Change is good

How to make a successful jump from a traditional working relationship to a flexible and rewarding remote career

You’ve all heard the saying before from the French Scientist Jean-Baptiste Leroy, “but in this world, nothing can be said to be certain, except death and taxes.” Said even more concisely, I believe that there is only one constant, and that is change.

As we all know, change can be a force hard to reckon with. Not usually because its physically hard or strenuous—although I suppose it could be—but because it’s scary. And that fear is often the one thing getting in the way of our achieving our fullest potential. An example of this might be when an individual aspires to change careers.

By the time most of us hit a wall at our present job, discover a new passion, or arrive at any of the myriads of reasons one might choose to go a new direction, we’ve likely been thinking about it for some time. Even though job jumping is at an all-time high, so many of us get stuck in a cycle of thinking, not acting.

“Don’t think. Act. We can always revise and revisit once we’ve acted. But we can accomplish nothing until we act.” —Steven Pressfield

But never fear, change is good, and as a society, I think we are starting to embrace it—at least with respect to work. In the past, it wasn’t uncommon for our grandfathers and great-grandfathers to put in 40-years at the factory and claim that shiny gold watch as the sun set on their careers. But in recent years the amount of time people spend in the same company has changed dramatically. According to an Economic News Release from the Bureau of Labor Statistics, “the median number of years that wage and salary workers have worked for their current employer is currently 4.6 years. However, this longevity varies by age and occupation: The median tenure for workers age 25 to 34 is 3.2 years.”

Part of this shift in longevity has to do with the steady evolution of the business landscape in recent years. Jobs that simply didn’t exist in the past now do, and one modality, in particular, that is quickly on the grow, is that of remote work.

For many a career-swapper, the prospect of detached work can be quite appealing. On it’s face anyway, the idea of being able to do your job from the comfort of your La-Z-Boy looks pretty darn good when put against that monochromatic cubicle you’ve been reporting to for the last 12-years. It’s true, because of advances in technology—and studies that prove efficacy—more employers than ever are working to offer remote positions. In fact, according to Forbes, “Remote work arrangements are no longer an exception. They are an expanding reality. In 2019, 66% of companies already allowed telecommuting, and 16% operated as fully remote teams.”

But like any job, remote jobs can be great or super sucky. The flexible schedules and freedom to move about are definite perks. There are also negatives associated with being a teammate apart. Loneliness, challenges when communicating and collaborating, distractions-a-plenty, and staying motivated, to name a few. That said if you are thinking about dumping your old office job and making a run at going fully remote, allow me to offer some useful insight.

How to find work

You’ve decided to go remote. Cool. But now what? I guess it’s time to find work to do. Remotely. This can mean a lot of things to a lot of people, but here are a few places to start the hunt.

Ask your current employer.Happy with the job, but think you’d be more productive at home? Why not ask your current boss if you can work remotely? It sounds simple enough, but if your company isn’t presently set up to support an off-site team, it can be complicated to let you do so. However, if you can build a well-researched and compelling business case for how your detachment could serve the company better, an employer would be hard-pressed to dismiss the prospect entirely.

Ask around. If working remotely for your current employer is a no-go, take this opportunity to tap into your professional network and make it known that you are on the hunt for remote opportunities. People are often happy to help, especially those with whom you have real, authentic relationships with—versus online connections to which you have little or no actual contact. People who know you and who are in tune with what you bring to the table in terms of skill and ability will be most able to help you turn good connections into great opportunities.

Ask the interwebs. If the first two ideas haven’t born any fruit—or you are pivoting so hard that you are entirely new to the space you hope to work in—perhaps its time to reach out to our old reliable friend, the internet. As the popularity of flexible work relationships continues to grow, so has the number of places to look for potential work online. There are many comprehensive lists on the web that dive into each of the many available channels in great detail, so I won’t bore you with that here, but suffice it to say a simple Google search should yield results.

For the impatient among us who want to open a tab right now, here are a few places to start that grace many of the “best-of” lists I’ve seen floating around:

How to prepare

While you are on the hunt for that perfect gig, you should probably start to plan for your future life as a remote worker. While a job is essentially just a job, being detached requires one to pull from a range of skills different than your run of the mill desk jockey. While no two workers are alike, there are some basic things to consider regardless of your discipline. Take the items below with a grain of salt, understanding that your situation will be unique.

Reality Check. In the famous words of the legendary rapper Ice Cube, “You bettah check yo self, before you wreck yo self!” Some of the draw for people hoping to make the jump from a traditional working relationship to detached one are the creature comforts that can come along with it. The idea that you might be able to rock your bunny slippers through that morning meeting and watch Judge Judy while you prepare your TPS reports is glorious, don’t get me wrong. But a remote job, as I’ve said, is still a job. Fully-equipped with responsibilities and requirements. Just because your workspace happens to be flexible doesn’t mean you have the luxury of collecting a check without putting in the work. Maintaining an employer-centric mindset while working from home will help you create good habits that contribute to your success working apart.

Keep it professional. You might be working from home, but just as in a traditional office, you should put careful thought and consideration into your workspace. There is a battery of scientific studies that illustrate home-based/remote workers are more productive than their in-house counterparts. The reasons are many, but if you are to become successful as a remote worker, you have to set yourself up for the win.

You need to arrange your space in such a way as to be optimal for your style of work. I’m not just talking about Feng Shui here (although it might help), but be sure you have a place dedicated to work where you can work with minimal distraction. You should also invest in a good quality chair and work surface, good lighting, any software and productivity tools that aren’t being supplied by your employer, and of course, internet access. Connectivity is king, so if you don’t have great internet access or speed, get it. If you can’t get it at home, you may need to consider working from other locations like public libraries, coffee shops, or co-working facilities where access you high-speed broadband is cheap or free.

Develop routines. Simplifying your daily tasks by way of slick, efficient, routines can help ensure you make the most of your remote-working experience. In my more than 20-plus-years working remote, my routine has stayed pretty constant. Sure, the demands of each day move around and change a bit, but I try to ensure that at least the core tenets of my day are met. At this point, I’ve been working my routine so long that if I miss any part of my list, I feel a sense of disappointment. Logically I know I must be flexible, but I like the routine.

There is nothing particularly innovative about my routine, but it goes something like this:

6:00 AM - Wake up, get ready. Get dressed like I’m going to work. No jammies!

7:00 AM-8:00 AM - Make breakfast for the kids, get oldest off to carpool, and take youngest to school.

8:30 AM - First pomodoro of the day. Spanish Practice.

9:00 AM - Reading for two pomodoros. Always be learning.

10:00 AM - Writing and content creation for four pomodoros.

12:00 PM - Email, espresso, croissant (except when I’m low-carbing it).

12:30 PM to 5:00 PM - Work. Varies day-to-day.

5:00 PM to 9:00 PM - Family time, make dinner, run errands.

9:00 PM to 10:00 PM - Exercise.

10:00 PM to 11:00 PM - Write more if I have anything left in the tank.

11:00 PM - Bed.

As I mentioned, there is variability in there. Some days I don’t get to read, or write, or I have less time to dedicate to them, but that’s life. Generally speaking, however, what I’ve described is a good day for me. That said, I also have routines for specific days. For example, I only take meetings on Tuesday and Thursdays (rare exceptions apply), and Wednesday’s are dedicated to Podcasting.

Whatever your plan, it should be unique to you and designed to support your needs—and the needs of your employer. The more you can do to optimize your day, the more productive you’ll be, the better you’ll feel, and the more you will benefit positively from your detached experience.

Time management. Managing your time is a critical piece of being a productive remote asset. There are a million ways to do it. Your employer will dictate some, your body’s natural rhythms will determine others, but if you are going it alone, you’ll want to establish systems for tracking time and tasks that will help you get stuff done.

One method I like, as evidenced in the previous section, are pomodoros. Pomodoros are short, 25-minute, hyper-focused sprints on singular tasks followed by scheduled 5-minute breaks. Repeat that process four times in a row, then take a 15:30 minute break. There are apps galore that allow you to outline tasks, assign the amount of time—or number of pomodoros—you estimate you’ll need to finish any given job and track your progress. I use an app called Focus To-Do. It’s simple to use, and the chime at the end of each pomodoro is oh so satisfying. By way of disclaimer, I am not paid to promote their app. Buy it, or don’t. They may even have a free version, but that one works for me on my iPhone and my Mac.

For the purists in the crowd on the other hand, pomodoro is the Italian word for tomato. It refers to an old, tomato-shaped kitchen timer that the man who created The Pomodoro Technique, Francesco Cirillo, kept in his kitchen. So if you’d prefer to go analog versus downloading yet another app, swing by your nearest Sur la table then get to work!

Build community. One of the most common issues that many remote workers must contend with is that of loneliness. It’s not usually one of the things you consider when building fantasies about what your future remote-work life might look like, but I assure you it is a genuine concern. Being alone all the time may seem liberating at first, but over time the seclusion can become a real issue for some.

One way to combat the loneliness pervasive among detached assets is to develop community. I am intentionally excluding your co-workers with whom you communicate regularly as part of your job from your community, and for a good reason. Of course, you talk with them every day, you’re always connected, but despite technology’s promise of encouraging greater human connection, it simply cannot deliver. The seclusion that most feel when working apart isn’t because they aren’t communicating enough online. But it has to do with the fact that they aren’t spending enough time developing real, human relationships with people in person. A tweet will never replace eye-contact and knowing that we must step aside from our computers and smart devices now and again to engage in community.

Be on the lookout for conventions, events, industry-related meetups, and so on. These are great places to engage with and develop relationships within a community. Further, work with your employer to arrange travel and find the opportunity to meet with your in-house counterparts and physical “team” whenever possible.

You can do it

It takes a brave person to make a mid-career jump, pivoting to a new job, a new company, or a new field entirely. It’s another level altogether to consider going remote if you have never done so. But I greatly admire the person willing to make the switch. Fear of change will try to stop you in your tracks, but overcoming that fear by way of sound preparation and clarity of mission will afford you a life—and a new position—that will reward the effort.

Ready to jump?

Are you ready to make the change to remote work after a career working in an office? What is keeping you from making the change if you have trepidation? Want to talk about it? Let’s do it! Join our community here in the comments or feel free to find me on the socials to take this conversation wherever the audience most suited to hear it can get involved - I am @ryanroghaar on Medium, Twitter, and Instagram and click here to find me on LinkedIn.