10 Things I learnt from 50 days of failure

I’d never had a tarot reading before, and I didn’t know how much I really bought into it, but my friend had been studying to do it professionally so I gave it a go.

At the start of the reading, he said, ‘You really like your comforts, don’t you?’

He told me he saw an image of me in a hammock in the middle of the jungle. Instead of exploring, I was choosing to stay where I was safe and cosy.

‘I tell a lot of people that they need more comfort and calm in their life, but you I want to kick up the arse and send out to explore, take risks and push yourself. You’re too worried about losing face.’

This message really resonated with me. I was like a foetus, hiding away in a soya matcha latte amniotic sack, pepping up my spirits with carrot and orange cupcakes.

I knew there was so much more I could do, and wanted to do, but that I wasn’t doing in case it was uncomfortable, embarrassing or unsuccessful.

So a few days later, I set myself a challenge to do something every day that I might fail at, for 50 days; something that would stretch my comfort zone. I announced my intention on Facebook and asked for challenges.

People loved the idea and I soon had lots of suggestions. That was just over 50 days ago. I finished my challenge on Friday.

It’s been an absolutely life-changing experience. I’ve earned 2.5 times what I’ve ever earned in a single month before; I’ve massively expanded what I believe is possible for me; I feel more confident, excited about life and fulfilled than before; and I failed to fail — meaning I succeeded — a lot more times than I was expecting.

Here are 10 things I learnt from the process:

  1. When I fail, people don’t point and laugh

At my secondary school, this was what happened. If I made a mistake in front of the class, I was often ruthlessly mocked and heckled and I felt deeply embarrassed. Note to self: never risk making a mistake in front of others!

My first challenge was to rap for three minutes about failure, which I improvised on the spot, in one take. One of the lines was ‘Maybe I’ll have to do something scary/Maybe I’ll have to meet a woman called Mary.’

It was more Alan Partridge than Jay-Z.

Part of me was waiting for the mockery, but I received so much love! People thought it was brilliant that I was willing to look a bit silly, and be imperfect and vulnerable. Knowing that people I barely even knew were behind me made the whole challenge so much easier.

2. People want to help you, but you need to be clear what you’re asking for

When I asked for help with something from my network, I realised that the level of willingness and the unexpected links people had were amazing. I just needed to be specific about what I was looking for.

One of my challenges, for example, was to teach mindfulness in a prison. I did not imagine that many of my friends had connections to that world, but lots of people did, and it’s only a matter of time before I get into one.

It made me realise that many times in the past, people hadn’t been able to help me because I hadn’t clearly expressed what I wanted to do or who I wanted to find.

3. Courage is the key to success in business, relationships and health

It takes courage to pick up the phone to a potential client, be ambitious or increase your prices. A successful salesperson has to go through a lot of rejection.

It takes courage to talk about something awkward or uncomfortable in your relationships that is eating away at you on the inside.

There’s a little voice of resistance that needs to be overcome to go running when you don’t feel like it, to resist the junk food, or go to bed instead of watching another episode.

Generally, what I’ve found is, the bigger the resistance, the bigger the reward. If you do the thing that scares you most it will propel you forwards the most.

4. There’s almost nothing I can’t do

OK, so I’m very unlikely to win the lottery, write a number one hit single or jump onto the moon with a pogo stick. But none of those things really matter to me. What matters to me is feeling like I’m making a tangible positive impact on people’s lives and and getting paid well for it.

As a coach, I often ask people what their dream future is, and while it might be radically different to their current life, it is always totally realistic if they’re willing to really pursue it.

Some people make things happen, others make excuses.

I learnt that when you are prepared to take risks, make mistakes, be criticised and take consistent action towards something, there’s almost nothing you can’t do.

Only a few weeks ago, I never would have imagined I could be a guest on a podcast about success in business, have a whole room laughing at my stand up comedy or nearly triple my income in a month. But all of those things were much easier to do than I imagined. I had to dare and I had to put the work in.

5. How much I earn is more to do with my mindset than how many hours I work

When I used to think about people who earn a lot more than me, I imagined they must either do far more hours, be very lucky or have some skill that I don’t have and never will have.

I learnt to make struggling for money a way of life. I’d created a whole belief system around it — my own ‘poverty mindset’.

I’ve made great strides in overcoming this, but it has been quite incremental. As part of my challenge, I set a target of earning 2.5x what I normally aim for in a month, and I hit it, almost exactly, without working more hours.

I put this down to expanding the realm of what I believed was possible. When I used to think that earning a certain amount per month was all that was possible, that is what happened. I surrounded myself with other people who earned that much, adjusted my lifestyle accordingly and convinced myself of a whole load of excuses as to why I couldn’t do much better.

It turns out that I can choose what I think is possible, it just takes some retraining, courage and putting myself in the right conditions.

6. Fail before it matters

One of the challenges I was most nervous about failing was doing five minutes of stand-up comedy. I did not fancy the idea of cracking joke after joke and being met with a room full of stone-cold silence.

Fortunately, I know a few experienced comedians and I asked for their help.

I wrote a script, and performed it in front of my friend Chris Smith.

‘It needs to be… funnier. It needs more jokes’, said Chris. I put that in my routine!

It was helpful and unhelpful. I knew it wasn’t funny, but I didn’t understand how to make it funnier.

I completely rewrote it and shared it with another comedian friend, who didn’t laugh either! But he did give me lots of specific feedback about using similes, metaphors, making things extreme and acting things out, which helped me to understand how to turn a story into a funny story.

I ran the next draft past two other people, so that by the time I had performed it, I’d failed four times. That meant that when it mattered, I succeeded in making the whole room laugh, almost all the way through my set, which was far beyond my expectations.

7. How to help the homeless

My sixth challenge was to help a homeless person off the streets. I was really nervous about this one because I’d never engaged with a homeless person before. I was worried they might be aggressive, dismissive or unpredictable in their behaviour.

It didn’t take me long to find someone, sitting outside a pharmacy on Old Street, near the roundabout. He said his name was Tim. His hands were black with dirt and he smelt of urine.

I felt profound sadness and hopelessness while talking to him. His story was that his wife had taken the house as part of the divorce.

I asked if there was anything I could do to help. He said he didn’t need money, he needed somewhere to live.

‘What if I could help you with that?’, I asked.

‘That would be a miracle’, he said.

That sounded like a good challenge to me, so I rang some homelessness charities there and then, and was advised to call StreetLink.

They told me that they only come and pick people up at night to take them into shelters, and I handed the phone to Tim so he could describe where he was going to be.

A couple of weeks later, I saw him again and he said they had taken him in somewhere, but he didn’t like it, so he was back on the street.

These issues are clearly very complicated, but I learnt that it was meaningful and worthwhile just stopping and talking to a homeless person, and that there is something you can do to offer them an alternative to sleeping rough.

8. Being told to ‘F off’ is not a big deal

My 46th challenge was to walk in a straight line down Oxford Street and not get out of anybody’s way. It was an assertiveness exercise, and with 45 challenges behind me, I really had the wind in my sails and a clear, purposeful stride that most people made way for.

In fact, I thought I was doing something wrong, because it was too easy! I walked from Oxford Circus to Tottenham Court Road, and decided to double the challenge by walking back again. I bumped into my a friend, by coincidence, who said he’d been weaving all over the place, so I was reassured that it was actually a difficult thing to do.

A few paces later, I came face to face with a woman about my age and stopped. We looked at each other and she said ‘Are you just going to…?’, as if she was about to say, ‘Are you just going to wait for me to get out of your way?’

‘You’re a knob’, she said, and walked around me.

I reflected on it and decided she had no more right of way than me, so I wasn’t doing anything wrong. Given my conviction in what I was doing, I didn’t mind being criticised. That was a great lesson.

The next day, I tried selling mindfulness door to door, and noticed how much resistance I was feeling to getting started. I was anxious about having the door shut in my face and being told to ‘F off’.

But remembering my experience from the previous day, I reminded myself that as long as I have conviction in the integrity of what I’m doing, that’s okay. How flimsy is my passion and drive if I’m only willing to do things I’ll never be criticised for?

In fact, everyone just politely said, ‘No, thank you.’ It wasn’t a big deal!

9. Things are far worse in your mind than in reality

I felt a lot of resistance to doing challenge 8: trying to sell a mindfulness session to someone in McDonalds. The person I chose was busily writing an important email, and didn’t want to be interrupted by me asking him what he did for a job and telling him about what I did. It was quite awkward, but it wasn’t that bad.

I was really procrastinating on challenge 11: asking ten strangers ‘What do you long for?’, which I did in a pub in Hampstead Heath. I think I feared it being awkward, them telling me to go away, feeling embarrassed… But in the end, I had one of my most enjoyable evenings in the pub ever, engaging strangers in meaningful conversation and having a laugh with them while I was at it.

10. Life expands or shrinks in proportion to your courage

A lot of people in the pub said that they longed for an exciting, fulfilling life. Well, courage is what’s needed to live such a life. The challenge gave me a sense that anything is possible for me. If life feels predictable, my dreams impossible and my relationships frustrating, then it’s up to me to show the courage to change that situation.

What you need to do is choose a goal, embrace failure and learn from it.

My challenge to you:

Think deeply about what you long for in your working life, your health and your relationships. What would give you a strong sense of meaning and purpose? And what is the fear that’s stopping you from taking action towards it?

For some people, it’s starting a business or going freelance. It might be learning to sing, moving to a Greek island, asking for a pay rise, asking someone out on a date or telling someone you love them.

I think everyone’s got some kind of dream they don’t dare to pursue.

Whatever the fear is, do it anyway. If you want to be successful at anything, you’ve got to learn to fail.

Below the full list of challenges I did. You can see all the videos on my Facebook page:

  1. Perform a 3 minute rap about failure

2. Lie down in a public place for 3 minutes

3. Get a meeting with your ideal client

4. Apply for Britain’s got talent

5. Say hello to everyone I see when I go out for a run

6. Get a homeless person off the streets

7. Do 5 minutes of stand up comedy

8. Sell a mindfulness session to someone in McDonalds

9. Get 10 stranger’s phone numbers

10. Get into a sold out event

11. Ask 10 strangers the question ‘what do you long for?’

12. Sell a painting for £10k

13. Get a homeless person off the streets

14. Get a free coffee

15. Free hugs in Canary Wharf

16. Be 10 minutes early for all my appointments

17. Admit my shame to room full of people

18. Make eye contact with someone on the tube and then give them an orange

19. Eye-gaze for 20 minutes

20. Answer truthfully when asked how I am

21. Earn £10k in May

22. Sell a 121 coaching programme

23. Get interviewed on a podcast

24. Double your prices

25. Slack lining

26. Do a challenge every day

27. Have a clear next step after meeting my ideal client

28. Beat a 7 year old at one on one football

29. Sell two workplace mindfulness workshops

30. Write a comedy script

31. Get people to come to my comedy gig

32. Teach mindfulness in a prison

33. Teach mindfulness in a prison

34. Pitch a documentary idea to the BBC

35. Do 5 minutes of stand up

36. Pitch a documentary idea to the BBC

37. Perform the Thriller dance after a 10 minute youtube tutorial

38. Win a round of boxing

39. Get a TV interview about mindfulness

40. Get a refund full refund for a £210 shoddy bike service

41Teach mindfulness in a prison

42Get a high profile person to support your business

43. Contact every secondary school in islington and offer them mindfulness

44. Negotiate a discount in a high street shop on a £50 jumper

45. Hold your breath for 3 minutes

46. Walk in a straight line down Oxford Street

47. Sell mindfulness coaching door to door

48. Win a round of boxing

49. 5 Random acts of kindness

50. Get a TV interview about mindfulness

My work is all about love. Loving yourself, loving other people and loving the earth. I do that through writing, podcasting, coaching, running workshops.