A Time for All Things: Knowing When You’re Ready

Our Quest for Purpose

During a recent podcast discussion, our conversation turned toward the concept of “Following the Signs.” Those of you who know me or follow what I write, know that “following the signs” is a core tenet of my personal philosophy and frequently comes up in conversations, posts, and presentations. I believe it continues to resonate because we all struggle with the future. What should I be doing? When should I be doing it? Is this the right path? Am I the right person? Is this the right place?

Often, our struggle with the future revolves around our more elemental quest for a sense of purpose. We alone among animals are gifted with the self-awareness to be concerned, not just with what needs to be done to survive, but also with our own fulfillment or self-actualization. Along with such self-awareness comes the imagining, planning, hoping, dreaming, willing, and behaving in such ways as to attain our higher state of being. We want to move with what William Blake calls our “firm persuasion” toward that state of fulfillment. Such aims give us, and our life, a sense of purpose and, hopefully, move us to attainment.

Alas, purpose is rarely so obvious, measurable, or tangible. The “why” of our existence will likely take a lifetime to discern and will evolve continually along the way. Even clear cut “why’s” such as choosing to live a life of silent, meditative, prayer in a monastery or focusing on a mission to shelter and feed the homeless will undoubtedly evolve along the way. Neither we, nor the paths we choose, remain static. The sands of our journey are continually shifting under foot. We begin to discover that purpose is more a reflection of our personal philosophy, moral compass, world-view, or religious priorities than a finite point along a curve. It is a collection rather than an object.

Once we understand that our “why” is a collection rather than one thing, then we can start to break those actions, objectives, and situations down in a more meaningful way. We can start to look for purpose in the things we do rather than lose ourselves in some grander sense of ultimate being because that ultimate being is formed from all of the little things we do along the way.

Trusting the Path

What is the right path for me? What should I be doing? When should I be doing it? Am I doing what I should be doing? Self-awareness can be such a curse! Our introspective journey can be maddening because it so often yields more questions than answers. The bottom line is: how do I know? We’ve been taught that “if you don’t know where you’re going, any road will get you there.” The message: know your destination, plot your course, go someplace with intention. Makes sense, right? We are smart enough to know what we want and create a plan to get it. Then all we have to do is execute and it will be ours.

The problem with our intense focus on “beginning with the end in mind,” is that, in a life offering so many great beginnings, middles, and ends, how do we know the right one? Obviously, if I want to end up on the beach, I pick a beach, map out the path, and head in that direction. Ahh, but which beach is right? Conversely, if I know which beach, how do I discern the best path? Do I want shortest time? Most interesting landscape? Traffic? Weather? Construction?

The curious thing about our destination-driven approach is that we don’t allow for what might happen along the way. What if I get pushed off course? What if my car breaks down? What if I change my mind and no longer want to go to the beach? We are often so focused on managing to our particular end that we miss things along the way: compelling side roads, points-of-interest, unforeseen opportunities, new places, new people, new signs. Along the way, we begin to realize that our plan is evolving and the control we sought is elusive. We learn that we have to release our grip on the way and the destination a bit and trust the path to get us where we need to be. Even if it isn’t where we first thought we were going.

Formed Along the Way

One of the curious things about watching for signs that indicate the right path is that they are often very hard to discern. There may be billboards hiding in plain site that we just don’t notice. The call to another direction might be more of a whisper than a shout. The reality is that we miss many more than we notice. The casual acquaintance. The unexpected, but inconvenient, invitation. The flat tire, road block, detour, or traffic jam that is so maddeningly annoying that we don’t see the oasis sitting on the horizon. We busy ourselves with the distractions that entertain and tune out more meaningful signals. Or, we only see the signals for which we’re looking because we already know the answer.

During our podcast discussion, my interlocutor asked me about when I first launched into the world of being an entrepreneur. He asked if there were signs. Yes, yes, yes! It look me a long time to see them but they were there. Why so long? Because I was looking for specific signs, the ones I wanted, or the ones I thought were the “right” ones. Then he asked me: “what role does experience play in following the signs?”

What a fantastic question! He is right, I had to have a degree of experience to see the signs, let alone be able to respond to them. The signs of our lives are progressive; they evolve as we evolve and are not static. As we change, as we grow, as we are formed into that next version of our selves, the indicators are changing right along with us. We are formed along the way and that formation enables us to recognize and respond to the next mission, opportunity, or barrier presented.

Knowledge is knowing of the things that might be valued, wisdom is knowing how to value them. We must realize that there is no shortcut, no quick answer, no “silver bullet,” when it comes to walking the path, recognizing the signs, and then responding to them. We have to learn, grown, and become all along the way.

Am I Ready?

I often describe the years before I launched Northwind as my time of “throwing myself against the rocks.” This captures my sense for how I approached career and work in those days. I kept chasing the same things, getting the same results, and living with the same disappointments. I kept throwing myself against the rocks rather than looking out to sea, to all of those places yet to be discovered, or possibly even considered. It wasn’t until I surrendered control, in the sense of my own predetermined expectation of purpose or mission, that I was able to see a new pathway.

Are you ready? To answer that, let me ask another question: can you see it? Can you see a different end? A different way? A different version? A different answer? You have to see it first. The sign can’t appear if you’re not ready. What is readiness? There is another form of surrender. You must be ready to surrender your assumptions on the beginning, the middle, and the end. There is no straight path and the course you set will not be the course you take. Sure, law school, an MBA, or the apprenticeship certainly show a pathway but that’s only a beginning. And possibly not THE beginning.

For the goal-obsessed, the single-minded, or the control freak, this kind of surrender is extraordinarily uncomfortable. You cannot will the result into being, manage to the final end, protect yourself from failure (or injury, or disease, or pain, or disappointment), or control your destiny. You can only begin, adjust, fall down, fall behind, and try again. Readiness is ongoing, evolving, and relative.

It’s Time

There is a time for every season and all things appear in their time. There can be purpose in everything you do and mission for everything you move toward. There can also be meaninglessness. You get to decide both in the way you consider them and act upon them. Are you throwing yourself against the rocks when there are new lands to be discovered? Are you listening for the whisper or waiting for the howling wind? Do you remain annoyed at the people or things that seem to be barriers or see them for what they might be: signs?

The time is now. Now to begin. Now to end. Now to consider. Now to pivot. Now to listen. Now to see. You must walk forth, even when the end is unknown. You must step out, even when uncertainty weighs upon you like an anchor. You must surrender the control you think you must have to the control of what you really need. You must trust that you will be formed along the way even though you have no earthly idea what that looks like or what it might produce. You must remember that you will be ready when the time comes and that the time will come when you’re ready.

As for me, what do I know? I’m still just a novice, struggling to see my own signs, surrender my own assumptions, and trust enough in the way ahead to take that next step. I suppose that’s how it’s supposed to be. Fulfillment really does lie beyond that next step. Or the next 1000. Or, perhaps, it really lies in feeling grateful for the chance to take the next one. Whatever it may be for you, I wish you purposeful sailing today in whatever direction you choose. Especially if the seas look rough.

Showing 2 comments
  • Jennifer+Gleckman

    Nailed it once again Mr. Berry. In every way imaginable, nailed it. Kudos, thank you and happy sailing. Do I throw on my life vest again this week, hold on for dear life and navigate the waters with cat-like reflexes, or pull a Leonardo Dicaprio and lean out over the bow, arms out, screaming I’m Queen of the Universe! Whatever I do, I do it with gratitude to have and to take the opportunity, yes! 🙂

  • Liz Thomas

    I feel like you just captured the last year of my life in this blog. One thing I can say is it may be hard to see a sign as a sign, but trust in your gut, trust in your prayer. Know when something just isn’t working or you feel like you’ve put so much into something and you’re constantly hit the brick wall, it may not be the WHAT you are doing, it might just be that it isn’t your WHY. Great read!

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