All of us want to win. We have aspirations for ourselves, our businesses, our families. We want financial success without sacrificing our health and relationships. We dream of thriving across all dimensions of life – not just surviving on one front while sacrificing the others.

But what happens when, despite your best efforts, you find yourself trapped in a cycle where victory feels perpetually out of reach? When you've implemented every tactic, read every book, hired every consultant, and still find yourself running faster just to stay in place?

I see this pattern repeatedly in my coaching practice, and it's one I've experienced personally too. The mounting frustration as we try harder and harder without seeing the results we seek. The growing suspicion that perhaps we're fundamentally flawed or incapable. The slow surrender to a reality that feels less than we know is possible.

This can be one of life's most isolating experiences – the gap between where you are and where you want to be, despite doing everything "right." And without the proper framework to understand what's happening, this frustration can drag on for years until we eventually give up and settle for mediocrity.

I believe in these situations we're often focusing on the wrong question entirely. And this realization has the power to change everything.

Two Questions That Shape Your Life

When you strip away all the complexity, your strategy for winning – in business, relationships, health, or any domain – comes down to two fundamental choices:

1. Where will you play? This determines your environment – where you live, what work you do, who you marry, which friends surround you, what communities you join.
2. How will you win? This shapes your approach within that chosen environment – your daily habits, your systems, your tactics for getting what you want.

The mistake most of us make is focusing relentlessly on the second question while treating the first as fixed and unchangeable.

In my coaching practice, I often describe "where you play" as drawing "bright lines" in your life. These bright lines create the container within which you operate – they define the boundaries of your playing field. They might include who you're in a relationship with, what job you hold, whether you work for yourself or someone else, where you live, how much you drink, when you go to bed, or which communities you belong to.

We try new productivity hacks to squeeze more from our 24 hours rather than questioning whether we're in the right job. We implement elaborate communication strategies with our spouse instead of confronting whether the relationship is fundamentally aligned with who we've become. We hire help to manage our overwhelm rather than examining if we're committed to too many activities.

This happens because redrawing these bright lines feels risky, disruptive, and often scary. It's much easier to tinker with how we approach our current situation than to fundamentally change the game by drawing new boundaries for ourselves.

When Tactical Solutions Fail You

Let me tell you about a brilliant mortgage broker I’ve worked with for the last few years from Atlantic Canada. Year after year, he has been one of the most decorated professionals in his industry. 

But after starting a family five years ago, his definition of winning had shifted. He wanted to be home by 5pm to spend quality time with his daughter. He wanted evenings free after his daughter went to bed – time to pursue personal interests, connect with his wife, and actually enjoy his life instead of answering emails.

With a team of seven people, he had capacity within his organization. So we spent our first few months together implementing various "how to win" tactics:

• Hiring an executive assistant to manage his emails and calendar
• Building more structure into team meetings and one-on-ones
• Bringing on additional producers to take pressure off his performance

Despite these changes, he remained overwhelmed. While leading his team, he continued meeting with clients every week – something he excelled at but that kept him perpetually reactive. The unplanned needs of new clients and personal referrals kept him up late, at the office longer than expected, and living in a constant state of hypervigilance.

With his second child on the way, he knew something had to change. But more "how to win" tactics weren't going to do the trick.

Then during one coaching call, as he launched into what had become a repetitive conversation about his stress, I changed the direction:

"I think it's time we change where you're playing, not how you're trying to win."

This simple statement created an opening for a different conversation. What emerged was the realization that he was holding onto a belief that he personally needed to meet with clients for his business to succeed. This belief was not only compromising his personal aspirations but creating a ceiling for his company's growth.

That day, he made a decision: he would no longer meet with clients. Instead, he would focus solely on coaching his team and developing investment projects that aligned with his vision for the future.

Within a month, the transformation was remarkable. After two weeks of transitioning his client meetings to his team, he found himself home every night by 5pm. The overwhelmed, disappointed energy that had characterized our calls was replaced by lightness, possibility and a renewed sense of pride.

Three months later, his company was up 70% year-over-year without him meeting clients himself anymore. They were attracting top producers from competing brokerages. And most importantly, he was winning on his own terms – present with his family, free from constant stress, while his business thrived.

By changing where he played, everything shifted. After months of trying to optimize how he played, he realized he was working on the wrong level of his strategy.

Beyond Business: Where We Choose to Play

This principle extends far beyond business leadership.

I've seen people struggle for years trying to make a relationship work through endless communication exercises and date nights, only to discover a profound sense of peace when they finally acknowledge it's time to separate or divorce. The relief that comes from changing where you play can be immediate and transformative.

I've watched families exhaust themselves juggling competitive travel sports schedules – hiring babysitters, coordinating complex carpools, missing weekend after weekend of downtime – until someone finally asks, "Is this game actually worth playing at this level of intensity?" The space that opens up when they choose a different path often reveals possibilities they couldn't see before.

I've even experienced this myself, spending years trying to moderate my relationship with certain social circles that left me feeling drained and inadequate. I tried showing up less frequently, setting time boundaries, even preparing conversation topics in advance. Or predetermining how many drinks I might allow myself to have. None of it worked until I finally recognized I could simply choose to play in different social environments altogether.

These aren't easy decisions. They involve grief, uncertainty, and fear. They require facing the sunk cost of time and energy we've already invested. But they also create the possibility for alignment that no amount of tactical optimization can achieve.

Signs It's Time to Change Where You Play

How do you know when it's time to question where you're playing rather than how you're playing? I look for these indicators with my clients:

1. Your efforts to change aren't moving you closer to your definition of winning. Despite implementing new strategies and systems, you still feel stuck in the same patterns.
2. Your resentment continues to grow. You find yourself increasingly frustrated, not just with circumstantial challenges but with fundamental aspects of your situation.
3. Your self-talk has become consistently negative. The voice in your head regularly expresses discontent, doubt, or resignation about your circumstances.
4. You've tried multiple approaches with minimal improvement. After attempting two or three new ways of doing things, you're still experiencing the same problems.

When tactical solutions repeatedly fail to create meaningful change, it's time to consider that you might be playing the wrong game entirely.

The Courage to Change Games

I think about courage differently these days. Sometimes the bravest thing isn't persevering against all odds – it's being willing to walk away and start fresh.

If you're feeling stuck, try this simple exercise with me. Take out a piece of paper and write down where you're currently playing – your job, your relationship status, where you live, how you spend your time.

Now, rather than immediately jumping to how you might improve your approach, ask yourself: What are two completely different environments where I might play instead? What would it look like if I made a significant change?

Don't worry – this is just an exploration. You don't have to act on anything yet. Just allow yourself the freedom to imagine alternatives.

Next, sit with your fears. What makes you hesitant about these alternatives? Get really honest. Sometimes our fears point to important considerations, but often they're simply protecting us from necessary growth.

Then, let yourself dream a little. If making such a change went extraordinarily well, what would become possible that isn't available to you now? How would your daily experience be different? How would you feel waking up in the morning?

Finally – and this is the question that often breaks things open – how will you feel two years from now if nothing changes about where you're playing? This question reveals the true cost of staying put.

When my mortgage broker client imagined himself in the same role, struggling with the same issues three years later, the physical response in his body was immediate. His face flushed, he held his breath. The prospect became unbearable, creating the internal tension necessary to overcome his resistance to change.

I've sat with clients as they've imagined their future selves, watching the subtle shift in their expression when they recognize a truth they've been avoiding. That moment – that small internal acknowledgment – often contains more power than months of tactical adjustments.

The Temporary Nature of Strategy

Here's the thing about changing where you play – it's not a forever solution. At some point, my mortgage broker client will hit a new ceiling, face new challenges, and need to reconsider his strategy again. That's the nature of growth.

The game isn't finding a permanent solution – it's recognizing when you're trying to solve the wrong problem. Sometimes the most profound transformation comes not from doing things differently but from doing different things entirely.

The question isn't whether you can succeed where you are – with enough force of will, perhaps you could. The real question is whether winning where you're currently playing will create the life you truly want.

Sometimes the bravest strategic choice isn't figuring out how to win at the game you're playing. It's having the courage to play a different game altogether.