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Plunging in to freelance work..? (Development/DevOps)

edited February 2016 in Not Sports Related
I've decided it's time I take a step forward and look at contracting and doing some freelance work; as a Software Developer I've had the fortune to work in a few different environments so have some confidence with different roles and technologies. I also ran infrastructure for a cloud company's flagship product - so can pretty much market myself as being able to carry out technical services from conception through to deployment and continued maintenance/patching.

Although contract work is very attractive financially, it still keeps me trapped in the essence of a normal 9-5 role - something which limits my ability to try and get the above off the ground. I'm pretty sold on remote working and using co-working spaces for the social vibe.. and further networking.

That said - if I could go remote and work freelance, I'd like to devote a percentage of my time to trying to launch my own company - offering cloud based hosting with some software offerings on the side. Launching such a venture whilst a freelancer would also allow me to begin to create a network of clients who would be interested in such a business.

Unfortunately, I seem to have found myself stuck in a bit of a catch-22... my current "network" - as it were - is obviously centred around permanent employees and companies that rely upon permanent employees. Recruiting agents are very good for contract (i.e on-site, 9-5, essentially a temp employee) work but this is something I'd rather steer away from in favour of more flexible/remote opportunities.

Any tips/advice from lifers who have made the leap themselves? I have a decent understanding of paperwork - i.e the Ltd company route, but my knowledge stops pretty short after that.

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    edited February 2016
    I've just done a similar thing in the States, though I'm lucky that I've been working with dispersed teams and clients for a while, so I've been able to adjust well so far.

    I recommend Dice.com, I know it's big in the states, certainly worth a shot.

    Unfortunately I am four years in to working for/with the US Government and public entities, so my network for people who can even consider hiring foreigners is currently poor, though something I'm look to expand on. If you want, add me on LinkedIn, it's one of those "you never know" type things (I'm Alex Seelig).

    On the cloud (I'm assuming IaaS) services stuff, are you thinking you'll have a third-party host it, then do the management? Stand up your own thing? On a larger scale it's a really crowded market, but I've been working on large scale, specific security type systems for so long that I can't see the forest for the trees, always wanting to learn though.

    I'll think on it, I'm at the end of a day of packing for a move. I'm sure the corporate cultures between the US and England are different, but there are always commonalities. Certainly all the best, eventually this should result in you having more flexible hours, and do keep us updated.
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    The key is to develop something that you can market to companies. I don't know what your experience skill set is but if you've worked on software and you think you can develop something better then go for it. Think of a way that you can submit fixed priced bids to companies. You know, if a company needs a system (HR, payroll, a Financial Settlement System whatever) then look at what would be needed from soup to nuts and get a bid put together. You probably wouldn't be able to do this on your own but if you know, say, good developers, analysts and a solid Project Manager you'd have a nucleus of a team there. Then think of some sort of a software package that you could develop from soup to nuts and then look for companies who would be interested in buying into what you have to offer. You'd need to present it as a business plan so lots of details/documentation would be needed.

    You could also develop something that would be a competitor for something that is already out there. You could do this on your own if you could think of something to write and package. You'd have to put your thinking cap on. An example would be mobile apps for smart phones for companies. You've probably missed that boat but you get the idea. For this approach you'd need to get creative and think of something that is different, or just better, or at least marketed as such. It's all about the marketing and getting a bite.

    That's the best way of getting out of the 'temp employee, 9-5' mentality of IT consulting.

    Not sure if that makes sense but I know people who have made a lot of money doing this kind of thing (millions).

    Good luck.
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    By the way, Dice.com is used for something that it sounds like you are trying to get away from. Namely, the 9-5 temp employee IT contractor. It's an IT contract finding site.
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    Rob said:

    By the way, Dice.com is used for something that it sounds like you are trying to get away from. Namely, the 9-5 temp employee IT contractor. It's an IT contract finding site.

    Not entirely my experience, but it certainly leans more that way (and again, I'm in a different country).
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    I live in California as well
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    Absolutely brilliant responses guys, and I apologise for the absolute age it's taken me to reply. I've wanted to set aside some time specifically to give you both a real reply - as I genuinely appreciate the time taken to give me advice.

    I’ll follow this post up with replies to both of your responses, but before I do that - I’d just like to express my gratitude again. It’s obviously a decision I’ve been mulling over for quite a long time, and to finally pluck up the courage to take that desire further has led to a mixture of feeling a bit excited as well as genuinely worried.

    I’ve been a bit more proactive in nailing out the basics that I should’ve been doing anyway - i.e writing recommendations for people I’ve worked with on LinkedIn - and I’ve been positively surprised by the sentiment I’ve received back. On top of that I’ve thought more about what exactly I wish to offer, and gone ahead and registered a company and thrown together a site, and today I should hear back from Santander regarding a business bank account. I’ve even got a few networking events penciled in to my diary! I may have broken a calculator out and HMRC guidance documents at one point too.. truly living the highlife! ;)

    Ultimately, I’m still looking at sustaining myself via Freelance/Contract work whilst I formulate a solid product-cantered business plan. I can match my current salary working 11 days per month, even with taxes accounted for. Although, I’d quite like to spend some time contributing to a few Open Source projects I’ve become aware of - I’m currently writing some automation tasks for one actually.

    Due to the boredom I get during jobs, I’ve benefited from working in a real variety of environments - something I hadn’t quite realised. It still means most of my network are still permanent employee’s working in established companies though, unfortunately!
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    SDAddick said:

    I've just done a similar thing in the States, though I'm lucky that I've been working with dispersed teams and clients for a while, so I've been able to adjust well so far.

    I recommend Dice.com, I know it's big in the states, certainly worth a shot.

    Unfortunately I am four years in to working for/with the US Government and public entities, so my network for people who can even consider hiring foreigners is currently poor, though something I'm look to expand on. If you want, add me on LinkedIn, it's one of those "you never know" type things (I'm Alex Seelig).

    On the cloud (I'm assuming IaaS) services stuff, are you thinking you'll have a third-party host it, then do the management? Stand up your own thing? On a larger scale it's a really crowded market, but I've been working on large scale, specific security type systems for so long that I can't see the forest for the trees, always wanting to learn though.

    I'll think on it, I'm at the end of a day of packing for a move. I'm sure the corporate cultures between the US and England are different, but there are always commonalities. Certainly all the best, eventually this should result in you having more flexible hours, and do keep us updated.

    Dice.com looks good, whilst it does seem predominately contract on-site based - it’s not something I’m ruling out at the moment. It may prove to be a good approach for a transitionary period. I will definitely look you up on LinkedIn though!

    Regarding the cloud services, it’s a weird situation because.. I’ve seen the problem I wish to solve first hand, but I don’t know how best to conquer it. I headed up a team in - possibly one of the UKs largest B2B SaaS companies - and the complete and utter headache that I had inherited was a real eye opener to how badly architected a lot of existing companies must be at the moment.

    After doing an audit, we managed to get rid of 20 (yes, twenty) out of 35 servers - and reduced the costs immensely. On top of that, I’d managed to get reproducible environments via automation (Ansible), automated builds and testing (Jenkins) and managed to remove a dependency on a third party operations company. (Who were supposedly “managing” our infrastructure - and tried “down-selling” me on a Raspberry bloody Pi for load balancing..)

    I left after I got my team established and there was a new project underway, but I took pride in the effect that I managed to have. I’d also got an internal project fully containerised and deployed to a CoreOS cluster, with container orchestration done via systemd. Furthermore, I got another fancy new deployment strategy via Red Hat’s OpenShift approved before I left, and that makes deployment such a breeze whilst removing low level headaches.

    I know that financially I saved about £30,000 p/a on “management fees”, physical server rental and associated costs. Not to mention the development team no longer refused to deploy the application they maintained! I guess I’ve spent a lot of time thinking about that role and realising I must’ve worked on some pretty common problems there - from selecting the team members, setting up the tools they need to work (GitLab, Atlasssian Suite, Vagrant boxes etc) and then the actual technical aspects.

    I loved it, and the thought of getting paid to identify and consult on these issues would be perfect. To develop a product that can bring in recurring revenue whilst enabling people to avoid these issues? Even better - but I don’t know -how- yet!

    Thanks again :)
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    Rob said:

    The key is to develop something that you can market to companies. I don't know what your experience skill set is but if you've worked on software and you think you can develop something better then go for it. Think of a way that you can submit fixed priced bids to companies. You know, if a company needs a system (HR, payroll, a Financial Settlement System whatever) then look at what would be needed from soup to nuts and get a bid put together. You probably wouldn't be able to do this on your own but if you know, say, good developers, analysts and a solid Project Manager you'd have a nucleus of a team there. Then think of some sort of a software package that you could develop from soup to nuts and then look for companies who would be interested in buying into what you have to offer. You'd need to present it as a business plan so lots of details/documentation would be needed.

    You could also develop something that would be a competitor for something that is already out there. You could do this on your own if you could think of something to write and package. You'd have to put your thinking cap on. An example would be mobile apps for smart phones for companies. You've probably missed that boat but you get the idea. For this approach you'd need to get creative and think of something that is different, or just better, or at least marketed as such. It's all about the marketing and getting a bite.

    That's the best way of getting out of the 'temp employee, 9-5' mentality of IT consulting.

    Not sure if that makes sense but I know people who have made a lot of money doing this kind of thing (millions).

    Good luck.


    Hi Rob,

    I must admit - I laughed at your post - not for it’s content though - but the fact I worked for a very successful chap (who, you’ve inadvertently reminded me to email!) who was also called Rob and had done exactly what you describe! He’d seen a gap in the market for a cloud based Hospital Management and EMR package - he pitched his idea (without a product) to Bupa. Bupa loved the idea, in fact they loved it so much that they accepted his bid - even on the understanding that no product existed. His company is going from strength to strength, is of a very good size and (in my mind) is the model of a perfectly run tech firm.

    So in response to your last point - it makes perfect sense to me. I agree that this is potentially one of the best ways of getting a product out there, having a sense of ownership whilst also having some security - or as much as can be expected - at the same time.

    One of the best things of the job I mentioned to SDAddick, was I worked very closely with a Business Analyst to form a business case for a lot of the work I undertook - to win the board over for us to freeze development. By the time we finished we’d actually hashed out something very similar to a business plan, and it’s an experience I should be able to draw upon going forward.

    Thanks again :)
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