When Life Doesn’t Go According to Plan
What I’m Learning From Starting Over
Sometimes the bravest thing you can do is take a chance on love. And then the second bravest thing you can do is acknowledge when it’s not going according to plan and might need to change. This is more than just some 'big sky' idea from me. It's something I am living through in this season of my life.
The Risk I Took
Earlier this year, I did something that felt both terrifying and exactly right. After over ten years of friendship with someone I deeply cared about, we decided to explore becoming more than friends. I quit my job in Tennessee, packed up my car and drove back to California to move in together and build a life.
It was a leap of faith. A risk worth taking. An expression of everything I believe about life being short and love being precious. And I have no regrets.
Within a few months we both recognized that while we made wonderful friends, we were wired very differently when it came to living together and building a romantic relationship. As a result, I made the decision to move back to Tennessee and essentially start my life over from scratch.
I’m writing this blog article still very new to that 'restart.' I’m still processing the pain and grief. I’m still figuring out what comes next. And I’m doing exactly what I coach others to do when their plans fall spectacularly apart: I’m not trying to fix it or get over it quickly. Instead, I’m working to (and committed to) integrate it.
The Aftermath: What Starting Over Actually Looks Like
Let me be honest about what “starting over” means in practical terms:
I’m living temporarily with close friend while I straighten out my housing. I’m job searching in a market I left months ago. I’m rebuilding routines and rhythms that were completely disrupted. I’m navigating the awkwardness of explaining to people what happened when they ask how California is going. At times I still feel terribly embarrassed and sick to my stomach.
But more than the practical challenges, there’s the emotional reality: I’m grieving not just the relationship that didn’t work out, but the future I had envisioned. The life I thought I (we) were building. The hope I had invested. The friendship that’s now changed forever, even if we both are doing our best to handle the ending in our own way.
Some days I feel surprisingly okay. Other days I feel the weight of starting over at this stage of my life. Most days, I feel both.
And here’s what I’m learning: this is exactly what I’ve been talking about in my coaching work for years. Life doesn’t follow our plans. Loss comes in many forms. Transitions happen whether we’re ready or not. And how we navigate these moments matters more than whether we avoid them.
What I’m Learning in the Messy Middle
1. Taking the Risk Was Still the Right Choice
Even knowing how it ended, I wouldn’t undo the decision to take that chance. Living according to my values - recognizing life’s brevity, acting with courage, taking risks on love - doesn’t guarantee outcomes. It guarantees that I’m living authentically rather than safely.
The FLOURISH framework I developed includes “Finite” as the first element precisely because I believe we only get one shot at this life. Taking the chance on love, even when it doesn’t work out, honors that value more than playing it safe would have.
2. Integration Beats Elimination Every Time
My coaching approach is built on integration rather than elimination - the idea that we don’t “get over” our experiences, we learn to work with them in healthy ways. I’m living this principle right now.
I’m not trying to quickly move past this pain or pretend it didn’t happen. I’m not avoiding the grief or rushing toward “being fine.” Instead, I’m sitting with the full range of emotions - disappointment, sadness, embarrassment, hope, resilience, gratitude - and letting each one teach me what it needs to teach me.
This is messy. It’s non-linear. Some days feel like progress, others feel like setbacks. But this is what healthy processing actually looks like - not the sanitized version we often imagine.
3. Even Coaches Need Coaching
One of the most important things I’m doing right now is practicing what I preach about interdependence. I’m not trying to process this alone or “be strong” by handling everything myself.
I’m working with my own team. I’m staying connected with trusted friends who can hold space for my process. I’m using my own FLOURISH framework to assess where I am and what I need. I’m being vulnerable about the fact that I’m struggling sometimes.
I don't think of this as weakness - but as wisdom. It’s recognizing that we’re not meant to navigate major life transitions in isolation. The strongest people are those who build strong communities around themselves and actually use them when things fall apart.
4. Pain and Growth Can Coexist
I’m learning that I can simultaneously feel heartbroken about what didn’t work out AND excited about possibilities ahead. I can grieve the ending AND feel grateful for what I learned. I can hurt AND be okay at the same time.
This isn’t compartmentalization or denial - it’s the full integration of the complex 'human' experience. Life isn’t either/or - it’s both/and. I’m both sad and hopeful. Both grieving and growing. Both wounded and healing.
5. This is Exactly When Coaching Matters Most
And here's what I'm most recognizing in this season: the worst time to try to figure things out ALONE is when everything has fallen apart. This is precisely when we need support, perspective and the tools to navigate the chaos.
When our plans disintegrate, we’re often at the most vulnerable and least objective position possible. We cycle through the same thoughts, question every decision, struggle to see possibilities beyond the pain.
And it's in these moments that we need someone who can:
Witness our experience without trying to fix it
Offer perspective when we’re too close to see clearly
Help us distinguish between healthy processing and destructive patterns
Remind us of our own resilience and capacity
Hold hope for our future when we’re struggling to see it ourselves
This is what coaching offers! And it’s exactly what I’m using right now, even as someone who coaches others.
Why Now is the Perfect Time for Support
Sometimes people think they should wait until they have their situation “under control” before getting coaching. But we can all see that’s backwards. The best time to get support is when things are falling apart, not after we've somehow managed to put them back together on our own.
Here’s why coaching is particularly valuable during life disruptions:
1. You Get Tools in Real Time: Rather than trying to figure everything out through trial and error, you learn approaches and strategies you can apply immediately to what you’re facing.
2. You Avoid Destructive Patterns: When we’re in pain, we often default to unhealthy coping mechanisms. Coaching provides accountability and healthier alternatives during vulnerable times.
3. You Process More Effectively: With skilled support, you can move through grief, disappointment and transition in ways that lead to integration rather than getting stuck in cycles of rumination or avoidance.
4. You Make Better Decisions: When everything feels chaotic, having someone help you think clearly about next steps prevents impulsive choices you might regret later.
5. You Discover Unexpected Possibilities: Sometimes the ending of one thing creates space for something you couldn’t have imagined. Coaching helps you stay open to those possibilities even while grieving what’s ended.
What Integration Looks Like in Practice
You may be wondering... "What is Keith actually doing to integrate this experience rather than just survive it?"
Here’s what my process looks like:
I’m Feeling Everything: I’m not rushing past the sadness, disappointment or embarrassment. I’m also not wallowing in them. I’m acknowledging each emotion as it comes, learning from it and letting it move through me.
I’m Using My Support System: I’m in regular contact with my own coaches, staying connected with friends who can hold space for my process and being honest about when I’m struggling versus when I’m okay.
I’m Maintaining Self-Care Basics: Even when I don’t feel like it, I’m walking, eating reasonably well, maintaining sleep routines and doing things that support my physical and mental health.
I’m Staying Present: Rather than obsessing about what went wrong or anxiously planning every detail of what’s next, I’m trying to stay present to this day, this moment, this step.
I’m Looking for the Learning: I'm not doing this in an “everything happens for a reason” way, but in a “what can this teach me about myself, relationships, resilience, and what I want going forward?” way.
I’m Holding Space for Both/And: I can miss the relationship AND be glad I took the risk. I can feel sad about the ending AND excited about rebuilding. I can be disappointed AND resilient. All of these can be true simultaneously.
An Invitation
If you’re reading this and finding yourself in a similar place - a place where life didn’t go according to plan, where you’re starting over in ways you didn’t anticipate, where the future you envisioned has dissolved - then I want you to know a few things:
1. You’re not alone.
So many of us are navigating transitions and losses that others can’t see. The brave face we show the world often hides the rebuilding happening underneath. Others are going through difficulties also, I promise.
2. Taking risks that don’t work out doesn’t make you foolish.
It makes you courageous. It means you’re living according to your values rather than playing it safe. The outcome doesn’t determine the wisdom of the choice.
3. This is exactly when you need support, not after you’ve “figured it out.”
The middle of the mess is the perfect time for coaching, therapy, community and for the tools that can help you navigate with greater clarity and health.
4, Integration takes time and doesn’t follow a linear path.
Some days will feel like progress, others like setbacks. This is normal. Healing and growth happen in spirals, not straight lines.
5. Your capacity for resilience is greater than you think.
You’ve survived 100% of your worst days so far. You have everything within you to navigate this transition, especially with the right support.
Where I Am Now
As I write this, still just a short time into starting over, I’m still very much in process. I don’t have everything figured out. I haven’t “arrived” at some place of perfect peace and clarity.
But I’m okay. More than okay, actually. I’m learning. I’m growing. I’m integrating one of life’s painful but important lessons about risk, love, compatibility and resilience.
I’m using every tool I teach others to use. I’m practicing what I preach about vulnerability, community, integration and healthy evolving. I’m proving to myself (and hopefully demonstrating to others) that the coaching approaches I offer actually work - even in the messy middle of starting over.
And I’m more convinced than ever that the times when life falls apart are exactly when we need support the most. Not because we’re weak or broken, but because we’re human and we’re not meant to navigate major transitions alone.
Your Next Step
If you’re in the middle of a similar experience - where plans have fallen apart and you’re figuring out what comes next - I’d be honored to walk alongside you in that process. Not because I have all the answers (I clearly don’t), but because I know what it’s like to be in the messy middle and I know what tools and support actually help.
Sometimes the most valuable guide is someone who’s walking a similar path and can say “I’m in this too, and here’s what’s helping me navigate it.”
If that resonates with you, let’s talk. Contact me at keithpagecoaching@gmail.com or (949) 701-3631 for a free consultation where we can explore how coaching might support your journey through whatever transition you’re navigating.
Because life not going according to plan doesn’t mean you’re doing it wrong. It just means you’re living fully, taking risks and being human. Congratulations and welcome to this journey. And sometimes the best thing we can do when plans fall apart is walk the path forward with someone who understands.
Keith Page is a professional coach specializing in crisis, grief, burnout, and major life transitions. He helps people integrate difficult experiences into authentic, resilient living—not by having it all figured out, but by walking the path alongside others who are navigating their own journeys of transformation.
