How to Become Self-Employed in 9 Simple Steps

Warning: Some of these steps are extremely effective. Be careful what you wish for.

Second Warning: some of these steps are utterly ineffective. I’d even go as far as suggesting you consider skipping them completely.

I won’t tell you which is which because I’m cruel and will enjoy seeing you suffer.

Ha. Just kidding. In reality, I have confidence in your ability to decipher effective from ineffective.

“Man, Matt’s a great guy!”

Yeah. I have my moments.

Ok, the steps. Here they are:

1) I thought about becoming self-employed.

I actually remember thinking this when I was about 15, but it was always followed by “yeah, maybe one day.”

In case you’ve never read anything about self-improvement on the internet ever, let me tell you something motivational: “one day” isn’t a day of the week.

*drops mic*

2) I realized I wanted to become self-employed.

I was working for the biggest private company over here in the UK, in an extremely stable job, with virtually unlimited room for progression and enough money to go out every weekend and  chat up women (unsuccessfully).

So, I should’ve been happy.

But, to paraphrase the ever-eloquent Tony Robbins, I ended up “should-ing” all over myself.

I was unhappy. There was no denying it. With my actual job, yes. But especially with working for that particular company. With “having” to be in the exact same place, every single day, at a specific time until a specific time. With having to get all my fucking work “approved” by all kinds of people.

It just wasn’t “me”.

3) I realized I needed to become self-employed.

A couple of years later, and still at the company I didn’t want to work at, I got promoted. It was something I’d wanted for a while – or so I’d told myself – and it had finally happened.

And I’d be doing a job that had been specifically created for me by my new boss.

And I’d be managing a graduate, something I’d been pushing for.

And I’d be earning a lot more money.

I was happy.

Wasn’t I? I mean, why wouldn’t I be? Right?

I’d tried to convince myself I would be. Because of all those reasons above. And because my boss told me I’d be a Director and earning 6 figures after a few years. Because because because.

None of those reasons mattered. I thought they would, and I thought they should, but no.

And that’s when I realized I’d gone from wanting to be self-employed to needing to be self-employed. I’d never be happy if I wasn’t.

4) I didn’t do much about becoming self-employed.

I scanned some articles, subscribed to some blogs, read some books, went to some “networking events,” reached out to a few people.

I’m not knocking those things, by the way. They’re important (apart from maybe the “networking events”). But they’re not enough. Not on their own. If all we needed was information we’d all be self-employed billionaires with ripped abs, to paraphrase Derek Sivers.

I wasn’t all in. I was a bit in.

Why though? Isn’t this what I wanted? What I needed? How could I not be all in?

Well, I was scared. What if I couldn’t do it? Wouldn’t I be a failure?

I was entitled. Because I should’ve just been able to quit my job instantly and be successful right away and not do any of the work that every single successful person ever had to do to get to where they were.

Being scared and being entitled stopped me from going all in.  

5) I took advantage of my luck.

The company I worked for, one of the biggest private employers here in the UK, “lost” over 250 million pounds (for all you Americans, that’s the British currency). The CEO was fired, a new CEO was ushered in almost immediately, and a bunch of executives were suspended.

In other words: things were changing.

Everybody in the company was offered voluntary redundancy. That meant we could apply to be made redundant – and essentially be paid to leave.

I couldn’t believe it. I’d wanted so desperately to leave, and now this? I could get paid to leave? Was this real, or had I eaten the wrong brownies again?

It was very real. And yes, I was extremely lucky. The perfect opportunity had dropped right into my lap through no doing of my own whatsoever.


I still chose to apply for redundancy. I still chose to take it. I still chose to leave. If I’d done nothing, if I’d continued to lie to myself about how happy I was, I wouldn’t have been “lucky”. I would’ve been someone who saw the perfect opportunity and – to paraphrase Eminem – let it slip.

6) I worked hard and without strategy.

I was writing about 3,000 words a day, every day. For my own blog, for various publications, on Q and A websites. Writing writing writing. More writing. Always.

Because I was “building my audience.”

Do you ever say a word or a phrase so much that it either grates on you or loses all meaning?

Yeah. “Building my audience.” Ugh.

Here’s something I wouldn’t admit to myself: I didn’t know what I was building it for. Did I want to write another book? Did I want to create some kind of online course? Did I want to offer my services to people?

I didn’t know. But as long as I was building my audience (please make it stop), things were ok. Or something.

7) I burned out spectacularly.

While I was building my audience (ok it hurts now), here’s what else was happening:

  • I was recklessly spending my redundancy money. On food, mainly. I do love pizza.
  • I had no income. Like, at all. And I didn’t want to freelance because I was building my audience (kill me) and I needed to spend all my time on that. And, honestly, I thought it was beneath me. I was better than being a mere “freelancer.” Told you I was entitled.
  • I was barely seeing my friends, wasn’t meeting women, and definitely wasn’t having any sex.

Extreme as it is, I felt like I was sacrificing everything for nothing. Because I really was working hard, but for what?

Good fucking point, I thought.

I wondered what I was doing it all for. I worried every single day about how I was making approximately £0.00 per year.

I wondered and worried and worked and worked and worked until it was all too much.

Writing became a chore, not something I enjoyed. Social media became a painful reminder of everything I wanted but didn’t have because I kept seeing all these “successful” people who were killing it and here I was, failing. I stopped going out anywhere because I just couldn’t face seeing anybody and having to “deal” with them.

I lost the fire. My determination to succeed. Something that had been there for my entire life.

That kind of scared me, but not really. I was too exhausted to feel scared, too fed up to give a shit about anything at all, including myself.

My life was shit and I was a fucking loser.

8) I stopped.

After I finally told some people what was really going on with me – which was painful and embarrassing – I felt relieved. Because I knew what I had to do.

I had to stop.

I’d tried pushing through and that hadn’t worked. I’d tried working harder and that hadn’t worked. Stopping was about the only thing I hadn’t tried, and really didn’t want to try.

But I didn’t care about myself, hated my life, and was completely broke. What was there to lose?

So I stopped. I stopped working, I stopped pitching clients, I stopped mindlessly scrolling on social media, I stopped writing.

I just. Fucking. Stopped.

At first, it was weird. I felt guilty. “I should be working”, I’d keep thinking. Every time I thought that, I’d take a deep breath and remind myself I needed this rest and what would happen if I refused to rest.

After a couple of days, I knew I’d done the right thing. I was feeling better already. I’d stopped beating myself up for not working and started actually enjoying all the rest and relaxation I was finally getting. 

To take the pressure off myself? To stop berating myself for not working all the hours in the entire world? To give myself permission to slow down, and rest, and actually relax?

To stop fighting myself?

It was glorious.

After a week or two, something else started to happen.

It was the fire.

It was burning again.

Was I… back?

I started making arrangements to see my friends. I started to go out and meet women. I started to incorporate routine into my life once again because I knew now more than ever that, as Jocko Willink says, “discipline equals freedom.”

I’d managed, somehow, to keep the only client I had through all of this. I was grateful. And I wanted to show them gratitude by doing a great fucking job, much better than before. I did, and they noticed.

I started planning out how to become a self-employed freelance writer. Because it was clear to me now: that’s what I had to do. I already had one client, so I knew I could do it. I just needed a few more.

My entitlement had been destroyed by humility. Pain will do that.

9) I started.

Yes. To paraphrase Michael Jordan, I was back. (Humility, Matt. Humility.)

I reached out to people I knew and asked if they had any freelance writing work they could give me, or if they knew people who’d be able to give me freelance writing work.

Here’s something crazy: it worked. How about that – asking people for help and them actually helping you! It’s almost like we’re human beings.

They gave me work, or pointed me in the right direction, and then – and this is vital – I did the best job I could. Easy to say; exhausting, time-consuming, and hard to do.

And rewarding. And exhilarating. And business-building. Because word-of-mouth marketing works.

I’ve become self-employed because I asked for work and did great work, essentially. Those clients told other clients about me and now, here I am, earning more than I ever earned in my 9-5.

Oh yeah, and I’m happy.


Matt Hearnden

Matt Hearnden is a freelance writer and marketer from the UK. He loves basketball and Freddie, his Siamese fighting fish. He burned out spectacularly in Summer 2016 and hated himself and life for a while, but, similar to Michael Jordan, made a dramatic comeback.