You Can’t Have True Success Without Alignment

StevenMiyao
2 days ago
5 min read

Updated: 1 day ago

Exploring fear, clarity, midlife thresholds, identity shifts, and the courage to choose alignment over momentum — with Ret Taylor

Spotify, Apple Podcasts, Substack

What happens when the life you've built starts to feel disconnected from the person you're becoming?

That question shaped my conversation with Ret Taylor, a successful entrepreneur who sold his business to pursue a deeper, more personal calling. He pivoted to work with leaders, founders, and seekers who feel called to step away from the noise and reconnect with the person beneath their identity by taking them into nature. He pivoted as he grew aware that success, on its own, was no longer enough; it needed to align with who he really is.

In this episode of The Midlife Remix, we explore what it means to reach a midlife threshold—a moment when the momentum that’s carried you this far no longer feels like the right guide. Ret’s story is about what happens when you stop striving long enough to ask: Is this still mine? Or am I just continuing out of habit?

We covered a lot of ground together:

How fear shaped his early identity and fueled decades of achievement
What clarity feels like when you have it
The discomfort of letting go of what works, but no longer fits
The power of solitude and silence to help you listen differently
And the discipline it takes to choose alignment over momentum

A Childhood Vow That Set the Course

Ret’s story begins in a bus station, in the middle of winter, with his mother and two younger sisters. They were moving again, cold, hungry, and uncertain. At ten years old, he made a vow to himself: I will never be in this position again.

“That night set a tone,” he told me. “I decided I would learn how to do hard things. I would work, push, prove, whatever it took to avoid that kind of instability.”

And that’s exactly what he did. He built a career from resilience. He became what the Enneagram calls a “3”—a high-achieving, goal-oriented performer. He succeeded. And for a while, that success felt like safety.

But over time, fear stopped being a helpful motivator. It became a weight.

“It was with me for 35 years,” Ret said. “And even when I started to sense it wasn’t serving me anymore, I was afraid to let it go. I wondered, If I’m not driven by fear, will I lose my edge?”

The Clarity of Letting Go

Change didn’t come in a single moment; it came in layers. First, there was the retreat he led in the Colorado mountains. He showed up without a script or presentation, just himself, and felt more in flow than he had in years.

“There was ease, confidence, and this sense that I was doing what I was meant to do,” he said.

Then came a multi-week expedition to Denali. One night, at 18,000 feet with a storm approaching, he lay in his tent, fists clenched, wrestling with whether to push toward the summit or turn back.

“That was when I realized I’d been white-knuckling my whole life,” Ret said. “Rowing upstream, trying to control every detail, every outcome. I saw it clearly in that moment—and I let go.”

He describes seeing the oars fall from his hands, metaphorically and mentally, and letting the river carry him—trusting that it would take him somewhere better than all that striving ever had.

This wasn’t about giving up. It was about choosing a different kind of strength.

Midlife as Threshold

We often think of midlife change as a crisis. But more often, it’s a threshold, an in-between place where we’re no longer who we were but not yet who we’re becoming. It’s uncomfortable because the old story is still running even as we begin to question it.

Ret’s work now centers on guiding people through that space—using solitude, stillness, and a structure that indigenous people call a vision quest.

Participants spend several days alone in nature, fasting and unplugged, with no distractions, not even books. It’s not a “suffer-fest.” It’s about removing the noise long enough to hear yourself again.

“Food is a distraction. So are our phones. Even thinking too much can be a distraction,” he said. “When you remove all that, what’s left is what’s real.”

The core of the experience is what Ret calls:

Reconnect — to the part of you that existed before the roles, goals, and expectations.
Refine — by letting go of the patterns and beliefs that no longer serve.
Rise — not to become someone else, but to fully inhabit who you already are.

Why It’s So Hard to Choose Alignment

We both agreed: it’s not easy to let go of what's working, especially when it’s been working for a long time. There’s a risk in changing. But there’s also a cost to staying.

“We’re often afraid that if we stop pushing, we’ll lose our identity,” Ret said. “But what we find is that something else comes in—something quieter, but more sustainable.”

For many high performers, the discomfort isn’t just in change, it’s in not knowing what comes next. We’d rather keep rowing than sit in the uncertainty of drifting.

This Is the Work

The conversation reminded me of something I say often in my own coaching practice: success without intention eventually becomes misalignment.

We can run at full speed for years before we finally stop and ask why. And when we do, it takes courage to listen honestly to the answers.

“Sometimes the moment that feels like unraveling is actually a re-entry point,” Ret said. “A way back to the parts of us that got buried under all the striving.”

A Few Questions to Sit With

If you're at your own threshold, consider:

What fear has quietly shaped my decisions more than I’ve realized?
Where in my life am I continuing out of habit, not alignment?
What might I hear if I gave myself real silence?
What would it look like to trust my own direction?

Ret’s upcoming book, The Vision Quests (2026), will explore these ideas even further. I’m looking forward to continuing this conversation with him when it’s released.

But for now, what I took away most was this: The cost of continuing without clarity is often higher than the risk of starting over.

Success is only meaningful when it reflects who we are, not just what we can do. And alignment isn’t a destination. It’s a daily decision to live on your own terms.

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