How to Know When It's Time for Change in Your Life

When do you know it’s time to make a major change in your life? How do we find the courage to make the changes in our life we know are needed?

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Some say it's when the discomfort of staying the same finally outweighs the discomfort of change. Others believe it's a quiet moment of clarity that arrives unexpectedly, like morning dew appearing on grass overnight. For me, it was both gradual and sudden – a slow-building pressure that finally cracked the dam.

I had spent twenty years building a career and business that looked impressive on paper. But each morning, the weight in my chest grew heavier as I readied for work. Each night, I'd lie awake wondering if this was all there was.

The fear of failure wasn't just a concern – it was a constant companion. What if I left everything behind and discovered I wasn't capable of anything else? What if security was the best I could hope for? I couldn't remember the last time I felt truly alive.

Change requires both planning and leaping. I began with small steps – researching alternatives, having honest conversations with myself, getting out of debt, setting aside emergency funds. These all take time, but as I, and so many others have proven, they are possible. But eventually, there comes a moment when you must jump without knowing exactly where you'll land. For me, that moment came when the last of my debt was paid and I realized freedom to choose a less practical path was now possible.

The real risk, I've come to believe, isn't in taking the leap—it's in never jumping at all.

Looking back, I realize my definition of failure was fundamentally flawed. I saw failure as a destination, a final verdict on my worth. But what if failure is simply information? What if it's just feedback on what doesn't work, pointing us toward what might?

When I finally made the decision and took steps toward that fateful leap into the unknown, I had a moment when I felt brave. But bravery suggests an absence of fear, and fear was my constant shadow during those first uncertain months after I'd made my decision. What I had wasn't courage but clarity: the understanding that the pain of regret would eventually outweigh the temporary discomfort of uncertainty.

There were false starts and moments of panic. Days when I questioned everything. But there were also moments of unexpected joy—the kind that arrives when you're living in alignment with your deepest values rather than someone else's expectations.

I wish I could offer a neat formula for knowing when to make a life-changing decision. The truth is messier. Sometimes change finds us before we're ready, through loss or circumstance. Sometimes we must actively choose it, fighting against powerful currents.

What I can say with certainty is this: when you find yourself diminishing to fit within the confines of a life that no longer serves you, it's time to consider a different path.

When you catch yourself saying "someday" about the things that matter most, it's time to ask when "someday" might actually arrive.

The gap between who you are and who you're pretending to be creates a tension that eventually becomes unbearable.

I'm not suggesting everyone should quit their job tomorrow or make dramatic changes without preparation. That's recklessness, not transformation. What I am suggesting is an honest assessment of what's working and what isn't—a willingness to acknowledge when you've outgrown the life you've built.

For me, the journey began with small questions that grew larger: What would I do if money weren't a concern? What activities make me lose track of time? When do I feel most like myself? The answers might surprise you, or perhaps you’ve had the answers all along and fear held you back.

There will always be bills to pay and challenges to navigate. But what if you met each day with presence rather than resignation, with curiosity instead of dread?

What I've learned is that change isn't a single decision but a practice. It requires constant recalibration, honest self-assessment, and the humility to admit when something isn't working. It also requires the ability to ignore those whose negativity hold you back and commit to the path you have chosen. The courage to change comes not from a single burst of determination but from a hundred small choices, each one a decision to honor what feels true rather than what feels safe.

Sometimes I ask myself if I regret waiting so long to come to this great realization, and it’s a complicated question. Those years weren't wasted—they were necessary. They taught me resilience, gave me skills I still use today, and perhaps most importantly, they helped me recognize what I truly wanted. We need the dark to appreciate the light.

Following your bliss, I believe, isn't about seeking constant pleasure or avoiding difficulty. It's about balance—finding the path that speaks to your authentic self, even when that path includes struggle.

When we make decisions from fear—fear of scarcity, fear of judgment, fear of the unknown—we build lives that require us to be less than we are. But when we make decisions from a place of self-knowledge and truth, we create the possibility for wholeness, even if that path is more challenging.

Start with Small, Manageable Steps:

• First: Make a list of three of the most important things in your life that you cannot live or do without. Then, add two more 'wish-you-had' things.

• Second: Ask yourself if what you're doing now with your life allows you to fully embrace and nurture those essential things on your list. Are your daily habits, routines, and choices supporting the people, passions, and priorities that truly matter to you? If the answer is no—or even a hesitant maybe—it might be a sign that change is needed.

• Third: Identify one small action you can take today that aligns more closely with your core values and priorities, and where you want to be in your life. It could be as simple as setting aside time for a loved one, dedicating a few minutes to a hobby, adjusting your schedule to reduce stress, or taking the first step to build a foundation of a business you've always wanted. The key is to start small, so the change feels achievable and sustainable.

Remember, meaningful change doesn’t have to be overwhelming. By breaking it down into manageable steps, you build momentum and confidence, making it easier to navigate bigger shifts when they come.