What I have learned from my biggest failures in life

15 minutes reading time

They all say you shouldn’t be afraid to fail, since failure is an integral part of success; if you want to succeed, you simply have to go from failure to failure without giving up. Next to that, we can also find a very popular view on failure saying that you can usually learn much more from your failures than you can from your successes. Both statements are true in a way.

But what you’ll hear much more rarely is that failing really sucks. It sucks big time. It hurts, it hinders your self-confidence and you feel really shitty about yourself for a long time afterwards. At least most people do. That’s also why most people give up after they fail big a few times. It’s totally understandable that you become more cautious and cold if your heart gets broken a few times.

On a logical level, all the cool quotes and sayings make sense. You fail and you try again and again all the way until you succeed. Nevertheless, persisting from failure to failure is more of an emotional than an intellectual challenge. You can either use negative emotions that come from failure to additionally motivate yourself or you can let them drag you down. You either get motivated to learn more and master the fire or you simply don’t want to get burned ever again, meaning you go back to the average life – zombie life.

Three sources of motivation to overcome failure

There are only three major cases when negative emotions of failure really motivate you without hindering you. (1) The first one is if you were raised as an emotionally healthy person with strong self-confidence and many competences, so you have no doubts that you can make it next time. By nature, you have a great level of believing in yourself. You don’t take it personally. Unfortunately, not many people have that kind of privilege.

(2) The second, strongest one (even better if in combination with the first one), is when you have a strong vision and a powerful why. Your big vision, clearly seeing how you want to contribute to the world and why you want to do it from a godlike personal mission you have in this life. And when you have a mission bigger than yourself, it helps you transform negative emotions of failure into pure new motivation. It doesn’t matter if you’ve failed, you know what you were born to do in this life.

(3) The third case includes all the people fighting their inner demons. When you’re fighting your inner demons, you’re usually addicted to outer approvals, be it in the form of money, praise, power, respect, sex or any other. In most cases, all these things are only surrogates because you lack the capacity for deep and loving relationships. But when you’re fighting your inner demons, there’s no failure that’s going to stop you from feeding them.

  1. Beliving in yourself
  2. Having a big vision and powerful why (your why eats any obstacle for breakfast)
  3. Fighting your inner demons

Well, the point is that persisting in spite of failure is an emotional challenge and as such, you have to pay attention to your emotions. If you aren’t fighting demons (I hope not) and if you aren’t ultra-confident and emotionally strong by nature, there’s only one option left that will drive you through all the failures. You need to form a strong vision and a powerful why that drives you through all the obstacles in life. You need to find a mission that’s much bigger than your life.

Emotionally processing every failure

But even if you have a strong mission, failure sucks. It sucks big time. Whether you want it or not, you have to go through five emotional stages when facing every failure, based on the Kübler-Ross model.

You start with denial, convincing yourself that you just don’t care, and then you have to deal with anger, bargaining and depression. Acceptance is the last step after a long road. But you really need to take time to deal with all the emotions and then move on. If you don’t systematically deal with every failure, no matter how small, by going through all five stages, you only suppress your feelings and consequently, you’re slowly becoming an embittered person.

Kubler Ross Change Curve

Kubler Ross Change Curve – Navigating Change, Source: HappyMeal

When you fail, you have to take time to recover. Fail fast, but recover slowly. It’s the only way to come back to the game stronger.

Learning from failure

While emotionally dealing with your failure, you of course have to ask yourself what you’ve learned from it. Despite that, I’ve often seen that people find learning an easy and convenient excuse for failing. Oh, I failed, but at least I learned something. And yet next time, they try to tackle a challenge in the same way.

If you don’t change your behavioral patterns, you haven’t learned anything from failure.

That’s why you need to make sure your learning from failure is validated. Saying only “I’ve learned something from my failure” isn’t enough. You cannot improve something if you don’t diligently measure it and share what you found with others and compare it with their experiences.

Don’t just say “I’ve learned a lot from my failures”. Ask yourself how you could approach things differently, which of your assumptions were wrong, where you have gone against yourself, which forces in the environment contributed to your failure, how will you change your behavior, what kind of emotional damage was done to you and others etc. You need to deeply analyze what happened and you need some metrics to really learn from failures. There are no shortcuts to emotional recovery and there are no shortcuts to really learning something new.

The key takeaways are:

  • Don’t deal with your failures on an intellectual level, but rather on an emotional one. Take time to process the failure and make sure every failure strengthens your vision, why, strategy and tactics. Afterwards, you should have a clearer picture of what you want in life and how you should make a pivot.
  • Don’t use learning as a fast and simple excuse for your failures. Extensively analyze every one of your failures and validate what you learned about yourself and the world. Afterwards you should know exactly how you’ll change your behavior.

My big failures in life

Now let’s look closer at my biggest failures (in business) and what I’ve learned about myself and life.

You want to have control

When you’re young and naïve and make the first steps in the business world, it’s not hard to be convinced to join multi-level marketing (MLM) or, to be more exact, some kind of a pyramid scheme, although everybody is trying to convince you that it’s not a pyramid scheme, but ironically only a funnel. I joined one of MLMs and was one of the most successful salesmen for a year. I subscribed many people and it felt good to see the results of my hard work. Then after a year and a half, the network went bankrupt (like most new MLMs do), which was quite a traumatic experience.

For three months, it hurt so much I didn’t even want to leave my room. I invested all my money into the network, I convinced many people to subscribe (without getting any products), I even convinced the girlfriend I had back then to invest money. Then they were gone, overnight. It was a very painful kind of failure, even more painful because it was the first one. I thought I was doing a good thing, that we’ll build a big happy business family where everyone will get rich, but I was so young and naïve.

Galvagin Congrats

Being one of the best salesman in MLM at age 19. FACEPALM

I definitely learned how to sell, which is a valuable skill. But I could also have learned that skill in a different and better way, without the bitter experience of failure. I analyzed what happened substantially and there’s one much more important lessons I took away from this failure. You must have control in business and there are no in-betweens. You either have control or you don’t. If you’re not driving, you’re in the passenger seat and someone else is in control. When someone else is in control, the only thing you can experience are sudden unexpected crashes. No control, no say, no power. And choice is the most powerful form of control that you have in life.

Never go against your values

Back in the day when there was still no incognito browsing and there were malware threats everywhere on the internet, we came up with an idea with a group of hackers to make an incognito browser based on bootable Linux CDs. You would simply put a bootable CD in your computer, the browser would load in its own operating system, you could browse anything that you didn’t want to leave a trace of on the computer and afterwards simply reboot your computer by taking the CD out beforehand and you’d be back in your operating system.

The project was called Freya and it was really the first incognito browser way before there was any incognito option in most popular browsers, which is a standard function today. With a team, we put some money together, developed a product and even got a very good distributor. But at the end of the day, we never launched the product on the market. The product was there, the distribution was taken care of, the marketing materials were prepared, but somehow things just stopped. The motivation went south and the project was slowly dying. Everyone had enough of other opportunities so we just forgot about Freya. The project failed.

Freya Main Screen Mockup

Freya Main Screen Mockup

Again, I analyzed the situation extensively and for me, the project failed because I was trying to go against my values. To be honest, the perfect target users for the product were in the porn industry. I definitely never saw myself in the porn industry, incognito or not. It probably was and still is a big and rich industry, we may have had the right product at the right time, but there’s no money in the world that can make you go against your values. The product simply wasn’t consistent with my values and therefore I subconsciously sabotaged it.

The lesson I learned was to never, ever go against yourself. Listen to your guts and instincts. Think of the final outcome and whether that’s something you really want. Your emotions are the compass that lets you know if you’re going in the right direction or not. Never go to war with yourself. After this failure happened, I went against myself a couple more times and I always hurt myself badly. Really badly. At a certain point, I decided to never do it again.

Wrong assumptions are the mother of all fuckups

I went to the U.S. for a few weeks and what I saw there is that every elite university has its own alumni club. In Europe, that wasn’t and still isn’t that popular at all. I decided to found an alumni club for one of the most elite high schools in my country that I had attended. I gathered a team of people, invested some money, and we happily started the project.

Back then there were no lean methodologies yet, so we did it the old way. I founded a not-for-profit organization, we built a website, marketing materials, gathered all the yearbooks for contacts and prepared the program for the first year. We had an opening party that was quite a success. It all looked so cool and awesome. But then we really went out of the office and onto the market. What happened was best described with the quote noting that everyone has a plan until they get hit in the face.

Basically the whole project was built on wrong assumptions. I assumed that the high school would be excited about the project and support it. Wrong. They basically threw me out of the office. I thought that people would be happy to see their classmates. Wrong. They have new busy lives now. We even performed a survey among more than 1,000 people (we gathered so many e-mails) on what kind of events would be best, on which day in a week, at what hour, and so on. We organized exactly what the survey showed and only four people out of more than a thousand applied.

Alumni Gimb

Alumni club of my hi-school was a big failure. But at least I got to know the most successful actress from Slovenia.

I decided to end the project. What I learned was that wrong assumptions really are the mother of all fuckups. Before formally establishing an institution, website and all marketing materials, I could have gone and talked to the school, I could have tried organizing a few informal events, I could have gone out of the building and saw it for myself. But I was so full of ego. Don’t assume anything, go out and test everything, in business and private life. Minimize your risks and gradually commit based on the feedback you get from your personal emotions and your environment.

You want full commitment from all partners as well as yourself

More than a decade ago, internet was booming. Everyone wanted to have a website with CMS (Content Management System). With two of my friends, we cofounded a web design agency called Core Solutions. We were really good at it. We had a lot of happy clients. We had knowledge about SEO, UX and other web design stuff way before the competition. It was clearly a big opportunity, but we somehow never really took advantage of it. After successfully finishing a few projects and making some money, the motivation simply ran dry and we stopped the project. Core Solution went into the grave.

I was more interested in startups than web design. I had big interest in both, but startups were higher on my value chain. I saw a bigger opportunity in helping to build one of the first university incubators and the startup ecosystem. It also seemed like the more prestigious thing to do. Internet was probably a much bigger opportunity financially, but startups were simply deeply in my heart. Other two members of the team also had other projects and opportunities, and their focus shifted. We were good, competitive and combative, but we were simply not committed enough.

Core Solutions

Interested does not equal committed. The first thing I learned is that if I don’t do only projects I’m really committed to, I’m wasting my precious energy. Nothing big was made in the afternoons. It may begin that way, but at some point, you have to fully commit and focus. In order to undertake projects that will motivate you in the long term, you need to know why you’re doing something. For startups, I had my powerful why, for web design I didn’t.

You also want full commitment from others. First of all, you have to observe what people do not what they say. Actions are the ones that show commitment, not words. Invested resources are commitments. Money, time, ideas, hard work etc., those are commitments. Nice words are not. Moral support is not. You should only do projects with people who are fully committed. They can be merely interested in the beginning, but when things are going in the right direction, they must be more and more committed and deliver results.

Timing is everything

When the Seedcamp startup accelerator began in the UK in 2008 (today the most popular accelerator in Europe), I wanted to do a copy-cat in the region. The project was called iTime – investing in telecommunications, internet, media and entertainment. I got 10 investors to commit to invest in the winners of the pre-selection process, but the investments didn’t happen at the end. The applications weren’t good enough.

Thus the project was adjusted to being just an accelerator without any investments, only functioning as an educational and mentoring program. But an accelerator without money isn’t really an accelerator. Well, me, my team and partners were running the iTime project for several years as a mentoring program until it got outdated. Later, with the same team, we started Start:up Geek House, which is a successful startup accelerator today, but with public-private money. iTime back then was a failure.

iTime Accelerator

Trying to do a Seedcamp Copy-Cat back in 2008.

There’s an important lesson hidden in this failure. Timing is everything. If you’re on the market too quickly, you’ll definitely fail. You must be ahead of time, but only a few steps, not a few miles. You know we were expecting flying cars in 2015, but all we have is 140 characters.

On the other hand, if you’re on the market too late, you may be getting only breadcrumbs. You can always innovate on established markets, but it’s much better to innovate and hit the right timing, the right market at the right time. A rising tide lifts all boats. The right timing on the market is like an accelerator, the best leverage you can have.

It’s the same in other areas of life. You have to take timing into consideration. When asking for a raise, when asking a person on a date, when deciding for a baby or starting a business. You also shouldn’t confuse the mantra “it’s never the right time” with the importance of hitting the right timing. The point of there never being the right timing is to motivate you to move out of your comfort zone. To not be a zombie. To take action and not be a scared pussy. Nevertheless, it doesn’t encourage you to take stupid decisions. Not analyzing your environment and failing to aim for the right timing definitely isn’t smart.

Markets always win, never go against a market

It was back in 2008-2009. Financial markets were crashing. Investment funds were getting closed. GDP went down, all markets basically collapsed. And I was super confident and super cocky. I decided to go against the market. Together with a few business angels we raised a 6,000,000 € seed VC fund as investment managers (target amount was 4 mio €). It was nothing but a ticking bomb.

Many financial companies went out of business, which was good for us. There were so many projects to invest into. But I was betting against the financial markets. Of course many LPs couldn’t meet their commitments because of their own financial problems, so we had to liquidate the fund. Afterwards I wasn’t so cocky anymore.

In many cases, you definitely have to go against the flow. You have to be different, different and better. You have to look for opportunities where others aren’t looking. You have to be greedy when other people are scared and you have to be scared when other people are greedy. Well, on second thought, you should be neither scared nor greedy, but you get the point.

But never go against the market. When a great team meets a lousy market, the market wins. When a lousy team meets a great market, the market wins. When a great team meets a great market, something special happens. It’s called product/market fit. Rather than going against the market, make sure that you have superior insights about the market. You have to understand markets better than other people do.

That’s the secret of success. You should use the same philosophy in all areas of life. Understand the markets, find your fit, but never go to war against the market, the same way you should never go to war with yourself.

Everything costs and takes at least π-times longer than you think

A few years ago, my friend and I started an ecommerce business selling food supplements called SimplFit. We imported the products from a few trusted brands from the U.S., UK and Germany, built a website on the Shopify platform (which I really recommend) and started the sales. We liked the products, the shop was sexy, we did some content marketing and made partnerships agreements, and so on. Things looked good.

The timing was maybe a little late, but there was still room on the market. There was another reason why the project failed. Everything took more than three times longer than we expected. We were burning up money three times faster than we expected. Sales were going up three times slower than we expected. There was at least three times more work than we expected with all the administration, inspection, importing, content marketing etc. The upside potential of the project was simply too limited. Small projects got in the way of potential bigger ones. That’s why we killed it.

SimplFit eShop

eCommerce for Food Supplements First Page.

It’s the same in all other areas of life. It called the π-effect. Everything takes at least 3.14 times the resources than you expect. If you want to have a quality relationship, you’ll have to work at least three times harder for it than you anticipate. If you want to live a healthy lifestyle, it will take you at least three times more effort than you think.

Whatever challenge you undertake, it will take so much more time, effort, resources, and so on. That’s why you have to be resilient and persistent in life. You have to know which things could go right, but you also have to know which things could go wrong. According to Murphy’s laws, they usually go wrong. That’s why success means going from failure to failure without giving up. That’s why you need to have your powerful why that’s bigger than you and that will drive you through every obstacle and give you the courage to invest and engage all the necessary resources.

The conclusion

Failure is inevitable. You’ll fail many times in life. The more successful you want to be, the more you’ll probably fail, at least in the beginning. Because good decisions come from experience and experience comes from making bad decisions. If you want to be successful faster, you probably have to double your rate of failing. That’s how you learn faster as well.

If you persist from failure to failure long enough, you shall find your success sooner or later. But you have to fail fast. You must not build false hopes on your ego and naivety. You have to be brutally honest with yourself, honest about whether something works or not and where you’re going.

You need a strategy, you need metrics and you need to learn fast. Last but not least, you must know that failing sucks, and you have to take time to emotionally process every failure, otherwise you can only slowly become a very bitter and unhappy person. That’s something no money or success can undo. It’s true that good times make soft people and tough times build character, and so you can build your character going through failure, but being under stress for a longer period of time is also how you burn yourself out and fail too deep to stand up again. Therefore you need a superior life strategy and a system for dealing with failure – a system for validated learning and healing your wounds.

BTW, besides a few big failures I managed to successfully complete many projects. You can find the list here.

About the author

Consulting and management coaching

Blaž Kos has managed venture capital investments over the past 12 years and participated in the development of the start-up ecosystem in the region. Today, he advises companies on growth strategies, process optimization, the introduction of lean agile methods and the digitalization of business. In addition to the Slovenian blog, he also writes an English blog, which was selected among the 50 best bloggers in the world in the category of personal and business growth.
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