Reader Case Study : Freedom through Self Employment

financial independence

Here at The Escape Artist we’re talking about how to achieve freedom and happiness.

There are different routes to these destinations. I’ve written about holding down a stressful job and investing your way to financial independence because that’s what I did.

But there are other ways to achieve greater freedom in your work and in your life.  You could freelance, be an interim, work part- time, you could have a side-hustle.

You could do those things right now. You don’t need to wait to have >25x your annual spending. But all these things are WAY easier when you have a financial safety net. So getting your financial shit together and your money working for you are essential.

I helped one of my coaching clients to do just that and he has now quit his full time job and is  successfully working self-employed. He kindly agreed to share his story. Enjoy!


OTR cyling

A few months ago I gave my employer notice that I would be leaving and working for myself.

The reason was not that my net worth and passive income was enough to retire on yet.  I’d love to be in that position and I’m working hard to achieve that.  I’ve just taken a different path to financial independence to the one TEA took.  I’ve sort of escaped – you could say that I’m “On The Run”.

Who cares about some guy who set up a small business?  The fact is that plenty of people go off and work for themselves, but there are also plenty of people who are considering making the move but just can’t get over the line and pull the trigger.  There might be some stuff in here which resonates with some readers and helps them make a bold move. That would be great.

A bit of background first.  I’ve spent 15 years working in a profession that, on balance, I rather like.  I’ve worked for some good companies and a couple of OK ones.  I’ve worked hard, I’ve ‘gone the extra mile’ on projects and for people, I’ve made some money for myself (and more for others).  I’ve basically worked really hard and in the process built a reputation within the profession for being a good guy.

I also saw the light at some point during those 15 years and decided to try to hang on to some of the money I earned.  I’ve managed to avoid lifestyle inflation.  I drive what some people might call a ‘shit car’, don’t own a 42 inch TV, and I don’t go and buy something every time somebody hurts my feelings. 😉

I have a financial safety cushion, partly because I don’t spend to show off.  I’ve also been lucky.  Our house has gone up in value a lot and since 2008 the rising tide has lifted my boat when it comes to shares and other financial assets.

So, why did I leave a reasonably lucrative job, if I’m aiming for FI?

I wanted to be happy. I’ve always wanted to do my own thing.  I’m independent minded, and ‘one day’ I wanted to be self-employed.  I began to think ‘if not now – when?’  Lots of people will do cool things ‘one day’ but it was time to put my money where my mouth was.  I was at risk of postponing happiness because my thought process was that I’d be happy when I saved enough for FI.  I realised I was wrong.  I decided that I could be happy and be working at the same time – if I made some changes.  And those changes revolved around bringing more autonomy into my life.

Happiness is important, but it’s achieved on a daily basis, it’s not a result of achieving a goal – which is what we’ve all been taught.  The truth is that happiness is at the end of a rainbow, but it’s at this end. It’s a choice.  Alan Watts explains the way we’ve been conned all our lives about happiness.

I decided that becoming self-employed will give me some things that make me happy, FI or not.

I could.  I might not be fully financially independent, but I’m not deep in debt.  So, basically, I was in a position whereby I could leave my job and bad things wouldn’t happen immediately.  I’m also in a profession where I don’t need to rent a property or buy loads of stock to get into business.  I’ve got a mobile phone and a computer (and a flat surface to put the computer on), and I can go and see people, so I made the investment (and the risk) to get started as low as possible.  I still have a mortgage, but rates are low so the money’s cheap.  I’ve only just recently achieved some FU money.  I’m super grateful that I have, and as readers of this blog know, that typically is the result of a few years of hard graft and sensible living.  I’m truly benefitting from the shade tree I planted a few years ago.  The best time to start investing is 20 years ago, the second best time is now and all that.

I want time with my kids. I wanted to do more pick ups, drop offs and attend more assemblies and open days.  When they’re 21 they’ll find that a bit weird, so I’ve decided to set life up so I’m in a position to do it while they’re still primary school age.  They really will only be young once.  I’ve chosen to be there a bit more often by working a bit more on my terms.  If I miss sports day, it’ll be because I chose to, not because The Man wanted me at the meeting where we look at a spreadsheet on a screen in a room while eating biscuits.

I hate commuting. Hat’s off to anyone who commutes into London every day or most days.  I’m not a fan of the London rush hour and decided that I’d just rather not thank you very much.  A very wise friend of mine helped me realise that the value of not having to make that commute was pretty high.  Commuters – think about it for a moment.  What would you pay (or what pay cut would you be willing to take?) not to have to commute anymore?

I have a supportive spouse. They say that behind every successful man is a surprised mother-in-law.  Behind this moderately successful man is Mrs OTR. Mrs OTR is very supportive (tip; listen carefully for support, it can be expressed in different ways, such as “can you stop fucking moaning about this and just either set up on your own or not?”). She is also a cheap date – I won’t lie to you.

What I do suits self-employment. I work in a branch of Human Resource consulting that is quite specialist.  While most large organisations have a need for what I do on occasion, they tend not to employ people in permanent jobs to do it for them.  What I do is also reasonably easy to buy; the buyers know what they’re getting (mostly) and can ask for for it in varying quantities.  I’m not trying to persuade people to buy into a new concept, I’m just offering myself as a service they’re likely to need at some point.  You could argue that I’m not changing the world. That may be true but it works for me.

I have a good network.  I’ve done good work for clients, I’ve helped a lot of people down the years, I’ve shared, I’ve done favours and introduced people to other people when I thought they might benefit.  I therefore have a lot of credit in the emotional bank account.  I get called a good networker, but I don’t really know what networking is if it’s not what I’ve just described.  I had reason to believe that some of that credit was available to be drawn upon. Give and you shall receive.

I like to have fun. I wasn’t having much fun.  That suggested to me that perhaps it was time for a change.

Sounds easy.  I had the financial cushion, which enabled me to do what I always wanted to do.  I had a wife who was supportive.  I knew there were buyers out there who trusted me.  I’d even got some ‘push factors’ in that I’d decided I wasn’t a great fit for my employer.  Easy peasy – hand in the notice and get working on the new life.

Of course, it really was not easy at all.  I’ve wanted to do this for about 5 years, been seriously keen for about 2, and after deciding to do it, took 2 months to say the words to my boss. It’s fair to say that, even though my mind was made up and I knew it was the right thing to do, I was shitting myself.

But I got over the line and it was a great decision.  I am (at the time of writing) more than busy enough.  I’m enjoying exploring.  I’m full of ideas about ways to make money and having fun while I’m at it.  I’ve got my mojo back.  The kids aren’t starving and we’re not living in a box under a bridge.  The previous sentence gives you insight into some of the deep seated fears I had to address in my decision-making process.

I’ve also bumped into a lot of people who’d really like to make the change.  Here’s some of the reasons they give as to why they don’t.

“I can’t afford to”.  If you’ve worked for more than 15 years in a professional job and you don’t have a safety net (aka FU money) then my friend TEA has some reading for you.

“it’s too risky”. If you have a job, you’re like a business with one client.  I’d call that pretty risky.  We advise businesses to get multiple income streams in order to spread risk, and yet most people have one job.  It’s puzzling.

I hate my job, but I want to get made redundant”. If you hate the job but want to hang on for a big pay off then I’d argue you’re kind of wasting your life.  Not many great lives were lived holding on and hoping to be let go by The Man in exchange for a cheque.  I’ve never been made redundant so I’m happy to be corrected on that one, but it just doesn’t sound very self-directed to me.  I’d just rather be in charge of my finances and life than allow the prospect of a payment at some point dictate my decisions about how I spend my time.

‘I hate the job but like my colleagues’ – You can still be friends. But that’s often not really what’s going on.  Underlying this kind of thinking is often some kind of loyalty to the employer.  My argument is that your true shareholders are your family and close friends, and I’d therefore argue that you should put their needs first, not your employers.  The employer might be less loyal to you if the shit hits the fan than you’ve been to them with your protestant work ethic, hoping they’ll reward your hard work.

“I’ve been in the job less than two years. I don’t want my CV to look like I’m a flip-flopper “ – 2 answers to this one.   A) you’re allowed a couple of bad moves on your CV, and the 2 year thing isn’t actually the rule of law as far as I know.  B) This one’s important; who cares? We’re all way more than our two pages of sunny-side-up bullshit.  Seriously, if your CV is your main concern, get some perspective.

“I don’t like selling”. This is probably a self-limiting belief.  The fact is that people love to buy, but hate to be sold to.  If you’re competent, have some war stories (social proof that you’re competent) and like to solve problems then you can sell.  If on the other hand you like being told what to do, really can’t cope with uncertainty and hate the thought that you have to ask for money, negotiate, chase invoices and talk about your business to people, then maybe it’s not for you.

“I don’t have the experience”. This one I will allow.  But not for everybody.   Mark Zuckerburg started his business at an early age, but for most of us without the ‘big idea’ we need to earn the right to sell our time and expertise through doing it for someone else for a bit first.  There is a fine line here; some people just don’t have enough to offer on their own yet.  But some do, and suffer from perfectionism, imposter syndrome or some other form of energy and confidence sapping thought pattern which is getting in the way of their success and clouding their decision-making.

So, there you have it.  My story.  Some reasons for going On the Run and pursuing FI self employed rather than as an employee…and some challenges to typical reasons not to.

I know some readers will be in the position I was in for a long time.  You want to pack in the job, but the guaranteed income makes it a difficult decision to take.  You want to make the brave move but you daren’t yet. No two people are the same, and there’s no set answer. What I’m saying is: think carefully about why.  Think carefully about why not.  Challenge the reasons why not.

What’s the worst that can happen?  I’ll let you know in due course (you can follow my progress at So far I’m really enjoying finding out.

Good luck and all the best in whatever you decide.


  1. dawnmartyne · · Reply

    well done to you and i wish you every success.
    thanks for sharing
    i always learn something .

  2. Very good article with a lot of sage like advice.

    I went freelance in IT over 23 years ago because I realised very quickly after starting my career that it wasn’t the job I hoped it would be. 23 years on I’ve worked in many different companies, with many different people (some of whom are close friends now, and one is my wife!), had some great contracts and some less so, and realised three things:

    1) That initial job wasn’t the wrong career, it was just the wrong company to place my career with.
    2) You will always find work, it may be great role or it may not be so good, it may pay a small fortune or it may just get you by, but there is always work out there if you look for it and are flexible.
    3) Working freelance forces you into the thinking about the future and possible periods of being out of work in a way that having a permanent job doesn’t.

    Point 3 was what led me to FI, which I reached quite a few years ago, though at the time I hadn’t discovered blogs such as this so didn’t even know there was a name for it (I thought I was a little weird with my goals around clearing the mortgage and building a massive nest egg when all my fellow contractors were buying a BMW M3 and a 6 bed detched!)

    Good luck with you new lifestyle, I’m sure it will be a great success.

  3. TheLuckyOne · · Reply

    Nice one. Love the fact that there are many ways to reach FI. I’m 2 years out of the camp and loving it. Sometimes doing new things or sometimes just more of the things I used to do without having to fit in time to eat the mans biscuits and typing shit into his computer.

  4. My husband had a similar story – he had thought about going self employed for years but finally took the plunge when he was pushed (redundancy). That was eight years ago and I don’t think he’ll ever go back to working for the man. He didn’t enjoy his job but saw it as a means to an FI end. He has always had a target for FI by 50 but hit it at 41, by a different route again (property rentals, shares and alternative investments) although we share many of the same characteristics mentioned here. We’ve avoided lifestyle creep, drive ‘shit’ cars and choose camping and UK holidays rather than cruises and disneyland. I’m also a cheap date who is lucky enough to love my job, and get paid pretty well for doing it, so there is no pressure from my side for him to become a walking wallet. I’d much rather keep him in good health so we can enjoy retirement together, than put him in an early grave through the stress of running on the corporate hamster wheel.

    Great to hear how everyone else is approaching FI

  5. Reminded me of this article:

    There are many paths to FI and having a business may be more enjoyable or faster for some.

  6. @Kamil – nice link. I agree that a lot of the FIRE crowd really just want autonomy over their time rather than a desire to retire in the traditional sense, but being self-employed is scary. Being frugal is intrinsically valuable, but I would agree, the whole 4% rule is prob too much of a time sink and therefore too risky (it uses up too much life) to be sensible. s and the author of the linked blog’s approach do seem more sensible to me. The argument that only 1 in 10 small businesses succeed shouldn’t strike the fear of god into you as those odds can be hugely tilted by the type and scale of the business enterprise you dabble in..

    A bit of everything is the answer, saving, investing, entrepreneuring – but what you shouldn’t be doing is wait, wait, waiting for some perceived future nirvana. Spend an enormous amount of effort on becoming time autonomous, thats my advice.

  7. I was wondering how you find work/contracts. Are there agencies you go through or is it just through the network you’ve built up? I work as an IT Consultant for a Service company. I get paid a salary but they charge me out per hour (i get paid about 27% of what they charge me out at). Not quite sure how to cut out the middle man. I’ve moved countries a couple of times so I don’t have a network to get work through.

  8. bluebluebluecat · · Reply

    Wondering where that island picture is from…

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