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The 7 Brutally Honest Questions That Lead to a Life You Actually Want & Business Over Guilt Plus More

One idea to Build your Business, one idea to Scale your life. Every Wednesday.

Welcome to Winformation Weekly. My 13 years’ experience of growing a business from £0-£100m, and the life that goes with it. All wrapped up, in one winning weekly email.

Today in 4 minutes you will learn:

1. ONE IDEA TO WIN IN LIFE: The 7 brutally honest questions that lead to a life you actually want

2. ONE IDEA TO WIN IN BUSINESS: Burned out, guilt-ridden, and tired: here’s the advice that saved me

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...

Have you ever seen the movie American Beauty? It’s a great watch, I'd recommend it. That is if you can still find a platform playing Kevin Spacey movies. Not exactly Hollywood’s poster boy anymore! In the movie there’s a scene where a plastic bag just floats through the air. It’s supposed to be a metaphor for something profound. But I can’t help seeing something else. It’s how the vast majority of people live their lives. Floating from one job to the next or staying stuck in bad relationships for decades too long. I really believe we all have the ability to design the life that excites us. In today’s One Idea to Win in Life I share 7 questions that you can ask yourself today to really get clear on the life you truly want. Let’s go old school with this. You will need to gift yourself an hour with a pen and paper, no phones, no distractions.  

Since our business has grown to over 100 people and £100m in revenue, I never thought when we first started that the main emotion, I would feel wasn't achievement or pride, it was GUILT. I have turned feeling guilty into an art form. In today’s One Idea to Win in Business I share why this is, and how to avoid it.

One Idea to Win in Life

The 7 Brutally Honest Questions That Lead to a Life You Actually Want

It’s so easy to let the 20, 30 or 40 years old turn into the 50, 60 or 70 years old without asking yourself “what do I actually want”. Some people are happy floating. If that’s you, I’m truly happy for you, and to be honest sometimes, slightly envious. For everyone else, here are 7 profound questions, that once you know the totally honest answers to, you can formulate a plan to get there. Exciting things happen when get totally clear on the below.  

  1. If money, time, and fear weren’t obstacles, what would I be doing every day? This strips away external limitations and forces you to focus on what truly excites and fulfils you. 

  2. What do I want to be remembered for when I’m gone? Thinking about your legacy helps define what really matters and guides your daily decisions. 

  3. What problems do I genuinely enjoy solving? Success and fulfilment often come from solving problems you care about rather than avoiding problems altogether. 

  4. What kind of people do I want to surround myself with? The people around you shape your mindset, opportunities, and overall happiness. 

  5. If I was the main character in a movie, what would the audience be screaming at the TV for me to do next? Remove yourself from “you” and place external eyes on your situation.

  6. What or who am I currently tolerating that I shouldn’t be? Before the “new” comes in, some “old” may have to be cleared.  

  7. What am I willing to sacrifice to make for the life I want? Every great life comes with sacrifices. Getting clear on what you’re willing to give up helps prevent future frustration.

One Idea to Win in Business

Burned Out, Guilt-Ridden, and Tired: Here’s the Advice That Saved Me

Since our business has grown and my responsibilities over the years with it, I have made "feeling guilty" almost an art form. A few years back I was probably one of the very best at finding an angle to ensure I started and ended my day with a big bout of guilt… sometimes justified, most of the time not. 

Guilty that I couldn't spend more than 5 or 10 minutes with anyone in particular. Guilty that with such a busy working day, almost all of my energy has left my middle-aged body by the time it comes to spend time with my young family. Can't see my parents at the weekend? Guilt. Can't go on a client visit when someone asks me to? Guilt. Can't donate to EVERY good cause that gets sent my way? Guilt. Guilt. Guilt. 

Nothing used to make me feel more guilty at work, however, than when someone accused me of "ignoring their email". I used to feel really bad, mainly because these accusations were usually made in person, face to face. You can't even hide behind a screen for that. Old-school 90s guilt right there. 

The worst recently being last week when I decided at 6am that the call of the office was too great, and I headed in very early to make a start on the day I had in front of me. That was until I totally forgot it was World Book Day and I had a FaceTime call from two very upset young boys that I hadn't been there in the morning to see them in their costumes for nursery. 

This was the turning point. I asked someone what do to, their advice was worth sharing: 

  1. Define what enough looks like. Setting clear boundaries on what counts as a successful day helps you avoid the endless chase of unrealistic expectations. 

  2. Schedule guilt-free time. Blocking out time for what matters most ensures you’re proactive, not reactive, with your energy and attention. 

  3. Stop being everyone’s emergency contact. When you create and communicate availability boundaries, you train others (and yourself) to respect your time. 

  4. Reflect before reacting. Pausing to check if something truly aligns with your priorities stops guilt-fuelled decisions in their tracks. 

  5. Celebrate the wins, not the inbox. Focusing on meaningful progress over constant responsiveness shifts your sense of worth from busyness to impact.  

So, fast forward a week and as I came out of a meeting yesterday morning, which ran from 9-12, I sat down at my desk, lunch in front of me, determined to crack on with my tasks for the afternoon. My inbox was tidy from the 6am start from my home office before heading to the office at 8am.

In walks another 50 emails. This was on top of the LinkedIn messages, two voicemails, 15 DMs from the weekend, Instagram comments to respond to, and let's not forget the usual four or five face-to-face "have you got a minute" questions that three hours away from the desk usually result in. 

I hadn't got the time to deal with it all. In the past this would have produced feelings of guilt that were next level.  

But… I refuse to feel guilt any longer. 

You are doing yourself, your team, and your family a total disservice by responding to everything that comes your way. The more you respond, the more that boomerang will curl round and head back your way. 

You are not a messenger manager, an inbox coordinator, or a WhatsApp. 

Next time someone comments that you take a while to email them back or return their call, take it as a compliment that for once you are prioritising your workload for the benefit of your team - and for once, when it comes to spending time with loved ones, you are putting what truly matters first. 

Until next week! 

Let’s win, together!

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