Remote work coach, Darren Cronian

About the author

This guide was written by Darren Cronian. Over the last 7 years, he has secured numerous remote jobs and built a successful freelancing business. Frustrated at automated rejections or struggling to find freelance clients? Your remote work coach is here for support.

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

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

Common Fears of Quitting a Job to Work and Travel
Uncertainty and lack of control

The simple reason why you will feel uncertainty and a lack of control is because you are taking your first steps out of the comfort zone.

It’s natural to feel like this, but remember that you cannot control the exact outcome on 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” and when completing a skills analysis with them, it becomes obvious 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 get over your lack of confidence is by helping someone else because this often enables us to forget about 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 have to return home

Changing your mindset about money is an important step to take before you quit 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 that is 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.

When you are bringing in a steady income you can then decide to quit.

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 travelling as a remote worker, it’s important 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 do if you were living a healthy life back home.

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

Lack of job security

Going from a regular monthly salary to not knowing when your next income is coming 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 an article written on how to deal with job security, this covers the topic in more detail. Realising 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 that are stopping you from deciding to quit 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 fear or it’ll be the realisation that it just needs a mindset shift to get you over the obstacle and move forward.

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