Planning for Flexibility Instead of Certainty

I Don’t Think About Planning the Same Way Anymore

A few weeks ago, I was looking at flights to South Carolina for another visit with my mom when I realized how differently I think about planning now than I used to.

For most of my adult life, I approached planning almost like an engineering discipline. My calendar was structured weeks, even months, in advance. Work commitments, meetings, travel, deadlines, events, and personal obligations were all carefully mapped out and “hard coded” into place. Once something was on the calendar, there was an implicit assumption that the surrounding structure of life would hold long enough for the plan to unfold more or less as expected.

Well, that’s no longer how I move through the world…

Over the past several months, I’ve been traveling from Portland to South Carolina every four to six weeks to support my mom as we navigate her memory loss. Increasingly, I find myself booking one-way tickets because I simply don’t know how long I’ll need to stay once I arrive. I need to assess the situation on the ground. How is she functioning? What appointments need attention? Is she steady emotionally? Is the house in order? Can I leave feeling reasonably confident that she’ll be OK until my next visit?

There’s something psychologically different about boarding a plane without a return date attached to it. It forces you to acknowledge uncertainty upfront instead of pretending it can be managed away through organization and preparation.

What I’ve realized through these trips—and through so many other experiences over the past several years—is that I no longer think planning is primarily about control. I think it’s about resilience.

Earlier in my career, I believed good planning could significantly reduce risk. And to be fair, preparation, strategy, and discipline all matter. Strong execution absolutely matters.

But repeated disruption changes your relationship with certainty — layoffs, entrepreneurship, economic downturns do that. Caregiving certainly does that.

At some point, you realize that even the most thoughtful plans are still operating inside systems you cannot fully control. On the business front, companies restructure, markets shift, and priorities change. In your personal life, health changes, family circumstances evolve. Entire seasons of your life can reorganize themselves around realities you never anticipated when you originally mapped things out.

For a long time, I thought planning meant creating the clearest possible path from Point A to Point B. Now I think planning is less about predicting the path and more about building enough flexibility into your life to absorb the inevitable turns along the way.

That shift has changed the way I think about almost everything.

Professionally, I’m less attached to rigid timelines than I once was. I still care deeply about goals and execution, but I’m more interested now in building structures that can survive volatility. That includes diversifying income streams, creating multiple professional pathways, investing in relationships and skills that travel well across industries, and being honest about when something needs to evolve instead of forcing it to remain what it once was.

Personally, the shift has been even more profound. There’s a humility that comes with recognizing that life will eventually disrupt even your best-designed systems. The answer is not to stop planning altogether. It’s to stop confusing planning with certainty.

Ironically, I think this mindset has made me calmer, not more anxious. When you stop expecting life to unfold exactly according to plan, you spend less energy resisting reality when it changes. You adapt and recover faster. You become more focused on stability and resilience than perfection.

That realization has been quietly shaping the early thinking behind a larger idea I keep returning to: the plan is the pivot.

Not because planning is useless, but because the most important pivots rarely arrive as dramatic, cinematic moments. More often, they emerge gradually through the choices we make when the original assumptions no longer hold.

These days, I still plan and prepare carefully. I’m still a fan of structure. I just no longer believe the purpose of planning is to eliminate uncertainty. I think the real goal is to build a life capable of navigating it.