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How to fail responsibly: lessons from the trenches

The way we fail will have the biggest impact on what happens next for us. Failure is f'ing hard. It sucks. It's a real feeling of loss & grief. The thing is if we do it right, we can build character, transform relationships & win trust & confidence so we can move on to the next thing with our heads held high.

I've watched founder after founder fail - I've even worked with a few of them - and observed failure close-up. I've failed in big ways a handful of times too & I am pretty sure I fail in small ways everyday. Failure is a part of life.

I've just seen a very public failure in New Zealand - founder raised $4m and recently sold for $60k a few years later. Shareholders are pissed off. Everyone is pointing fingers. The quality of the conversation around what happened has descended into what has become an all too common pattern on the internet; two camps, each thinking they're right & the other wrong.

I don't know the founder of this company, the shareholders or anyone involved however reading the story from the outside, I felt compelled to share some thoughts. There's too much at stake to not deal with failure responsibly. People's lives. The culture in the start-up ecosystem. Be very clear about this, how you deal with failure doesn't just impact you and those around you, it impacts future founders to come. Be responsible and learn to fail responsibly. Here's a few things I'd like the parties involved as well as all founders, teams, investors, advisers to think about in their own journeys.

#1 - Have some compassion; get some perspective
Failure happens for all kinds of reasons. It's a part of life. Beating up on yourself whether you're the founder, team, advisor or investor, won't change anything. Conserve your energy because you need to do more productive things with it like taking ownership & responsibility, having hard conversations & learning the lessons that need to be learned.

Be careful here though. Don't let compassion become self-pity etc. Compassion is productive. It's a launch pad for enquiry and learning. Self-pity is a waste of time. Don't park your car in the self-pity garage.

Practical steps:

  • Make a list of your strengths & things that went well with your startup journey; get some perspective because along the way you made some awesome decisions otherwise you would never have got to position where failure hurt so much.
  • Talk to a friend & get more perspective
  • Do the basics; sleep, eat, exercise, laugh. Get more perspective.

#2 - Remember how hard the game is you're playing & have more compassion
Entrepreneurship is f'ing hard. In fact I reckon it's one of the hardest mental pursuits on the planet. Read this to get what I mean: https://www.indiehackers.com/post/youre-an-athlete-but-you-just-don-t-know-it-yet-88d9d4599c

Just like the second rule of fight club is the same as the first, compassion matters that much!!

Practical steps:

  • Repeat steps from #1
  • Flip the script; what advice would you give or what would you say to your friend if they were going through what you are going through?
  • Look at the cold hard raw data of startup success & failure. Remember the odds were never in your favour!

#3 - Harness your anger in a responsible way
Anger is an emotion that if harnessed and channeled can create a HUGE AMOUNT of motivation for action. If not respected though, it can create way more mess than you need. Use your anger to motivate you toward learning & responsibility.

Practical Steps

  • Make a list of the things you messed up & everything that went wrong. REMEMBER: pointing the finger at other people and blaming, complaining or shaming is a recipe for disaster. Just focus on the things you had control over e.g. how you reacted to / responded to someone else's mistakes.
  • Make a list of the things you wished you did differently. Focus on the actions you could have taken but didn't and avoid endless commentary about all the mistakes others made or other external factors that resulted in failure.

#4 - Seperate what happened from your identity
The biggest trap people make when navigating failure is they collapse what they did or didn't do with who they are. We all do this. We say things like "I am useless" or "I am a shit founder/investor/adviser" instead of saying "I did and didn't do things that were useless" or "I did and didn't do things that a shit founder/investor/adviser would do".

Practical Steps

  • Step into the shoes of the observer so you can see your actions or inaction without the emotion you attach to them. You are no useless or shit. Yes, you can do things that are useless & shit but you can be whoever you want to be including being responsible, honest & courageous.

#5 - Don't make it all about you
Remember all those incredible people who started the journey with you and helped you get to where you got to. They're suffering too. Maybe they're suffering because of things you did or didn't do. Quit making the failure all about you and start thinking about what all those people are going through too.

Practical Steps

  • Make a list of all the impacts that others who were on your startup journey with you might be feeling right now.
  • Be bold, and highlight the impacts that you may have caused because of your action or inaction.
  • Flip the script; what would you want to hear from you if you were in the position of those people.

#6 - Avoid denial & the blame game
When we're scared & afraid about the future, our brains do some pretty weird things. Neuroscientists have proven that our left brain hemisphere distorts & denies reality to keep our identities safe.

They did an experiment with people who had had a right brain stroke and were paralysed on the left side of their body as a result. They first asked the individuals whether they were paralysed on their left side. They all said, "no, nothing is wrong." Their left brain hemisphere wouldn't let some perceived deficiency in them be acknowledged as some fault in reality. To be clear, they didn't even sense they were paralysed on their left sides.

The neuroscientists then said to the individuals they were going to inject a substance into their left arms that would cause them to be paralysed. It was a placebo of course. Next, the neuroscientists asked the same question as before, "Are you paralysed on your left side?" and as if by magic, the individuals responded with a yes!

The admission of fault / being wrong feels like death to our minds. So our minds looks for all the reasons outside of ourselves for why things are the way they are. That's why we blame, complain & shame others. We deny our parts in what happened. The thing is, when we do this we rob ourselves of power, learning & connection with others.

Practical Steps

  • Make a list of all your complaints, reasons why things failed.
  • Cross out all the line items that point to reasons outside of you for why things are the way they are.

#7 - Decide who you want to be moving forward
The character we play e.g. energetic, hopeful, trusting, drives our behaviour & shapes our experience of life. Ask yourself, who have you been being in the aftermath of your failure? If you're human, you've probably been being "fearful, irresponsible, righteous, cowardly". Look at what this has got you? Probably stuff you don't want right.

So, what do you want to happen moving forward and who would you need to be to create that? Do you want to have another shot at starting a company? Do you want people to respect you & be your champion in the future? Do you want to be someone who learns from failure? Well then you probably need to be some combination of "courage, trust, ownership, responsibility". Decide who you want to be moving forward and commit to it. Start filtering your thinking & actions through these ways of being.

Practical Steps

  • Reflect on the following questions
    --- Who have you been being and what has this got you?
    --- What do you want moving forward?
    --- Who would you need to be to make that happen?

#8 - Prioritise your relationships & get completion
All we have in life are the people that believe in us, that back us, that love us, that help us when we're down. You will ultimately be judged by the way you handle your relationships, especially with those who were part of your startup journey. The goal is to invest the time with those people who you backed and backed you so you get to the point where there are no more hard feelings. If you can do that, these are the people who will back you again. You build so much trust when being responsible with your people.

Practical Steps

  • Show up and connect with people
  • Follow all the steps in #9 (the next step)

#9 - Take responsibility, own your shit & say sorry
Using your list from #3, ask yourself, "Am I prepared to own everything I did or didn't do that contributed to the failure?" If you're struggling here, remember this. The only place we have any power in life is when we take responsibility for what is going to happen and how we react to what is happening. If we take the position of I am 100% responsible for what happened, then we can start cleaning up, reaching out to people impacted by what's happened & being the road to redemption.

Saying sorry is absolutely about acknowledging the impact your actions / inactions had on the other person however just as importantly, it's about forgiving yourself, and letting going of those big heavy rocks that are just going to slow you down moving forward. Be bold. Be courageous. Say sorry.

Practical Steps

  • Look at your list from #5 and prioritise who you need to contact, what action you need to take e.g. have a conversation, return money, acknowledge & thank, & start owning your shit.
  • Start getting on the phone. Set up meetings.
  • Get in action. Return money if that's a thing.
  • Be empathetic. Be kind. Don't defend. Don't squabble over the details. Just listen to what they have to say. Say "Sorry that's how it was for you. I totally own my part in this."
  • If there is something that you'd like to clarify or clear-up, ask if you could share your perspective with the other person? If they say no, just leave it. They're just not ready to own their side of things yet. That's cool. Check-in again in a few weeks.

#10 - Celebrate & make a plan for the future
So what are you going to do next? First, if you've take these steps. celebrate. Acknowledge yourself doing the responsible thing. Build a practical plan to get you moving forward. On this plan you should include the steps mentioned above but also practical things like employment, living situation etc.

Build a vision for what you want to create and get after it.


Remember failure is one of those inflection moments in life. If we handle it through the frame of responsibility, honour, courage & respect, failure transforms into learning, trust building & momentum.

If you are going through a failure and want support, get in touch [email protected]

  1. 1

    I think about failure often - wrote about it once.

    Founders with financially larger failures than I are always reaching out for help. Thanks for posting

    1. 1

      Hey thanks @Quinndawg I appreciate that man. The thing is, the road to failure often starts long before we even start our companies. There are undeclared & unconscious patterns of thinking & behaviour that cause us to take actions that slowly drive the car off a cliff.

      Failure can be avoided early or the size of the failure can be minimised by proactively addressing the core mental skills all high performers need to succeed. Ultimately, this is where I want to help.

      If you know any founders / investors that are getting started or are at the end of their journey and want to get on top of their mental skills game, it would be great to connect with them.

      Interested in your story of failure - can you flick me a link to your post please?

      Cheers

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