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I'm a freelance web developer and I've been working exclusively for one client for about 8 months now. They have a massive website that they wanted rebuilt from scratch and I've been hacking away at it. The main requirements are almost completed and I'm curious about my future.

The client pays well, on-time and is generally great to work with. Having a long-term client like this has been a financial windfall for myself. I've socked away a decent amount of savings and I'm considering making some financial moves.

The timing and extent of these financial moves would depend on the stability of my income. The client has additional requirements he'd like me to pursue after the new site is launched and has hinted that he has even more ideas that he'd like me to work on. I'm just not sure about how long-term he'd keep me on.

Is it okay for me to ask the client about my job security? If so, how should I phrase it?

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    Maybe better for Freelancing? – Philip Kendall Sep 12 '17 at 11:45
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    Are you billing by the hour, or by project milestone? Makes a difference. – Xavier J Sep 12 '17 at 19:11
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    You are a freelancer, remember, an independent businessman, there is really no job security for you, what you are feeling is merely an illusion. So, no you cannot ask the client abount your notional 'job security'. What you can do is ask your client what are the next things he is planning to work on as part of his business, even if it is not web development can you help in any way. As a businessman you should try and expand your business, approach the conversation in that tone. – Ironluca Sep 13 '17 at 10:43
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Is it okay for me to ask the client about my job security?

You can always ask, but you need to interpret the response correctly.

Anything that isn't specifically codified in a contract you should consider as opinion, subject to change at any time.

For example "Well, we have plenty of work to do that could keep you busy for a long time." could all end quickly if a key account falls through, the economy changes, or management decides to bring the work in-house. (I had a contract end abruptly 1 month early. I have reason to believe that it was due to management wanting to make their numbers look good so that they could attain their annual bonus. They dismissed all contractors.)

Part of the appeal of bringing in contractors/freelancers is that they can be easily dismissed as soon as conditions change.

If it were me, I'm not sure I'd bet my financial moves based on a single client. If you had a stable of dependable clients, it might make more sense. (It's not unlike holding stock in a single company, versus holding diversified index funds.)

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    Agreed. The OP should not rely on only one client....it will go bye bye at some point. – Mister Positive Sep 12 '17 at 16:02
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I think you are in a good position but you may have slightly the wrong mindset.

You are not an employee and as such you don't have job security in the same way you would have (or not have) if you were employed.

You are a contractor who has a good relationship with a client. You can and even should ask them about what work is in the pipeline. A good relationship goes both ways so they will want to keep you on if they can.

However, this is not always possible as often external resources, like yourself, are not financially viable in the longer term.

What you can do is be proactive about the situation:

  • Suggest features, opportunities you have seen, ways that you can make their product better and provide good value for them. They may have some things in the pipeline but you can always suggest more. You are a domain expert so can provide them with valuable insight.

  • If it looks like new work on the site is not going to be possible suggest a maintenance contract. Offer a set number of days a month that you can set aside for minor work and bug fixes. While this will be less income for you it keeps a relationship going with the client and they will know they have someone to help with the product. It will not preclude you from doing other jobs as well. And it leaves the opportunity open for more major work with them in the future.

  • It is also possible that you could change your relationship with the client and join as a permanent employee, while this would likely see a drop in your income it could provide more security and give you a more reliable stream of income.

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You can ask. If you are working with decent people, then they will tell you correctly what will most likely happen, in their opinion. They may be wrong. As a contractor, your job can be gone tomorrow. But asking is perfectly fine.

Take a sheet of paper, and write down what will happen if things go fine, what will happen if things go bad, and what will happen if things go really bad. You should do things so that "things going really bad" will not be a disaster for you. Bad, but not a disaster. For example "things going really bad" could mean "the client will stop the contract and I won't find a new job for six months, so I have to cut down my expenses, going out for dinner is McDonalds once a month", that's not a disaster.

Doing something that would turn the six months without job from "bad" to "disaster" would be a bad idea. That's what I would base my decision on.

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I would suggest you ask the client indirectly. My approach will be to ask:

There is another opportunity coming my way which looks great, but requires a long term commitment in a different city. I really like working here, is there any thing which can be done for me here?

That should get you a hint. Of course you need to be careful how you word this, you might end up losing what you are getting at this client.

Assuming you have good relations, this should get you a feeler on whether the client will be willing to make a long term commitment to you or not.

I will also suggest not to rely on verbal commitments. It may happen that the person you are talking to today gets moved to some other department or may change job, without doing a proper handover. It may happen that business environment may change and the work you are doing suddenly lose funding. Freelancers are not required to be notified. Until you have work handed over to you there is no guarantee.

Asking directly also may work. But there is nothing on which you can hold the guy accountable. You also need to look at the time. Most businesses get yearly budgets for IT. This financial year is ending in December for most companies. Until next year's budget is approved, it may be hard for anyone to commit. They may have a feeler, but it will be just that.

Every year, businesses may also be given cost reduction targets. Are you ready to work on reduced rates for guaranteed work? Would you like to work on a one year contract rather than freelancing? You could explore these aspects if you need a longer commitment.

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    And what do you suggest the poster does if the client calls their bluff and says "well, you've got another opportunity, thanks, bye, don't call again"? – Philip Kendall Sep 12 '17 at 12:51

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