When to quit your job and go freelance

I had a long list of potential blog topics to write about this week, but for some reason I just kept coming back to this one question:

Did I make the right decision to quit my high paying job as a business consultant/ analyst to go freelance?

Don’t get me wrong, I absolutely love working for myself and anyway, it’s still early days in the life of my startup. However this got me wondering… is there a right time to quit your job as an employee to start your own business? And if so, when is the right time?

The catch-22 of going freelance

This whole issue raises an interesting catch-22 situation. Do you quit your job now and focus 100% of your time on setting up and running your business? Or do you keep your day job until your business starts generating revenue but then have limited time to work on the business.

And how can it generate revenue if you have no time to market and sell the business? What’s more, this second scenario would be virtually impossible if your business is a service-based one, as mine is, which requires you to deliver a personal service to clients.

My story

Ironically, for me it was a fairly easy decision. I had just finished an 18 month assignment as a senior business analyst on a large and fairly complex government project and wasn’t too keen to jump straight back onto a new project. So I agreed to help out my sister who runs her own business with her husband.

I spent a few months helping them with refreshing their business strategy and plan, and implementing various operational improvements. It was a real eye-opening experience to see first hand how a small business ran its operations, compared to the corporate world. And finally, after some initial teething issues, I discovered that small businesses are simply crying out for real solutions to their business problems, with hands-on help to implement those solutions.

So I was empowered to do my best to provide that to them. After a couple of months sorting out my finances, writing a business plan and strategy, and creating my business brand and online presence, I was (driven probably by excitement more than common sense) ready and open for business.

The time is now…?

So when is a good time to go freelance? Well, I say NOW! …with a few conditions…

The conditions

It should go unsaid that this is a big decision and shouldn’t be entered into lightly. You absolutely need to have a few of your ducks lined up before you even contemplate leaving your paying job and starting a new business.

  1. Get the basics sorted. Read my 10 questions to ask yourself before you start a business. At the very least you need to know the answers to all these questions, and have a business and marketing plan roughly worked out. This is no small task and may take months to do, as it did for me. But believe me, you will be very pleased that you did all this work up front.
  1. Define a trial period. This will depend on your business and industry but decide how long you’ll try your new business out and what conditions need to be met before you declare it a failure. For example, I’ve given myself until the end of March to generate a specific target sales figure per month.
  1. Work out your fall-back plan and be prepared to do it. This is Plan B. Ask yourself what will you do if this all goes pear-shaped and the venture fails. Go back to your day job? Raise additional funding to keep trying? Get a partner in? Remember, it has to be an action that is realistic and that you are prepared to take.

Then what?

So, your ducks are all in a row, you’ve defined your testing timeframe and have a fall-back plan. Now what?


As often as I hear about people starting a business without the proper preparation, I hear the opposite as well. Fear and anxiety prevent would-be entrepreneurs from going ahead despite having done all their homework. Here are some simple techniques startup and small business owners can conquer their fear and anxiety.

Of course once you’ve launched your business, all the real work begins and the juggling commences! However, as I mentioned earlier, if you’ve done a lot of your homework up front, all you need to do is just follow your business and marketing plan.

Final thoughts

When things aren’t quite going to plan and you start to doubt whether you have made the right decision, here are a few final thoughts that may help you, as they have helped me.

  • Try not to panic – you have your fall-back plan.
  • There is no shame in trying something out and failing. At least you tried. I truly believe that every experience in life is an opportunity to learn something new.
  • Trust that good things can take a bit of time. Stay true to your business plan and trust that it will happen.
  • There’s usually help around the corner – in the form of a friend, partner or business expert – so make sure you reach out to them rather than suffering alone.
  • And finally, this one came from one of my business colleagues: “Feel the Fear and Do It Anyway” (thanks Annie!).

* Feature image sourced from Gratisography.

Peer-Business-Consulting-Angeline-Zaghloul-5What did you think of this article? Post your comments and questions below. And if you found this useful, please share with your networks.

About the Author: Angeline Zaghloul is an expert in business strategy, client management and business processes, and is the Principal of Peer Business Consulting, a Sydney-based consultancy providing strategy and operations support to startups and small businesses.

* Portrait by Markus Jaaskelainen.

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