🎯 Work Smart Wednesday - April 23, 2025
How to take strategic risks, positioning vs messaging vs copywriting, and a quote on breaking out of routine
Work Smart Wednesday
👋 Hey there!
Here is your fortnightly dose of Work Smart Wednesday.
In these emails I will share with you 3 things to help you work smarter.
🆕 NEW FEATURE: What I did instead
When people learn that I run a successful business yet I only work 12 hours per week the first question they usually ask is, “What do you do with all that free time?”. So, now I’m going to show you.
For the next few editions of Work Smart Wednesday I will include a little section at the end showing what I have done in the last two weeks. Take a look and give me your feedback, I’d love to know what you think.
1. 🎲 How to take strategic risks
Strategic risks are critically important to your success, both as a person and as a business.
You have probably already taken some strategic risks before - strategic risks are the difference between people who merely talk about starting businesses vs people who actually successfully start businesses.
But for some reason, entrepreneurs either forget how important it is to take a chance - or worse, they forget to make the most of their wins.
To get around this problem I like to intentionally allocate 10% of my time to rolling the dice, and I often recommend to my clients that they do the same.
Here’s the rule of thumb I live by (and teach):
90% of your time goes to what’s already working.
10% of your time goes to testing things that might work.
If you ignore this ratio, you run into one of two major problems:
You fail to roll the dice, you stay in the 90% loop forever
🧱 doing the same lead gen
🕰️ same client experience
📦 same packages
😕 wondering why your business feels boring and stuck
You roll the dice too much, you live in chaos chasing the 10%
✨ chasing shiny ideas but none seem to work as you lack focus
🧩 never building systems, so everything always feels chaotic and confused
📊 never mastering the boring stuff that actually drives revenue
The sweet spot is doing BOTH intentionally.
90% of your week should be dedicated to repeatable process
🎯 sending proven warm outreach messages
🏆 delivering your core offer with excellence
📊 tracking your key data to spot improvements and trends
10% should be reserved for experiments
🧪 testing a new lead source
🧠 crating a new “bridge” offer
✍️ rewriting your onboarding flow
🤏 niching your messaging for an offer
🙋 creating a loom video for a dream client
🎁 adding a limited-time bonus to your current offer
🔥 optimising how you share proof of results with clients
That’s what creates sustainable growth.
Not a rebrand.
Not a shiny new name for your offer.
Not a new website you’ll spend 3 weeks perfecting.
Small, intentional risks.
That’s how innovation happens in a service business: while the engine runs, you keep improving it.
When I want to grow faster I know not to try to do the 90% even harder, instead I go out to collect better data and make smarter bets.
I stay focused on delivering the core business, but I’m always making small, intentional, bets to fuel growth and improvement.
What are you testing right now?
Jen’s business is stable so let’s roll the dice (45 seconds)
2. 📍 Positioning vs messaging vs copywriting
Positioning. Messaging. Copywriting. Same thing? Not quite.
They’re related, but confusing them is a common (and costly) mistake.
Here’s the quick breakdown:
Positioning = where you fit and why people should care
Example: you’re writing a book, positioning is your genre.
Messaging = what you say and how you say it
Example: In your book, it is the big idea behind the story
Copywriting = the words that bring it all to life
Example: In your book, the words that make you want to read on
If your website or offer feel off, it’s probably a positioning problem.
If your content sounds scattered, that’s a messaging issue.
If no one’s clicking or buying, copywriting might need work (though check the positioning and then the messaging first!)
Examples? Let’s say you’re opening a pizza shop.
🌜 “Saucy After Hours” - The late-night slice:
Positioning: Only wood-fired pizza open past midnight.
Messaging: “You’ve had a long night. You deserve pizza that actually tastes good at 2 AM.”
Copy: “Soggy drive-thru burgers at 1:52 AM? Nah. Grab a wood-fired slice before last call.”
💚 “Pizza My Heart” - the purpose-driven pie:
Positioning: Organic ingredients, giving back to food insecurity programs.
Messaging: “Pizza with purpose - because good food should do good”
Copy: “Every slice makes a difference. Try our fan-favourite truffle mushroom pizza and give back with every bite.”
Same product. Totally different strategy. Your words should reflect that.
A few common mistakes:
❌ No clear positioning → “I help businesses grow.” (Yawn.)
✅ “I help indie retailers in Yorkshire grow on Instagram without chasing trends or paid ads”. Be something nobody else can be, say something nobody else can say.
❌ Inconsistent messaging → polished website, meme-heavy IG, robotic emails
✅ One tone, everywhere. Everything sounds like it is by the same person.
❌ Clever > clear → “Your workflow, but make it seamless!”
✅ “Track projects, invoices, and emails all in one place”. People often say “it is like you’re reading my mind!” when your copy is right.
How to fix your positioning, messaging, and copywriting:
Positioning: What’s your niche + differentiator? Put it on your homepage.
Action step: Fill in the blank → We’re the only [type of business] that [unique differentiator]. Now, check your homepage. Does it match?
Messaging: Pick 3 key phrases your brand should always communicate.
Action step: Write three phrases you want your audience to associate with your brand. Make sure they show up on your homepage and about page.
Copywriting: Make sure your site actually sounds like you and supports the above.
Action step: Pick one key website element - your homepage headline, about page, or service page - and rewrite it to reinforce your positioning.
Go positioning-first if you’re in a crowded space and need a clear differentiator. (Your homepage should make it instantly clear why you’re the best choice.)
Go storytelling-first if your brand is built around a belief, movement, or emotional connection. (Your about page should feel like a manifesto, not corporate fluff.)
Positioning, messaging, and copy all often evolve over time. Customer preferences change, as do your own preferences and experience levels. It is important we stay up-to-date.
How this need to evolve has applied in my own business:
I realised around 5 years ago I didn’t really like working with product businesses so I shifted my positioning to be a service-business specialist.
I am currently shifting messaging slightly from reclaiming time to more specifically helping entrepreneurs build “calm” businesses. It feels more in line with what I enjoy and what I am best at - building calm businesses that are highly profitable, very low stress to run, and give you lots of free time.
Today in this very email I am making a copywriting-type change to trial a new feature to show people the benefits of a calm business - that is the point of the new “What I did instead” section. No accidents, strategy.
When positioning, messaging, and copywriting work together, your brand clicks for people and your audience “gets it” instantly. Conversions become easy.
You convert through clarity and alignment.You make the right people feel seen, you invite them in, you show them what’s possible and how you can help - that’s how trust becomes revenue.
How would you like to evolve your positioning, messaging, and/or copywriting?
This post was heavily influenced, only slightly adapted, from an excellent article I read last week by Stacy Eleczko. I highly recommend you check out
and read the article.
P.s. when I asked ChatGPT to give me names for pizza places for each positioning type, it definitely excelled at pun-y names for purpose-driven/eco pizzerias. Honourable mentions go to Earth, Wind & Flour, The Crust Fund, and Lettuce Turnip the Beet Pizza Co.
3. 💡 Quote I'm pondering
"Comfort has killed more dreams than daring ever did - risk can be dangerous, but routine can be deadly ” - Ian Arber
Risks are necessary for progress, but should be calculated. Without risk, you and/or your business will fade into obscurity.
I rarely begrudge a person I work with for trying something new once in a while, but I will begrudge someone for resting on their laurels.
🆕 What I did instead
Here are some photos of things I have done in the past two weeks with my free time, the things I chose to do instead of working more.
What did you do with your free time?
What did you think about how I spent my free time?
What would you like to do more of if you had more time?
Let me know in the comments below or by replying to this email.
👋 Want to work together?
When you’re ready, here are 2 ways I can help you:
🧩 Your Work Smart Scorecard - what is holding you back? - Fill in this quick quiz to easily see what your productivity problem is. Clearly identify what you need to focus on to improve your life and business.
🔍 Clarity Call - We will discuss your situation and create a step-by-step action plan together so you know exactly what you need to do next for maximum impact.
That's it! I can't wait to hear what you think. What did you find most useful? What do you want more or less of? Reply to this email now and let me know.
Also, if you have anything interesting to share, I want to know about it😊
Have a great week,
John
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