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Why self-employed is the way to go!

I was pushed into self-employment, having been made redundant twice in a row—this was 20 years ago. I just decided that I wasn’t going to beg for yet another job running a factory (job interviews are basically begging aren’t they, and they’re not even fair; even though I’m quite good at them, I hate the process, it’s so phoney).

Without the redundancy I’d probably still be working as a factory manager or as a university lecturer, and I’m SO glad I’m not. Those jobs are OK, but they aren’t GREAT like my current work is. Here’s why:

1. You keep all the money

Tiny plastic model of a man reading a newspaper, sitting on top of a pile of actual coins.
Photo by Mathieu Stern on Unsplash

If you’re employed they are keeping the profit they make from you. This is how capitalism works, they only employ you if they can make money out of you—and that’s fine, we all understand the rules, and why SHOULD they employ you if you are a loss-maker! So when I worked for the university I used to present management courses to local companies, and we charged them £1000/day and I was paid £200. That’s when I realised that there could be better arrangement!

2. Tax advantages

Just while on the theme of money, legal tax arrangements can work much better for you if you’re self employed.

3. Freedom

This one is HUGE! Once you’re self-employed you can choose your customers, choose your working hours, choose the type of work you do. I don’t get up till 9am, and I often go to the beach in the day time, especially if the sun is out, but I often work in the evenings—that’s just how I like to do it, it’s how I work best. Depending on what you do, you could even work on your laptop or run Zoom sessions from a beach in Thailand, at least some of the year, if you wanted to. It’s great to have the freedom to work and live in the best way for you.

4. Reduced bureaucracy

Yes, you have to do your own admin, (or pay a PA like I do) but no more management meetings, no more budgets and targets, no more culture workshops or whatever—you can just get on with working.

5. Security

This one surprises people but it’s true. You have a skill you’ll always be able to sell, you have a number of customers so if you lose one you hardly notice, or maybe you make a bit less money but that’s still fine. And you have control—you can work harder and get more work if you want to. Unlike when you’re employed, all your eggs are in one basket and someone else is holding it—they can get rid of you if your face doesn’t fit, or if someone else in the company does a bad job (low sales, bad marketing, bad product, bad customer care, whatever) or if the market dips by 10% and the company becomes loss-making. That’s too scary for me!

6. Justice

If you are lazy and doing a bad job then you’ll struggle, and if you work hard and do a good job you’ll prosper mightily. I like that. It’s Darwinian, and 100% fair, unlike the politics and random reorganisations of a large organisations where often it’s the good people who lose out. If you want 100% justice then you have to do it yourself.

Chris Croft with his dog, standing at a gate with the beach and sea in the background.
The author (and his dog) on a typical working day…

7. Ownership

Once you’re self employed, your work is what you are, not just somewhere you have to go every morning. You’re building something for yourself, not for an ungrateful boss (or bosses’s boss who doesn’t even know you). Your work has more of a point, and is much more satisfying.

8. Holidays 

You can choose your holidays—where and when. No more 28 or 35 day limit (in the USA I think it’s only 20!). I usually go on holiday 5 or 6 times a year, and I take August off and three weeks for Christmas and New Year. So that’s about 12 weeks a year, or 60 days. And if I want a chunk of six or eight or 10 weeks I can just do it, no permission needed. Who owns your life—you, or an organisation that doesn’t really care about you?


I’ll admit it’s not all perfect. You don’t get sick pay (if you’re prone to a lot of that then don’t go self-employed) or holiday pay (although who cares if you earn more each year in total). You’ll need to think about a pension. You’ll probably work more hours than when you had a job, but only because the work is so absorbing and you own it. You’ll have to be a bit of a jack of all trades and learn about your own IT and accounts and marketing etc, but that’s useful to know, and actually quite interesting. (And of course you can pay people to do whatever you don’t want to do or don’t know how to do). There will be a time lag before you can be up and running and making a living so you’ll have to have a buffer of money or some support to get through that period. And you’ll need some knowledge on how self-employment works.

And finally, you’ll have to find something you can do—and also be able to sell it. If you can do THAT, then I would say absolutely you should go for it!

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