How to Get Remote Work at Any Age

age blog how to get Mar 15, 2021

I spent twenty-plus years as a corporate trainer working on employee development and career advancement programs before I left everything behind in 2016 to travel full-time in an RV. Then I reinvented myself for twelve different remote jobs. Now, I teach and coach others how to trade traditional work for remote work. I’m so passionate about this topic that I could talk your ear off over coffee sometime. Until then, in this article, I want to focus on the most commonly asked questions, if you too are looking to work remotely or pivot your career.

If a 77 year-old feisty guy can work remotely, you can too

Allow me to start with a story about a 77 year-old man named Arnie. He probably doesn't want me to share that with you, but I think he should wear his wise age loud and proud. 

Arnie is a musician who plays the flute and saxophone in a funk and soul band. He also uses his talent to teach teenagers—no easy task.

When COVID hit, his students essentially vanished. He had been going to their homes or meeting them as music studios, but of course that all changed when the pandemic hit. 

Arnie reached out to me to see what he needed to do to take his instruction online. 

And Arnie fought me. He fought me on a lot of things, like: 

  • this will never work. 
  • I have to teach in person.
  • How will I be able to watch the kids’ hands playing on scales? 
  • How will I be able to help them adjust? 

I said, “Look, I know so many music instructors who already teach online, it's already happening. And if they can do it, so can you.” Arnie fought me a bit more until I said these dreaded words:

“Look, the reality is you have no choice.”

Many people want to work remotely, but no one wants to be forced into it before their ready. Sometimes though, “being ready” means someone getting real with you.

That reality-check seemed to do the track, and Arnie jumped in full-force. 

He started with really basic technology—calling the kids on Facetime. Then he got fancy and started sending them lessons in advance to practice, then having them play for him live on camera. As he got more comfortable with this new model, he got more creative and eventually...started having fun!

Arnie now works 100% online. He doesn’t have to drive anymore. So he saves gas money. He saves time. He can reach more people. He's worked out all these creative ways to help students.

And now I want to tell you one more thing about Arnie—he happens to be my dad. I tell this story because if my dad can figure out how to work remotely at 77, then so can you.  

I hope this inspires you. Arnie is typical of a lot of people I work with. Perhaps a little more advanced in age, but has similar qualities like starting over, feeling overwhelmed, unsure of his online skills, and the dreaded this will never work mindset. Then, eventually dips a toe in, figures it out, and finally gets creatives and dare I say excited about what’s possible.

Avoid Doing This if you want to Get Remote Work

Another reason why I wanted to tell you the Arnie story is because I see people make a lot of mistakes when starting their remote work journey.

People often start by asking me “what types of remote jobs are out there. And are they real?”

Looking at the job market first is never the way to start. You can overwhelm yourself with options, feel like there are no jobs, not the right jobs, or they always want you to have a skill you don;t have. It’s downright discouraging. 

So, when I am asked this question, I always kick these questions back—

What do you like to do? 

What inspires you? 

What brings you joy? 

What can you do well or even good enough?

Here's the reality. You've probably been working at a job or a set of jobs you haven't liked in years. And if you start by looking for new jobs without pausing for some reflection, you’re likely to land at any old job you don’t like any better than the one you had.

The Best Way To Start Your Remote Work Search


You will likely need to reinvent your work identity a bit to get remote work. Or at least the type of remote work you actually like and that pays you what you need (and are worth).

Reinvent yourself so that your work aligns with who you are and the lifestyle you want to live. This is going to require that you do a little bit of skill-searching. Maybe but soul-searching too but that’s an article for another day.

You can “Skill-Search” by doing an inventory (or a few inventories of your top skills and strengths. If you aren’t sure where to start, check out this article 5 Reasons Why You Are More Qualified to Work Remotely Than You Think (links to article #1).

We often take our own strengths for granted. We think that because things are easy to do for us, they are easy for others, and therefore not valuable.

This couldn’t be further from the truth. And the way to get to that trust is to get objective about your own skills.

Seeing what you are good at on paper can increase your confidence, give youmreo to work with on your remote resume, and help you in an interview so you can improve your chances at getting the type of remote work that you want.


I hope you found this article both inspiring and practical. Getting remote work can be overwhelming sometimes, but if you take a step back and reevaluate your skills and strengths, you will start to see yourself with a fresh perspective. And that can help you reinvent yourself for remote work that you actually enjoy.


For more information click here to get the free Remote Work Training. It will help you get remote work so you can have income to enjoy your flexible lifestyle.