Why can’t I get a remote job?

While doing research for a new program I’m creating to help people get full time remote jobs, I spoke with a middle-aged gent about making the transition from office work to remote work.

He had been interested in working remotely for a while but, even after months of interest, had not taken any steps to get an interview with a remote company.

I’ve heard this story before. People are interested in working remotely but aren’t interested in getting the actual interviews to make this happen.

This guy had a lot of experience, too. About twenty years of sales experience. So it wasn’t a lack of experience that was holding him back. It wasn’t even his resume, cover letter, or low volume of applications.

The reason he wasn’t making any progress with working remotely is because he didn’t have a good reason for doing so. There was just no motivation to push him forward.

After he told me he was struggling to make the time to find remote work, I asked him: Why do you want to work remotely?

His answer: “Well, to cut out the commute time. I just find it inefficient. I could use that time to be making more sales calls.”

So you want to work remotely to work more? That’s not very inspiring. I told him this as politely as I could. And then I told him that it helps if you have a good reason for working remotely — something that is inspiring.

In addition to inspiring you, a good reason will inspire hiring managers to push you along in the interview process, because hiring managers often ask this question: Why do you want to work remotely?

If you answer by saying that you want to work remotely to work more, you might think hiring managers want to hear that, but it’s forgettable. And if you say you want to work remotely to “have more freedom” — that implies that you want to distance yourself from work.

I asked my new friend: What are your hobbies? What gets you going? Your family, a hobby, travel? He didn’t expect me to ask this. He thought our conversation was going to be “all business.” But he thought about it, and replied with, well, I really like comedy and standup.

“In my free time,” he said “I like to think of comedy sketches.”

“Do you write those sketches out?” I asked. “No,” he said. “They are just all in my head. But I really like thinking about it and I really like comedy.”

And then I planted the seed: “What if you used that time saved from commuting and office humdrum to work on your sketches and explore comedy.”

He didn’t say no. I could see his wheels turning over our video chat. And then he proceeded to share one of his sketches with me.

After this — after having at least an idea of a very specific and inspiring goal for working remotely — I could see he was more excited about putting in the necessary work required to get a remote job. Further, when he was on interviews for a remote job, telling hiring managers his comedic aspiration would set him apart and make him memorable. And even further, when he had a remote job, he would be less inclined to get bored and lonely with all that extra non-commute time. He would be less likely to become one of the many fresh remote workers who get bored and lonely and return to the office.

In this example, the bad reason to work remotely is cutting out the commute. That’s not original. It’s not inspiring. And it doesn’t answer the question: So what will you do with your extra time? A better reason for working remotely is realizing a childhood dream or picking up a hobby, much like this guy thought about picking up comedy and writing sketches.

To get your own wheels turning, below are some examples of good ideas to work remotely. (They are general, so make them specific to your interests and own goals)

Good reasons to work remotely

• To travel. This was my initial reason. I found a program that took remote workers to 12 countries in 12 months with other remote workers. This sounded like quite the experience. It inspired me to get my first remote job. Hiring managers also thought it was cool.
• To explore a hobby or side project. Do you want to learn Spanish, learn to play a new instrument, or start a side business. These are not silly reasons to work remotely, especially if you live in an area with long commute times and need to drive back and forth every day. Also, the companies you want to work for will think you starting a side business, project, hustle—whatever you want to call it—is cool.
• To spend more time with family. Another person I talked to during the research phase of the program I’m creating said he wanted to work remotely so he could stay close to his family in Hawaii. For anything in life, what better reason than family?

There are more, many more. These are just a few. If you have other reasons you think are good, please let me know about them in the comments!

Bad reasons to work remotely

• To have more freedom. This often comes across as you wanting to distance yourself from your work, which alludes to a different problem. You don’t like your work, or you don’t like to work. Working remotely will not solve this issue. Before exploring the idea of working remotely, you should explore different career options.
• To cut the commute. The commute is not usually the problem unless it’s eating up hours of you day. You can do a lot of productive things in the car, like practice clearing your mind in the midst of chaos, listening to podcasts that make you more aware of important topics, and calling you family or friends to tell them how much you appreciate them. Mild humor aside, seriously: Forget about the commute. Think about what you’ll do with your extra time.
• To get out of the office. Ok, but why? Is it because your manager is looking over your shoulder or you have shitty lunch breaks? The issue is not the office; it’s the company. Believe me: You can be micro-managed and stressed AF while working remotely. Video calls exists. You’re only a dial away.

Freedom itself is great. The non-commute is great. Not being stuck in an office is great. Don’t get me wrong. The point I’m trying to make is: Don’t think working remotely will solve your issues. Use remote work for a specific purpose. And if you find you don’t have one, that’s fine! There are plenty of cool companies that have offices. I’ve worked in those, too!

Because I’ll be releasing a paid program soon, it’s not in my financial favor to tell you this, but it’s the truth. Find an idea that excites you. Go after that. And if remote work helps you get that, go after that too!