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Is Success Scarier than Failure?

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Images shot with Super-Takumar 55mm f1.8

The idea that success is scarier than failure is not a new one.

This post is not introducing a never-been-heard-before concept.

But it’s something I’ve been thinking about a lot recently, and that makes me want to explore it further.

I understand for some people failure means not putting food on the table or keeping a roof over their heads. And that probably is scarier than success.

I’m not really talking about that. I’m talking more about creating things. Be it art, a product, a side business, or even a blog like this.

Things that only cause change when they work; when failure means nothing changes. That’s the crux of the theory.

The reasoning goes along the lines of success bringing:

  • change
  • expectation
  • pressure
  • exposure
  • criticism
  • work

It means your life may take a new direction. It means people will expect more from you, and an increase in pressure on you to deliver.

It means being exposed to a greater audience, which increases the chance of someone criticising what you do. It can also increase your workload to a level you find unmanageable – unless you learn how to say ‘no’.

You know how many of these things failure brings?


For creatives and side-hustlers – or those who can afford to fail – failure brings comfort. It brings you the right to pat yourself on the back as you sit in your pants watching Casey Neistat or Steph Curry or whoever else is doing exactly what they (and maybe you) want to do every day.

Because at least you tried. God loves a trier. It’s not the winning, it’s the taking part. You’ll get ’em next time, champ.

Failure gives you license to massage your ego in your safe place while those who get success are the ones being torn apart by people happy to never try.

Which one is scarier?

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My (imagined) success being scarier than failure

The title of this post is a question – Is Success Scarier than Failure?

For me, the answer is ‘yes’.

I did some freelance writing for a while, and had the worst client acquisition system possible. That’s not to say I didn’t get any clients, but I had an awful way of going about it.

More importantly, I felt awful doing it.

It basically involved being a dirty spammer. Sending a cold introduction email, BCC’d to around 200 companies at a time. I don’t recommend you do the same.

The idea of success being scarier than failure came in what I wanted to happen with regards replies – if we take a reply as success.

I kinda didn’t want any.

No replies would mean nobody telling me to stop spamming them.

I needed work, but I’d wake up and hope for an empty inbox if it meant nobody criticising me. I wanted the endeavour to fail.

It’s ridiculous looking back. I was sending emails I didn’t want to send to people who didn’t want to receive them, and kinda hoping these people wouldn’t reply to them.

Seriously, WTF.

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More recently, I’ve been working on an eCommerce store. Again with limited success. In fact, by the time you read this, it may be no more.

(Update: it is indeed no more.)

One thing I’ve noticed is the longer I’ve been trying to make a success of it, the scarier the idea of making sales has become.

In the beginning, I imagined every sale would result in a happy customer.

Now, the fear a sale will lead to a complaint is almost as strong as the desire to make a sale in the first place.

But hey, at least I tried. I got the store up and running. It’s online and it gets some traffic. It’s not my fault if people don’t buy anything.

There’s not much more I could have done anyway – I’m too busy patting myself on the back in my safe place.

This website is similar.

What if nobody reads this article? No worries, I guess. At least I wrote it. I did my bit. And it’ll be nice not to be ripped apart in the comments or on Twitter by people who disagree with it.


hong kong jewellery store

Faux-psychoanalysis on success being scarier than failure

I’m no more qualified to talk about the idea human attitude, mannerism, experience, and thought is largely influenced by irrational drives that are rooted in the unconscious than anyone else who can go to the psychoanalysis page on wiki and find that very quote.

But I’m going to throw out some ideas about why success might be scarier than failure anyway.

Looking back at my own experience, it reads like a confidence thing.

There was another fear at the time of the cold emails. A fear of successfully getting some work, and then doing it poorly.

This was unfounded in any of the clients I did get. Some asked for minor edits, but none told me I’d done a bad job.

They may have thought I had, but they never told me. So there was absolutely no reason for me to fear a successful email reply based on the quality of the work I would do.

On more than one occasion, I took on work I had no idea how to do. Like writing actual sales copy instead of simple SEO articles.

The cliche of jumping off the cliff and building your wings on the way down was put into practice. And it always worked out. I said ‘yes’ before googling ‘how to’. And nobody complained about the work I returned.

But still I was scared of landing work I knew I could do, and do well.

monochrome street photo bus

This lack of confidence idea leads to another well-worn term: impostor syndrome.

“Despite external evidence of their competence, those exhibiting the syndrome remain convinced that they are frauds and do not deserve the success they have achieved.”

I’d imagine there’s a connection between confidence and impostor syndrome and the idea of success being scarier than failure. But I’d also say there’s more to it than that.

Some people genuinely don’t care what others think of them. Or are so driven towards success that the idea of it being somehow scary is completely alien.

Lucky them.

I’d think they’re in the minority. I’d think more people have personal insecurities that could lead to a fear of success than don’t.

Issues of not wanting to be judged. Of not wanting to hear criticism. Of not wanting to open up. It’s not easy to get over these.

I know. I have them myself.

Fear of success as a self-fulfilling prophecy or not

The first time I heard the idea of success being more scary than failure was a real moment of clarity.

I began to think about why I’m really, really good at starting projects but never finishing them. Perhaps because the failure of not publishing something is more comfortable than the success of it being seen and judged.

I’ve worked long on things without success. I sometimes think I can see it, but there’s always something stopping me from taking the last few steps to get it.

Or rather, something stopping me opening up and allowing others to judge whether I deserve it.

I’m still guilty of this.

I fear one danger for all of us, now we’re aware of the theory of success being scarier than failure, is that it can become a self-fulfilling prophecy.

That it can become a crutch, or a ready-made excuse for people to remain in the comfort of failure.

That instead of dissecting and using this understanding of fear of success as a way to fix our problems, people can use it as justification to keep failing.

Because now someone has told us we are scared of success and it’s okay and natural to be that way, and that it’s one reason why we fail, it’s easier to just accept it and wallow in it than to change.

If you suffer from a fear of success, the other option is to, you know, at least try to do something about it – however that manifests for you.

I can’t tell you that you’ll definitely get past it though.

I can’t even tell you if I’ll get past it yet.

But taking a breath and hitting Publish is one way I’m trying.

What about you?


Update: I’ve actually changed my mind. I don’t really think the fear of success is a thing now. Or if it is, it’s really the fear of failure in disguise.

Come learn why in this post.


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Surely not. Everyone's scared to fail. That's why we never do anything, right? If we knew for sure we'd succeed, we'd have finished already and be wallowing in rewards and adulation. Spoiler: I disagree. The concept of success being scarier than failure is not a new one, but it's something I've been thinking about recently. I wanted to explore it from my own perspective. So I did. Hopefully, I guess, with some success.


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