Yesterday, a first-time founder reached out to me asking for help with being their own biggest saboteur. Here's a paraphrase of their question:

Out of all the questions I field from first-time startup founders, this is the one I get most often.
Perhaps it shouldn't be a surprise: in my experience, the most successful founders are the ones who are incredibly self-aware. They are self-aware of their greatest strengths, but also self-aware and hungry to fix their blindspots. It's what separates them as winners from the rest of the losers, who are more keen to following the strategy of being ostriches sticking their head in the sand. Yikes.
Struggles are actually common growth signals, rather than failures. When founders learn to embrace the struggle and love the pain, it helps them push past fear of failure. This is the only way to be remade into the leader you've always wanted to be.
There are three things I recommend to every founder I work with: going through a paraphrase of The Work by Byron Katie, learning how to recognize cognitive distortions from Cognitive Behavioral Therapy (CBT), and Fear Journaling.
I'll explain each of these below.
Paraphrase of The Work
The Work is very simple, and I use an adapted version of it.
- When you're in fear, start by looking at the judgment you're making about someone else / about a situation.
- Ask yourself, "Is this true?" (It usually isn't.)
- Ask yourself, "Can I really know it's true?" (It's almost impossible to know that something is actually true.)
- Then, challenge: "What is a truer statement than the first one?" Try flipping it, reversing it, going with the opposite thought (see below.)
- Most powerful part of The Work: "What would my life be like without the initial thought?"
Here's an example. Let's say you're thinking, "The A-players on my team don't respect me or think I'm learning quickly enough as a leader to keep up with them and guide the company in a meaningful direction."
Let's take that initial thought and feed it through the steps outlined above.
- Is it true? "Yes," your fear brain replies.
- Can you really know it's true? "Well, no. I can't mind read."
- What's a truer statement than the first one? "My team does respect me. They do think I'm learning quickly enough. I am learning as quickly as I can. I spend a lot of time learning and leveling up."
True, true, true. Probably truer than, "My A-players don't respect me / I'm not learning quickly enough."
- What would my life be like without the initial thought? "I would feel so free. I would feel like an unstoppable leader. I would probably get out of my own way."
If you have a split second to do one thing when you're in fear or making a judgment on someone else, just ask yourself if it's true, and what is a truer statement.
There's something fundamentally powerful of transforming, "My team is in my way" into, "I am in my own way."
Cognitive Behavioral Therapy
Cognitive Behavioral Therapy (CBT) is a clinically proven form of psychotherapy used by many therapists around the world.
It is considered the gold standard for treating various mental health conditions, such as anxiety, depression, PTSD, OCD, and many more. Numerous randomized controlled trials (RCTs) and meta-analyses have found that CBT is super effective, often equally or more effective than medication for many conditions in the long-term.
The essence of CBT is:
- You spot when you are in fear mode, and notice what cognitive distortions you're employing.
- You then cognitively restructure your thoughts after recognizing the distortions.
- If you're avoiding something due to the fear, you go through exposure therapy to slowly reduce your anxiety around those situations.
For this write-up specifically, I'm going to focus on the distortions and restructuring parts. My observation is most founders get around to doing the exposure therapy part out of necessity.
Here's a list of the most common cognitive distortions we fall victim to. There are dozens of cognitive distortions - we use many of them automatically every single day. It's the reactive thinking, aka your amygdala.
Figure out your triggers and identify them. The sooner you're able to recognize your own patterns, the funnier it becomes when they show up. For example, the ones I personally fall victim to the most are:
- Catastrophizing. Everything is over.
- Black and white thinking. It's all or nothing.
- Crystal balling. I can see and predict a scary future.
- Mindreading. They probably think this about me.
There was a YC company many years ago called Quirk. Though they are no longer around as a startup, they have open-sourced the original code on Github, and you can make a fork of it to continue using it on your own. If you want to download the app to use, you can do so here.
I always liked their methodology of employing CBT though, and found it wildly useful in my own early startup journey days. Here are the questions Quirk would prompt you with:
- What is the automatic thought that you are having?
- What cognitive distortions are you falling into? (Select one, or multiple - usually, there are a few distortions that are fair-game in any distorted thought.)
- How can you cognitively restructure your thought? In other words, what's the non-automatic thought?
That's based on my memory of the app back in 2018-2019, but it's close enough that this will get you pretty far. Try it out and see what you think.
Fear Journaling
One of the reasons your fear holds you back is because your brain locks in more often on when things go wrong, than when things go right.
Every day, millions of things go right. You wake up, and you are alive. You have basic utilities and needs met. You take your workspace for granted. You have people who love you. You are in good health. And on and on.
But your brain locks in on the one thing that went wrong, or even the one thing that possibly went wrong (without even confirming if it's really wrong or not.)
Here's an example: your colleague didn't smile at you over a Zoom call.
Shit - do they hate you?
They must think you're dumb.
Did you do that thing that pissed them off?
Man, maybe someone on your leadership team said something to them, and now they don't respect you.
What did you do to piss them off???
Of course, later in the day, they smile at you and say, "Rough morning, right? My caffeine hadn't kicked in yet. Wild how we're crazy people without coffee, isn't it?"
You laugh to yourself and think, Oh, they just didn't have caffeine yet. But then just as quickly, you move on and forget you had this fear in the morning that your colleague hated you.
We allow our fears to win, primarily because we don't take the time to affirm when it is, in fact, wrong.
Fear journaling changes that. It allows you to make a running log of how often your fear is inaccurate. At worst, your fear is wildly blown out of proportion. And at best, it's just flat-out wrong and lying to you.
Here's how to fear journal:
1. When you have a fear, write it down.
Write the story you are telling yourself. That's all it is. By framing it as a story, it allows you to recognize that just because you had the thought, it doesn't make it gospel, fact, or even true. It's just a story your brain made up.
Allow yourself to write it all the way down to the core fear. For example, in the scenario given above, if you were fear journaling it, you might say:
- This person doesn't like me
- They must not think I'm good at my job
- What if I'm no longer in a position for growth?
- My boss will fire me / no one will want to invest in my company
- I'm going to be a failure and no one will want to be my friend, and then I'll die alone.
Your fear journaling will usually end with something that sounds like: I'll die alone, I'll be unloved, no one will ever want to work with me ever again, I'll be a failure and never recover, etc.
These are our core fears: all humans want to be loved, respected, and understood. Outside of true psychopaths and hardened sociopaths, every person has these fears at some point. This does not make you weak. It makes you human.
The more honest you can get with yourself on what you're really most afraid of - being unloved, unwanted, alone, a failure, shunned - the more you can shift out of reacting and into responding.
2. Then, identify your cognitive distortions.
Remember the CBT stuff above? It comes into play here.
Where am I making assumptions, guessing, projecting, or catastrophizing?
3. Make a bet with your fear.
This part is really important: write down what you think is more realistically the case. Here's what I think is probably more accurate than what the fear is telling me.
Allow your non-fear brain to govern what you actually do. This is the part where you choose to respond, rather than react. It is shifting away from fast thinking, into slow thinking. You are using the prefrontal cortex in this state rather than your lizard amygdala brain.
4. Revisit the fear later.
Let life play out. If you're afraid of a specific event or occasion in time, evaluate once the event has passed. If it's a general fear with no real deadline, evaluate after a few days or weeks.
Revisit the fear you wrote in the past. Was it true? Was it a lie? Was it exaggerated?
This will create a running log of the sheer number of times your fear is wrong. You will likely laugh at the absurdity of some of the things you were afraid of.
If you want proof that this works, think back to a time when you felt very afraid, a few years ago. You might have thought your life was over. You might have hated the people you had to deal with. Perhaps your investors wanted to screw you over. Maybe you had an ex-boss whose guts you hated. Maybe you thought your co-founder had it out for you, that they were here to ruin your life.
With time, the fear fades and allows us to see our situation with more sober eyes.
In hindsight, if you are being very honest with yourself, it is likely you will be able to say, "Yes, that time of my life was stressful, and I was scared, but my reactive behavior probably created a lot of the problems I dealt with."
Or, you might say, "Yes, that time of my life was stressful, and I was scared, but it actually isn't so bad in hindsight...mostly because those people/situations/things don't really matter much to me today."
That is your unofficial fear log telling you that your fear is often exaggerated or wrong. Now, go write it down, and build a real fear log.
I suspect you will do this for about 1-2 weeks, and then stop. This is because if you are doing this properly, there will be many incidents in your personal and work life that show up daily where you are triggered into an anxious or afraid state of mind. You will have multiple logs and entries by the end of the week. And you will see just how wrong so many of them are.
I once had a coachee who did fear journaling, and he lasted about one week. The following week, he told me the most powerful part of fear journaling was realizing how often he was holding his company back and not swinging hard enough. The fear journaling caused him to make a huge pivot in his company, which sent the company's DAUs soaring higher than they could have ever imagined.
What could you do if you weren't afraid?