The Dark Moments of Doubt: Learning Not to Quit

This is a moment every founder and business person faces. When nothing seems to be working in your business despite all of your team and your own superhuman efforts. When the investors aren’t returning your calls, customers are dropping out, that is if you even have any to begin with. Your family and friends are openly questioning you about this life path. 

Doubt starts to fill your mind and it’s so easy to quit. Especially in the late and darkest part of night. You are wracked with anxiety and wonder what to do. You are in this weird fugue state of panic and helplessness. It’s way more common than people think but few successful people talk about this. They actively try to forget or they want to protect their egos. 

I face this myself as an investor. Getting a bunch of NOs from potential LPs in your fund or when a bunch of your startups die. In one case, it was 4 in one week back in early 2022. You wonder what’s wrong with you. What you are missing. You really question yourself. 

And of course, as per the rule of 3, there usually are other small and big things that go wrong in your life. Your phone breaks, you have family issues or something else crappy in your personal life. It’s so easy to feel like every aspect of your life is going wrong. 

So what do I do to get past this? 

At that moment, you have to decide not to decide on anything. Important decisions should not be made when you are feeling down and especially when it’s late at night. I then meditate to calm my monkey brain. I also take some melatonin and try to get a good night's rest. I tell myself that tomorrow is a brand new day. 

And surprisingly, it works most of the time. My subconscious brain works at what was a previous intractable issue or problem. 

I do my morning exercise routine which gives me new energy to go forward. 

I review my vision board and mission which is a reminder of my why: why I do what I do.  I then focus on the small specific tactics to regain momentum in my life and business. Even if it’s a tiny movement back in the right direction. 

It could be a call to your team or biz partner. Or you reach out to an old or new client. Maybe you post new useful content on your social media. Or you publish a new post on your blog or newsletter. Every little bit helps. As Ben Affleck in the excellent sales movie “Boiler Room”: “Move around. Motion creates emotion.”

Taking smart action the next day is usually the cure that stops me from even thinking of quitting. This way I can treat my previous doubts like a bad dream that I can move on from.