The freelance interview – insights into the gig economy

In this exciting new series of ‘freelance interviews’, we’ll be delivering invaluable insights and top tips from pre-eminent freelancers from many different genres; sharing their thoughts, practices, and observations in order to create a collective knowledge base for the benefit of all.

Our inaugural interview is with Simon Short – a successful Project Manager delivering technical hardware and software projects to central government organisations.  Simon has 11-years  of experience in software development and the delivery lifecycle; following a successful 20-year career in Electronic Engineering.

Simon, welcome to The Furious Engineer; and thanks for taking the time from your busy schedule to talk to us.  Can I start by asking what type of freelance services you offer?

I offer mid-term IT and Communications contracts that are delivery-focused.  So if someone has a need to deliver some change in their organization with projected timescales above 3-months and below 24-months then I can help them out.  Anything above 24-months is too much commitment so I wouldn’t be involved in that.

So would you say your role is more Project Management, Change Management or both?

It’s Project Management  – but the boundaries are starting to blur slightly because the way we deliver change is different.  Before, it used to be large requirements done up front – 2-years of requirements gathering and then a load of meticulous planning before entering the delivery phase.  Now it’s done in much smaller chunks; more agile – agile thinking, agile delivery.

The ‘project management’ term is disappearing – gradually becoming replaced with ‘delivery management’.  This changes your business analyst role, your project management role – and these boundaries start to blur a little. I struggle sometimes to define what I do; and it can often depend on who is asking the question!

The term ‘Project Management’ sits nicely with the people that usually hold the budgets and want to employ people; but once you’re on the shop floor it’s more ‘Delivery Management’ and it’s focused on delivering the required change.

So what qualifications do you need or would you recommend for your line of work? What do you need to be a freelance Project Manager, Change Manager or Business Analyst?

So for working in the IT domain, you obviously need to be IT savvy –  but let’s go from the top…for Project Management; ‘Prince 2 Practitioner’ and ‘Prince 2 Foundation’ are still very well-recognised qualifications to have, and then if you get into Agile then you require things like ‘Certified Product Owner’, ‘Certified Scrum Master’, ‘Safe Agilist’, and if you’re managing multiple teams then things like ‘Scale Agilist’.

Then quite frankly it is down to experience.  Clients want to see that you have experience in delivery – delivering real change in a safe way; to budget, to agreed timescales, and moreover, to quality.  In terms of qualifications, and in addition to Prince 2 I would recommend that a freelancer get as many of the Agile qualifications as possible – get your ‘Certified Scrum Master’ if you want to manage a team or if you’re a certified product owner and want to carry out the Business Analyst role – helping you with managing the change or the direction and speed of change.

So what’s more important then – your PM skills or your IT and Communications skills?

Your specialism and in-depth knowledge of your genre matters – it really matters.  You’re expected to have a thorough understanding of the domain that you’re changing.  Imagine: a client comes to you with a problem; you need to be able to firstly understand the problem and the risk this poses to your timelines – or how it may affect the budget or quality.  If you’re a little bit blind and don’t fully understand the IT domain then you won’t necessarily understand the impact of what you’re being told.

Some people understand Project Management to be mainly about managing Gantt charts – do you agree?

I absolutely disagree – that’s Project Scheduling (an entirely different skill set).  Qualifications like Prince 2 will give you the framework to operate – but how to remove impediments and deal with slippages is a totally different ball game.  A knowledge of the Prince 2 system will tell you that you need to write an ‘Exception Report’ or put an article in the Risk Register.  This is purely academic though – you need to know how to manage it.

Project Scheduling tends to be the remit of a Project Management Office (PMO), and that type of scheduling with an eye on documentation, and ensuring due process is carried out is done by them.  However, many smaller projects do not have a PMO; in fact I’ve never yet been in a position where there’s been one – I’ve always been expected to carry out both roles.

How do you ensure that you stay relevant in your genre?

It’s all about Personal Development.  It’s reading the right articles, keeping your knowledge relevant.  There’s a new phrase in town – the Dojo.  Dojos are now the go-to place for professional development.  Derived from a martial arts term, a Dojo is where professionals gather to hone their art.  There are software Dojos, Agile Dojos; and they’re were like-minded professionals meet up once a month.  You get a Guest Speaker in – who talks about their experience and what has worked well for them (or not).  Often these speakers are well-known and highly-respected in their field – other times someone will volunteer to make a presentation/speech with ‘this is what I do, this is how I rock and roll’.

What’s great about these Dojos is the conversations that break out afterwards – where people talk about similar issues and how they’ve solved them.  You should really go to these events – they’re held up and down the country and are all free.

Other than Dojos I read widely and listen to a lot of Audio Books (as I’m on the road all of the time).  I apply the Kaizen principle of self-improvement – a Japanese term that stems from Toyota and is widely used in the software world where one ‘inspects and adapts’.

Following these principles means that every time you finish a task, you chunk your work into things called ‘sprints’ and hold a retrospective meeting to establish:

  • What went well;
  • What didn’t go well;
  • What aspects did you like/dislike;
  • What did I learn?
  • What did I loathe?

Then you build on the positive aspects – things that went well and that you liked; and you try to switch around the negatives for the next task.  This honest, introspective action is a key part of Kaizen – a sort of ‘lessons learned’ but more proactive.

Rather then waiting for the end of a project when the ‘lessons learned’ become ‘lessons ignored’ –  as the file you create becomes a dust-gatherer in a dark and never-again-opened project file; Kaizen principles aim to enable learning as the project progresses – learning in ‘sprints’.  This way you fail early and fail fast – you inspect, adapt and do things better with the next task – all because you’ve chunked it down into 2 or 4-week sprints.

Following Kaizen, a person should constantly re-evaluate and ask ‘what did I do wrong’?  Did I not brief the team well enough? Did I not adequately manage the situation?

I thought you might discuss academic or vocational courses – do you consider these at all?

I’ve done two courses this year; including a Kanban course.  Some courses result in a qualification – but you don’t necessarily need to be constantly going on courses.  Any course you consider must be of more value than a monthly dip into someone else’s world (at a Dojo for example) – where you can gain an invaluable insight into their experiences; emerging yourself in their world for a while, which allows you to make meaningful improvements in your own.

Why did you decide to go freelance?

Freedom.  Freedom from the politics of an office.  Freedom to deliver without being impeded and without having to ‘play office politics’.  I like doing what I do, and I like to add real value to a process; but there’s nothing worse than having to fight with bureaucracy or fight with internal wrangling – the whole inertia of what an office can bring.

As a ‘permie’ you’re sort of trapped into that. As a freelance contractor, you’re brought in to do a specific piece of work.  Because you’re brought into deliver specific tasks, the money is ring-fenced – it’s secure.  I really believe that freelancing is a securer way of working.  In my world, I’m brought into deliver a specific change, and in addition to having the money to pay for it being secured, the scope of the task is tightly bound and well-defined.  And the beauty of it is – I just crack on and deliver it.  It is so rewarding.

You’re clearly well established in your field; but when you were starting out – did you have any fears or concerns?

Self confidence.  Can I actually do this?  I would often consider that ‘I think I have something to offer’ – but until you’re actually brought in to deliver a contract, and you’ve satisfactorily answered the question ‘so what would you do?’ you do worry whether you can cut it.

There was a fear over whether I knew my stuff – as a freelance contractor you’re expected to be the expert the client has paid for.  If I was the permanent staff member, I would expect my contractors to be subject matter experts in their domain; to be able to deliver straight away – and with only a minimal learning curve.  I’m not talking educational learning either – just the learning required to adapt to process (i.e. this is how we do business).

You’re expected to come in ‘fully armed’ and ready to deliver.  There was one contract I had at the National Archives (for the Ministry of Justice).  My first day started at 9 o’clock (you never start at 8 on your first day!) – my security pass was waiting for me, my IT was set up and ready to go and so I logged on.  I opened Outlook to find a meeting had been scheduled for half past ten that morning – and I had an action on me to deliver a talk in that meeting with my opinion on a matter (that I won’t disclose).

I was productive within an hour and a half of getting there!  That particular engagement was for 4-months – and that kind of activity never stopped.  The work and the value they got from me was relentless – it was fantastic; I loved it!

That kind of engagement is great for your confidence – but that would have worried me before I started – the nagging question of ‘can I pull this off?’  But the thing is – I could.  But that didn’t stop me feeling a little concerned in the early stages of my freelance career.  You have this nagging thought in the back of your mind – a worry that ‘they’re going to find me out’.

The thing is we’re all the same as everyone else – we’re just people.  There are things we don’t know and things we do – there are skills we have and those that we don’t.  But you do sometimes think ‘surely to goodness this can’t be right’ – we do get fairly well paid for what we do – and so you worry whether you’re bringing good value to the client.  My wife, Paula was great during the times when my confidence was a bit low; and she asked me a simple question – ‘Simon, have you ever been unable to answer a question?’ And I hadn’t.  Sometimes I had been clear that an immediate response wouldn’t be possible – that I would need to take time to come back to them with a full and measured response.  But I’d never been unable to give an answer.  ‘Well that’s why you’re being employed, Simon’.

Did you have to make any sacrifices personally or professionally when you started out on your freelance career?

Yes.  Personal.  The whole work/life balance was going to change massively as a result of the lifestyle choice I made by working on freelance contracts away from home.  I’ve not brought my kids up for the last 7 years.  So absolutely – massive sacrifices.

So how do you manage your work/life balance?

Poorly, I think.  My wife is an extremely busy and successful business woman.  In some ways it was easier when she didn’t have Beauty Boulevard – because she had more capacity to deal with the kids and I didn’t have to feel so guilty.  Now her business is thriving it’s harder – I do feel massively sorry for the kids.  They sometimes get the short end of our attention.

When I’m home I try to give them my unbridled attention.  The danger is that sometimes you try and buy it.  Sometimes you say ‘let’s go out and have a pizza and have some fun’ – but you try and pay your way out of your guilt.  Because you do feel guilty that you’ve not spent much time with them – and you try to throw money at it.  But they don’t want that – they want nothing more than time in your company – to have that emotional connection with you.

You mentioned professional sacrifices earlier – but there have been none whatsoever.  Professionally it’s a win-win situation; and this is the best thing about freelancing.  All of the decent pieces of work, all the new projects being brought in; because business often don’t have the capacity to resource these tasks – they bring in ‘externals’ like me; and I get to do all the funky new stuff whilst the ‘permies’ get to do the rubbish, mundane stuff – all the ‘business as usual’!  I’ve only ever come across one contractor who was brought in to progress the ‘business as usual’ whilst the existing team delivered the change.

As a freelancer we are spoilt – from a professional point of view; if you want to be working at the top of your game doing the funky stuff, then freelance contracting is the way forward.  But it does come at a cost to your family life unless you’re lucky enough to get a contract close to home.

I was offered a role close to home when I first started out.  It was local but a permanent position.  The thing is though, I wouldn’t have accepted it even if it was freelance – I wanted to spread my wings and discover whether I could ‘do it’.  It was a conscious decision to work away from home in the best roles I could.  I’d love something a bit closer to home now though!

How did you get your first client?

Erm…not my finest piece of work I’m afraid! I went onto the internet – to Monster Jobs or whatever it was, looked at the roles and thought ‘this is great – I can see myself in loads of these roles’.  So, I’ll just send off my CV and sit back and wait for the calls to come rushing in.

Of course, this didn’t go anywhere – but it took me a month (I feel so thick looking back) to realise that my CVs weren’t getting read; they weren’t even getting sifted.  I realised that I had to start ‘phoning these people up and establish a relationship with the recruiters; let them know I was available; that I was good – and moreover that I was the right person they were looking for.

I made it my job to ‘find a job’, so I’d ring the same set of recruiters every day and pester them until I started getting interviews.  In the end it was 80 CVs that I sent off, 8 interviews and 4 contract offers.

“I made it my job to ‘find a job’, so I’d ring the same set of recruiters every day and pester them until I started getting interviews”

I was delighted with my first contract offer, and took my foot off the accelerator – but what I didn’t realise at the time was that the contract offer was not in fact that firm!  It was reliant on the supplier being successful in their contract bid.  There was actually no job there – although the supplier was confident they’d win the bid.

So – I was sat at home for a week or so wondering what was happening with my start date.  Then of course came the notification that they hadn’t actually won the work and I had no job offer.  That was a huge lesson for me – you don’t stop seeking work until the day you’re in and you start work.  Until you start on day one of your contract – there is no firm guarantee of work.

To this day I still accept interviews right up until the day I start work.

With the second job offer, the money fell through…I can’t remember what happened with the third – but it was the 4th job offer on which I actually started work.

It is all about networking and building relationships with suppliers and clients.  Once I had my first contract, and my name was known, then ‘I was in’.  It’s then just contract after contract – and I’ve never been out of work (apart from when it was my decision to take a break) since I’ve started.

It’s all about output.  As long as you deliver quality work and ‘do what it says on the tin’, then people want you – just keep delivering.  I’ve had around 6 medium-term contracts since I started – all in different locations with different clients; delivering different packages of work.  It keeps things fresh, keeps it challenging and rewarding; and it’s also tax efficient to move around before the 2-year point any way (so you can continue to reclaim mileage and other T&S costs).

You’ve discussed efficiency in terms of taxation – but is there an App or piece of software that you use to maximise the efficiency of your output?

No not really.  The software I use to organise myself is just the run-of-mill Office based software.  For collaboration with clients and team members I use Podio (free).  Trello is another one – these are productivity tools rather than any ‘management tool’.  Trello is a sort of Kanban board with swim lanes that denote specific activities.  But to be fair I use whatever the client is using – as I’d be expected to.

I guess this also links back to the question of what makes you qualified to do your job – on top of the skills to enact the task, you need to be conversant in the tools that the client is using – Visual Studio Online, Sharepoint 2013, Ice Warp etc.  It’s not just being a Prince 2 Practitioner; it’s what tools you can use.

Looking back with the knowledge and experience that you now have, what advice would you give to the novice freelancer that was Simon Short as he starts his freelance career?

Don’t be scared.

I don’t know.  I’m relatively happy with the way my career has progressed so far.  I think I took some baby steps at the start; but I think I needed them.

Ah…here we go: when going abroad, do your bloody homework!  I did a contract in Belgium working for a new team over there, and you think ‘right – what’s my day rate in the UK?’  and factor in costs. I kind of knew what my expenditure would be, so l added on an other £100 a day to cover T&S (Eurostar tickets, accommodation etc.).  I was happy with the work – and so I went for it at that price.

What I hadn’t realised was how different the Belgian tax regime was to the UK’s – and suddenly I had no idea about how I was going to ‘get my money out’.  I genuinely didn’t know.  All of a sudden, I discovered that it was going to cost me another £1000 a month to get my fees out in a tax efficient way that made the contract financially viable (from a Clearing House).  I then realised I would also need to employ the services of a Belgian Accountant (as well as my UK one) at further cost.

I was also blind-sided by the high cost of living in Belgium – I was paying over €2,000 a month for an apartment!

Needless to say I didn’t make much money out of that contract; but I learned some invaluable lessons.  I accepted two contract renewals out there and was able to increase my daily rate each time, but the first year out there was painful.

Next time I go to Belgium on a contract I’ll know much more about how to price myself and how to get my money out efficiently.  When you say it out loud it sounds bleeding obvious, but when you’re in the UK and being offered a ‘glamorous’ overseas contract for the first time – it isn’t that obvious.

My advice?  Do your homework before you decide on a daily rate.

So if you could give one piece of advice to someone who is contemplating a freelance career, what would it be?

Do it.  Do it early.  Don’t be afraid.  If you’re good at what you do then you will suit freelancing.  If you’re no good – you will soon be found out.  I’ve not come across many – but I’ve seen some freelance contractors who weren’t very good; and they were gone in a heart beat.  This is a key advantage to a client when employing freelancers – don’t cut it – you’re gone.  You need to deliver.  You need to deliver, and show that you’re providing value to the client, otherwise you’re gone.  And I don’t blame them – I really don’t.

But if you know your stuff, just do it.  Its great.

Simon, thank you for your time.

So, what advice do you have to offer? Maybe you have some of your own burning questions you’d like answering?  Let us now in the comments section below.

Get the latest Furious Blogs delivered straight to your inbox for free once a month – simply enter your email address here.



Andy Paddock October 5, 2015

A pity this wasn’t a video interview.

the furious engineer Author October 5, 2015

Do you think that would work well?


Leave a Reply

Your email address will not be published. Required fields are marked *