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The Dark Truth Behind Lifestyle Businesses No One Talks About & The Power of 5 Whys

The information to Win in Business, the information to Win in Life, all wrapped up in one winning, weekly email. Winformation Weekly.

My 14 years’ experience of growing a business from £0-£100m as well as the life that goes with it.

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Today in 4 minutes you will learn:

1. ONE IDEA TO WIN IN BUSINESS: Choosing to stay small? Here’s what no one tells you about lifestyle businesses

2. ONE IDEA TO WIN IN LIFE: The easy, free method that helps you stop making the same mistakes

3. VICTORY VAULT: If you are here for all my free Cheat Sheets, Guides and E-Books, your exclusive key to the Victory Vault is at the bottom of this email!

Simon Says

Winformation this week...

We all love the idea of freedom, especially when it comes wrapped in the glossy packaging of a “lifestyle business.” But what if the thing you built to give you more life ends up taking more of it instead?

Below, in this week’s One Idea to Win in Business, I’m telling the story of a holiday that revealed something surprising: the smaller the business, the harder it can be to escape it. We’re unpacking why the dream of a balanced, low-stress business might be the very thing keeping you from real balance and why aiming higher could actually set you freer, faster.

Whether you're just starting out or you've been at it for years, this one's worth your time. Because sometimes, the biggest wins come when we stop thinking small.

In this week’s One Idea to Win in Life, we’re diving into a deceptively simple life tool called the Five Whys. Invented by Sakichi Toyoda (yes, the Toyota guy), it’s a no-cost, low-effort way to actually solve problems rather than just crying into your beer.

One Idea to Win in Business

Choosing to Stay Small? Here’s What No One Tells You About Lifestyle Businesses

A few years ago, I went on a group holiday. In our party was a friend who had a lifestyle business. He had always been vocal about keeping it on the smaller side. Understandably, not wanting the stress and time toll a larger operation always seems to have on the founder. At the time, the business I co-founded had 60 employees and a £70m turnover. For the 6 days we were away, he received 3 or 4 calls a day, often into the evening, from the small team he had left behind to allow him to take a short break in Europe. In comparison, I didn’t receive a single call. Not one.

 96% of UK Businesses...

Of 5.5m private businesses in the UK, only 4% will ever hit the £1m mark. So, that tells me, 96% of business that don’t hit this milestone fall into 2 camps. Those that strive for years to get there and don’t (and I'm hoping all my free content can help with this). And those where the conscious decision of the founder/operator is to create an intentionally smaller operation or a lifestyle business.

A lifestyle business is primarily set up with the intention of maintaining a certain lifestyle for the founder, its existence is one of a supporting role to the owner, rather than having growth ambitions of its own. Now, that's fine...but I have another way of looking at this. Hear me out.

Creating a Smaller Business For "Balance"

In terms of the strain on your life and often your sanity over the long term, I personally think it’s harder to maintain a lifestyle business at sub 7 figures for 20+ years than it is to grow something way into the millions and beyond before the decade is up. At that level, you have choices and a management team hungry to learn and take things on. Lots of people talk about balance, and maybe they create intentionally smaller business to ensure a work life balance?

This is ironic, because I see far less balance for my friends who run an intentionally smaller business. I don’t see work life balance in terms of my day, week or even year, I see that balance will occur at some point over a lifetime. Put it in now, and later things will ease…maybe when the business gets far larger. If you hire ambitious people to drive your business forward, then they will also want to feel part of a growing, winning team. Constantly replacing people who outgrow what your business can offer them for their career and their life also takes a huge amount of time and resources.

Lifestyle Businesses Are Great...Until

It could be that you are about to embark on your entrepreneurial journey, or maybe you are years in. You may have wrestled with this conundrum before. But…if not, it’s something worth thinking about. In my experience, lifestyle businesses are great, until they continue to interfere with your lifestyle!

Key Takeaway: Rethink the “Lifestyle Business”

🧳 Small doesn’t always mean stress-free

📞 Less scale can mean more daily pressure

🔄 True balance may come after growth

💡 Ambitious teams thrive in growing businesses

⚠️ Greater effort upfront could mean bigger “balance” back end.

One Idea to Win in Life

The Easy, Free Method That Helps You Stop Making the Same Mistakes

Sometimes life can leave a few banana skins for you to slip up on, usually when you are wearing your best shoes. So, what do you do? Curse your luck to anyone who’ll listen? Go hide and hope the problem goes away? Or get to the root cause of the situation to help you solve it? I’ll give you a clue, the first two suggestions might make you feel better for 10 minutes, but they won’t help you. The last will. Especially if you use a method called the five whys, which was the brainchild of Sakichi Toyoda, the founder of Toyota. Not only is the process of asking why free and an easy way of getting to the root cause of a problem. It also stops you from making the same mistake again.

Here’s how it works and why it can be so useful.

  1. Identify your problem. What is the issue? A complaint? Something not being achieved? A gap in your plan? Make sure you are clear on what the answer is. Do so by creating a clear and concise statement on what it is. For example, we lost 14% of revenue each quarter last year.

  2. Put a team together. This is not so you can purely delegate work to them. This is bringing together a group of people who are in the best position to talk in depth about the identified problem.

  3. Ask why once. For example, why have you lost 14% revenue each quarter last year? Are you following up on leads? Or, is our level of customer care high enough. For any potential root cause you pick up you need to ask why again, to find a deeper answer.

  4. Ask why four more times. This allows you to get to the crux and go beyond the symptom of a problem. Eventually, you will find your way to the root cause of it. Once you have that, it’s time for step five.

  5. Further determine the root cause. Taking our 14% revenue loss as an example again. Your five whys may have drawn you to discovering that you need to rethink your approach to customer service and how it is carried out.

  6. Get together for solutions. Now you have uncovered all this information you can start to get thinking about ideas to overcome the causes, along with choosing the most effective way of doing so. The great thing about this method is that it works across any industry and it encourages continued improved performance.

Key Takeaway: Use the Five Whys Method

❓ Ask “Why?” five times

🔍 Get to the real root cause

🧠 Prevent repeat mistakes

✅ Simple, free, and effective

💼 Works in any industry

Until next week! 

Let’s win, together!

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