Transition to Self-Employment Without Going Broke

Financial Autonomy - Blog
Transition to Self-Employment Without Going Broke

I’m hugely excited to share with you the release of Entrepreneur You – Transition to Self Employment Without Going Broke, our new online program in the Financial Autonomy Academy.

It’s the first course we’ve created that combines one-on-one coaching with self-directed online learning modules. The feedback I’ve received from our beta testers has been fantastic and I’m super excited to launch it out into the world.

So why consider moving to self-employment?

Our mission here at Financial Autonomy is helping you gain choice. Of the options available to gain choice, becoming self-employed offers the potential for you to achieve success quickly, without huge financial investment, and provides the greatest potential financial upside.

But transitioning from being an employee to becoming self-employed is a mine field. Let’s look at some of the challenges and what you can do to overcome them and achieve the success you deserve.


1. Getting lost in the weeds

SEO, social media, business plans, balance sheets, influencer marketing, taxes, budgets, branding. These are just some of the items thrown at those starting businesses, each apparently super urgent. It’s easy to get overwhelmed.

In module 1, we focus on developing your clear north bearing so that as you develop your strategy to transition to self-employment, everything is aligned, consistent, and self-reinforcing.


2. Reinvent the world, or stick to what you know?

We’ve identified 5 different pathways to reach self-employment, which we explore in module 2 of Entrepreneur You:

Same Profession – own flavour
Same industry – new take
Grow a side interest or hobby
Pursue a passion
Reinvent the world

Determining the best pathway for you is a key step in de-risking your transition to self-employment.

My journey involved the Same Profession – own flavour pathway. I was an employed financial planner, and I set-up shop running my own financial planning business all the way back in 2006. Perhaps you’re a barista who starts a coffee roasting business (Same Industry – new take). Maybe you’re a passionate fly fisher who starts a guiding business (Grow a side interest or hobby). Or you’ve always loved writing and decide to start a blog and work on a book (Pursue a passion). Or maybe you’ve got an idea that will change the world.

Being clear on your pathway to self-employment is an essential foundation in developing your strategy.

3. What do people want?

You might love your idea but if no-one else loves it, there’s not a viable business in the offing.

The Entrepreneur You program is about transitioning to self-employment without going broke. We’ve developed a framework to maximise your chance of success. Depending on the pathway you are pursuing, using a Side Hustle approach to perform experiments and gain feedback is an important way to achieve success and something we dive into in module 3.

4. Plan to fail or fail to plan?

How to create a business plan that doesn’t end up gathering dust in a bottom draw? That’s the challenge we address in module 4.

I’m a huge believer in the concept that the best opportunities aren’t evident until you’re in motion. To succeed you need to adapt as you gain feedback on your business idea. Our 1 Page Business Plan is designed to be easily refreshed and re-jigged. As a very small business a key advantage you have is that you can be nimble and responsive. Long winded business plans set in stone work against this advantage you possess and are therefore to be avoided at all costs.

Module 4 is also where we have our first coaching call so you can get impartial feedback on your business plan and we can iron out any other issues you have to this point.

In the free sample that we have produced, I cover the framework used in the Entrepreneur You program so you can see where things like the business plan fit in. Request a copy here.

5. I’m no good at selling

Which is more important, the business plan or the marketing plan? There are plenty who would argue the marketing plan is what it’s all about. To succeed in your move to self-employment you need your ideal customers to know you exist, and you need to convince them that you can solve a problem that’s troubling them. You then need to make your solution so appealing that they are prepared to hand over real money to have you solve it for them. This is a challenge not to be under-estimated.

Developing your marketing plan is the focus of module 5. We have a 1 Page template and various resources to help you succeed.

6. I need income from day 1

If you’ve got a family to feed it may be that building a business from zero is not viable. In module 6 we explore the process of buying a business. As a former business broker I share the details of several transaction I was involved in and explain the process involved in buying a business.

I show how to value a business and, in your workbook, provide an example for you to run your own numbers.

Buying a business can be a great way to hit the fast-forward button and greatly reduce your risk in transitioning to self-employment.

7. Financial Controller – huh?

The largest module in Entrepreneur You covers all things dollars and cents. Most people making the jump to self-employment won’t be familiar with reading financial statements, monitoring key financial metrics, deciding on the best business structure, determining prices, and preventing fraud.

The lack of these business foundations is a common reason for business failure. It’s essential that in your plans to move to self-employment you accept that one of your new roles is that of Financial Controller for your business. The good news is, through a combination of solid foundational knowledge, suitable software, and a good accountant, succeeding in those role is within your grasp.

8. Battling the mind games

The difference between the number 1 and number 4 tennis player in the world is likely not their inherent skill. To have reached the top 5 in your chosen level of specialisation necessitates skills at a level few others enjoy.

But what separates the number 1 player from all the rest is almost certainly in the mind. Whether it’s how they handle pressure, or how long they persist at training, the deciding factor amongst most athletes is in their head.

Success in your transition to self-employment requires a mindset change. No longer will you have a manager to report to, or work colleagues to confide in. How will you win the mind games?

In module 8 we explore handling failure, defeating loneliness, time management, and worst-case scenario planning to put you on the path to success in the mindset game.

This module coincides with our second one on one coaching call. We can discuss where you plans are at and overcome any hurdles together, so you can launch your new business successfully and make your transition to self-employment.

Moving to self-employment certainly provides the potential for you to gain choice and happiness in your life. But it’s not without risk. Having a clear framework to follow, and the support of someone who’s been through it before, will improve your chances of success immeasurably. That’s why we’ve built Entrepreneur You.

Learn more about the program here.

Request a free sample of the program here.


In my book Financial Autonomy – the money book that gives you choice, we step through the framework below. The content covered in this blog and podcast explore each of these steps. Learn moredown a free sample of the first chapter here.

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