How To Leave a Permanent Job to Become a Freelancer

Estimated reading time: 4 mins

Leaving the safety and stability of a permanent job is a daunting task. Thousands (like You?) don’t chase their dream of being their own boss every day because they just don’t know how to make that leap of faith and hand in that resignation letter that’s gathering dust in their minds!

The risks are enormous…. well that’s the perception. The thing is, in our minds full of doubt and uncertainty, we can make the problem feel much worse that it really is. But of course, unless you’ve done it before, it’s also difficult to believe that statement! No matter how ready we might feel to actually make a success of a freelance venture, quitting can rarely seem the easier task. Maybe these things are going through your mind…

  • I don’t have large SAVINGS account
  • I am scared of doing the WRONG thing
  • I am scared of FAILING
  • I don’t want to end up working harder than I already am
  • I don’t have a business that could replace my income
  • I am worried about what my family will think if I left my JOB
  • I am worried about what my friends will think
  • I don’t know what I want to do that I really LOVE

Sound familiar? So what do you do?

Do you:

  • Keep your job until some magic event waves away all the fear? No.
  • Leap anyway even though you don’t know what you will actually do once you have? No.
  • Forget all about it. Maybe this permanent job where I am told what to do isn’t so bad after all. NO!

Here is the Answer…

If you can muster the courage (and save up some money) then the best way forward is to seek help from someone who knows how, and knows all the pitfalls to avoid.

Your leap of faith, like a bungee, needs a safety cord.


Your ‘safey cord’ is getting help from an experienced entrepreneur or business coach .

Finding a Business Coach

If you want to improve your golf swing, who do you see? That’s right, a golf coach. If your kid if falling behind on math, what then? Yes, you bring in a math tutor. A Business Coach is someone who has helped people with this challenge many times over .

Your situation is unique, yet a business coach will know how to help you make the leap after only a few sessions. Your business coach will prompt you to discover the real issues behind your uncertainty and provide you with ideas to overcome them. It’s so much easier, and quicker, to deal with these complex problems with someone who has experience.

Business coaches should be easy to find – sometimes as simple as looking in the Yellow Pages, and I also recommend you use your network or social network to find a coach in your local area that comes with recommendations. You could even tweet that you’re looking for a coach – try it!

Business coaches will charge varying rates, from as little as $50 per hour right up to $5,000 per hour ! Obviously, find a coach that you can afford, but don’t necessarily go with the cheapest if you can’t find a recommendation.

An Alternative…

Let me introduce you to something I found recently: ExitMyJob .  Here is where Bryant Jones shows us how to successfully exit from your permanent job and enter the realms of freelancing and entrepreneurialism through soul-searching, careful preparation and skillful execution.

It was not that long ago I was struggling in a JOB I loathed… – Bryant Jones

This isn’t a guide on how to set up your new freelancing business (there is a great one here, so use that one), rather, it is a coaching program that prepares you for the change by helping you examine your dreams and desires, plan how you want to escape permanent, deal with challenges and resistance and build up a team of associates.

It’s not a template for a resignation letter – it’s far more than that! What I like about ExitMyJob is that it guides you through all the stages you will take to do a proper job of exiting the workplace, step-by-step. It does this by making sure that you are ready and able to quit, by taking you through a journey of self-analysis and self-testing. It’s also more than the typical module-based self-study course; with Bryant you will thoroughly engage with him to get right into the psychy of the challenge you face, through 12 live job sessions where . And more than that too – with Bryant you will develop a life plan that takes you beyond the resignation to form a roadmap of your ‘dream life’.

It isn’t cheap. ExitMyJob is priced at $497 (reduced from $1,997) but I think that this is a good price if it delivers its promise to you. Even then, if it doesn’t deliver, you can ask for your money back with the 100% guarantee. So $497 could offer you great value if it means it sets you on the road to be your own boss and enjoy the benefits and lifestyle of a freelancer.

ExitMyJob is perfectly suited to a frustrated permie who has a compelling desire to be a freelancer, but isn’t confident in making the leap.

5 thoughts on “How To Leave a Permanent Job to Become a Freelancer”

  1. I guess the course seems expensive, until you compare it to the costs of a business coach. Now it looks like a great deal! How do you think they compare Simon?

    1. simonstapleton

      Hi Asif. A business coach has the advantage that they focus on you only during the time you pay them for. This means that the coaching and advice is tailored just to your own needs. The downside to this is that they tend to share advice of the basics upfront as they would to most of their coachees, which you pay for at the same price as you do when addressing more of the advanced topics, and of course you have to pay for the time that your situation becomes understood whilst you get to know each other. In other words, the first few sessions are much lower value in terms of solving problems than the later ones.

      With ExitMyJob, the components of the process are very common to most people, so even though you’re learning from a course, most of it applies fully, so it’s an inexpensive and more valuable means of preparing yourself and making the first steps. If the course ended there, then I would argue that a Business Coach offers you more value later on as you would deal with nuanced issues specific to your situation. However, the ExitMyJob program included live intereactive sessions and personal discussion so I believe the nuances are dealt with there. ExitMyJob is high value, whereas a Business Coach is a boutique proposition.

    2. simonstapleton

      Hi Asif – it does seem a good deal when you consider the alternative. Unlike a Business Coach, if you’re not satisfied you can ask for your money back, so you only pay if you get value from it.

    1. simonstapleton

      Hi Jason – do you use a RSS Reader? Yahoo provides one for free, as do Google (Google Reader), and Newsgator is a popular online reader too ( You can even subscribe using Internet Explorer.

      Try hitting this URL in your browser and see if it offers you an option to subscribe:


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