FounderFuel: Mental models for founder survival in tough times

I did the math and felt my eyes pop out of my skull. “This could cost us north of $10 million” I thought to myself, “we could never pay that!” Our bootstrapped brand had only recently found success, and now we were teetering on the edge after finding ourselves embroiled in a legal situation. 

While I can’t go into details about the situation, suffice to say that there were some legal loopholes (since closed) which made our company vulnerable, and someone was sticking a knife in. It felt like extortion. I couldn’t believe it was happening.

We had just gotten our feet under us, only recently achieving the growth we’d been pursuing for years, and now it could all disappear overnight. For weeks as the situation unfolded, each morning felt like waking up with a 100lb vest on. I was angry – this was unfair! I was sad – everything we’d worked to build could be washed away. I was afraid – what about our livelihoods, and those who work with us? Emotionally, it was one of the more trying times of my life.

As founder, you may have your own experience of coming to the brink of failure, or maybe even crossing it. These things can take a toll on our lives, both professionally and personally. What you may not know is that the hardships of entrepreneurship can be made easier by changing how you think.

Hard times are guaranteed. Suffering is optional.

The ancient Stoics thought a lot about hard times and suffering. You could think of them as some of the first self-help gurus, way back in 3rd century BCE. A central tenant to the Stoic philosophy is that your perspective informs your experience. Let me explain. 

To borrow a metaphor from author Shawn Achor, say you’re in a bank and a robber bursts in. He’s waving a gun around and it goes off. The bullet hits you in the arm. Of the 50 other people in the bank, no one else is hurt. How do you feel about your luck in this situation? Your average Joe or Jane might be peeved about the odds of the bullet hitting them out of all the people there (2% chance), or about their poor timing in visiting the bank. A Stoic, on the other hand, would be glad – glad that she didn’t get shot in the head, glad that no children were hurt, and glad that she’ll live another day. She would fully appreciate that things could have been far worse, and she’ll be at peace with what happened (although she may reconsider where she banks). Which of these perspectives serves its owner more?

For startup founders, challenges, setbacks and failures are 100% guaranteed. Suffering, on the other hand, is optional. Suffering might sound like a dramatic word, but I’m using it as a catch all for anxiety, fear, doubt, stress, anger, frustration, sadness, and all the other negative emotions that come from the curveballs our businesses can throw. These negative emotions stem from your perspective.

Using tools of perspective, you can change how you view hard times to find freedom from suffering. Shifting your perspective can harden your resolve, help you enjoy the journey more, and even help you make better decisions free from the cloudiness of strong emotions. 

Tools for shifting perspective 

Below, I’ll describe a few different tools for shifting your perspective. You can think of these as mental models for wellbeing, based on 2,000+ year old Stoic wisdom.

Dichotomy of control

This model states that everything in life can be divided into two categories: things under your control, and things not under your control. Your goal is to understand where things fall on that dichotomy, and then to avoid betting your happiness on things that aren’t under your control. 

Here’s the kicker: the only thing you ever control is your actions. Everything else can be affected by chance or unseen variables. So the list looks rather one-sided, with your actions on one side, and everything else on the other. It’s risky to bet your happiness on things not under your control, so the Stoic view means trying to be satisfied (or not) based on the quality of your actions, rather than what ultimately happens.

Applying this view to my legal situation, I’d say “Whether or not my company survives is not under my control. What is under my control, however, is what I do to defend us. Therefore, I’ll try to care less about whether or not the company survives, and try to care more about going above and beyond to provide the most outstanding defense I can.”

This is great for wellbeing, but it’s also practically useful too. Focusing on what you can control (your actions) is the most direct way to getting what you want. I wouldn’t win my legal battle worrying about it, I’d win it by taking action.

HOW TO USE IT: 

When you’re facing a difficult time, try using this little worksheet I created here.

You can dive into dichotomy of control more on my blog here

Premeditatio malorum

This is the Stoic practice of intentionally imagining bad things that may happen in the future. While that may sound like a recipe for misery, it actually has the opposite effect: it reminds you that even the worst case scenario usually isn’t as bad as it seems, and it provides a sense of calm when bad things do eventually happen.

Using my legal situation as an example, I’d practice premeditatio malorum by imagining upcoming conversations with the opposition. In my imaginary story, I’d say the wrong things & make the situation worse. Our company would need to be shut down with our equity wiped out. I’d be back at square one. After the most distressing scene, the one where I am shutting the company down, I’d ask myself “then what”. I’d hopefully recognize that while it would be an exceptionally crappy day, it wouldn’t be the end of the world. I could try again, my family would still love me, the sun would still rise, and my favourite foods would still taste good.

HOW TO USE IT: 

Write out a fictional story describing the worst case scenario of the situation you’re concerned about. Do this without using emotive language, just stick to plain descriptions of events. After you reach the most distressing scene in your story, ask yourself “then what?”. Try to shift your attitude from, “what if this happens, how will I cope?” to “ so what if this happens, it wouldn’t be the end of the world”.

You can dive into premeditatio malorum more on my blog here

With adversity comes opportunity

The Stoics were a very resilient bunch. A major source of this resilience stems from how they viewed hardships. They saw hardships as necessary to reaching one’s full potential. 

Here’s a quote from Stoic philosopher Seneca that captures this well: “I judge you unfortunate because you have never lived through misfortune. You have passed through life without an opponent—no one can ever know what you are capable of, not even you.”

A life without real challenges is an unsatisfying life. We know this to be true intuitively. Would you want to watch a movie about someone who’s life was just gravy, from start to finish? Sounds boring. Yet for some reason, we still default into thinking that if everything would just go our way then we’d be happier. If we could just get that next round of funding, if we could just get back onto a growth trajectory…

We default into thinking that hard times are nothing more than something we must suffer through, but in reality they are an essential part of a satisfying life. 

You can choose to see your adversity more completely by recognizing that adversity always brings opportunity. Your job in this exercise is to update your view of your hardship, and to find any opportunity hidden within. 

A perfect example is the birth of weare3sixty. Founder Christina Richardson experienced a mental health crisis as a result of red-lining stress for years on end. While I’m sure this was a terrible thing to experience, that adversity was the main driver for the creation of this organization, which has now improved the lives of thousands of entrepreneurs through connection and support. Weare3sixty was not born in spite of the adversity Christina faced, but because of it.

I had a similar experience with my legal situation. It started me down the path of creating & collecting mental models for wellbeing, a toolkit of exercises like these that I’ve used in many situations since. Even if I could go back in time and sidestep the legal situation, I wouldn’t.

HOW TO USE IT:

When you’re facing a setback & feeling low, reflect on some of the greatest triumphs you’ve had in your life. Would they have been as satisfying if they involved no struggle? Try to find some peace in knowing that life is a never ending series of problems, but that it wouldn’t really be a rewarding journey without them.

Now, how can you turn this adversity on its head? Is there a way you could succeed not in spite of it, but because of it? Open your mind & consider if this setback brings with it the chance to develop new skills or explore new avenues. Can you use this to your advantage?

PS – we survived, the brand is still alive and kicking 🙂