“How to win in life” gets hard when you stay on autopilot—busy weeks, vague goals, and quiet drifting that costs you years. In this article, Jef Menguin shares a simple strategy framework you can return to when your days feel full but your direction feels unclear. Practice it and share it with your people at work so you stop guessing, choose on purpose, and build wins that actually stick.
When I was younger, I had many wishes but no real way to win. I thought winning was something that happened to you—like you got lucky, met the right person, or stumbled into the perfect opportunity. I worked hard, yes, but deep down I was waiting for life to “open up.”
Maybe you’ve felt that too. You want a better life, you keep trying, but you can’t explain how it will happen—only that you hope it will. You set goals, you promise yourself things, you start strong… then life happens, and you’re back to surviving the week.
That’s when I learned something that changed my posture toward life: winning isn’t an event. Winning is a set of choices you repeat. And repeated choices are easiest when they’re built into a system you can return to.
So here’s a framework you can use without turning life into a spreadsheet.
The 5 questions that stop you from drifting
You don’t need to think of business to use strategy. This is just a way to stop guessing. A way to choose on purpose, especially when your energy is low and your days feel full.
Read these slowly. Don’t rush.
What does winning look like for me—right now? Where will I focus my time and energy? How will I win in a way that fits who I am? What capabilities must I build to sustain that win? What system will keep me winning even on hard weeks?
If you can answer these honestly, you stop outsourcing your life to chance.
1) How to define what winning means in life
Most people don’t lose because they lack talent. They lose years because they never defined what they were aiming for, so they end up chasing whatever looks respectable. When you borrow someone else’s definition, you also inherit their anxiety.
I once met a leader who got promoted—good salary, bigger team, nicer title. He was grateful, but in a quiet moment he said, “I thought this would feel better.” He wasn’t being dramatic. He was realizing he climbed a ladder without checking if it was leaning on the right wall.
Have you ever felt that? You got what you wanted, but it didn’t satisfy. Or you’re chasing something and you can’t tell if it’s really yours.
Pause and write one honest sentence:
“This season, winning for me means ______.”
Keep it human. Peace is a valid answer. Health is a valid answer. Finishing what you keep delaying is a valid answer.
2) How to choose a focus area in life (because you can’t win everywhere)
Here’s a truth that feels harsh at first, then strangely relieving: you can’t focus on every part of life at the same intensity at the same time. You can care about many areas, but you can’t push all of them without breaking something—usually your energy, your relationships, or your sanity.
This is why many people feel like they’re failing. They’re trying to fix “their life” as one giant problem, and the size of it makes them freeze. When you carry everything, you end up carrying nothing forward.
Let me ask you gently: where do you feel the most strain right now? Is it your energy? Your relationships? Your money? Your work direction? Your inner life?
Choose one. Not forever—just for now.
Write it: “The area I will focus on this month is ______.”
That one sentence alone reduces overwhelm, because it turns a vague life problem into a clear starting point.
3) How to win in a way that fits your season and personality
Some people try to win by copying the loudest person they follow. They borrow routines, pace, and standards, then feel guilty when they can’t sustain it. They call it lack of discipline, when it’s often just mismatch.
A new parent doesn’t win the same way a single 25-year-old wins. Someone rebuilding after failure doesn’t win the same way someone in a growth season wins. A quiet person doesn’t need a loud strategy to make progress.
So ask yourself: what kind of winning fits my real life right now? What pace can I maintain without resentment, and without needing a miracle week to catch up?
A plan that looks impressive but collapses is not a winning plan. Winning has to be repeatable, not performative.
4) How to build real capability (from the inside out)
When people hear “capability,” they often think resources—money, time, connections, tools. Those matter, yes, but they’re not where capability begins. Capability starts inside, then shows up outside.
Here’s the ladder:
Identity — who you believe you are. Mindset — how you interpret problems. Behaviors — what you do in real moments. Habits — what you repeat without thinking. Discipline — what you protect even when you don’t feel like it.
This matters because two people can have the same resources and still get very different results. One has an identity that supports winning. The other has an identity that keeps postponing it.
Let’s make it concrete. Say your focus area is Health & Energy.
You shift your identity from “I’m always tired” to “I’m someone who protects my energy.” Your mindset shifts from “Rest is a reward” to “Rest is a responsibility.” Your behavior becomes “I stop scrolling at 10:30.” Your habit becomes “phone stays outside the bedroom.” Your discipline becomes “I keep the minimum even on weekends.”
Do you see the flow? This isn’t about becoming a new person overnight. It’s about building capability like a ladder—one rung at a time.
Now your turn: what’s one capability you want to build this month—one that would make everything easier if it improved by just 10%?
Write it down in one line. Not five. Just one.
5) How to create a life system (because systems beat goals)
Most people don’t fail because their goals are bad. They fail because goals don’t carry you on tired days. A goal is a destination. A system is the way you travel—when life is noisy, messy, and imperfect.
If you’ve ever set a goal on a Monday and lost it by Thursday, you already know this. The problem isn’t that you don’t want it enough. The problem is you built an intention, not a rhythm.
Systems beat goals because systems are repeatable. They don’t depend on motivation. They create momentum through small actions you can keep doing even when you’re not in the mood.
A leader once told me, “I have goals every year. I even write them down. But I don’t follow through.” When we looked closer, he had no weekly reset—no moment where he reviewed his life, chose a focus, and decided what mattered now. He wasn’t undisciplined. He was unsystemized.
A life system doesn’t need to be complicated. It needs to be simple enough to return to, and strong enough to keep you from drifting. Think of it as your personal reset button.
Here’s a system you can actually live with:
Once a month, you zoom out and check your life areas. You don’t judge yourself. You just notice what’s loud and what’s neglected. Then you choose one focus for the month, so you stop trying to fix everything at once.
Once a week, you choose one shift that matches that focus. Not a big transformation. One shift that makes your week winnable. If your focus is health, your shift could be “walk after dinner.” If your focus is relationships, your shift could be “one real conversation a week.” If your focus is work, your shift could be “ship one useful output every Friday.”
Once a day, you do the smallest version of that shift. This is the secret: your daily minimum must be doable even on a bad day. Ten minutes. One page. One message. One walk around the block. Because bad days aren’t exceptions—they’re part of life.
Do you see what this system does? It replaces guilt with clarity. It replaces “I should” with “Here’s what I do.” It turns winning into something you can practice, not something you have to chase.
One shift can change everything
A shift is not a motivational line. It’s a change in how you act when real life happens. It’s the bridge between who you are today and who you want to become.
Instead of “I will fix my life,” it becomes, “I will take a 10-minute walk after dinner for the next seven days.” Instead of “I will be more present,” it becomes, “I will leave my phone in another room during meals.” Instead of “I will grow,” it becomes, “I will ship one useful output every week.”
Do you see the difference? The second set is winnable. And winnable is what builds confidence.
So let me ask you: what’s one shift you know would help you right now—if you actually practiced it?
Start with Life Starter (so you don’t overthink the first decision)
If you’re overwhelmed, you don’t need more advice. You need a first decision.
That’s what Life Starter is for. It turns “my life feels messy” into “this is my focus.” It helps you choose where to play first, define what winning means there, and commit to one shift you can repeat with a daily minimum that’s realistic.
Don’t treat it like homework. Treat it like a reset you can return to—especially when you feel lost.
Your 24-hour challenge (so you become a user, not just a reader)
Before you sleep tonight, write these two lines:
1) “This season, winning for me means ______.” 2) “This week, I will win in ______ by doing ______.”
Then open Life Starter and pick your focus area. Choose a winnable shift, define your daily minimum, and run it for seven days.
Because winning in life isn’t about intensity.
It’s about a system you can repeat—one shift at a time.
If you’re tired of knowing but not doing…
Let’s make one shift easier to live daily.
→ Shift Experiences
