A year of transformation: Hard, but Good

By Matthew

· 8 min

As I closed year three of Hook Strategy, I started setting out some more transformational ambitions. This is, I suppose, the progress report!

It’s also a personal record of a time that’s been challenging and rewarding in new ways. The soundbite: it’s been hard, but really good.

And looking back at what I wrote a year and a half ago, and standing at the close of a hectic year, ‘hard but good’ is what I was starting to search for.

Leaving the advertising company life had brought with it an energising burst of freedom. But the shadow side of it was always going to be the challenging lightness of lost context, of removed constraints – and potentially of diminished purpose.

Well, while ‘purpose’ may been have losing its ascendancy in marketing, this has certainly been a year of re-doubled purpose for me. And purpose is often hard!

Nailing my colours to the mast

I stated a set of ambitions just over a year ago, in an attempt to make myself accountable to them!

I’m rephrased them a few times, but they were broadly…

  • To shift my project base in favour of not-for-profit
  • To put more long-term skin in the game
  • To lean more deeply into networks and partnerships

Each of these areas has involved moves outside my comfort zone. At a time when the consulting and freelance market itself has been challenging, I’ve taken a series of steps onto less-known ground.

The outputs have been joyful and nourishing. But the process has been genuinely hard. I’ve felt stress, confusion and doubt much more than in previous years, and not all of that has been pleasant to deal with.

But I’m genuinely proud of where I am at the end of the year. So, for those who have been following this story (thanks!), here are a few glimpses behind the curtain.

More purpose, bigger impact

I’m certainly no moral absolutist, and I believe there is sometimes plenty of purpose to be found simply in helping teams of people to find clarity and make progress.

But the world is full of enormous challenges, and blind faith in capitalism certainly isn’t going to solve them.

This year I’ve been able to immerse myself in some profound issues: the implications and illnesses of an ageing population; the mental health of an industry in periods of rapid change and toxic legacy; the quietness of communications for good in a world of polarisation and misinformation; the incompleteness and fragility of the truth that we see about the world.

I’ve always held two tensile thoughts about strategy – that in order to do it well, you need to retain some emotional distance from your decision-making, but also that you can’t understand the picture unless you are able to approach it with wide-open empathy.

Of course, that makes this kind of work much harder. It takes more out of you.

My best project of the year was also my hardest. Co-running a consultation on the mental health of the advertising industry was stimulating, rewarding, and challenging.

I spent many years as leader in the advertising industry, and the entire nature of this project was to look in the eye some of the human implications of how the industry is led. I always tried to lead with good intent, with integrity, with positivity. But so have many, many others – and despite that, there are clearly many corners of the advertising industry that are not in a good state of mental health. And given that I’ve both had some small hand in making it, and that I’ve also been able to experience this industry at its very best, that brings a sense of sadness.

But – a life with purpose can’t be a life without processing and engaging with challenging questions like this. Hopefully, we’ll be able to do something collectively to fight against the headwinds, and make the industry a better place to work. Maybe that’s a hard but good objective for a few of my readers in 2024?

I’ll certainly look to do more of this, and more of this kind of thing, next year. Which I fully expect to be hard…but good.

Putting more skin in the game

Have I mentioned that I’ve started a new venture, a transformation business called LookUP?


The nature of an independent consulting business is that beyond a degree of branding and propositional rigour, it’s infinitely supple and agile. That’s what makes it such an effective way of solving infinitely varied problems. But it’s not always a good vehicle for building value in a way that accumulates and scales.

LookUP is something totally different. It’s a way of accumulating wisdom around key areas like building the future, communities and stories in a way that is constantly enriched, enhanced, and scalable through different themes and through organisations.

This is a totally different mindset – it’s a product mindset. That means investing massive amounts of time and emotional energy, to realise the benefits in the future. It involves much more risk – putting on events, speculative costs. It involves a lot more selling, and all the emotional vulnerability that comes with that too.

The risks and the rewards, the work and the payoff, don’t come together. This is familiar to anyone pursuing the product-led entrepreneurial life, and having been (again for the first time) a deeply involved advisor and investor in a tech startup this year I’ve watched with deep admiration the ingenuity and relentlessness of the Shimmr.AI business as they’ve pursued this journey.

But – at the end we have built some products that I think are profoundly powerful, and that have extraordinary potential to do something different. The roadmap ahead is long (!) but this is a deeply proud achievement and I can’t wait to push on in the New Year.

Product building is hard…but good!

Leaning into networks and partnerships

One of the things I have most enjoyed about the first few years of independent life has been building networks of mutual support.

In particular, I love knowing that at my back I have a galaxy of superstars with incredibly diverse backgrounds, skillsets, outlooks, and that together we can do extraordinary things. 

Far more of my projects have involved these kinds of teams of galacticos this year, and it’s been a privilege. It’s also a joy to create good opportunities for other people, particularly in a year where good, well-scoped, properly-and-promptly-paid work has been incredibly difficult to find, even for practitioners who are absolutely at the top of their game.

What, in truth, I find a lot harder, is getting used to intense, everyday collaboration.

Behind the scenes, my working styles can be…idiosyncratic! I work on a complex system of post-it notes, Sharpie-diagrams, and relentless second-guessing and re-drafting. 

I sprint, and then recuperate – and during those sprints, my appetite for workload can be extreme (and therefore so is my need for reflection and recovery.)

And it’s been many, many years since a peer has reviewed and edited my work. In the Jumptank dream team of 2010-2012, this was commonplace – since then I’ve mainly either been the boss, or I’ve been on my own. It’s taken a bit to open up again!

So, the biggest shift this year has been having for LookUP a proper 50:50 business partner and collaborator in Caroline Keylock. And not just a partner – but someone just as ambitious, fired-up and relentlessly high-standards as I am (if not a little bit more). And it’s been challenging, but also incredibly rewarding, and an essential source of support in some of the more challenging moments.

Proper collaboration is hard, but good!

Transformation – the life impact

This is a lot of transformation for one middle-aged man to take on in one year.

And obviously this is only a slice of life – I’ve also been able to put a lot of energy into the twists and turns of helping my kids grow, of making a bit of a step-change in my health and fitness.

Some things had to give. An early casualty of the year was my creative endeavours – not a lot of songs or stories got written this year – and that’s something to address in 2024.

And, occasionally the casualty was my own serenity! I’ve been frequently somewhat exhausted, and at some points at an unusually low ebb. I’m not always a good boss – I’ve got a tendency to ask a lot and not always give a lot back.

But this has been a transformational year. I think one I’ll look back on a few years with great fondness.

It’s been hard. But it’s been good.

Happy holidays everyone.

Hook Strategy helps organisations to move forwards with shared strategic clarity. If you are an organisation seeking unified thinking, get in touch at or by calling +44 (0)7780 481717.

Let's Talk

Get in touch


By submitting you agree that Hook Strategy Limited can securely hold your data in accordance with UK GDPR regulation and our Privacy notice.

This field is for validation purposes and should be left unchanged.