A step-by-step guide to finding your dream life and actually making it happen with Simon Squibb
episodePreviously titled “A step-by-step guide to finding your dream and actually making it happen” — renamed by the publisher on Aug 2, 2026
Transcript
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What is the main topic discussed in this episode?
What is up? I'm Grace Beverley and welcome back to Working Hard, the podcast-shaped guidebook on how to improve your own life and achieve what you actually dreamed of doing, because life's too short for boring podcasts and bad advice. What is up and welcome back to Working Hard. Guys, I'm so excited for you to listen to this episode. I want to start with something that I think a lot of people will relate to. There's that feeling of knowing that there's something you want to build or create or do, but constantly finding reasons why now isn't the right time. And the person I'm speaking to today has spent his entire career trying to prove that wrong. Simon Squibb went from sleeping rough at 15, starting a small gardening business and step by step building business by business,
and eventually experiencing a life-changing business sale. Since then, he's dedicated his life to funding strangers' dreams on the street and built a global movement around the idea that everyone deserves a shot. If you're confused about your path or you've got an idea that you just can't shake, this episode is a proper step-by-step guide to building your dream. We get into what freedom actually means, how to figure out what you actually want, how to start without quitting your whole life and what failure really teaches you. But before we get into the episode, please make sure you're following the podcast on whatever you're listening to it on right now. It means a lot to us, but it also means that you get a new episode in your feed every single Monday completely for free with no paywall and means that we can keep it that way.
Simon Squibb, are you currently more working hard or hardly working?
How did Simon Squibb's early life experiences shape his entrepreneurial journey?
I'm doing both, I think. It doesn't feel like work, so I feel like I'm hardly working, but I'm actually working hard. But I think that's why purpose helps you work without feeling it.
Yeah, and I want to dive into that because your story is incredible. Even just like going through the bullet points of where you've been and everything. I want to go right back to the beginning because I feel like that context around your relationship with work is so important. And you've spoken about being 15 and having the harrowing experience of watching your father have a heart attack and becoming homeless and unable to find a job. Can you tell me a little bit about how that shaped your relationship with what I guess was then you just being thrust into this idea of work as an essential way of keeping you alive rather than maybe leaving school and being able to dawdle around a bit and work out what worked for you?
When I think back to my early days, I would probably describe myself as having an unlucky start to life. But I think luck is a strange thing. Sometimes luck can be perspective. But my father died and I found myself three weeks later homeless. And I did what the system told me to do. The system tells you, go get a job. You can get a job. Or the system tells you if you can't, and I couldn't get a job, by the way, because I don't have a national insurance number and I didn't have an address. So no one will give me a job. And so then the system tells you go to social benefit, go get social security money and they'll give you a home and it will be fine. So I went to the social benefit system and they just basically said no.
In fact, they said, I think, which is kind of worse than no. They're like, no, because... there are six other people in front of you that all have kids and they need housing first. And in my head, as a 15-year-old, I thought I was a fully grown man and I totally understood. I didn't get angry. No, you've got to give me a place to stay. I'm a kid. I didn't think that. I was like, oh, right, absolutely. People who have kids need somewhere to stay. I will be all right.
What does freedom mean in the context of following your dreams?
I can sleep outside. So it didn't even occur to me that the fact the social system didn't and couldn't help me It didn't occur to me that that was wrong. And so then I just moved into this third area, which is like an area that I'd never really been taught, which is why I'm so angry today.
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Chapters
8 chapters
1
What is the main topic discussed in this episode?
0:11–1:38
2
How did Simon Squibb's early life experiences shape his entrepreneurial journey?
1:38–3:46
3
What does freedom mean in the context of following your dreams?
3:46–5:23
4
How can someone identify what they truly want in life?
5:23–7:46
5
What practical steps can you take to start pursuing your dreams?
7:46–9:10
6
How does failure contribute to personal growth and entrepreneurship?
9:10–11:19
7
What mindset shifts are necessary to embrace entrepreneurship?
11:19–13:52
8
How can you balance security with the desire to follow your dreams?
13:52–1:11:33
Speakers
3 identifiedMore from Working Hard with Grace Beverley
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The lies we all tell ourselves about our careers with Jemma Sbeg (LIVE)
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A Doctor’s guide to eating for your health (a full food reset with Dr Rupy)