Rosie Sherry - Reckless Mother

Hi All - in this episode we talk to Rosie Sherry. Rosie is a self-declared introvert and community builder extraordinaire. She is best known for the Ministry of Testing, Indie Hackers, Rosie.land and RecklessMother.com

Rosie builds communities and has done so for more than 15 years. It includes the Sherry community of Rosie, Graham and their 5 kids aged 17 to 3 - none of whom go to school.

It’s not that Rosie is looking to rebel. It's just that she seems to be clear about how she wants to spend her time and a conventional path would not allow her to live life, her way. So she designs her own made to measure life with little or no reference to the way most people live theirs.

Rosie’s approach is one where she just does stuff. If she enjoys doing it, she’ll spend more time doing it and then, because she’s spending the time she works out how to get paid to do it.

Rosie is half Columbian, half Irish, sounds Scottish, was born in London, grew up in London, Indonesia and Columbia, moved back to London with no qualifications because she avoided school and now as a reaction to her unsettled childhood, has settled near Brighton on the South Coast of the UK.

She had an entrepreneurial and spiritual mother and a father whose life was changed by an accident. It resulted in financial insecurity but the upside was that along with her brother, Rosie was forced to be independent. It seems her kids are pretty independent too. Their unschooling, as Rosie calls it, requires them to self-direct their own learning, with a little nudge from Mum or Dad here and there. The set-up means their kids teach each other but it’s still a time-consuming endeavour.

Rosie’s clear that successful communities are places where there’s trust, a common goal or set of interests and a way to simplify things. She’s also a big believer that communities can solve most problems.

Rosie works on herself. Like all of us, she doubts she can achieve things but doubt does not prevent her from taking steps forward. She tries to remain positive. She believes things can change.

Financial security is important, it’s a reaction to the financial insecurity of childhood. And because it’s important and she has the ability to change herself, and although she is by no means rich, she does now have enough security to do what she wants to do, what she’s passionate about. She is not afraid to lose her job or quit a job if it means doing what she wants to do.

Easier said than done. It took her 4 years to leave her own company, the £1m + revenue - Ministry of Testing

This conversation got me thinking. What can we do when we realise a job has reached the end of its natural life?

Option 1 - We can hand in our notice and have faith that something will turn up. All well and good if you’ve squirrelled away a war chest that allows you time to find the next positive step but the fear of not being able to pay your rent or mortgage can force us to leap from the frying pan into the fire of another unsuitable job.

Option 2 - We can stay where we are and save. This is a real option. If you know why you’re doing a job (to save money or acquire skills for example) it helps us to get out of bed in the morning. I imagine prisoners of war planning their escape have better mental health than those who are resigned to their fate.

Option 3 - We can be open-minded about where we live and the lifestyle we live. There are always less expensive ways to live. Kids and other relationships don’t always make this easy but accommodation is much more flexible these days, if you are. We’ve had conversations with quite a few nomads who work as they travel. In many senses it’s about working out what we’re prepared to let go of in order to grow.

If I’m not prepared to make any sacrifices in return for a better working life or a better life in general then I’ll struggle to change. But letting go of this and that, might not be as painful as I imagine. In fact, my experience is that letting go of one story and replacing it with a better story, a story about what’s important and what’s not, is an uncomfortable process but not as uncomfortable as continuing to value stories or ways of behaving that fail to serve me. This process is me surfing the edge of my comfort zone. Resmaa Menakem, author of ‘my grandmothers hands’ talks about the uncomfortableness of change as clean pain and the uncomfortableness of avoiding change as dirty pain.

The problem with avoiding change is that it becomes a rut, that becomes deeper and deeper, more and more difficult to get out of. Confronting your rut early is helpful and flirting with what you could do differently is often enough to climb out.

I love Rosie’s approach. She experiments. She does what she wants to do and then she finds a way to make it work financially. She started her newsletter Rosie.land and got frustrated with her ability to build a writing habit, s...