Ok, I have a bit of a work dilemma and am having a tough time making a decision. Apologies, long post!

The situation is that I’m currently employed half the week in a super-secure job in the education sector (but not teaching), and the other half of the week I’m self employed. Combined, my income is fairly decent. However, the self employment isn’t 100% guaranteed (depends on finding clients, etc), but it is well paid and interesting… and the education job is very stable and safe and predictable, but isn’t brilliantly paid (although it does cover the main bills by itself). So, I’ve got a good mix of employment and self employment, and stable stuff and exciting risky stuff there.

However, something else has also landed on my plate and I’m trying to decide whether I should give all of that up for it.

At the back end of last year, I sent in my CV to a company that was recruiting. Long story, but it wasn’t because my current work wasn’t going well – it was way more comedy than that. I’ll not say who this company is, but they’re literally one of the biggest names on the web. Most people will have heard of them, and even if you haven’t you’ve likely used their products without realising. Last year they raised funding at a valuation of over $1bn. So, they’re big and growing, they’re morally and ethically sound, they’re fully distributed around the world (no central HQ) and it’s the kind of place where a lot of people would give their right arms to work.

So, my application was a complete long shot and they took a while to reply to me, during which time I naturally assumed that they’d filed my application in a bin under a desk somewhere. Until they invited me for a 2 hour interview in January and I managed to get through that ok. They then asked me to do a test project over a week or two, which I was pretty sure I’d screw up. Unbelievably, that also went well because they next invited me to work with them (paid) for a trial period.

I started that trial a month or so ago, but had to delay it after a week because I had too much of my own client work on. I picked it up again for a little while and have now had to delay it for a second time for another whole month because we’re moving house.

To be honest, I’d have thought they’d have told me to do one after the second time I asked to postpone the trial, but their feedback was that it was going really well and they’re adamant that they’ll holding it open for me and are really looking forward to getting me back in.

Yep, I’m still struggling to believe it myself. They’ve even already paid me for the work I’ve done for them.

If I got the job, it should pay a good chunk more than my current income. The benefits are good. I’d be based at home. There’d be a month or two of expenses paid global travel spread across the year. And they give you a whacking budget for IT and home office gear.

On paper, it sounds like a no-brainer, but I’m actually in two minds about whether to carry on with the trial. One of my biggest issues (weirdly) is that I’d be working almost exclusively with 20-something yanks who say ‘awesome’ and ‘you bet’, and high five each other, waay too much for my liking.

But seriously, I’m also not entirely sure I want to lose the mix of self employment and super-safe employment either – and like I said I’m having a hard time weighing each of these options up.

What would STW do? Or am I being a dick even thinking about not carrying on with it?

Jump at it. I’ve done employed, I’ve done self-employed, I’ve done 50/50. Even I would give it a shot (and I’m really old) and I’d soon get the hang of hearing young Americans talk.

You’ll regret it all your life if you pass it up.

a super-secure job in the education sector

if it helps you make a decision, there are no jobs like that in education now.

The high flying one just on the off chance I bump into Cpt Flashheart in an airport somewhere exotic.

I assume you could always get your job back if you left or something similar and you will not lose your client base immediately so easy to return after say 3 months ?

Can you take a long holiday and start work then ? x

In life you t”spares and repairs” doesn’t mean you can sell something that’s not as described

PS AWESOME DUDE like totally stoked for you

its not webcam work for one of the online smut pedallers is it ?

I’d be working almost exclusively with 20-something yanks who say ‘awesome’ and ‘you bet’

Sounds like you’ll fit in perfectly well…

super-secure

I assume you could always get your job back if you left or something similar and you will not lose your client base immediately so easy to return after say 3 months ?

Yeah, that’s a fairly realistic way of looking at it. I suppose there’s always a way back.

its not webcam work for one of the online smut pedallers is it ?

Ha! How’d you guess?

Sounds like you’ll fit in perfectly well…

I’ve been self employed for 15 years or so, and the industry I work in has been through some pretty tough times (especially between 2007-2010 ish). I’ve only been in the ‘super-secure’ job for about 3 years and to be honest, getting a regular salary paid into my bank account every month has been a bit of a novelty for me – and one that I’ve gotten used to!

And when I can combine that with the higher paying – but not guaranteed – self employment that I’ve been doing for the last 15 years, then I think I’ve finally got the right mix of stability and fun/interesting stuff, plus I’ve got half the week where I can do other things than work if I want/need to, like getting in the water or getting out on my bike.

It’s that mix that I’m not entirely sure I want to give up.

wife? kids? how would your personal life be affected? less leisure time?

I would go for it.

You are only secured in education sector because you get peanuts as performing monkey or in your case you have another source of income apart from teaching.

If they are willing to pay you well then go for it.

😛

wife? kids? how would your personal life be affected? less leisure time?

Yip, Mrs and 3 kids.

I’d be based at home – apart from the few weeks across the year when I’d be travelling. It would actually be easier all round on home life, and the Mrs is right behind it!

I just wouldn’t have that flexibility in the week where I can take a full day off and go for a surf if there were waves. I’d be tied to a desk/terminal/Skype/Slack/confcall/whatever, albeit at home.

Tough one.

Apart from the money what’s the real benefit of working for the new company? What would your average day look like and would that suit you? Would you feel like you were part of a team or out on a limb, and would that suit you? How much face to face contact would you have? What is the culture like, will they expect you to be available out of hours? Have they specified any of these things?

Unless you actually need more money then the daily experience of the job and work / life balance should be the main consideration IMO.

Get off the internet and crack on with all three.

Isn’t this the plot to a Steve Carroll movie?

US companies are well known for pushing you to your limits, plus being ruthless when they need to be.
I’d do some research around them first.

Weird – all the way you are downbeat on your chances etc yet this company are bending over.

Why? They are definitely kosher?

If they are as keen to have you as they sound, then might you be able to give them all you ‘self-employed’ time for a while, but keep your safe job too?

Nice problem. I’m sure you know better than me, but ime tech companies are flexible as long as you can complete projects, work properly with others and get the job done, so keeping the education/research job might be a possibility. Another option – take a long-term sabbatical of sorts from education? Assuming it involves tech, the institution should be keen to keep you as a contact/link.

Edit: on the Americanisms: I’ll take high fives over whiny cock bags.

Weird – all the way you are downbeat on your chances etc yet this company are bending over.

Yeah, fair point. Completely kosher. Part of the problem is confidence. I’m completely self-taught in this area and still can’t believe I’ve gotten this far. I keep thinking they’ll discover that I’m a fraud.

It’s a bit of this, I think: http://en.wikipedia.org/wiki/Impostor_syndrome

If they are as keen to have you as they sound, then might you be able to give them all you ‘self-employed’ time for a while, but keep your safe job too?

That’s pretty much what the trial is all about. I keep trying to swerve client work to fit it in, but urgent jobs keep cropping up.

tech companies are flexible as long as you can complete projects, work properly with others and get the job done,

Yip, they’re very much ‘output-oriented’ rather than a company who measures performance by clocking time spent sitting at a desk. The division I’d be in would mean constantly speaking to their clients, so there would be a large degree of ‘being available’.

I think I’ll give it a crack – you’re right, I’ll only regret it if I don’t. There’s still a chance I’ll not be successful after completing the full trial, but I think I’ve done pretty well to get this far at least!

Reckon I know who it is. If they’re anything like Google et al, they’ll likely expect full on commitment to the point of it being your reason for living.

It sounds like it would be a good experience, and something that might open up a lot more doors. I suppose the question you need to ask yourself is what would be the impact if it doesn’t work out and you find yourself wanting out after 3 or 6 months. Would you be able to find other work quickly, and could you afford to have a gap will you look for other work?

Reading between the lines of your post it sounds like you already know what you want to do but just need to summon the courage to make the change. Go for it I say! Someone smarter than me once said something like “better to regret something you did than something you didn’t”. Having said that, if it was me, I’d probably be too chicken 🙂 good luck!

But seriously, I’m also not entirely sure I want to lose the mix of self employment and super-safe employment either

Do it.

As you said – he who dares wins.. and it is better to regret the things you’ve done than the things you haven’t done. And as I say – you progress your career by changing jobs.

I used to be a contractor – self employed, and I was briefly pretty depressed about taking a job with a huge company. Best thing I ever did though – I really love being part of something, where really good stuff is happening. Even though there is still a lot of the same shit I had when contracting, there is a lot of brilliant stuff too.

And, if they are that hard to get into, even if you only do it for 6 months you’ll gain serious cachet that will help your next role. Solid gold opportunity, by the sound of it.

Maybe see if you can hook up with some people who work there on some kind of IT professional site – anonymously of course – and see what it’s like working there. My wife’s uncle works for the same company I do in a pretty senior role. He does have to attend calls with clients, but he often does it from his ‘cabin’ in the woods. And he has been known to attend conference calls whilst sitting in a hunting blind… Not all US companies are slave drivers in all roles.

my only career regret is a job in scandinavia that i never took (bottled it) and it still winds me up. Go for it, sounds like you want to anyway.

my only career regret is a job in scandinavia that i never took (bottled it) and it still winds me up. Go for it, sounds like you want to anyway.

I’ve got a similar one. I went through a full process at a global ad agency with a Euro HQ in Brussels a few years ago. Was offered a good role that would have taken me places but gave it a swerve for a couple of reasons (one of which was the silly tax thresholds in Belgium, another was the big salary rise my current employer offered me in response). That decision still really winds me up too. I don’t want another one on my conscience that I’ll regret every day!

I used to be a contractor – self employed, and I was briefly pretty depressed about taking a job with a huge company. Best thing I ever did though – I really love being part of something, where really good stuff is happening. Even though there is still a lot of the same shit I had when contracting, there is a lot of brilliant stuff too.

^ This makes a lot of sense.

Maybe see if you can hook up with some people who work there on some kind of IT professional site – anonymously of course – and see what it’s like working there.

Already done that as part of the trial – I’ve been working with the team as if I’m in the role. I’ve also had unfettered access to all of their internal comms channels and plenty of opportunities to speak to people (off the record) who’ve been through the process and are now working there. All seems good to me. I’m just a tad nervous about swapping what I have now for something else. :o)

FFS! Take their money already!

I was fortunate enough many years ago to go on a development programme with my then time employer, the top performers in the company where selected for this programme and the chief executive came to talk to us (he is now knighted so a very successful business man). Anyway I asked him about taking risk and he explained that prior to setting the company up we all worked for he was chief executive of a global organisation with household name and brands and he said the biggest risk was leaving that job, borrowing millions of pounds and setting up his own from scratch. He justified it by saying that he knew how to be a chief executive for a global Plc as she had already done it so if his own company didn’t work he knew how to get back to where he left off. He went on to say that he hoped his company would provide us with the opportunity we sought but if it didn’t and those lay elsewhere we shouldn’t hesitate in taking the risk and go where we wanted as we already knew how to work for him. The point being if the opportunity interest you (which I believe it does) then you should take a leap of faith, worst case scenario bing it doesn’t work out then retrace your steps to where you are today.