Interview: Jordan Carroll on Getting Your First Remote Job and Being a Successful Remote Worker

8 min readMay 30, 2022


Photo provided by Jordan Carroll

Jordan Carroll is a remote work expert and job coach connecting high-performing individuals to remote-first opportunities. He creates content courses and coaching programs for candidates to help them sharpen their skills.

Jordan is also currently working on his book, Remote for Life. He has an active Kickstarter account to fund the project and is also on the road promoting the book.

We talked to Jordan about landing a remote role and cultivating the right mindset to succeed in a remote-first environment.

You’ve been working remotely since before it was cool, what do you think of the widespread adoption that happened to remote work over the last couple of years?

I love it. I think more people are going to be able to prioritize their life and do things they enjoy. The widespread adoption is good for a lot of people. I rarely see jobs that are listed as ‘on-site’ now.

I think it’s going to do a lot to make our society more borderless. What’s going to end up happening is that when people don’t have to live somewhere because of a job, they’re going to choose where they live based on a wide variety of other factors.

We’re going to see regions, countries, cities, and counties all having to push to try to get new people to inhabit their areas. There’s going to be a lot of competition among countries. That’s going to change a lot of the ways our society is bordered, which I think is one of the most exciting things.

Digital nomad visas are one example.

What are the top soft skills employers look for in remote workers?

Asynchronous communication is probably the most important skill you can acquire. That starts with your writing ability. So if you work with people from all across the world and across different time zones, in order for you to push a project forward, you need to give them everything they need to be able to do that when they wake up and that comes with really good asynchronous communication.

So being able to do that is one of the most important things and that is shown through the job search process. A lot of people don’t consider that.

But every little email or every little message you send to a recruiting or hiring manager is very important. You’re giving them a preview of what it’s like to work with you. And if you take these little details really seriously, they’ll recognize that. Remote-first companies prioritize being asynchronous.

What are some examples of limiting beliefs that aspiring remote workers have?

Let’s just take an example of someone who hasn’t worked remotely before and hasn’t been in an industry that’s typically remote.

They may say to themselves, oh well there are no jobs that are remote!

And yet, they’ll go and skill half-heartedly try. But if you don’t believe in yourself, you’re not using an actual strategy. So of course you’re going to fail. It’s predestined at that point. Whatever people believe comes true.

If you believe you can’t do it, or if you believe you should expect failure, or even if you’ve been through a lot as an applicant and nobody is getting back to you and you’re just getting discoursed, then no, this isn’t going to work well.

Because you’ve told yourself that.

So I think your strategy is very important. And that means not just applying to a bunch of jobs, but rather using your network to get referrals, and building a personal brand, and figuring out what the other intangible parts of the job search are.

Because just clicking on a button doesn’t have a personal feel.

Having limiting beliefs about your job search becomes a bit of a self-fulfilling prophecy. As with most things in life, people who really believe in themselves and believe in success are often successful.

So what are some ways people can develop that self-belief?

It starts with self-awareness. I think a lot of people who are early on in that journey of becoming aware don’t actually realize they have these beliefs. When I talk to somebody, I can pretty much hear in the first few minutes what their beliefs are and what they believe about themselves.

They’ll say things that really disparage their own worth. Or they’ll be self-deprecating and negative.

These beliefs need to be reframed. Journaling is a great tool to use for that. I journal every day and I find when I am constantly journaling, especially within a positive frame, I start focusing on the good things rather than on what I lack. That’s a really good way to start changing patterns around limiting beliefs.

What are some tips you have for remote workers struggling with a lack of structure and routine?

For me, my calendar is key. Everything is in my calendar. I’m very structured that way. I would definitely advise using a calendar. Start with all things you need to get done every week, and all the things that contribute to you having a great week.

For me, the non-negotiables are exercise, meditation, breathwork, and eating lunch. These are things that are really going to contribute to your well-being or things that need to be done from a work perspective.

Another way to find structure is through the social accountability of coworking. You could use an online coworking app, like Focusmate, which lets you schedule 25-minute or 50-minute sessions with people all over the world.

You schedule a block, you tell the person you’ve connected with what you’re going to do, they tell you what they’re going to do and then you just work together and there’s no talking. And in the end, you review how it went.

I’m in Croatia in a co-living space right now and we just did a session right before this. We ended about five minutes before our call. It’s just very helpful because you have other people who you can see working and you’re going to be motivated to work yourself.

And that’s why I like working remotely.

It can be tough if you’re by yourself, but if you’re purposefully connecting with others, and focusing on work, it’ll help you be productive.

And it depends on the person. Some people are really good at motivating themselves. But even then, I personally like the social aspect of it. I like the pressure and gamification of being like, hey, I’m going to get this done in 50 minutes, you’re going to get your task done in 50 minutes, boom! Let’s race.

How does productivity differ in the office versus in a remote-first space?

I mean, it kind of depends on what you mean by remote. Remote can mean I’m working from a coffee shop. Remote can mean I’m working from home. Remote can mean I’m working from a co-living space. Remote can mean so many things

Typically, for me, I am most productive at home when I’m not traveling.

I’m much less productive when I’m in a co-living space like this, than when I’m in my own apartment in Mexico or California. So I think just knowing yourself helps. It comes back to self-awareness and understanding.

Where are you most productive? When are you most productive? Are you a morning person or an evening person? Can you structure your schedule and your environment to help you succeed?

Because if your environment doesn’t give you the tools to be successful, for example, if you don’t really have strong WIFI or you’re easily distracted, or you go to a place that’s really loud, then you can ruin all ability to be productive just by that environment.

What’s your advice for people who need to let go of the 9 to 5 mentality to find their flow ?

If you work for a company that allows asynchronous working, I would look at it as a huge positive, and not as a detraction. There will be a learning curve.

But what I would say is, what could you do with your life if you had autonomy over your day? What would you want to do?

I often have clients write it out. It’s called the ideal day exercise. So if you were to look at any ideal day and just imagine it and visualize it, you’d walk me through that day and write it down to the 15 to 30-minute intervals.

And once you write that out and actually see it for yourself, you begin to realize you could actually live that day.

For me, that’s how I looked at my life too. I was like, what do I want to be able to do? What are things that are important to me?

I feel like I get pretty close to the ideal day for me often.

And what would you say to companies that are still reluctant to adopt remote work, let alone go asynchronous?

At this point, if you’re reluctant to do it, I don’t know what to tell you. It’s going to be a major part of any candidate’s decision at this point. Anyone who’s thinking about working somewhere is wondering about how flexible the job is.

I would ask them to consider how important they think keeping their business afloat is. Then, they should think about instituting a flexible policy. The issue that I see most often is the indecision of how the policy is going to be built and the definition of what remote means to the actual company.

There’s also a difference between what I call remote-ok and remote-fist. There are the companies that offer remote but do not really support their employees with remote work. Then there are the companies that give you a stipend to work from home, offer coworking memberships, adopt asynchronous working, limit meetings, and center all their policies around remote working.

The companies that are going to be the most successful in the coming years are going to be the ones that really adopt this mindset.

And they’re going to get the best talent because the best talent is going to want to work where they have the most choice and autonomy.

And finally, where do you see remote work in the next five years?

Remote work will become the default in the next five years. People will be able to work from anywhere.

There are a lot of companies that are working on global payroll right now to make it easy for companies to hire anywhere. So I think the default company that’s going to get started, especially when it comes to tech start-ups, will have a work from anywhere policy, rather than work from X, Y, and Z.

I think that’s going to open up borders. That’s going to open up travel. That’s going to open up a lot of things. So I think remote is going to be in a really good place in five years.

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