It’s the age of the gig economy and the portfolio career, so we’re told.

Yet, judging by the number of people still streaming off the 7.13 to Waterloo and the recruitment angst pervading LinkedIn, a lot of us are still ticking those traditional career boxes; get qualified, get a job, get fed up with that job, look for another job, repeat until retired.

That was me until a couple of years ago, when things changed.

If that sounds like the start of a motivational spiel about how I broke free from the rat race en route to my first billion, rest assured it isn’t. At last count I’m still the odd £999.9 million short, and quite happy to stay that way.

However, I have stopped ticking those boxes, and a lot of the change is down to the power of the internet in helping us make connections and get noticed.

It’s made me think about the potential of our digital world to transform all aspects of how we go about earning a crust, from finding work through to filling in our tax returns.

I’ve been surprised by two things: firstly, how easy digital makes it to get work outside the traditional rigmarole of CVs, screening and interviews, and secondly, how far a lot of work-related paraphernalia, from recruitment to taxation, needs to go to catch up with this new way of working.

I guess I shouldn’t be surprised. In a world of innovation and business disruption, some things, especially the less sexy ‘box ticking’ things, can easily end up left behind until we discover we actually still need them.

For example, when buying online became a thing, we were happy at first to trade the convenience of getting stuff delivered to our door for the value of seeing the product before we bought. A few years on and Amazon has started opening physical stores.

Contactless payment is so handy that we don’t care too much about the fact that it takes away a layer of security; we’re just waiting for biometric authentication on phones and smart watches to put it back in.

How does this cycle of innovation and catch-up relate to the world of work, and to my experience?

For me, ‘innovative’ was hardly a word you’d apply to my career.

I trod the common privileged path from university to milk round to graduate intake to trainee to doer to junior manager to middle manager, before sensing the way the wind was blowing with my employer of thirty-odd years and opting for a package.

For a while after that, I carried on ticking all the job search boxes; honing my CV and TMAY, getting my LinkedIn profile humming, networking, scouring job boards, wooing recruitment agencies and all the usual stuff.

Then I suffered a minor stroke; one of those things which makes you stop and think a bit. The outcome of my stopping and thinking was that I took an early pension, stopped chasing work and started doing more of the stuff I like.

I’ve always enjoyed writing and acting, so I started a blog and a couple of other writing projects, and signed up with a couple of agencies as a film and TV extra.

What has surprised me is that, whilst I haven’t been run ragged with paid work since then, I’ve been far from idle. I’ve done a bit of consulting, some copy writing, and quite a few days on film sets.

None of this work has come through the traditional route of formal application, CV and interview. One way or another it’s all stemmed from my online presence, and I probably wouldn’t have done any of it a few years back because the barriers to entry would have been too high for me to have bothered.

The consulting gig stemmed from an approach by a former work colleague who I’m in touch with through social media, the copy writing came from someone who had enjoyed my blog, and for the film work I just uploaded some photos and went through a straightforward online DBS check. Now I just sit back and wait for those jobs where my face fits.

This passive approach to getting work feels a bit odd after all those years fretting over how to quantify my achievements and get the right font for my CV.

It was a bit like spending years mastering the subtleties of fly fishing before realising that dangling a hook in the water while you snooze still gets you the odd fish.

I know that, for all the hype about portfolio careers, I’m still an outlier in the labour market stats. If you’re on the recruitment treadmill and trying to pay the mortgage I sympathise, and I understand if you take this with more than a pinch of cynicism.

On the other hand, if you find yourself in a similar position to where I was a couple of years back, I hope my experience might encourage you to relax a bit, just leave those hooks in the water and not stress so much about flicking that fly. Like me, you may be surprised at what bites.

You may also be surprised as I was at how ill-adapted our work management processes seem to be to deal with this work model.

For all the talk of the gig economy and the rise of the portfolio career, the mechanisms supporting the process of getting and managing work, from recruitment to taxation to insurance, still seem to put us in boxes.

We are either employed, unemployed, self-employed or in a defined non-employed state such as student, retiree, carer or full-time parent.

Being self-employed is largely taken to mean you’re running your own business with a specific function, and most likely with assets, running costs, turnover forecasts and all the associated paraphernalia.

When it comes to form-filling, my kind of “dangle a few different lines and see what bites” approach doesn’t seem to tick the expected boxes very neatly. (I hasten to add that it does so well enough for me to fulfil all my obligations, just in case any tax inspectors are reading this).

In fairness, it would be hard to adapting the mechanisms and paperwork to reflect this greater diversity of working patterns without creating unmanageable complexity.

Alternatively, you could make greater use of all that data which makes up our digital footprint to start to bypass these, mostly proxy-based, processes and mine the data you need directly from its source.

Quite a few years back, I attended a presentation by an HMRC IT guru who laid out a vision of a world without tax returns.

When every financial transaction and record is online, the taxperson only needs access to that data to work out what tax someone needs to pay, and the authority to deduct that tax directly from the individual.

In principle, I reckon you could do the same kind of thing with all the box-ticking elements of getting and transacting work.

When I buy insurance for the vehicle I use for work, matching my actual pattern of use to the risk profile of others with the same pattern would give you a much more accurate basis for setting my premium, without having to resort to the blunt proxy-based instrument of asking what I do for a living.

The same principle could be applied to pretty much any type of insurance. I may need to give some baseline information initially, but after that it’s all over to the algorithms.

Even the sacred cow of the recruitment process itself, with its application forms and covering letters and CVs and screening tests and interviews, could be replaced with a bit of data mining and AI matching what each candidate has actually done against the profile for the role.

As with so much of our automation revolution, the main barriers to achieving this are social, not technical.

There are the hefty ethical questions like whether we are prepared to purchase a free pass from completing tax returns by giving the authorities carte blanche to scrutinise our financial activities directly.

The answer is probably not, at least not yet, although our recent history of willingness to trade privacy for convenience suggests that may not always be the case.

And what would happen to all the people who make a living from supporting these proxy processes – the recruiters and job coaches, the accountants and insurance underwriters, the tax officers and consultants?

To my mind, the usual automation work displacement rules apply – in the medium term, there’s scope for moving these roles further up the value chain, away from just feeding the proxy process, and in the longer term, there’s retraining, or I can recommend a good casting agency.

We may be getting a somewhat distorted view of the extent and speed of the move away from traditional to portfolio careers, simply because they’re relatively new and thus get more attention in the media, social and otherwise.

They’re definitely a trend, though, and there will come a point when our legacy mechanisms for transacting work will have to adapt to keep up.

When they do, in my view, it’s questionable whether our traditional proxy based approach will be able to keep up. When that happens, maybe it’ll be time to hand over the box-ticking to the machines.