Dear World: If You're Thinking About Giving it All Up to Do Something Different, *This is for You*
10/19/2025
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hi, i'm ash!
Creator of the New Travel & Design Series, 'OTHER PEOPLE'S HOUSES.'
Travel writer & host, cultural explorer, and architecture & interiors freak.
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I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈
I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈ I THINK YOU'RE REALLY GREAT ✈
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But I have a question. From your vantage point today, in those moments when you know you’re looking for something different, but you just haven’t figured out what that “something different” is, do you quietly work in the background, or set up an experimental station in full view of everyone, and risk looking like someone who can’t seem to ever make up their mind.
I’m pretty sure I can anticipate at least part of your answer.
I could not help noticing that over the last few months your Substack went through a bit of, um… trial and error. It was interesting to watch someone with such a long history as an online entrepreneur do this tinkering in public. Usually, what you get is the old website quietly swapped for something slick and professional looking that’s been taking place in the background (as Ann Handley did today). Tada! A new me, freshly baked and perfect.
I have also been experimenting in front of my audience a little bit, hoping to find new trajectories and following promising routes. But they have not panned out in the way I thought they might. Not just in terms of audience response (though there’s that), but in sustaining my own level of excitement. Some things look great in the future, and I professed myself to be passionate about them. But now that the future has arrived, I feel a bit deflated. Or that I picked up too many tools that now feel cumbersome.
Is it me: do I love beginnings but hate middles? Or is it the projects? Did I make things unnecessarily complex for myself? How do you know when you’re giving up on something too early? Or is it better to cut your losses and move on to something else, even if for a few weeks (months?) your website looks like it has schizophrenia?
Totally feel this as well – your post Ash and your thoughtful reply Justyna. I love novelty in my work – trying out new services/products – but that means living with the nerves of being considered a dabbler. In midlife, I’ve chosen to ignore this and experiment with things that look imperfect and unfinished. Super-impressed that you learned swimming skills through reading Justyna. Gives new meaning to diving into a book 🤩
🤣 I hadn’t thought of it that way!
I love the fact that midlife (and beyond) is time for experimentation.
I’m just so done with gloss and perfection and trying to seem bigger than life and all of the logos and all of the performance. I’m just out here having FUN. Substack is such a…low-stakes place to tinker. As you know, I’m a huge fan of experimenting with *everything*, because how else will you know what lands? For you, for them? Honestly, with “real websites,” it’s super easy to run experiments with copy because you can use tools like VWO and Optimizely and now Right Message that serve different messages to different audiences based on all sorts of factors so you can see what converts better – but no body knows it’s happening behind the scenes. 🙂 Here on Substack, though, not the case. It’s been fun trying to learn a new ecosystem and see what kind of writing / packaging lands here. I’m not even slightly worried about fidgeting around with this: one thing that makes me good at what I do is that I am able to pivot quickly and move fast, and ditch what isn’t working and KEEP GOING. My personal opinion? I prefer doing it in public because I am DOING IT, rather than thinking about it in my head for years and not being able to pull the trigger because I’m too overwhelmed with competing ideas. Know what I mean? Sometimes, the “doing it” is what offers clarity, as you work your way through. And if you get there and you realize you’re not as into it as you thought? So what! Onto the next one! You are a human being who is evolving and growing, and so should your ideas. Don’t feel bad about it: celebrate it! You’re this much closer to knowing what you DO want.
Rooting you on, always!!!!!!!!! -Ash
Thank you. Yes, I know exactly what you mean. The second half of your response is like a mini personal coaching session. Especially the gaining clarity through doing part. I already know that intuitively, but I needed to hear it.
You got this. You’re brilliant. Let the world know!
Bravo – an ode to thinking outside the box, or simply smashing it!
“I think about the people who are constantly reading the bible, trying to read themselves into being a better person.” Christ on a cracker, Ash, the things that come out of your mind and onto the page. I just love how you jolt me into thinking about things in new ways.
I am sooooo impressed with you! And I’m sure that I’ve been doing this, though not so much with excavators as with other risks.
I traveled Europe on a Eurail pass on my own for 2 months – AND I took trains across Russia (when their very own serial killer was still not caught…). I pressed the button to blow up a car (someone else set the explosives – and boy did that fly high!) Never learned to hang doors (you either yet 🤣) or excavate my driveway (never owned a driveway)…
This entire post is one big YES!!!! 💕🙌
I’d been out there learning by doing for years, and I STILL felt the need to get credentialed, even though I didn’t need credentials anymore. You are so right, Ash. You gotta get out there and do. And where did I end up when I could choose to end up anywhere?… A teeny, tiny house in Scotland.
I laughed out loud about your hostage voice joke.
I really wanna live in Edinburgh in an old cottage! And try mudlarking, too. Yes, please, raises both hands, jumps up. 🙋🏻♀️
If you are moving to Scotland, you have to read Kelley Armstrong‘s “Rip Through Time” fiction, which takes place mostly in Victorian Edinburgh.
Looking outside the box!!!! Smashing the box!!!! Burning the box on fire!!!! I shall applaud myself for these things and ALWAYS applaud you Lady Ash!!!! xoxo
This hit me:
Maybe real courage isn’t about applause at all—it’s about building a life you’d still choose, even if no one ever noticed. And even if no one claps for you… you’ll have a life that makes their applause irrelevant.
I love how deeply relatable your writing is for me, and who knows, maybe we’d become neighbors in Scotland, because living there is on my to do list!