Existential Wednesdays


Aspiring and new entrepreneurs are frequently told of the mental challenges that accompany the entrepreneurial journey. Indeed, while the highs are exhilarating, the downs can be grueling and debilitating. The experience is akin to riding a colossal roller coaster—a sensation that may not fully resonate with you unless you’ve personally experienced it.


In my recent conversations with acquisition entrepreneurs, I have talked about what we used to describe as “Existential Wednesday” when Searchfunder was getting off the ground.

What is an Existential Wednesday? It’s a moment that doesn’t adhere to any calendar schedule; it can emerge unpredictably, on any day, at any hour. For some people, the moment happens like clockwork, but my experience is different. It could happen at 2 pm on Tuesday or on a Thursday evening during a meetup or conference.

My routine might be proceeding flawlessly, and I might feel like I am seamlessly executing against my plan. Suddenly, without any forewarning, an event or thought plunges me into a profound reassessment of my entire life’s worth of decisions. I’m talking about choices stretching back to when I was about 16.

Every. Single. Choice. I’ve ever made is up for harsh scrutiny. As I write this, I’m fully aware of how it may sound, especially coming from a graduate of MIT, Harvard, and Stanford. Yet, that’s the reality of my Existential Wednesday.

In essence, an Existential Wednesday reduces you to the shell of your being. It brings forth the questioning of whether your endeavor, the very pursuit you’ve dedicated so much of your life and soul to, should continue forward even for one more minute. This introspection isn’t just a trivial matter. Given that we, as entrepreneurs, often intertwine our identities with our businesses, the impact can be especially profound and destabilizing.

It is not pretty. It’s not fun. And, if not handled well, it’s not productive.


Over time, I feel like I’m gradually honing my skills at recognizing the onset of an Existential Wednesday—though it remains a cunning and elusive adversary. Before I can grasp what’s happening, I might find myself mired in self-doubt and recriminations. It stuns me before I even know what hit me.


Initially, these episodes could engulf an entire day. Now, armed with awareness and a few mental strategies, I often can cut down the time spent in the turbulence of Existential Wednesdays.

First, I assess my physical state: Am I tired, hungry, or in discomfort? Venturing too far into an Existential Wednesday while grappling with basic needs is a surefire recipe for emotional doom. Thus, I perform a comprehensive wellness check to confirm that I haven’t overexerted myself, that I’m healthy, and that my fundamental needs for sleep, nutrition, exercise, and relaxation have been met.


Next, I evaluate my mental process: Am I aimlessly spiraling, or actively seeking solutions? It’s crucial to distinguish between futile worry and the necessary haze of pursuing a solution to a specific problem.

Am I just spiraling through issues, fears, concerns, and self-doubts? Or, am I stuck on a specific issue that if I could “phone a friend,” I could perhaps get some help?

As it turns out, more often than not, I am problem-solving. Buried in the muck of my consciousness is an intractable problem that I am trying to solve. I just need to sift through that muck to figure out what exactly is the question. If I can’t ascertain what is gnawing at me, I will ask, “If I could wave a magic wand, what would I fix right now?” Invariably, calling my one friend who knows the subject provides an avenue to something I can experiment with as a solution.


Altering my environment often provides significant relief and a path toward problem-solving. It’s nearly impossible to not feel joy watching my two poodles happily swishing their tails on an unexpected afternoon stroll around the block. By the time we’re back at my office, I have a renewed sense of energy and vigor.

Could be:

  • Going for a stroll
  • Walking the dogs
  • Hopping on a bicycle
  • Engaging in a workout session

Whatever you choose, a change in scenery can remarkably diminish the duration and intensity of Existential Wednesdays.


If none of those options work, I reassess the business: Does the business case still make sense? If something has changed, what is it? Typically, the fundamentals behind the business case remains sound and unchanged. However, on occasion, answering the question helps me identify shifts or emerging trends needing my immediate attention.


As an entrepreneur, you’ll want to come to recognize your version of the Existential Wednesday and develop plans for how you can best navigate the experience. For instance, I’ve heard some searchers say that they also try to manage the highs of the search experience to not let them get too high to help buttress the lows. At this stage in creating Fetch Strategies, I tend to celebrate every high as a win.


If you do find yourself frequently wrestling with Existential Wednesdays, it’s imperative to seek the necessary resources to safeguard your mental health and overall well-being.

I’m still learning to navigate my own. I am sure others have wonderful tips and strategies, so please feel free to comment and share them.