from the recorded episode. Portions of the episode such as opening or closing comments may be excluded for brevity.


Jonathan So, wherever you are, whether you are just starting out, or you’ve been remote for a while and looking to transition to another opportunity, we’re going to talk through some things to consider and really set you up for success.

Starting off, I’d like to have you take a moment and envision what it is you want to get out of remote work. And if you’re envisioning a laptop on a beach, I think you need to get a little more practical.

Ari Definitely, that doesn’t happen for everybody. That’s a here and there kind of thing, unless you just happen to get that job.

Jonathan Yeah. There are those out there that achieve it, but there are very few of them. So, let’s get a little more practical. What is it that you want to get out of remote work? Is this a career decision for you? Are you wanting to shift your entire career really towards a remote trajectory? Are you looking for some work on the side to pick up some extra cash and make some extra money? Or are you looking for really, like, a flexible schedule? Which is common among remote work.

Ari Definitely there are those companies that, you know, if you’re working for an actual company, there are those that are just looking for part-time people to work, maybe, to fill in the evenings, sometimes for support or things like that. Also, extra cash is something you can get by opening up your own little remote business, doing some freelancing.

Jonathan Yeah. Ari, I know that you... So, you currently have a commuter job, as we refer to them on the show, but you’ve also done some freelancing on the side. What does that kind of look like for you?

Ari Well, you know, I’ve done some traveling for that, but I’ve also pretty much had the flexibility of—you know, flexibility is the key word, I think, here—the flexibility to sit down and work at my dining room table, on my couch, wherever it is, at a desk, you know, and hack away a little. I’ve done a little bit of that web development and some other related things, and just the ability to do that from any location. I can do it in the evenings, after my daughter’s gone to sleep, after my wife’s gone to sleep, usually, as well. And then I put together some project. I get it out there and hopefully get paid.

Jonathan Yep. That is always the other important part of it.

Ari Yes. And I was just going to say, that’s the big risk with the freelance side of it sometimes, is that, you know, if you’re looking for extra cash, freelancing doesn’t always provide an easy, steady stream of income.

Jonathan Yeah. That is for sure. I’ve definitely been there, chasing people down. So, with this, one thing to considering is that, really, what stage are you in your career? Are you looking to transition remote to a setting and a situation where you have already acquired the skills and experience needed for a job? Are you looking to transition careers completely into a new career? Are you an entry-level person just right out of college and looking for your first job? Or are you more of a senior executive and you’re looking to transition out of that corporate into more of a remote-type engagement? So, these are all things that can affect, really, your strategy for finding remote work. My personal recommendation for this would be to have some type of experience in the area that you’re looking to get into. And there are some opportunities to get into a position without the experience, and I’ll talk about that later. But at this point, the goal is, in my particular case, I’m a web developer and a JavaScript developer. And so, it’s easiest for me to get into remote jobs that are for JavaScript developers, where I already bring the experience. If I were to transition into a social media-type position, I don’t have enough relevant experience. That would be a lot of on-the-job training. And so, that would be a more difficult remote position, and especially a difficult first remote position.

So, that’s one thing to consider. Really start crafting what it is, the type of engagement that you’re thinking about. And also, that you have some type of remote experience. So, start small, and maybe pick up a side project or two to start getting comfortable with the process of remote communication and kind of the whole management side of it, managing yourself and your time, and to be able to put some remote experience on your resume, which we’ll talk about in a little bit.

Ari Sure. That remote experience is definitely a big helper, because remote work is very tempting to a lot of people. It’s something which a lot of people look at it and say, “Oh, I’d love that. The flexibility,” like we talked about. “Oh, I don’t have to go on the commute. I don’t have to do that.” But there’s a certain accountability that has to go with this. Actually, we were talking about that earlier today before the show. We were chatting a couple hours before about focusing, getting your head down, and just focusing on that task for a while. And you know, when you’re at least in an office, sure, maybe you’re sitting at a desk in your own space, and if you’re focused or not, nobody’s really going to see it. But when you’re at home or at a co-working space or wherever it is that you’re working from remotely, there’s nobody there to walk by who you might think, “Oh, I better make sure I’m working so they don’t think anything bad about me.” So, not everybody has that self-discipline. So, you also have to make sure that’s something that you’re up to, and that’s why sometimes, little remote projects of your own is a great way to get into it and kind of see if this is something that you can really do long-term.

Jonathan Yeah. I totally agree, Ari. And I wrote a blog post a couple years back talking basically about the concept of leadership of self, that when you’re working remote, you really do have to have that self-discipline, and it’s an opportunity for you to personally develop. So, that resonates well with me. So, talking about some of the mechanics now about it, so online job boards, they are everywhere. It seems like a new one pops up almost daily, if not hourly, and it can be a little bit overwhelming waiting through all of that to find opportunities that you feel are a fit and a match. And there’s basically a lot of noise that’s available.

So, my first recommendation for looking for an opportunity is leverage your referral network. Leverage your existing professional network. I personally, every single job or contract that I’ve landed has been through my referral network. I have cold applied to a number of positions, and honestly, I haven’t got... I’m trying to think here. There isn’t one that I have actually landed a job. I’ve gotten close to the final couple interviews, but it always ends up that the top person picked is one that comes from a personal network. So, there’s great values in that.

Ari Sure. And that goes to the classic...with all job hunting, whether it’s a commuter job or a remote job, it’s not what you know; it’s who you know. And that plays even more so... It’s an interesting mix of that when it comes to remote work, because who you know definitely plays huge into it. Because remember, once you’re applying for a job where you can work remote, instead of just applying as one of the people in the area that happens to know that field, now you’re competing against, at least across the entire country that you’re in, possibly internationally, everybody that can do your job. So, you always have to keep that in mind. So, it is who you know, because you should get to know people in that field, relating to what you’re pursuing, whether it’s other web developers, or you know, other support people, other...whatever field it is that you’re going into.

But also, it is about what you know, I think more so with remote work, because when you get to know these people, these people should look at you and say, “Oh, I see he’s got that track record,” or, “she’s got that track record of doing this, this, and this in the past, so I know this person’s a good support person, a good web developer, a good JavaScript developer,” or whatever, a good C developer.

Jonathan So, my next tip is, when you’re applying for an application, when you actually are filling out one of those online job application forms, really take a lot of care and time to answer all the questions well. There’s going to be a high number of applicants that fill this out, and your application can rise to the top if it is evident that you took the time to actually care about your response. This is the part that is very much like running a marathon. It takes a lot of time and application after application that you fill out. Everyone’s going to be a little bit different. You’ll be able to reuse some parts of it. But overall, that is kind of the first step to rising above the huge applicant pool that exists.

Ari Right. So to speak, you have to personalize that application for each company, for who you’re sending it to. I’ll tell you from experience, one job that I applied to... Now at this point, I can’t remember which order it was, but it had specifically, it said in the directions, “Put in your name, and then the job title that you are applying for.” And I sent in my application. I took a lot of time with the letter, very careful, everything. I sent it in. And it took a long time to hear back. And I was saying, “This is too long.” I spoke to some people, again, utilizing my network of people who knew the company: “What’s going on? What’s the deal?” He says, “Well, you know, you’ll hear back soon, hear back soon.” I said, “This is taking too long.” I went and I looked back and I double-checked, and I realized I had swapped the job title and my name in the subject, and I am positive that that is what got me rejected on that first try. I sent the same email with the subject flipped, and I think within a month, I got a response to at least set up an initial interview. So, little details really do matter. So, pay attention. Pay attention.

Jonathan Yeah. And especially making sure that your name is actually your name. Like, for example, you could have changed your name to your job title, and then it would have been legit.

Ari [Laughs] That’s true. And there are those companies... That’s the thing with some of these more modern companies, that they’re doing all this stuff. They’re saying this is a basic job description, but you can go for whatever title you want. So, I guess I could have tried to say that my name was also my job description, but...

Jonathan That’s horrible advice that I gave, so everyone else, please disregard that. I personally do have some affinity for Kim Dotcom, who legally changed his name. That’s impressive.

Ari Yes.

Jonathan The next point that I have to make is that your digital footprint is really important when you’re working remote. You’ve heard of companies that will Google you. Well, they will absolutely Google you again when you’re working remote. And so, it’s really important to make sure that you have relevant information up there. I recommend to everyone that they have their own web page, even if it’s just one page long. You need to have your own web page. And even if you don’t have your own domain name, it’s fast and easy to throw up an About.Me page. So, that’s one example. You can basically put links to your social profiles up there. You can put a blurb and a photo about yourself. But something to start giving depth and show that you’re a real life person. That is key. So, Ari, what are some other ones that you can think of?

Ari Well, I did mention earlier in a previous episode a company called Book Like A Boss, which is taking About.Me kind of a step further, where you can actually, if you want to kind of get into the freelancing and do some other stuff, you can actually schedule people. I’m not going to go into it in too much detail here, because people can click the links and look at it, and we’ve mentioned it previously. But suffice it to say, you can go in, set up a page where it talks about what you do, what your services are that you’re doing, and even you can set up, “Hey, for this much money, you can get an hour of my time to do something. I can do this kind of a project for this amount of money,” and little things like that. And just having that nice little page set up and just saying, “I can do X, Y, and Z,” that’s another way to set yourself up.

Jonathan So, this next section is related to your resume, and really, skills of interest for remote work. So, to apply to remote work... You’ve heard before to craft your resume for the particular position that you’re applying for, and that still applies to being a remote position, and you need to craft it so that it looks like you will do well working remote. So, for remote work, the type of things that are important are that you’re an independent person, that you’re a problem-solver, that you are somewhat tech-savvy in that you’re able to get connected to the internet, basically, that you won’t have to call someone else when your router breaks. Also, that you’re adaptive and able to adjust with changing schedules and just the chaos that sometimes comes with working remote. And then also, that you’re proactive about communication, that you take the initiative to say, “This is where I’m at and this is what I’m working on, and just want to let you know I’m still here and I’m still working.” That’s a key trait there that’s important.

Ari Yeah. So, I was just going to say, communication, I think, is one of the absolutely most important things in remote work, again, because you’re never seeing the other people you’re working with, in most cases. So, actually going and contacting the other people, whether it’s a text option, like HipChat or Slack, or any type of other reports or other things that you do, any way you can prove or show, or any way that you can list that you’re good at communicating, that you’re good at...especially in written form it really does help to show that.

Jonathan That’s exactly true. And then the last part kind of adds onto that, and that is the personable trait, and shows that you’re able to connect with people and that you don’t hide behind an avatar. This is one thing that’s hard to do when you work remote. It’s easy to put up a picture that is of a fun character, and there’s a time and place for that, but I highly encourage you to actually use a real picture of you. That’s important. And showing that you are relating and working with other people, not just the latest favorite Star Wars character.

Ari Sure, sure. You know, the thing about being personable and all of that, in connecting, a lot of these companies also have a certain culture surrounding them, which is partially because they’re remote, but also it’s just the certain culture. You find this with commuter jobs, too, often. There’s a certain culture. But I seem to see this more so with these remote jobs, and you know, you want to kind of show that you can fit with that culture. So, it’s not only... Going back to what we talked about about examining the situations that you’re going into, knowing the’s knowing the culture before you apply and making sure it’s a good match for you, but then showing that also on your resume, that it is a match.

Jonathan That’s exactly right. And culture’s really a key part, because we’ve talked before about the different types of remote teams. There’s ones, organizations that are fully remote. There are ones where there’s a hybrid approach to it. I’ve worked in both situations, and I can tell you that a hybrid approach to remote work is definitely a challenge. Those are the projects where communication easily happens, that you have no way of being aware of, because it just happens in a particular office or a situation like that. So, also, the tools that an organization uses says a lot about its culture, whether it’s a very enterprise-driven type of environment, or if it’s a lot more fluid and innovative. So, that is one thing to ask as you start interviewing with a company and exploring them, that...what tools are they using? How do they use them? And that type of thing.

Ari Sure. In fact, I know it’s interesting to see how the interviews take place. And I know we’re going to talk more about interviews in a little bit, but in relation to the whole communication idea, some companies strictly have text-based chat interviews, because that’s the way they communicate as a company, and part of that process is seeing that you can actually communicate in that text-based manner, just like everybody else in the company does.

Jonathan Yep. That’s exactly true. And I personally find that to be a challenge. I like the high fidelity of video and audio, and you are able to understand people’s tones and their mannerisms. And it makes people come to life. But that is very much a cultural thing of the company and the organization. So, it’s important for you to think about what type of organization and what type of culture is it that I’m looking to engage with. Part of that culture discussion is, what does the feedback process look like? Basically, you can ask, how can I find out that what I’m doing is great, and what can I improve on? Because some organizations, that is a huge void, and that proves to be a huge challenge in remote work.

Ari Yeah, there’s definitely a mix of that. Especially some of these remote companies are young. They’re not as fully-developed in terms of this kind of HR system, in terms of performance reviews and all of that. And so, you may run into a company where you go ahead and start working for a remote company, and you know, how do you show that you’ve completed tests? How do you get feedback from your supervisor, or whoever might whatever hierarchy system they have, how do you get any kind of feedback that, “Hey, you’re doing a good job, we’re moving along here real good, you’re fitting in nice”? You know, there are some companies that have a structure. They have once a month, you sit down with the manager via video chat and you go over this stuff. And there are some where, if it’s a young company without the HR system developed, you don’t know when you’re going to hear back.

Jonathan So, another thing that’s tightly coupled with an organization’s culture is its benefits package and how that all plays out. And that’s definitely something worth considering. So, the first question relating to benefits is, do you need to bring your own laptop, or do they provide one for you? I’ve worked at places where both has been the case, ones where they said, “Yeah, you can bring your own equipment and you’re good to go,” others where they provide the equipment and the laptop. It just depends on the culture of the environment. But that’s something to consider, because if you don’t have the latest and greatest laptop and you’re starting a new job and they expect you to have something that will be able to accomplish what it is that you’re doing, that is an added cost that you need to be aware of up front.

So, the other thing that has been a growing trend, I think it’s safe to say, has been the concept of unlimited vacation.

Ari Right. And I’ll actually take that a step further. I’ve seen some places now having mandated vacations, because of the remote work idea that you can... You see people who go in to do a remote work job, and they find not that they’re working their eight hours a day, their nine-to-five, so to speak, but they find themselves working 12, 15 hours a day because there’s no structure around them of getting out of the house, getting in their car, going to an office, leaving the office, coming home, and all that. Depending, obviously, on what else is going on around you in terms of family life and so on, there’s people who will do that. And then it just goes on day by day. You lose track sometimes of the weekends, things like this. And therefore, the idea of actually a mandated vacation has come up in some companies, where they’ll actually say, “You must take a week or two weeks of vacation time. We’re going to make you do it once a year. Doesn’t matter what you’re working on. We’re going to find a way to get you away from us for a couple weeks, when you can actually break away from working on this job as many hours...” Who knows how many hours you’re putting in.

Jonathan Yeah. And the next part of this is pay and compensation. So, you think, okay, I live in Chicago and I’m working remote, and I should be able to get a Chicago-based salary or an equivalent of. Well, in some cases, that may be true; in others, not so much. So, where I fall on this spectrum, there’s really two approaches. There’s variable pay based upon a region or has some influence in the region, or there’s really pay that’s just based on the market rate, and that’s kind of the larger market. I personally prefer to fall on the larger market, and this is based on value-based pricing versus kind of commodity-based pricing.

So, value-based pricing would come and say basically, you are providing value and service—that’s why you’re working or accomplishing this particular task for a company—and therefore, if you are sitting in Chicago, versus sitting in the middle of Iowa, there really should be no difference, because you’re providing the same value. That is very much tied to a culture of the organization. I’ve seen some organizations that say, pretty much, we have a standard pay scale and it doesn’t matter where you live. I’ve seen others that have a standard pay scale with a modifier that will take into account geography. So, for example, if you live in an extremely expensive place, such as San Francisco or that type of thing, they may give you a five or eight percent above the rest of the position, or above the standard rate, if you would, to account for that.

And then there are some companies that take it, I would say, to the extreme, and pretty much factor in your location. And so they say, “Well, you live in rural Northern Wisconsin, Jonathan, and so your market rate is going to be what the market rate is where you live.” And I can tell you that there is a huge gap in the market rate for where I live, because there are not many web developers up here, nor a great need of them, compared to a larger metropolitan area. So, that’s something to consider, and again, plays into the culture and something to inspect and check out before you apply for a particular role or gig.

Ari Right. So, there’s definitely, if you’re kind of looking into that, there’s definitely been a move towards transparency with a lot of these organizations. Buffer is a prime example of that. If you go to Buffer’s website, they have a table which says, “If you have this position and this number of years, you’re getting this salary,” and that’s it, so you know everybody in the company that meets those requirements is getting that salary. And then they do have those modifiers, like you mentioned, Jonathan, where, if you live in a place that does cost more money, major metropolis like LA, I guess, San Francisco, New York City, places like this, they’ll modify your salary accordingly. There’s also companies that I’ve inquired into, in terms of remote work, where each person speaks with the CEO as part of the final interview, and the CEO not only makes the determination in how they’re going to be placed within the company and whether they’re going to be hired, but also makes that final determination based on that discussion of what their salary’s going to be, you know, based on your salary history, based on what the job that you’re doing is, and so on.

Jonathan Yep. That’s exactly true, Ari. And we’ll throw a link in the show notes to that Buffer. They have a whole blog post about it that breaks down their philosophy very nicely.

Ari Yes.

Jonathan The next part of benefits is health benefits, and that is a hot topic, no matter who you talk to. And there’s a wide spectrum of how that actually plays out in practice. In the United States, there is a lot of regulations between states in how health benefits play out, and so it’s worth considering and finding out ahead of time how their particular insurance plan will actually affect your insurance and where you live. Same thing, I’m sure, applies to other situations. But again, check that out up front and be proactive in that. Don’t let that be a surprise after the fact.

Ari Yeah, there’s definitely some variety there, like you said, with every state having their own rules and regulations on that. And of course, it applies even more so if you’re getting a job working for a company...if you’re a U.S. citizen, you’re getting a job working for a company that’s based in another country that might not account for that. And that actually kind of goes back a bit to the salary thing as well, is that we’ve been talking a lot kind of on a U.S. focus, which is what we’re coming from here a bit. But sometimes, when international hires are made, they’re hired as contractors, and that can play into it, also, in terms of health benefits. If you’re going to go work for a company based out of London and you’re living in rural Wisconsin, they’re probably...unless they have a U.S. presence, you’re not getting any health benefits with them, actually. So, I mean, these are all things to take into account. You’re just going to be a contractor.

Jonathan And then you run into situations where you have exchange rates and everything else. In a previous organization that I worked with, we had a contractor who lived overseas. But they were able to establish a U.S. bank account. They were a U.S. citizen and they established an account before they moved overseas, but we would pay them and then they would determine when the best time was to exchange the money out, based on exchange rates. And so, that was a benefit to them, and they managed it and it worked out well. But definitely something worth considering there.

So, one other benefit relevant for remote working with an organization is if they offer a stipend for co-working spaces or internet or just general office needs, if you would. Some companies offer this. Others don’t. I personally have always provided my own internet connection for work and any associated cost with it. I just consider that part of the commute cost, if you would. I’m not paying for a daily commute for gas or transportation or anything like that. And so, I invest in my internet connection instead.

Ari Nothing like a good high-speed internet.

Jonathan As fast as can be in remote Wisconsin.

Ari Yes, or in your case, it’s two internet connections at high speed, if I’m correct.

Jonathan Yep, that is correct. I do have two connections for redundancy purposes. So, the final, as we’re getting closer to wrapping up here, the interview process... Take time to clean your office. That is key. When you first start interviewing and if you’re doing a video interview, your office will give a good perspective of who it is that they’re hiring. So, take time to clean your office.

Ari Right. You gotta remember what they’re seeing behind you when you’re talking to them. And for that matter, going further on that, it’s the noise levels also around you. You consider that, how if you have pets, like dogs that bark a lot, you might want to have somebody take them out for a walk while you’re doing an interview.

Jonathan Yep. Very, very relevant advice there, for sure. And I’d also encourage you to do audio/video calls. Start trying to get as personable as you can. That is the thing that is key. And if you’re uncomfortable with video calls, run some practice calls with a friend and make sure that you’re confident in the technology. So, when you have those interview calls, you’re able to not be like, “Oh, hold on a minute. It’s not working. My video won’t turn on or my audio’s not working,” or whatever it is that’s happening. Those are regular occurrences when you’re using video and audio to communicate, but really, try and own it, and master it and don’t be afraid to dive in and learn something new with that.

Ari Right. And I’ll add to that, especially one you schedule that interview and you know how you’re going to be connecting, that’s the best time to be doing that, because you don’t know if they’re going to want to use a Google Hangout, if they’re going to want to use Zoom, or any of these other products out there to connect with you, or who knows what’s going to come out along the way in the future, you know, what video method or audio or anything else... Try to find an opportunity to familiarize yourself with whatever kind of technology that they say they want to use for that interview specifically.

Jonathan And based on the technology, not all of them offer this, but some do. They’ll offer a test call service, so you can actually kick off a call with basically a fake person at the other end, and verify that your audio is working. Skype has this capability. I think it’s the first user that shows up when you sign into Skype. But do that ahead of time, and if they don’t, you can even ask the company that you’re working with, “Is there anything I need to download or install prior to this video call?” They are typically using this technology every day, so those aren’t things that they think about, but they say, “Oh, yeah, you need to go here and download this plug-in or make sure that you install this video driver,” or whatever it is, that’s required. That will show that you’re proactive and really comfortable with the technology.

Ari Definitely.

Jonathan So, our final point in this outline here really is defining success, and it can be daunting, considering a new career or a job change, and remote work can easily add to that anxiety. So, really, I want to encourage you... We’ve had previous guests that have recommended this, too, but being patient to wait for the right opportunity, not just the first one that comes along. Assuming that you are employed and had the luxury of time, really take the time to find the right opportunity. Do your research, investigate the companies that you’re working for, leverage your network to find people that may work for that, either as a first degree or second degree connection, and be confident. This is an awesome opportunity, working remote.

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