Starting Over: Tragedy or Adventure?

10.05.20 09:03 PM By Heather Kleinschmidt

Ah, the promise of a fresh start. A new hero’s journey on which to embark. The dream, the danger, the potential — all of the unknown, wrapped up in a single new adventure.

In our lives, this takes form at various levels:

  • Transitioning to a new job, role, or even an entirely new career.
  • Trying out a new relationship or entering a deeper phase in an existing relationship.
  • Moving to a new town, or getting to know the neighbors or sites in our current town that we’ve never before explored.
  • Learning an entirely new skill or digging deeper into an our existing specialty.
  • Going on a vacation, whether to passively relax or actively explore.
  • Picking up a new book, whether for information or entertainment.

We’re story-driven creatures, and there’s something about new possibility that calls to us.

Without a sense of purpose or direction or adventure, we stagnate.


The Feeling of Starting Over

There are two main characteristics built into the experience of a fresh start: disorientation and intrigue. Newness is highly stimulating — it taps into our most primal brain region, grabbing our attention and letting our body know that this is important and requires engagement.

Stepping into the new makes us two things:

  1. The Newbie
  2. The Adventurer


The Newbie

The Newbie is out of his depth. He doesn’t yet have mastery in the new domain. She doesn’t yet belong in the community. The Newbie is at the bottom of the competence hierarchy and therefore at the mercy of the rest of the community, at least until mastery begins to develop.

When you do something new, you are — by definition — new. You don’t get the luxury of status. You don’t get the luxury of stability. You don’t know what you’re doing, and you don’t get to pretend you know what you’re doing. You’re at the bottom of the barrel, and if the world comes to an end, you’re the first one who gets fed to the zombies.

You’re the one holding everyone else back. You’re the one receiving charity. You’re the one pouring everything out and still barely keeping up (or not keeping up), while someone else might only put in half-effort and still will outperform you.

You’re also the one driving your own fate. If you don’t figure this out, you get left behind. If you don’t figure this out, things may actually fall apart for you.

Being the Newbie requires humility. You won’t make any real progress without it. When you’re new, you’re like an infant, incredibly dependent on the good nature of the others around you. If you don’t learn to integrate well in the new environment, you risk being left behind.

The Adventurer

When you do something new, you’re also the Adventurer. The Adventurer is driven by the vision of what could be. She’s driven by purpose. He’s driven by the desire to attain something he lacks.

The Adventurer is alive. The Adventurer has a transcendent purpose. She is experiencing, seeing, engaging, learning. She is there for a reason, and no impediment or friction will dissuade her from pursuing this new path.

As the Adventurer, you have the opportunity to lean into the thrill. You have the opportunity to make something become that doesn’t yet exist. You bring fresh insight. You have the space to really grow exponentially. You can take on totally new mastery and use it to do really cool new stuff.

Being the Adventurer opens up new horizons not only for you but for those around you who will see you go on this journey and may decide to set out on their own Adventure.

Being the Adventurer requires openness — both openness to the things you’ll encounter (that you’ve never encountered before) and openness to adapting your behavior in response to the environment.


The Narrative of Adventure

In his book The Seven Basic Plots, Christopher Booker discusses Aristotle’s assessment that there are only two ending types available that can resolve a story: the tragedy and the comedy.

The tragedy often begins with what appears to be nothing but good fortune. One thing after another goes well for the hero, and it at first appears that will never change. But then the hero’s trajectory turns downward — and never recovers. Down and down the hero goes, to an ultimate destruction.

The comedy, on the other hand, may begin in a number of ways, but rather soon, complication after complication pulls the hero into a tangled mess of frustration and pain. But then things begin to turn around… By the end of the story, the hero has not only attained the treasure or victory he sought, but he has lived a thrilling and meaningful life in the process.

Booker writes:

To say that stories either have happy or unhappy endings may seem such a commonplace that one almost hesitates to utter it. But it has to be said, simply because it is the most important single thing to be observed about stories. Around that one fact, and around what is necessary to bring a story to one type of ending or the other, revolves the whole of their extraordinary significance in our lives.

We need to live an adventure. It’s one of the pillars that give life meaning. But it’s important to consider whenever you embark on a new hero’s journey whether you’re setting down the path of a comedy or a tragedy.

Because tragedies are real. If they weren’t, we wouldn’t have them in our vocabulary. And real people live tragedies all the time. The scary thing is that many people never saw it coming — until it was too late.


Where Starting Anew Goes Wrong

Starting over can be an incredibly meaningful experience — when it’s done right. When you approach the new thing with both openness and humility, you live the Great Adventure that the new thing can be.

Not all new things are wise choices, however. There is a distorted version of starting over that generates only destruction, regret, tragedy.

This is the form of starting over that exists solely in the domain of immediate and non-intentional gratification. This is the False Adventurer— and this orientation in life is a non-starter.

We can know we’re operating from this perspective when we’re stepping into something new and we’re not able to identify a personal purpose for doing so. If we can’t articulate a personally-felt value associated with this new action, or if the only benefit we can identify is a short-term gain, it’s likely that this path is going to backfire in a big way… eventually (but not until later, which is what makes it so appealing).

If you’re telling yourself that “No, this won’t backfire for me — I know exactly what I’m doing; I’ve got this handled. And besides, it’s such a small thing. No way this becomes a big deal.” You're wrong. You’re just flat-out wrong, and you’re going to regret it. When you take on the path of the False Adventurer, you’re headed for tragedy.

The False Adventurer gets the reward — the thrill, the benefit — instantly, but then things start trending downhill. And without a value-grounded purpose for engaging with the challenge, the False Adventurer is likely to bail. Or to become bitter. Or domineering. Or a victim. Or some other unsavory type. And in the process, he has lost his path — his real Adventure — which can be much harder to rediscover once it’s been abandoned.

When you abandon your real Adventure for the allure of the False Adventure, it can be a painful road before you rediscover your true path of passion and meaning.

Any time you start over, it means you possess no mastery and/or no belonging within that realm for some time at the beginning. If you don’t have a well-grounded purpose that can stabilize you and fuel your progress, you’ll be left to wander from new shallow thing to new shallow thing — without purpose, without meaning. Only left to a tragic narrative.


Recognizing When It's Time To Start Fresh

While keeping that sobering reality in mind…

There's a real Call to Adventure that we must answer if we're going to live meaningfully.

We can know it’s time to start something new when:

  • Transitioning to a new job, role, or even an entirely new career.
  • Trying out a new relationship or entering a deeper phase in an existing relationship.
  • Moving to a new town, or getting to know the neighbors or sites in our current town that we’ve never before explored.
  • Learning an entirely new skill or digging deeper into an our existing specialty.
  • We feel a deep internal pull toward a new direction, and we can verify that the impulse is not for short-term gain. We can identify at least one deeply held personal value that is calling for us to step forward into this thing.
  • We are wholly confident that we are not taking this step out of avoidance of something else. Sometimes, we avoid the next step in our real Adventure because... well, it's scary. The Life of Adventure is not always easy, and it's not always pain-free. There is real struggle involved, and sometimes there are real losses and failures. These are the moments when the False Adventure can seem sooo appealing, and when we must remind ourselves that the False Adventure ultimately leads to tragedy.

Starting Over... the Right Way

The Life of Adventure is a constantly evolving story, and you'll be repeatedly stepping into new things along the way.

With each new phase, there will be unexpected twists and turns  some of them joyful, some of them painful, but all of them meaningful.

Whenever we step into a new phase, it's important to remember humility and openness  remembering that we are new and unseasoned here, and that we can learn and expand our identity and our understanding of the world.

To start something new the right way, our steps must be value-grounded. We must be able to identify a personally relevant reason for taking this action.

We also must know and remember that we're getting ourself into it. This won't be easy. Because this is new, we won't have high-resolution heuristics to guide our behaviors in the new reality (which is good  but also challenging). We're going to have to struggle through being the Newbie if we ever want to master the new reality.


The False Adventure is alluring, but it ends in tragedy. It begins strong and will seem like the best decision you’ve ever made — until things start to turn south. Then it becomes increasingly difficult to turn the ship around and get back on track.

When we hear the subtle but powerful call to real Adventure, however, we know we’re on the right track. When we step into something new while grounded in conscious value, we can not only endure the temporary suffering, but we can thrive in it. There will be a real struggle, where things seem to become more and more complicated — but as we keep our eye on the prize, our struggle will pay off and things will — eventually — work together for the good.

Each week, I do a deep-dive into the question of living meaningfully.

To receive the next publication, sign up below: