About the author

Darren Cronian, the author of this guide, has spent eight years securing remote jobs and building a successful freelancing business. His goal is to help people escape the office. Read more >

Quitting a job to travel and work remotely will be one of the biggest decisions you make in your life. You must deal with the fears and mindset issues early to move forward.

After coaching several people, these are the common fears of quitting a job that is brought up in the sessions.

Common Fears of Quitting a Job to Travel and Work Remotely
Uncertainty and Lack of Control

You will feel uncertainty and a lack of control simply because you are taking your first steps out of your comfort zone.

It’s natural to feel like this, but remember that you cannot control the exact outcome of any aspect of your life – what you need to have is a plan, which is why having a proven exit strategy will take away a lot of your fears and give you back some control.

If you expect the worst, you’ll probably feel too negative to notice opportunities. If you expect the best, you’ll create a life that’s hard to live up to. Focus on what you’ll do to create what you want to experience.

Lack of Confidence in Abilities

One of the more common statements when coaching a client is, “I don’t have the technical skills to be a remote worker,” when completing a skills analysis with them, it becomes apparent that they have more skills than they give themselves credit for.

Grab an A3 pad and pencil, then write down skills from current and previous employment.

Another way to overcome your lack of confidence is by helping someone else because this often enables us to forget our inabilities.

It feels good when you can make a difference for someone else. Instead of focusing on your weaknesses, volunteer to mentor, assist or teach another, and you’ll see your self-confidence grow the more you help.

Run Out of Money and Return Home

Changing your mindset about money is an essential step before quitting your job. You cannot run your business from a place of fear.

You will make decisions based on bringing money in quickly rather than having a long-term approach where you focus on the needs of your target audience.

There are steps within my exit strategy taught to clients that make sure you put plans in place to avoid stress around money, such as creating your business as a side hustle while working full-time.

You can decide when to quit when you bring in a steady income.

Fear of Health Issues

You might be taken ill because it happens in life, but you cannot live on ‘what-if’ type scenarios; otherwise, you will live a lifetime of regret. While traveling as a remote worker, it’s essential to make sure you purchase adequate medical and or travel insurance so that your medical bills are covered.

Avoid any health issues by exercising regularly and eating healthy food just as you would if you lived a healthy life back home.

Having diabetes does not hold me back – traveling with medication means my sugar levels are controlled, and exploring the places I travel to, results in regular exercise. Regular annual checkups are essential for pre-existing conditions.

Lack of Job Security

Going from a regular monthly salary to not knowing where your next income comes from is a huge mindset change. When you transition into a freelancer or an entrepreneur, you lose that job security, and it’s important to know how to deal with this change before you quit your job.

Recommended is a read of this guide on how to deal with job security. This covers the topic in more detail. Realizing that there is no such thing as job security anymore will make you feel confident about the decision.

How to Deal with your Fears

Sit down with a pad/pencil and brainstorm the fears stopping you from quitting your 9-to-5 job to work remotely and travel. Be honest with yourself and make a note of everything, no matter how small you think it is.

  • What would help you get over that fear?
  • What’s the worst thing that could happen in this situation?
  • What tasks would you put in place?

The only way to deal with your fears is to fight them head-on.

There will be solutions to deal with the common fears of quitting a job, and being actionable will result in you coping with the anxiety or the realization that it just needs a mindset shift to get you over the obstacle and move forward.

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