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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Simon Says

Winformation This Week...

I get it. You’re a start up, or even an established business hunting for top talent to drive your growth. You’ve offered flexibility that the big corporates couldn’t. You’ve stretched the salary because their old employer can’t break the bands. Maybe you’ve even dangled a tiny slice of future ownership. All good.

But here’s where most of us stumble and it feels so harmless. You hand out a flashy, over-the-top job title. Suddenly your Finance Assistant becomes Head of Finance. “It’s just a title, right? Free, compared to the perks and pay we’ve already offered.” Wrong. The most harmless, casual “cost free” perk becomes a ticking time bomb as you grow. Before you make your first (or next hire), you have to read today’s One Idea to Win in Business.

I’ll be honest 2025 has been… okay, at best. Both in business and in life, there have been some tough moments. A lot of it was self-inflicted, thanks to the layers of complication I’ve added to my own life. Running a £100m business on top of a goal list of 25+ items is not something I plan to repeat next year.

I’m looking forward to a more stripped-back, simple life and workflow in 2026. In today’s One Idea to Win in Life, I’m sharing the small changes I’m planning to make to simplify how I tackle work and boost productivity.

One Idea to Win in Business

Something to be Careful of!

The Hidden Dangers of Big Job Titles for Early Hires & What To Do Instead

I’m speaking here directly from the heart, and directly from my own experience. Our 5th hire we called our new Finance Assistant “Head of Finance” - this was informal at first, but we had unknowingly placed a trap in our own path and threw it a few years up the track. Please don’t do this. Here is why:

1. Titles set expectations....unrealistic ones

   When you hand someone a senior-sounding title, you set a tone. Head of, Director all suggest decision-making power, budgets, strategy. But in most small businesses, the same person might also be running social media, ordering printer ink, and writing copy at 10pm. That mismatch between the title and the day-to-day creates confusion and ensures your new hire will only ever look to wear one hat, when you need them to wear way more.

2. The awkward moment when you grow

   You scale up, and suddenly your “Head of Finance” now needs to report to an actual Head of Finance. A qualified one. Your Finance Assistant can be forgiven for thinking “well I thought that was me” - and yes in a way, it was...when we only had one finance related person in the building. Good luck with that conversation. Once someone’s got a senior title, it’s very hard to take it away without denting their pride. This makes building proper structure later on unnecessarily messy. Resentment will flow, trust me!

3. It can confuse your clients and partners

   A “Director of Sales” on a team of three gives the wrong impression. It might look like you’re trying too hard. Authenticity always beats appearance. Clients don’t care how big your team is they care that you deliver what you promise.

4. You cap their career progression before it starts.

   When someone hits “Head of Something” in year one, where do they go next? You’ve accidentally built a ceiling over their head. Any future change in title sounds like a demotion, even if it’s really just aligning the structure properly.

5. Salary expectations spiral

   Big titles attract big pay expectations from them and everyone else who applies later. Before long, your internal salary bands are impossible to maintain, and you end up paying for a title rather than performance. Your “Head of Marketing” will natural google other positions with the same title. Chaos will rein.

6. You invite ego into the building

   Titles should reflect contribution, not compensate for it. When people are motivated by recognition rather than results, culture starts to slide from “we win together” to “I need my status.” You don’t want that - especially early on.

What to do instead:

• Focus on clarity, not grandeur.

• Use descriptive, honest titles - Marketing Executive, Finance Assistant, Operations Lead.

• Give people growth paths that lead to senior titles, not ones that start there.

• Reward progress, not position.

• Doing this early...or at least from your next hire is key!

One Idea to Win in Life

Something to Make Things More Simple

The Freedom of Fewer Choices: How Simplifying Boosts Your Focus

Sometimes freedom and growth can come from fewer choices. It’s not always possible to have a simple life, but when simplicity is an option, it’s worth taking. Here are five tips on how living simply can improve your life.

1. Limit distractions

   We have spoken about the occasional digital diet being beneficial, but we aren’t only distracted by screens. It could be a certain food, person or even colour that messes with your focus. It helps to know where you work and exist best. Some people can happily work in a busy café, for others that is unadulterated hell. Be aware of what triggers you and avoid it.

2. Think about your environment

   For many of us, an uncluttered space is an uncluttered mind. But we are all different. What does a good home and work environment actually look like for you? Lighting and space are two key elements, as is sight and smell.

3. Healthy habits

   It is possible to get stuck in routines that do not help us. You don’t have to be like Steve Jobs and have a wardrobe of the same outfit, to save time on choosing what you are going to wear. You don’t even have to meditate or take a cold plunge. Something as simple as a short morning walk, where you can gather your thoughts and intentions for that day can get you off to a healthy and positive start.

4. Quality over quantity

   Even if you have had a windfall, consider how you spend. This isn’t about being tightfisted with money, it’s about choosing quality and value and items that support your growth. Think also about experiences and relationships rather than only material possessions.

5. Step by step

   As the old phrase goes, how do you eat an elephant? Answer? One bite at a time. Not only does it feel fulfilling to give your full attention to whatever you are doing, it is also how you progress. Don’t fool yourself that you are being productive when you have 17 tabs open on your laptop. It’s great to book your calendar with jobs you need to do, but it pays to make sure the tasks you’ve given yourself are specific. So instead of saying, I’ll work on my website, better to hone in on something, like I’ll finish the landing page.

Win or Wonder?

Ask Me a Question…

No matter where you are on this mad journey. Starting out, scaling up, or somewhere in the messy middle feel free to ask me anything.

Business, life or mindset, I read and reply to every question. The best ones will get featured in future editions of Winformation, with your permission of course!

To ask, just hit “reply”, type your question and send. That’s it. No forms. No fuss.

Until next week! 

Let’s win, together!