What I learnt In My First 3 Months Of Being Self Employed

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 on 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 straightforward. 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 (full-time 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 full-time 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!