Self employment lessons - bye bye boss!

One day, after a year of planning, I decided to leave my job. I told my boss that I need to get more control over my life and need to jump. She was very understanding and was thankful for the 7 weeks’ notice I provided. 

The idea of not having a stable salary was exceptionally daunting, but I was determined to make this work. 

I have done all my work with due diligence – I had 1 stable client that would cover my expenses for 3 months and another also coving my expenses with monthly work flowing from Australia.  

Are you freaking out yet on my behalf?

It’s just crazy at times. 

I would like to reflect about my first three months being self employed in this post – my journey. 

Maybe you can learn from my mistakes. 

These are my self employment lessons.

Quitting your job: Backups of backups

I love the way people talk about entrepreneurs like they all work in the same way. Guy Raz explains in his book “How I built this” that not all entrepreneurs work the same way – Check out the apple podcast here and his website here

He uses the image that some entrepreneurs jump from a plane and build the business on the way down – and if they don’t fly, they will die. Others have backup plans. I fall into the latter category. 

I have backup plans for my backup plans. Some of my backup plans included:

  • 2 x clients that would each cover my expenses before I quit
    • That would mean for a minimum of the first 3 months I would get twice my monthly expenses as income
  • 2 years of expenses saved up
  • Conversations with other smaller clients for little projects
  • A sideline project to keep me busy when I don’t have work
    • This happens when you’re self-employed
  • Marketing: I hired a company to do LinkedIn marketing for me. Not that I needed it, but for the future pipeline.

Filling up the sales pipeline

With my prior knowledge, I knew that I had to work on my pipeline. A pipeline works like this: If I know that I need 3 months to convert a lead to a client, then my pipeline is 3 months long. In software development, this pipeline can sometimes be more than a year long!

For this reason, I employed a marketing firm specialising in LinkedIn marketing to connect me with people that would likely use my service. I outlined my company mission and vision, where I would like to go and what I want to do. They connected me with the most interesting people – only one that converted into a R 4 000 deal. This was a fraction of what I paid them! But it will be worth it in the next few months – it’s not converted yet.

You will need to juggle marketing, sales, customer service and the actual work (which is coding in my case). If you have a lot of work that needs to be done, you shouldn’t drop the ball on your marketing or sales – or you will be out of work in a few months. 

Keep that pipeline full!

The business language

One thing I realised early on is the language that business people use is strange and not straight forward. Here are some examples:

  • “Synergy” / “Mutually beneficial”  – Check if we have something that you would want to buy from us
  • “Please send me your company profile” / “Could you send me your rate card” – they’re polite but don’t have opportunities
  • Engagement models – this refers to how do you charge, e.g. per hour or per job. 

This one you only pick up with experience. You need to learn how to communicate. I started playing stupid with some of the LinkedIn queries:

  • “What exactly do you mean with ‘opportunity that might be mutually beneficial’…?”
  • “Hi there, I would be more than willing to meet with your team. Do you have a software development project in mind with which I could assist?”.

In my opinion, it’s very similar to hanging out with software developers: you get to know the terms they use and pick up their language.

Money and working for free.

Now that I am working for myself, I need to think about quoting for jobs. Previously, I would do freelance work because I enjoyed it – as a form of extra cash on the side. At this time, it now means food on the table.

Remember: you will not be busy every hour of the day. You need to make up for those times. For this reason, I am not able to do jobs for R 500 anymore. I have generally taken my hourly rate at my previous job and multiplied it by three. 

The cool thing about being self-employed is that you really do earn every penny. And you get to choose what you do and don’t do. 

Remember: charity is charity and work is work.

Doing nothing

I was working very hard last month. I clocked some seriously good hours. Then the client didn’t send through any more work for 3 weeks. 

I’ll be honest: I was freaking out emotionally. The thought of my recurring client being unhappy and leaving is terrifying. It turned out I just worked ahead of schedule without knowing it. 

This happens. 

And sometimes you need to cope with the silence. 

Paranoia and resting

After working 2 jobs for a while (fulltime and freelance), I now only had freelance work. I have worked maybe one weekend since going on my own. I find this so strange. Previously, I used to have freelance structures in place: 3 days a week after work, Saturday mornings (08.30-14.00) and Sunday mornings (05.00-10.00) would be freelance time.

Now that I don’t have a fulltime job, it feels like my world has been freed up and turned upside down. 

I sometimes feel like “what have I done?!”.

When I don’t have loads of things to do, it just feels wrong. It’s like I am not using my time well – or that I am not making money. 

After my experience at my previous employer, I realised that I need to look after myself. And taking a day off every now and again is not a bad thing. 

Looking after yourself is so important! 


Getting clients is not easy. 

Closing deals aren’t easy.

Living with regret is not easy.

I am happy with the choice I made to work for myself.

And I have more self employment lessons that I am learning every day. 

Happy investing!

Frugal Local

Frugal Local runs his own company (Effectify). He does software development and helps small businesses and startups with digital solutions. He enjoys writing articles and simplifying complex things - such as the article you're reading!