Getting a proper job after 10 years working for myself - how to sell it?

[mattster]

I've been making a (modest) living selling my own software online for nearly ten years now, and the (rather niche) market that I am in has changed considerably over that time. I'm not making the money I was, and I don't see it getting better in the future (the nub of it: what was a small niche with enough potential users to make a living and not enough money in it to interest the big boys has now been incorporated directly into some of the hardware products I used to write software for, rendering my software of use only to an ever smaller subset of users).

This leaves me looking for a real job - not a pleasant prospect - with a "gap" of ten years on my CV. Of course, it's not really a gap - for many of those years I worked harder than I ever had in a paid position, and have been using much of the same tech (WPF Windows dekstop - web has rather passed me by so far). Obv prefer contract, and my record before this job is fairly strong - most recently a 5 year permie-tractor stretch in a hedge fund research dept, before that other finance in the city (mostly trading).

So how to sell this on my CV? One route would be to just list the last ten years as any other job, under my Ltd Company name, list the techs, responsibilities (everything) etc, and make some passing reference to the fact that it is my own company in the blurb above the skills. The other would be to really emphasise the "own company" thing (also listing tech etc), but make more of a thing of running everything myself (website, sales, support, documentation etc). People I know who are in hiring positions universally say (to me, at least) that they would be very interested in a CV from someone who had done similar, however I suspect the biggest hurdle will be getting past the agents' automatic buzzword/cv gap/recent experience detectors.

Advice appreciated, especially from anyone who has done something similar.

[SueEllen]

What skills have you actually got? Sales?

[northernladuk]

Wait until you see a role you want and that you can do and then just list the relevant experience from what you've been doing for the last 10 years as your last role.

If you are going for a coding gig they won't be interested in the sales, marketing and other activities, only what you can do for them. You are only as good as your last role in contracting so the stuff before 10 years will be largely irrelevant but still need to make sure it's got a smatering of the keywords in the gig you are going for.

Let the role profile of what you are going for dictate how you write your CV rather than a generalist list that an agent won't bother reading.

[mattster]

What skills have you actually got? Sales?

Definitely not, otherwise I'd probably still be in business. I'm just a dev really, 20 odd years of mostly finance C++ thru C# .NET now, mostly Windows.

[TheDude]

Definitely not, otherwise I'd probably still be in business. I'm just a dev really, 20 odd years of mostly finance C++ thru C# .NET now, mostly Windows.

Is there still significant income to be made from the software you have been selling for the last ten years?

If not stick it on github and reference it on your CV.

[mattster]

Is there still significant income to be made from the software you have been selling for the last ten years?

If not stick it on github and reference it on your CV.

Yeah, not quite ready to do that since it is still a primary source of income but the writing is on the wall. Hopefully even when it is no longer my primary income in the future it can bring in a few grand a month with minimal extra effort from me, for a few years at least.

[BlueSharp]

Same advise for anyone else. List and tailor your ten years experience what ever the job title your applying to then in the description drop in that you were also owner of the company. BF father was in a similar position, but the advise does not change to any other job application. Tailor it to the job your applying for. It might be easier to contract so you don't get the usual what's stopping you shipping out in a years time.

[d000hg]

It sounds like your best option could be the companies who have rendered your work obsolete - they'd know exactly what you have been doing with your time? Do you have any way to leverage your unique expertise and insider knowledge?

Or failing that list yourself as working as lead dev for the last 10 years on the CV. You only need to get to interview then you can be more open and any decent company will want you, if you have the skills... and aren't a lone-wolf who's fallen behind on modern methodology of course.

How long do you have left before retirement? Is this a career relaunch or a "just need one last job" for a handful of years?

[TheDude]

and aren't a lone-wolf who's fallen behind on modern methodology of course.

I haven't worked with one of these for a while but back in the early days of Java I worked with a lot of guys who struggled to pick up new technologies and would resort to bluster and war stories about archaic systems they once worked with when challenged.

[mattster]

..and aren't a lone-wolf who's fallen behind on modern methodology of course.

ahem!

How long do you have left before retirement? Is this a career relaunch or a "just need one last job" for a handful of years?

Well I'm not quite 50 yet, so it could be viewed as a career relaunch I suppose - early retirement not looking as likely as it once was with the current war chest!