"Real" remote work jobs

Remote work is on the rise causing more people than ever to jump into the travel lifestyle. People of all ages who want to travel or have more flexibility in their day, have more options than ever to try something new and different. While new and different can be exciting, it can also be an emotional experience, too. This article explores the emotional journey of becoming a remote worker, and offers tips to manage the experience if you choose this path.

What is “Remote Work?”

Remote work is the ability to work anywhere, and perhaps even anytime you want. The changing landscape of the economy in the last decade, along with improved internet connection has resulted in an explosion of remote and flexible jobs.  If you’ve been paying attention to the job market lately then you know that not only is unemployment low (3.8% according to the U.S. government https://tradingeconomics.com/united-states/unemployment-rate), but that remote job opportunities are growing rapidly (see graph below).

Growth of remote jobs

Remote work growth data.

People are working from their homes, RVs, coffee houses, overseas, libraries…heck, I’ve even worked from bars (while drinking only water of course)!

Not all remote jobs have to be online, either. Remote simply means “not location based” and for some people that means traveling and working in one place for a while, or picking up seasonal work before moving on to the next place. The point is, you can define the perfect remote work situation for you. It’s the freedom of choice that this work type allows.

Click this link for more remote work ideas.

What is the “Emotional Journey?”

The emotional journey is a phrase that I use to describe the emotional process related to a life change. For example, ditching your house and walking away from a good paying job to work remotely and travel full-time (oh hey, that was me!).

I didn’t make this concept up. With a master’s degree in counseling psychology and over twenty years working in corporate training, I’m well versed in change models like the Kubler-Ross 5-Stages of Grief. I might be the first, however, to actually blog about it as it relates to full-time RVing.

Why do people experience an “Emotional Journey?”

A big life change can trigger a range of emotions. Even positive decisions like getting married, or having a baby can produce feelings of fear or anxiety while you’re simultaneously experiencing joy and happiness.

This can be disorienting for people, and it gets worse if guilt sets in. Thoughts like, “I’m going to live my dream and travel the country so I should be thrilled not terrified,” is a form of self-shame that can create another layer of discomfort to the emotional journey.

If you’re in the midst of change and feeling things like anxiety, depression, fear, panic, or other strong or scary feelings, just know that these are normal human reactions. Change of any kind disrupts our sense of safety and security, and can trigger chemical reactions in our brain. If you can relate, check out the tips below to help you manage the emotional journey.

Common emotional reactions and tips for transitioning to remote work

1. Loss of Identity

Loss of identity is one of the top struggles that people share with me. This is especially true if you have worked in one job type, career, or had a job title for a long time. My title was “corporate trainer” or some variation of that for a long time. I tried to do other things, but I kept returning to my training “roots” because it was comfortable and I was good at it.

remote work job identity

My work badge, e.g. “job identity”

A strong work identity can limit your thinking when you want to transition to something new. It’s hard to see what else is possible when you’ve been calling yourself “teacher,” “truck driver,” or “claims associate” for a long time.

Tips to manage this:

Start by mourning the loss of your identity. That might sound weird, but you are literally losing a part of yourself when you give up your title. You may also be giving up work relationships, a paycheck, and a work culture, too. Honor that and go easy on yourself. Know that feelings of sadness, confusion, or any other feelings associated with loss are temporary, normal, and actually important to your new future.

2. Not feeling qualified

I was teaching a workshop this past weekend at an RV Rally. A man in the audience—let’s call him Joe—said, “But I’m 70+ years old and I can’t do technology. How in the world can I work remotely?”  

I get Joe. Technology is a real struggle for me, and I’m younger than him (I’m not a millenial though, so don’t go thinking I know what I’m doing). Additionally, people sometimes think that since they’ve never worked online or remotely, they just don’t have the skills to do it now. This holds them back, and they give up on their dreams because this remote job stuff just seems too complicated.

Tips to manage this:

Here’s how I respond to people like Joe: Do you log in to your computer and check email? Did you watch YouTube recently? Did you scroll on your Facebook feed? Guess what? You can work online!

Many remote jobs don’t require complex technology. Some don’t even require a computer. Some jobs can even be done with just your hands, like being a traveling lighting technician. I even once got a side acting gig (and I’m not even an actor!).

Lastly, realize you are more qualified than you think. People are multi-talented, and have many skills that can transfer from one job to another. The trick is to know what you’re good at, and how to talk to talk about your value.

Remote Work skills inventory

Example of a skills inventory exercise.

Click here if you want an exercise to help you determine your transferable skills.

3. Thinking that remote income may not be enough

When people think about working remotely, it’s often followed up with, “But I’ll have to take a paycut.” I’m not sure where this myth comes from. It may be because people think that remote work means low paying jobs, workamping, or Amazon CamperForce. For some people, these jobs are great and fit exactly what they need. For other people, the pay just won’t cut the mustard.

The underlying issue here is that people simply don’t know what’s possible. They haven’t had exposure yet to the remote job types that can pay the same, or sometimes even more than their “traditional” job. Additionally, people make the mistake of thinking the income they make now is the income they need in the future. That may not be the case.

Tips to manage this:

The reality is that remote income is up to you. It’s a matter of understanding what’s out there, knowing what you want to do, and then being able to communicate your value. There are jobs where you are fully employed that offer great pay, and there are jobs where you set your own pay rate and hours (if you’re willing to freelance). The bottom line is to do your research and follow a process to create opportunities. I offer a process inside of my Remote Work 101: Work, Live, and Travel Where You want course.

Lastly, consider not only how much income you’ll earn, but also expenses you can reduce to see exactly how much you need to make when you go remote. In my case, our expenses dropped drastically, which freed us up to freelance and withstand variable income—something we never even considered when living in our “sticks and bricks” before.

4. Feeling overwhelmed with learning curves

Another common theme I hear from folks is general overwhelm. People have this dream of traveling and working remotely, and before they can even get excited about it, they quickly shift into, “But how is that gonna work?” The minute you introduce “how” questions into the equation, suddenly the vibe changes from excitement to panic—especially if you start with no plan and just start looking for jobs online. The experience of going online into the massive sea of job boards can shut down the process entirely.

RV learning curves

Bryce learning how to fix our RV slide.

If you’re lucky to get through that phase and find a job, then the next phase is actually learning the job while also learning to travel full-time (if you’re headed that direction). Whoa, talk about learning overload! That’s a lot of learning curves. That much change is enough to make anyone feel overwhelmed—even if you like change like me! 

Tips to manage this:

The best thing you can do is go easy on yourself. Take the pressure off that you have to get this remote work and travel thing “right.” You’re in a huge transition to begin with, and the more you layer on the learning curves the more stress you are putting on yourself.

Understand that this is a process that can take time and involves some trial and error. Your first remote job may not be your last. And you may also discover that what you thought you wanted to do is totally different in a year from now.

Lastly, it’s ideal if you can stagger your learning curves. For example, try doing remote work a year before you plan to travel. Practice working in different locations. If you’re going to RV or travel, start by taking shorter trips and practice working remotely. That way, you can simulate what remote work and travel will actually feel like when the time comes. And you’ll be able to work through the challenges in advance, too.

5. Your new reality is uncomfortable

When people get on the road or make the transition to remote work, they often go through a period of discomfort. It’s different for everyone and ranges from a loss of identity, to missing family, to managing income and expenses differently, etc. What makes this period even more uncomfortable is when they start questioning their decision, and then beating themselves up or believing that their friends and family were right—they are crazy after all! And the self-shame that I mentioned earlier can lead to more intense emotions.

Tips to manage this:

I want you to remember how brave you are. Someone who is willing to make bold moves like working remotely when they never have before, or traveling part or full-time, or any new life change, is a special person.

Emotional journey art

Bryce’s alcohol ink painting.

Rather than question and beat yourself up, be kind to yourself. Say nice things about how brave and courageous you are, how you are living life on your terms now, and being intentional in your life. Do things like journal, create art, meditate, or take a walk to clear your mind and reset your energy. 

And remember, most of the time this is a normal adjustment period. Even a positive life change is still change, and can result in strong emotions. The key is to know that it’s temporary, and to practice healthy behaviors to help you manage the experience.


I hope you found this article on the emotional journey of becoming a remote worker helpful. If you related to anything in this article, please leave a comment below. And if you have any tips to share about how you manage the transition to remote work, please share those, too.

It’s important that I mention that while the emotional journey can be a normal human reaction to life changes, if you are experiencing emotions that are causing more intense feelings for prolonged periods, it’s time to seek external support. There are online counseling services that can be very helpful to you. Here’s a link to check out online counseling services.

If you liked this article and want additional support and guidance in your remote work journey, check out my course Remote Work 101: Work, Live and Travel Where You Want. I combine emotional management with practical remote work information to help you achieve your ideal remote work future.