What Is the Valley of Despair for Entrepreneurs?

The "Valley of Despair" is a term taken from a well-known graph used to outline growth and learning in any single skill. As the graph goes, you get started on your journey, all seems well, and you trend upward with a false sense of "I know what I am doing" - only to realize how much you don't actually know. As the graph shows us, you then trend down sharply into the valley of despair, and over a long period of time begin to trek back up this metaphorical hill until you reach your final goal or mastery.

For those seeking their own path, this graph covers more than just skill progression. It applies to your entire trajectory.

Over the longer span of your career, the graph isn't a nice, clean curve going up, down, and then back up. It is a series of what I call mental ruts. They aren't as harsh as full-blown rock bottom, but they are heavy enough to make you question if you are really doing what you want to be doing: Should I pivot? Is this team right for me? Do I actually need these people?

Now, this may sound like the occasional creep of self-doubt making its way into your mindset. But the pivotal difference with this feeling of mental bogging is that I do not doubt my own capabilities. I am just doubting if the current step in my trajectory is where I think it should be - specifically: Why am I not further ahead?

Why You Can Feel Stuck at Any Stage of Your Career

A mental rut may just be another way of describing personal angst with one's position in life. There is an accumulation of things that can trigger this internal fight, but using personal experience from my own trajectory, I have noticed there are really two distinct situations that bring this on for myself.

The first was when I was still working my sign-writing apprenticeship. I was waking up at 20 years old every day at 5 AM, driving through the quiet coastal town I lived in to go work with 50-year-olds still reliving their youth. Day after day after day. I knew I could do better and wanted to do better. I became so fed up with where I was in life that I was taking it out on the world around me and my friends, constantly waging an internal war in my head. That lasted until I finally decided to take action and change my position in life.

Secondly, the corporate world. For all the benefits of being in corporate environments and the executive positions you can hold within them - for example, I get paid to build products I think are most viable, meaning my own ideas, I get paid along the way, I get the upside in the form of equity and profit share, and I am protected from the downside since my own capital isn't on the line - yet I find it doesn't take much to get into that same state of a mental rut. Except here, it is typically brought on by frustration with others around me who I do not believe are as hungry as I am. Frustration becomes internal questioning: "Do I need these people?" or "I should just leave and go on my own." That then becomes a prolonged state of mental angst for the next week.

I use these two examples because to most people, they look like complete opposite ends of the spectrum in terms of positioning in life. But it doesn't matter where you are on your trajectory - whether you are a $14-an-hour apprentice or a C-suite executive - everyone and anyone has to deal with these mental ruts.

What Triggers Mental Ruts and Career Angst?

I think these moments of mental angst are most likely triggered by a deeper cause or an overarching mental mode that, once struck, puts you directly into this frame of mind.

For myself, my trigger state for mental ruts is almost always external things that create a feeling of a lack of control. As an unhappy 20-year-old, I didn't feel in control of my own life until I took control of it. Having made it all the way to C-suite roles, the slack in the chain of those around me causes that exact same feeling of a lack of control - because I cannot directly control other people's actions to progress toward the primary goal at my own faster speed.

A key to getting out of these unfavorable mindsets is to take a step back and look at the deeper cause:

• Is something creating the feeling of having no control?

• Do you feel like you aren't doing enough?

• Do you feel like the people around you are dragging their feet?

These can all be the trigger for mental angst. I haven't spoken to many entrepreneurs about this because, as you know from the internet, every entrepreneur online is perpetually stable, dedicated, and utterly driven. But in the real world, I cannot be the only one who feels this way from time to time, even when everything seems favorable on paper. If you face these ruts, reach out and discuss.

How to Avoid Poor Decisions in a Low Frame of Mind

The problem with fast-moving, driven individuals - to which you may be one - is that it can be very easy to take this mental rut and run with it, making poor long-term decisions.

At a level where you are fortunate enough to have options, the first bout of mental angst can have you automatically thinking: "I should pivot to another business," "I should leave and just do this myself," or "I'll call my recruiter and find a hungrier group of people."

In fact, I have had all those exact thoughts when going through these day-long internal conflicts. But you must stay grounded. Take an objective look at what's around you and where you actually are. Is there genuine ground to make a pivot? Has this mental rut brought on a real concern for your trajectory based on where you are (like the 20-year-old apprentice needed to solve), or are you just feeling a temporary lack of control over those around you while your underlying position remains highly favorable (like the corporate leader)?

A Field Guide to Navigating Mental Ruts

As I learn to deal with this onset mindset myself, I will write more and ideally provide better operational frameworks for handling or preventing it. But as a field guide written on a napkin:

Remember that it's normal to fall into mental bouts of "doom and gloom." Try to look for the deeper cause of these mental ruts - is it a lack of control, or the feeling of not doing enough? Take a step back and look at your position objectively. Has this been brought on by an actual cause for change, or is it relatively superficial in its depth?