Michael Ashcroft

Thinking Out Loud No. 50 // Tuesday 02 November 2021 // 5 minute read

Hello everyone!

I’ve been taking a little break from creating recently, but am excited to get some plates spinning again. This newsletter is a little life update as I start writing and making things again in earnest.

I’m embarking on a nomadic year

The big news I want to share is that, from February 2022, my partner and I will be embarking on a year of nomadic world travel, starting in Mexico for three months and then likely moving on to Austin, TX. The aim is to travel slowly, spending at least a month in each place.

This has long been a dream of mine and I’m enormously grateful that life has conspired to make it possible. Of course I plan to continue writing and making things! Hopefully I’ll figure out a mobile YouTube setup that isn’t an enormous pain to carry around.

I’ll share our location as we travel - I hope to be able to meet many new friends around the world.

Fifty editions of Thinking Out Loud

This is edition 50 of Thinking Out Loud, which has an air of a milestone about it. It’s also just over two years since I started writing online.

When I started this newsletter I had just started a new job at KPMG in the hopes it would help me recover from burnout at my previous job. I don’t entirely know what I was thinking, but I guess the absence of clear thinking was the thing I have been trying to fix.

Most of you know my story, so I won’t labour it again here, but I do want to say to anyone embarking on a similar path: what you want is possible. It may not be easy, but, for me anyway, it’s been well worth the struggles.

I’m coming to realise that part of what I want to do with my life is help others who want to pursue similar journeys. I felt various degrees of stuck for ten years, knowing that where I was wasn’t where I really wanted to be, but I never knew how to change my path.

If this resonates with you then please feel free to reply to this email. I’m really curious to hear your stories and, if I can help in any way, I’d like to.

Case study with Rob Hardy

I’ve been working with Rob for several months now in various ways. I was and continue to be his coach, while he has helped me grapple with some of the big questions surrounding what I want my fledgling business to look like.

Apparently what I’m doing with my business is unusual, to the extent that Rob, who is steeped in the practices of conventional online business, thinks it’s worth digging into and sharing. I should also stress that Rob himself is following an unconventional path, and if my ways of doing things appeal to you, then Rob’s work will also.

To this end I’m really excited to share that Rob and I are working on a case study following my own journey, which you can read about here at The Ashcroft Files (not named by me!).

I hope you enjoy.

Announcing Playful Creativity

I’m also excited to share that I’m working on a new email-based course called Playful Creativity. This is based on a framework I’ve been using with coaching clients to help them ‘get out of their own way’ with regards to creativity.

Here’s the context. For a long time I believed I just wasn’t a creative person. I sucked at art when I was at school and from there some kind of block emerged. Over the last few years I have slowly unwound this false belief. It’s not that I’ve become creative though; I’m figuring out how to get out of the way of my innate creativity.

I’m making Playful Creativity because I want to help people unlock the natural, sincere and earnest capacity for play that I believe is our birthright. That thing we had as children, but that so often has become hidden behind layers of effort, fear and internal struggle.

I believe good things will emerge if more people are able to bring a playful spirit to their own creative process, regardless of medium. Rather than seeing play as a frivolity to squeeze in occasionally around work, play is the fundamental mechanism through which we feel most alive and can access our capacities to create world-shaping things.

“This is the real secret of life — to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play.” — Alan Watts

My fundamental assumption here is that people are already naturally creative, it’s just that various things interfere with it. The course, then, will explore the nature of this interference and provides various tools to resolve it.

The idea of this course existing makes me happy, and that’s why I want to make it. I want to see more playfully creative people in the world and, selfishly, I’d love to be surrounded by people who have tapped into that way of being.

Stay tuned! I’ll offer a pre-launch discount for Thinking Out Loud subscribers.

Things I have made


More to come!

Things others have made

I want to give a shout out to the aforementioned Rob Hardy for creating his first YouTube video. This is a huge and vulnerable step and I applaud him for it. Go watch and subscribe!

And that’s all for this one. See you next time!



I publish a newsletter called Thinking Out Loud, which chronicles my journey as an online maker of things, but it's also is where I talk about whatever I'm interested in at the time.​ There are almost 1000 of us now, come play!