5 lessons from 5 years of being self-employed


January 31, 2023

I just realised, whilst on the phone to a friend, that…


That’s a milestone!

And it just kinna snuck up on me!

I remember wanting to work for myself so badly but also thinking there was NO WAY I would survive longer than a year because…

  • I didn’t have a business plan.
  • I was petrified of having the responsibility of doing self-return taxes.
  • And I was riddled with ‘what will they think?’ thoughts when I pressed publish on my first video.

But, I thought, I’ll give it a year and see what happens.

Five years later, I’m still here!

Who would have thought?

And with that, I thought I’d share 5 lessons I learnt from becoming self-employed.

1) Everything feels scarier before you actually do it.

I felt like there was a vast canyon between my 9-5 world and becoming self-employed.

But the scariest thing turned out to be taking the first step.

Once I made the leap and I was officially self-employed, the fear melted away and what came instead was pride for having faced my fear and euphoria!

I felt like I was on a year long honeymoon because I was finally free from the shackles of the 9-5 life.

I remember when I was an Executive Assistant to a CEO, I spent my life coordinating his diary and being jealous of the interesting people he was meeting, the freedom he had to meet and see people instead of doing admin chores.

That was when my vision was born – “I want to be Queen of my own diary”

And then I finally was! That’s why it felt like such a honeymoon.

I could work from anywhere, I could stretch out my morning routine instead of cramming everything before 9am, and I got to go those networking brunches that I’d always eyed up with envy from my desk job.

Takeaway- So if you’re thinking about taking the plunge but you’re scared, know that it gets easier. Like this picture below so neatly illustrates. And focus on all the things you’re gaining from working for yourself – that will make it feel like YOUR honeymoon year.

credit: Liz and Mollie

2) Being self-employed is the scariest, but also the best personal development journey you can go on

Before I was self-employed, whenever I came across a fear (eg. public speaking), I would first avoid it.

Next, I’d be all perfectionist about it and think I’d need to take a course on it (so I went to about 5 ‘Intro to Public Speaking’ course taster sessions), and those all made me think it would take YEARS for me to be a good speaker.

Then I became self-employed and there was nowhere to hide. I had to confront that fear right there and then, and get over it cos I needed to get out there and meet some clients!

And you know what? It comes back to point 1 – it wasn’t that bad at all.

I didn’t need years of studying.

I just needed to go out there and do it.

I know there are some of you who dream of the freelance life or being your own boss, but you hold yourself back because the thought of selling or being visible scares you, and you wonder how you’ll handle failure and rejection.

I’ll tell you now, not only will you handle it with more ease than you anticipate, but it also won’t take you nearly as long as you’re imaging it.

Learning by doing, and making mistakes, is truly the best way to grow exponentially.

Credit: Ferraro Roberto

3) Always be networking

Luckily, I loved networking before I became self-employed, but if you don’t love networking, start working on that now because your network is where all the good opportunities lie!

It is only through my network that I got contracts or speaking opportunities with big brands such as Lloyds, Sony, and Shoreditch House.

It was only through my network that I discovered how much other people were charging corporates and what phrases to say to make sure I wouldn’t be haggled down.

Sure, you could get lost in some deep Reddit thread and learn about these things. But they may not apply to your country or to your industry.

The beauty of your network is that it’s YOURS.

Custom-built to your interests and world.

So start networking now both in person and online.

4) Invest in yourself

I got the biggest results and made the most progress when I invested in a good course, a good mentor or a good membership.

That’s the golden trio that worked for me – a course to learn from, a mentor to ask questions and get feedback, and a membership to build a network.

But you can pick one to do at a time.

I will say, that it took me a while to invest because I was scared of taking the risk.

What if it didn’t work? What if I wasted money?

But that’s part of the process.

You need to get comfortable with taking risks and making mistakes.

And honestly, there’s no such thing as a mistake.

Just valuable FREE lessons, you didn’t know you needed.

In the times I didn’t have those three, I felt like I was doggy paddling – working lots but not moving forward with anything.

So my advice is – save yourself time and mental anguish and get help!

5) Trust your timeline

When I was stuck in a job-hopping cycle, trying to find my calling but failing miserably, I thought this hamster wheel struggle would never end.

I felt so behind in life!

It felt like it was taking ages for me to find my dream career.

It actually took me 5 years to discover coaching and then 2 more years to find my dream job (within full-time work) and then 2 more years to find the job I was actually meant for – being self-employed.

Looking back with the gift of hindsight, I realise my timeline was PERFECT.

I am glad it took me that long.

There were so many skills I learnt, things I experienced and tried in those years, that are serving me (and my clients) now.

Heck, I wouldn’t have specialised in career change if I just became a coach 1 or even 3 years after graduating. What workplace experience or life wisdom could I share at that age?

So if you’re frustrated at how long it’s taking you to arrive, know that this time isn’t wasted. Every book you read, question you ask in a webinar and idea you have, will serve you down the line. And when it works out for you, it will be the perfect time!

Credit: Liz and Mollie

I hope you’ve found this useful.

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