If you’ve ever said, “One day, I’ll get around to it,” this article is for you. Most people have a list of things they plan to do once life gives them a bit more space, money, motivation, clarity, or time. The problem is that “one day” keeps shifting like a dodgy satnav. You deserve better than a moving target. You need a plan that works in real life, not just in your imagination.
Goal setting doesn’t have to feel like writing a 400-page business plan or mapping a trek through the Amazon. You don’t need a colour-coded binder, scented candles, or a motivational playlist that makes you cry on the school run. You need a clear path, a few decisions, and the courage to move one step forward today.
That’s what Charting Course, one of the pillars of Winning The Game, is all about. When you learn to turn your dreams into a simple, workable roadmap, everything starts to shift. Not because life gets easier, but because you start playing with intention.
Let’s build your roadmap.
Start with a Dream You Actually Want
Dreams are free, which is why people often collect far too many. Before you plan anything, ask yourself a blunt question: Do I even want this, or does it just sound nice?
You might think you want a bigger house, when what you actually crave is more space to breathe. You might think you want a new job, when what you want is to feel valued. You might think you want to run a marathon, when what you want is to feel healthy enough to keep up with your kids.
Be honest with yourself. Strip the dream down to its real purpose. That purpose becomes your anchor when the work feels boring.
When I first started my business, people told me I should chase growth. Bigger team, bigger building, bigger numbers. I tried it and hated every minute. I realised my real goal was freedom, not scale. Once I admitted that, my decisions became much easier.
So ask yourself: What’s the actual point of this dream?
Break Your Goal into Clear Milestones
A dream becomes a goal the moment you give it structure. And structure doesn’t require complexity. You just need clear milestones that move you forward.
Think of it like climbing stairs. If you can’t reach the next step, you don’t leap six stairs at once; you fall and bruise your ego. You take the next reachable step, then the next. Goals work the same way.
Let’s say your dream is to switch careers. You can break that into small milestones:
- Identify three industries that interest you
- Speak to someone currently doing the job
- Take one short course
- Update your CV
- Apply for five roles
Each step is small enough to act on, yet large enough to feel meaningful. The list becomes your route map — not a mountain, not a mystery.
This is where many people freeze. They think they need to see all 50 steps ahead. You don’t. You only need steps one to three. The road reveals itself as you walk.
Add Rewards Along the Way
You’re not a machine. You need incentives.
Gamification is one of the themes in Winning The Game, and for good reason. When you link progress to rewards, you turn effort into something playful. You make the journey enjoyable, not just tolerable.
I once worked with someone who wanted to save money but hated budgeting. So he turned it into a challenge. Every time he skipped a takeaway, he dropped £10 into a “treat pot.” After eight weeks, he booked himself a night out he’d wanted for months. He saved money and felt good doing it.
Rewards don’t need to be big. A nice coffee after a tough task, a walk in the sun after you finish something you’ve been avoiding, or an early night when you complete a mini goal. You’re training your brain to recognise progress.
Ask yourself: What small reward would make this feel worth the effort today?
Give Your Plan a Timeframe
Dreams with no deadlines drift forever. Deadlines don’t make your life rigid; they make your plan real.
The key is to choose timelines that suit your life, not someone else’s. A parent with young children will move differently to a student. A business owner will move differently to someone working shifts. There’s no universal pace.
Instead of saying, “I’ll write a book this year,” turn it into:
- Write 300 words three times a week
- Finish chapter one by the end of next month
- Complete the first draft in six months
Clear, manageable timing beats vague ambition every time.
When you think about your own goal, ask: When do I want the first step done?
Don’t Hide From the Hard Bits
Every ambitious goal has at least one part you’d rather avoid. Maybe it’s paperwork. Maybe it’s asking for help. Maybe it’s admitting you need to start from zero.
If you avoid the awkward bit, your progress stalls. But when you face it early, the rest becomes easier.
I used to delay anything involving contracts, because I found them dull. Then one day, I blocked an hour, made myself a coffee, and focused on nothing else. I finished it faster than expected and spent the rest of the day in a better mood than normal. The dread ate more time than the task ever did.
Look at your goal and ask yourself: What’s the bit I keep postponing? Can I do it this week?
Stay Flexible Without Losing Direction
A roadmap isn’t a prison; it’s a guide. You can adapt it as you learn more.
Sometimes you start a goal and realise you want something slightly different. That’s not failure. That’s clarity.
If your plan needs adjusting, adjust it. Just don’t abandon it because of a wobble.
Most of the time, people give up not because they can’t do something, but because they lose momentum. A small correction keeps you moving forward.
Ask yourself: What part of my plan needs updating right now?
Ask for Help When Needed
You don’t need to hit every goal alone. If you want to run faster, speak to someone who runs. If you want to start a business, talk to someone who has built one. People love sharing what they know.
When I wrote Winning The Game, I didn’t sit in a dark room hoping the words would magically arrange themselves. I spoke to leaders, coaches, and people who understood the challenges I wanted to explore. Their insights shaped the book in ways I couldn’t have predicted.
Asking for help doesn’t weaken your independence; it strengthens your progress.
Who could help you take your next step?
Track Wins Every Week
Your motivation grows when you see progress. Even tiny progress.
Keep a simple log:
- What did you achieve this week?
- What moved you closer to your goal?
- What went better than you expected?
This builds confidence and helps you avoid the common trap of forgetting how far you’ve already come.
You might be further ahead than you think.
Start Today, Not Tomorrow
The perfect moment never arrives. You don’t need a new week, new month, or new year. You just need one action today.
One step builds momentum. Two steps build belief. Three steps change your life.
If you want a simple guide that ties all these ideas together with stories, humour, and real examples, Winning The Game walks you through the entire process of turning big goals into achievable steps.
Your dream is waiting. Let’s chart the course.