Last week I was on a call with a friend and the many ways he’s sabotaging himself were so painfully obvious.

For example, he’s not asking people to include his project in their blog posts since he doesn’t want to annoy anyone and feels like the project is not quite ready yet.

Or, there’s a beautifully simple playbook that leverages scripted interviews he could use to grow his project. But again, he’s not doing it since he feels like he would offend people by asking everyone the same questions.

You know, these kinds of things.

After the call my head was spinning: What if I’m doing the exact same thing?

I know that like most people, I’m very good at coming up with plausible excuses for almost anything I don’t want to do.

And this is of course also what my friend did. He was immediately able to come up with reasons for why he’s not doing these things.

So I sat down and tried to put the spotlight on myself.

Step 1: Answering the Unasked Question

At the top of a blank piece of paper I wrote: How am I sabotaging myself?

After 15 minutes the page was already full. There were just so many painfully obvious examples.

• A year ago, a VC fund had invited me to help with their research. But I never joined their Slack after they sent me the link.
• My days are always 10x better when I’m starting it with a short meditation session and avoid filling my head with others’ voices for the first hour after waking up. But on most days I give in to the urge to check my emails and Twitter immediately after waking up.
• I know that I should spend more money to grow my projects and start outsourcing so that I can focus on high-leverage tasks. But here I am, reposting stuff I’ve written on Reddit all by myself.
• A person I’m genuinely looking up to had started to send me emails, offering feedback and advice. And what did I do? I simply stopped replying.
• I had a project with clear signs of traction. But instead of doubling down, I hopped on to the next project.

The list goes on and on.

Now I, of course, had “good reasons” in each of these cases.

• The VC fund just wanted to exploit me.
• These emails are urgent.
• This is what bootstrap entrepreneurs do. Only VC-funded startups waste money on ads.
• I wanted to write a perfect, thoughtful reply but then eventually it was too late to send any reply at all.
• The new project seemed like a much better opportunity.

Yes, I know, I know. These are all weak excuses. They are on exactly the same level as the reasons given by my friend.

Okay that feels like a good start. found the unasked question (”How am I sabotaging myself?”) and started to answer it as honestly as possible.

Now it’s time to identify the real obstacle that is blocking my progress.

Step 2: Separate Problems from Symptoms

Now it’s time to identify the real obstacle that is blocking my progress.

What stands out when I’m looking at my list is that there’s no clear pattern. The only thing my examples have in common is that I’m doing things that clearly stand in the way of further progress.

So each of these self-sabotaging actions is just a symptom, not the root cause. And to really solve the problem, I need to tackle this root cause, not just fight the symptoms.

For example, when you’re struggling with headaches and low energy, you can of course fight the symptoms by taking ibuprofen and drinking lots of caffeine. But eventually these temporary fixes will stop working and all kinds of unwanted secondary consequences (e.g. stomach cramps) start popping up.

To really solve the problem once and for all, you need to get to the root of it. In this example, a good place to start would be drinking more water and fixing your posture. At least, that’s what worked for me.

In fact, it took me years to uncover that my headaches and low energy were caused by dehydration and bad posture.

I of course had tried to drink more water and maintain a better posture. But since there was no immediate improvement and my headaches kept coming back, I gave up after a few days.

Another difficulty was that there were actually two root causes, not just one. Hence I had horrible headaches even though I worked on my posture and hence assumed this was not the solution I was looking for.

Only once I committed to drinking 2 liters of water every day and made a conscious effort to fix my posture for several weeks, I was able to solve the problem once and for all.

Now I wake up every morning and feel like I can rip the world apart and only very rarely get headaches.

This was kind of a tangent but it was important for me to reflect on this story as it contains many important lessons for the inner battle I’m starting now.

Most importantly, I’m under no illusion that identifying and solving the root cause of my self-sabotaging behavior will be easy.

Moreover, just as I did with my headaches, I did some reading to learn what others have identified as the most common root causes for self-sabotaging behavior. It’s usually a good starting point to assume that statistics apply to you.

As for most search terms nowadays, the Google results for “self sabotage” are a clickbait dumpster fire. But after a few hours of reading I got at least a few ideas that seem like good starting points.

Popular explanations seem to be things like fear of success, fear of failure, fear of rejection, or fear of loneliness. But to me these seem like symptoms too, not root causes.

The most likely root cause seems to be a lack of self-esteem/self-love. Yes, it feels extremely cringy to write this in a way that only remotely indicates that this might be my problem.

But that’s precisely why there might be some truth to it.

If you have deep issues with your self-esteem, you will subconsciously assume you simply don’t deserve success. Moreover, it’s better to keep your head down as otherwise, the chances that others expose your flaws are much, much higher.

You might have a carefully constructed confident self-image. But if below the surface of your consciousness you’re riddled by self-doubt, you will always fear this image will be shattered as soon as it’s hit by the cold hard light of reality.

For example, I might tell myself that I can achieve anything if only I ever really tried. That’s my confident, conscious self-image.

But if there are deeper issues with my self-esteem my subconsciousness will assume that this is simply not true and hence help protect my self-image. This is why it feels right to self-sabotage.

As long as I never really try, go all in and really test the limits of my ability, my self-image remains safely intact.

This makes a ton of sense to me. I’m able to see how these patterns could’ve entered my mind as a result of my childhood. Obviously this is not the right place to talk about my childhood traumas but suffice to say that I‘m definitely able to connect the dots.

Now here’s the catch. If a lack of self-esteem is the root cause of my self-sabotaging behavior, it has to be on a deeply, deeply subconscious level.

I’m definitely not riddled by self-doubt. At least on any conscious level. My mental baseline is positive and when it swings, it’s only up. In other words, I’m generally in a good mood and don’t experience episodes where I’m consciously doubting myself.

My self-talk is positive and confident and I don’t have to force my thoughts in that direction. I’m not putting on a mask for the outside world.

So what can I do to tackle the root cause?

Step 3: Tackle the Root Cause

First of all, I think that writing what you just read already helped.

Previously, I might have had some vague feeling that something like this is going on. But now after I was able to spell things out in a coherent way, my confidence has reached a level where I’m taking the issue seriously.

The process of writing crystallized the fuzzy ideas I had floating around.

What else can I do?

Right now, I haven’t found the answer yet. But I started to collect ideas and will report back once I’ve tried them.

Therapy. This is the most common recommendation. But it’s also quite vague. There are lots of different types of therapy and for each of them there are dozens of different ways of doing them. I have no doubts that if you can find the right therapist and approach this can work wonders. But that’s a big if.

I have several friends who were definitely worse off after visiting a therapist.

Here’s an analogy. Let’s say you broke your leg as a child and since then you’ve never really been able to run properly. So you go to a doctor and he tells you in order to fix your leg, he has to break it again. Now maybe the guy knows what he’s doing and there’s a good chance you’ll be finally able to run afterward. But it’s also possible that the guy is a quack and you won’t even be able to walk after the surgery.

Moreover, many forms of therapy only seem to tackle surface-level symptoms rather than focusing on the root issues.

So I’m not sure what I’ll do. If I can find the right approach and practitioner, I’d be happy to give it a shot. But I’ll have to do a lot more research first.

Journaling and Debriefings. I will add the question: “How am I sabotaging myself?” to my weekly reviews and possibly also to my daily evening debriefing.

Simply putting the issue into the spotlight on a regular basis will keep it top of mind and help me monitor if things get better or worse.

I’ll also add the question “Why am I sabotaging myself?” to give myself space to reflect on the internalized beliefs and patterns from my childhood. Like I said, I’m convinced that there’s a lot of value in seeing lingering thoughts being spelled out explicitly.

More Meditation. I currently already try to meditate every morning. After each session I get into this state where I’m able to observe myself like a third-person observer.

Since self-sabotaging behavior is so painfully obvious to third-person observers, it’s easy to avoid it as long as I’m in this state. And in the rare cases when it happens, I can simply call it out, label it in my mind, and this makes me stop it.

But currently, I’m not able to maintain this state for a full day. Hence I will add a second and possibly a third meditation session spread out through the day.

Affirmations and Incantations. These techniques are definitely a bit more esoteric and it’s easy to write them off as new-age nonsense.

But quite a few people I’m looking up to are swearing they work. And the downside is very limited. At most I’ll lose a bit of my time.

So I’ll start by spending 5 minutes each morning writing down positive affirmations about myself. The odds that these will eventually trickle down into my subconsciousness seems to me at least not to be zero.

Possibly even more powerful are incantations. These are affirmations with a physiological component. You use your body and your voice to embody the meaning behind the words. I also want to try those even though this is gonna feel very weird at first.

Closing Thoughts

I wrote everything you read just for myself. But I’ve decided to put it (with some minor modifications) online since I believe there’s some value in seeing how someone works his way through a problem like this.

Maybe it inspires you to try something similar.

Anyway, that’s it for now. I’ll keep you posted.

Jakob