How I Learned To Love Failing

This is an absolute belter of a post from Penny.  And one that is hard to read, and cuts to the truth, and calls out anyone with a shred of the “compulsive overachieving” gene.  Failing is hard.  It’s not something we are taught to relish, or encouraged to do, not ever.  We shy away from taking risks because of our fear of failing.  And we end up as lesser versions of the people we could be as a result.    

Penny took risks.  She failed.  Here’s her story:       

I still remember the first time I failed. Standing outside my department head’s office in my first year of university clutching my first English essay paper of the year with its big fat F. Puffy red eyes and a snotty nose, feeling like I was staring into the abyss, that some horrible injustice must have come to pass. How had this happened? How could I, me, the clever person, write something that I really tried hard at and still fail?  Turns out writing an academic essay was a million miles away from my college trick of slinging together any old thing and getting an A. “Well done for writing in proper sentences and having an independent thought!” Oh that first year was a wake-up call.


I floundered at university, actually. Didn’t really make friends and languished in the middle regions of all my academic classes. I had never failed before, never even really been average. I hated it. My identity was tied up with As and success and coasting through life. If you took that away what did I have? I waved my brains like a flag to hide my weak personality behind.


Years later, flung into the world of work, I managed to get a good (rare) steady job in a creative industry and my life was back on easy street. Then five years down the line, everyone in my department got made redundant. Blinded by a fat pay-out and the belief that if I worked hard enough at anything I would succeed, I changed career. I set up as self-employed. I was going to prove everyone wrong, because all you really need is determination, right?


Nothing hurts more than investing everything you have, financially and emotionally, in something and having it flop. I chose to do fitness – something I loved that didn’t come naturally to me and was hard to market in a recession. It drained me. Three years on I realised I needed to cut my losses before I lost my home. Seemed I could work hard enough to make myself good at something, but that wasn’t enough to make me great.


My business had failed, I had failed. This was bigger than an English essay. This was three years of my life and thousands of pounds I would never get back. Three years I could have spent on the career ladder to something I was good at.


At first I took it personally. I hated that I wasn’t the best instructor, that I wasn’t the fittest, that people didn’t come to me to burn fat and work hard. Then I looked at why they did come to me, and I started to see something quite incredible. People at my gym came to me for emotional support with their weight problems, my personal training clients came to me to talk about their day. My aerobics and Pilates students came to me to have fun, to shoot the shit, to be different, to be themselves. These aren’t things people normally come to fitness classes for. I realised they were coming to my classes because I’d made them laid back and silly and not like a fitness class at all. And then I started to see how failing is great.

Failing isn’t just life telling you off. It’s the world trying to teach you about yourself. That English essay told me I needed to step up my game. And those three years trying to make ends meet taught me more about the person I am than I ever knew. That I love working with people, helping people, picking them up and dusting them off and sending them on their way. Would I have learned that spending another five years cooped up in a script office by myself? Probably not.


And now I’ve learned that what I do love is writing, because I carried it on through that whole difficult time, like a compulsion. And that’s why I’m sitting here writing to you on maternity leave from my new(ish) copywriting job. Writing to you when the baby is asleep and I should probably be sleeping too. Because I can’t help it. These words swim round in my head all day and I need to get them out. And now I’ve had three years of meeting people and talking to them and learning about life to inspire me.


This is why we can all learn to love failing. It’s not the end of the world, even though it really, really feels like it at the time. It’s just another step in your adventure.  And unless we learn to try and fail, over and over again, we risk never fulfilling our true potential.


So hold on tight and jump…


Categories: Life Experience, Money and Career
27 interesting thoughts on this


  1. Posted September 23, 2013 at 7:14 am | Permalink

    EFFING LOVE THIS!!!!!!!!!

  2. Posted September 23, 2013 at 7:55 am | Permalink

    Love you P!

  3. ChirstyMac
    Posted September 23, 2013 at 8:10 am | Permalink

    Oh my God. Right up to the writing bit I could have written this about me. Word. For. Word.
    Kinda scary when you realise that you and someone else out there is the big wide world (nay, someone that you think its pretty darned awesome actually) have trodden the same path.

    • Posted September 23, 2013 at 8:27 pm | Permalink

      Such a nice thing to say! I had no idea we had this in common (didn’t realise anyone I knew had such a similar experience in fact). It does feel better to know I’m not the only one too.


  4. Fran M
    Posted September 23, 2013 at 8:33 am | Permalink

    Yeah! Love all of this. And you’re certainly not alone.

    My tried-and-failed story was a journalism MA, which I’d planned and saved up for for a couple of years post-uni. Turns out I was miserable doing it and couldn’t handle going back to being a student after a couple of years travelling and working full time.

    At the fine, admitting defeat floored me and still feel a bit guilty about it now… But I’ve always known it was the right thing. Journalism isn’t for me, but I still write in my current job. It’s not perfect, but I’m slowly piecing together the puzzle of what it is I can and want to do. Nice to hear I’m not alone x

  5. Katie
    Posted September 23, 2013 at 8:47 am | Permalink

    Thank you for this Penny. Well done for being so positive and cheery. These are wonderful attributes. Xx

  6. Posted September 23, 2013 at 9:20 am | Permalink

    Love this, and just what I needed to read today x

  7. Posted September 23, 2013 at 9:32 am | Permalink

    Did anyone else just hear the Pause for Thought on Radio 2? It was perfect after reading this earlier! X

  8. Posted September 23, 2013 at 9:32 am | Permalink

    Glad you keep writing Penny! I feel like this about my couple of years working in telly. I wasn’t bad at it but I hated the stress of the job and deciding to leave the industry felt like I’d failed a bit. But actually I realise it taught me to deal with pressure, deadlines and generally cope with anything that’s thrown at me. Not sure I could have said that before. We live and learn

  9. Posted September 23, 2013 at 9:32 am | Permalink

    This was just the inspirational read that I needed on a Monday morning. I have always been scared of failure, yet I set impossibly high standards for myself. This has taught me to take more risks and embrace the things that I can learn when I don’t quite achieve what I set out to.

    Thanks Penny. And keep up the writing, you are clearly awesome at it!! xx

  10. Posted September 23, 2013 at 9:34 am | Permalink

    This is such a great piece. I keep reminding myself that I’ll regret NOT trying things more than I’ll regret trying and failing, but it’s not easy advice to follow. So a perfectly timed and inspiring reminder about how important failure is to making us into the best possible version of ourselves. Must try jumping more often…

  11. Fee
    Posted September 23, 2013 at 9:39 am | Permalink

    Penny, you’re so wonderful. And you sound like exactly the kind of trainer I would need! Or maybe just life coach?

    I identify with your experience – I was a classic overachiever until my mid to late twenties when I became very confused and disoriented. I still am a bit to be honest.

    This is exactly what I needed to read at the moment, you have made my Monday much better. Mwah!

    • Posted September 23, 2013 at 8:33 pm | Permalink

      I had a total meltdown in my mid-twenties too! I think it all reached critical mass and I sort of exploded. I’ve grown a lot since then, I definitely class success in a different way.


  12. Alison
    Posted September 23, 2013 at 9:51 am | Permalink

    At a point where I’m questioning my career future (also on mat leave) this is really inspirational. I’m wondering about going freelance (I’m a journalist) to fit around childcare but am terrified. So pleased to read you learned from your experience even though it didn’t work out. It takes such a strong person to work for themselves and to bounce back if it doesn’t work out. I believe whatever happens in your past -good or bad-gets you where you are in life now. And if you’re in a good place then it’s all been worth it.

  13. H
    Posted September 23, 2013 at 10:13 am | Permalink

    “My identity was tied up with As and success and coasting through life. If you took that away what did I have?”

    Yep, I can identify with this one. I worked hard at school and uni because I enjoyed it but also because I *bloom* with positive feedback. It does worry me how much I need to hear that I’ve done well, I’m not sure it’s healthy. When I first started getting professional feedback that wasn’t 100% marvellous, it was really, really hard to deal with and I still have to work at accepting it as an opportunity to learn. I also did an MA that was new territory for me and struggled with the fact that it didn’t come easily.

    Penny, thank you for writing this (and so eloquently!). Admitting that you’re not on the right path is the hardest part. I’m so glad you’ve found something new that allows you to do what you enjoy and that fulfills you. Wishing you all the happiness for your next chapter!

  14. Alice
    Posted September 23, 2013 at 10:33 am | Permalink

    This is a slice of perfection on a grim Monday morning :-)

  15. Posted September 23, 2013 at 11:20 am | Permalink

    For someone who has a ‘dream job’, and bizarrely gets asked to give careers advice to other people, I spend a lot of time feeling like a complete failure. It can be a bit intimidating sometimes, surrounded by successful friends! Life was all going so well until I became ill during my postgrad, came 1 mark away from failing it, and lost my place on a PhD. I’ve spent the last few years since I should have started it trying and failing to carve a career for myself in something, and failing. I’ve had 6 jobs in 5 companies in 4 years. I frequently berate my past self for choices I made!
    Reading this though before I left for work this morning has helped me think about everything and put it into perspective. I have learnt a lot about both myself and other people by being a ‘failure’. So, thank you for helping me to reflect. I certainly wouldn’t have gained so much experience and insight into who I am and what my values truly are without having royally failed and stuffed up so many things!

    • Posted September 23, 2013 at 8:30 pm | Permalink

      Stuffing up is definitely not all bad news. I think the point about successful friends is a good one – I think my lowest points came from comparing myself to my peers. We need to have absolute faith in our instincts and ignore the crowd!


  16. Jessie
    Posted September 23, 2013 at 1:00 pm | Permalink

    Penny, thank you.
    I am currently going through a massive ‘I’M FAILING’ phase. I’ve been coasting through everything for years because I would rather feel like I’m ‘too good’ for my job than challenge myself and feel like I’m failing. Then I got a massive promotion. This all sounds fantastic but I can’t lie, I hate the feeling that I’m not in control! And it’s hard for me to admit this to myself – let alone others.
    Interestingly I was recently clearing out some stuff at my parents’ & I came across my school reports – even at the age of 4 teachers had identified this fear I had of not being able to do things, leading me to suspect that this is so incredibly hard-wired in my personality I’m never going to be able to wean it out – I think I might need to learn to cope with it better though….maybe Life Coach Penny!!!

  17. Mira
    Posted September 23, 2013 at 5:54 pm | Permalink

    So very true! I also did very poorly in my first year of uni because I was so used to being able to get As without having to study… oops! Taught me a big ol’ lesson right there.

  18. Lexie
    Posted September 23, 2013 at 7:42 pm | Permalink

    Love this Penny, such wise words! X

  19. Posted September 23, 2013 at 8:40 pm | Permalink

    Thanks so much for all your awesome comments today. I think it’s interesting that in spite of knowing that we should know better, a lot of us still feel guilt and regret about things we’ve done that haven’t quite worked out the way we intended. It’s easy to think of these trajectories as time “wasted” rather than experience gained. How dull would life be if everything worked out? How would we ever grow a thick enough skin to protect ourselves and our loved ones if we never made ourselves vulnerable and got hurt?

    Love hearing other’s experiences. Thanks everyone for sharing.


  20. Posted September 23, 2013 at 10:23 pm | Permalink

    Right, it’s taken me ALL day to find time to sit down and comment on this as it deserves. Penny, first off, please please don’t ever stop writing. You actually make me saner with every word you type. Fact.

    This is so true, and so brilliantly written. I have always been such a chronic over-achiever, even now I’m still butting up against it, trying to remember that success isn’t achievement, necessarily. Success can be happiness, peace, joy. And those things aren’t quantifiable, which is a shame as I love to rate myself. I usually find that I could do better, funnily enough. You’ve reminded me, once again just as I needed it, that success comes in many forms, and that failing at one thing isn’t failing at life.

    KL xx

  21. Beth
    Posted September 23, 2013 at 10:41 pm | Permalink

    Penny this is awesome and very inspiring – I’ll keep this in mind next time I’m suffering from a massive lapse in perspective. Have you found any particular coping strategies or is that you’ve just reset your expectations? I know what you’re saying is right, have even given this type of advice to others but somehow still find myself blowing even small failures out of proportion.
    Seeing the flipside of any failure is such a great way to look at it.

    I can’t wait to read more things that you write. B x

  22. rachel JHD
    Posted September 24, 2013 at 11:19 am | Permalink

    Message for Ernie – Keep napping & sleeping so that your mummy can think & write & write.

  23. Posted September 25, 2013 at 10:21 am | Permalink

    Penny this is full on amazing. I love how you can take such a trying time and still manage to take something positive from it. You’re an inspiration my dear! Xx

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