Starting a business is a dream for many, but few make the leap. In his latest listen, How to Quit Your Day Job, Simon Squibb (bestselling author of What’s Your Dream?) provides a roadmap for unhappy employees to ditch their careers and become their own bosses. In this brief Q&A, Squibb tackles the mental roadblocks that wannabe entrepreneurs encounter on their journey, including losing a financial safety net, fear of failure, and uncertainty around AI technologies.
Rachael Xerri: You’re known for asking the question, "What’s Your Dream?" How does that signature question connect to your latest listen, How to Quit Your Day Job?
Simon Squibb: The first time I ever asked it out loud was in Tesco. I'd just signed up to TikTok a few weeks earlier and started posting business videos online. Not many were watching, but the ones who were watching valued it. I'd spent the last 20 years living my dream and building businesses. But posting on TikTok showed me just how many people needed help building theirs.
So when I saw a Tesco worker stacking shelves, I just blurted it out: "What's your dream?" She looked at me. Froze for a second, confused. And then she started to stand a little bit taller. She told me she wanted to open a care home. Her mum had died alone in her house, and she didn't want that happening to anyone else. I had £150 in my pocket that someone had tipped me on a TikTok live, money I felt bad about taking because I didn't need it. So I gave it to her and told her it was my deposit for when she makes it happen.
Five years later, and I've asked thousands of people that same exact question. Most have an answer. But that answer often falls apart the next morning, when they still have a shift to do. How to Quit Your Day Job is about that next morning.
So many people dream of being an entrepreneur, but few know where to start. How does How to Quit Your Day Job help listeners take their first step?
Honestly, most people don't even need a first step. They just think they do. What they're actually waiting for is permission. I went to Carnaby Street once with £2,000 in cash and offered it to anyone who'd quit their job that day and go after their dream. We were there all day and spoke to about 50 people. Only one took it. The rest all had dreams; they just had reasons, too.
In How to Quit Your Day Job, I've laid out the steps to move past the reasons all of us have for not taking that first step. Getting your costs down, the mental blocks we put on ourselves, the risks we need to take. None of it's complicated. It's just that nobody ever sits you down and explains it, so you end up assuming it's harder than it is and you don't start. I wanted this to be the thing everyone who has a dream listens to before deciding they can't.
You describe quitting your job as “cutting through your safety net,” an idea that is quite frightening to some people. At what point should someone take the leap from working for someone, to focusing on their own business, and how can they overcome that fear?
Look, the first thing to understand is what that net actually is. A job feels like a safety net, right up until your employer loses two big customers, and then you find out how fast you can be made redundant. It's someone else's net, and they can move it whenever they like. That's why I say cut through it—you're not losing as much as you think.
On timing: Go before you feel ready, but not before you've done the maths on the worst case. Natasha, the Vegan Patty Lady, rang my doorbell with a dream and a pot of savings she and her husband, Adonye, had put aside for a house. They sat with the bad ending, and Adonye said, "It's only money. If it takes five grand for my wife to follow her dream, then that's life." They put in £5,000, I matched it, and she's sold thousands of patties since. Fear stops running the show once you've been to the worst case in your head and worked out you'd survive it. And look, even if it does go wrong, you've had one job; you'll get another.
What do you want entrepreneurs to know about launching a business in the age of rapidly evolving AI technologies?
People are scared of AI and they shouldn't be. Will AI take jobs? Absolutely. But it's also just made building a business accessible to everyone. The entry bar has never cost less. You don't need a huge team, expensive equipment, or even new skills. Ben Francis, who I talk to on How to Quit Your Day Job, started Gymshark at 19 while delivering for Pizza Hut, with a sewing machine and a screen printer in his parents' garage and his grandma teaching him to sew. You can now build the site, the brand, all of it, in an evening, for almost nothing.
The tools are catching everyone up equally, so the only edge left is purpose. A person can't borrow your purpose and an AI can't simulate it. Nobody can copy the thing that happened to you that made you need this to work.
Is there anything else about How to Quit Your Day Job that listeners should know before they press play?
Only that I didn't make it for people who are already doing all right. There's a warning at the front of my book saying if you're genuinely happy, put it down, it's not for you and it might even do the opposite. Same applies here. I recorded this for the person carrying the thing they know they were made to do, but for whatever reason are holding themselves back. And if nobody's ever asked you the question, consider this me asking: What's your dream?
