Capturing Kairos

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The Hidden Struggles of Founders: From Inspiration to Identity Crisis

Many leaders experience isolation and loneliness, but for founders, the burden can be particularly acute. While, from the outside, many may perceive them as successful figures, they often face unseen challenges tied to their unique journey. I'm going to talk about the founders journey.

A company begins as a spark of inspiration. We all have these sudden bursts of inspiration - some of them better than others. What makes a founder is the person who knows what to do with the idea. At the very least they need to have people around them who can support them and make these dreams a reality.

So from the moment someone has an idea (and we've all felt this), they're flooded with excitement, purpose, direction, and confidence. But most of all, they believe they have found their value, consciously or subconsciously. Now this may ebb and flow over the course of business, but at the very root these are the prominent emotions. And "value" is the why.

While the company takes shape, something is happening in the founder as well. Founders pour everything they have into their idea until it's a company - from conversations, to financial modeling, to strategy, hiring or firing, and market fit. The idea slowly takes on a life of its own. First in thought, then in action, and eventually it becomes an identity.

And then one day it's over.


Whether it's by purchase, or failure, or retirement it's done. And because founders have spent all their time, energy, and effort pouring everything they have into this adventure, they may find themselves feeling lost or even depressed. Oftentimes they are lost and living in the past.

And this is emphasized, unknowingly, by those around them. The perception that close friends and loved ones have can be damaging; not out of malice but because they care so deeply about the founder. The founder has built a reputation with their success, but they also know the difference between success and failure is only a poor decision away. This adds stress to maintain perception.

On the flip side, if the venture is not successful everyone is watching their next move with judgment. Their next move is a make-or-break moment.

And so, those close to the founder don't understand the weight of what they may see as an insignificant question:

"What's next?"


Friends, family, and even strangers don't understand that the founder has likely spent sleepless nights ruminating this simple question, and more. Do these talents transfer? Will someone else find these skills useful? Can my health take another venture? Do people want my opinion? The ingredients were just right last time - can I replicate that? Is my career over?

This line of thought tends to tie a person's value entirely to their career, leaving little to no room for an identity outside of being a founder. Their mind is so busy doing and accomplishing things that they've never had a free moment to consider how they got there.

When the time comes to face themselves in the mirror - when they can no longer identify as the person they've seen themselves as for the last, fill-in-the-blank years - depression sets in. Grieving is required. Even if the founder has found relief or freedom after an exit, they still must tackle what's next. No matter the state of the exit. It's a loss of an identity. It's a turning point for better or for worse. It can feel like they're starting over.

This issue of internalized value being tied to external success is widespread, but it's particularly acute for high-functioning leaders. High functioning leaders often mistake their value as what they do instead of who they are. And by the time they realize this, it's often too late.

No matter who you are, at some point your body will no longer allow you to function at full capacity. It is inevitable. So what's left for a high-functioning individual if they can no longer function to meet their expectations? Identity crisis. Depression.

Here's the thing. Success and failure are perceptions. The perception of success and failure is fluid and can be self-defeating. It's vital for an individual to establish their own definition of success.

You may say, Meagan, success and failure are very clearly defined. A business has either failed or it is profitable. True, but this is conflating the individual and the company. We are not our business. Additionally, we often don’t get what we want, especially immediately. We get what we need. Sometimes we need to fail to move forward, that is part of the overall success journey.

Success is defined by the individual, subconsciously or consciously. They have either allowed outside influences to tell them what success looks like, or they've taken the time to define what success is specific to them.

I once met someone who lived in a teepee in the forrest living off the land. By their definition, they were a success. To be clear, I'm not telling you to live in a teepee in the forrest - unless you really want to.

My point is this: what the individual believes to be success should be built on their own values and not on the perception of others.

German philosopher, Arthur Schopenhauer said, "When you want to be praised sincerely, why be indebted to someone else? Praise yourself!"

If you are a founder, now may be the first time in memory where you have a quiet moment to reflect and what you find may scare you. Families are growing, health is failing, and everyone wants to know what's next - including you.

In the words of my business partner, Jacob Warwick, "You know too much."

Your background and experience demand that you see not just the tasks that need to be done but also the entire picture. You see the lows with the highs, the sleepless nights, the employees you'll have to let go, the lawsuits ... the list goes on.

This is a fear state.

You've lost the thing that's driven your value - your worth - but that doesn't mean you're worthless. You've simply misplaced your value in something that can be taken away from you. You are doing, instead of being.

Take a moment to realize that by trying something, whatever the outcome, you're already setting yourself apart from the rest. You've pushed yourself and exposed yourself in many ways, just as an artist does. You created something and you've shared it with the world more openly, and with more passion, than many artists. You are inspirational, whether you see it or not. What you have is a gift.

You've moved from the space of knowing how difficult running a business is to actually understanding it. This is a lived experience. It is irreplaceable.

Give yourself the time to explore what makes you happy. What's most important to you and your family. What gives you energy? What takes away energy? What went well and what didn’t work? What was your fault? How can you improve moving forward? What does less look like? And finally, what does success look like to you without any outside influence?

In the words of philosopher Michel de Montaigne, "No longer be concerned about what the world says about you but how you talk to yourself."

Success is a journey, not a destination. And for the truly successful, it's what you define it to be. To have others define success for you is freely giving up what you value.

Knowing your wants, desires, boundaries, and needs, will help you understand your own definition of success. Self-understanding is power, and no one can take that power away from you.

So what's next?