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  • jenniecashman

Why I’ve been feeling like a failure

For much of the last three months, I’ve felt like a failure.


This is despite spending my entire 30s and early 40s dedicated to building an organisation to continue my late husband's legacy; the Abram Wilson charity is an organisation that inspires, connects and opens doors to the music industry so that young people from minoritised communities can realise their creative potential.


Through my leadership, we have worked with over 200 performing artists through performances, coaching, mentoring and strategy sessions; 650 young people through music education workshops; and 10,000 pupils through live performances. Artists who I have directly supported over the years have signed with labels, set up their own labels, headlined festivals and won music industry awards. Young people I have worked with have grown in confidence and resilience, and through our efforts now see music and the music industry as an avenue for them.


Throughout this time the UK government has slowly been eroding arts provision in schools and more recently cutting back on the funding available to artists and arts organisations in London. Despite this, the Abram Wilson charity has evolved and continues to do great work, preparing to expand its music education programme into the North West.


Yet I’ve been feeling like a failure. Why?


At the end of May this year I decided it was time for me to step down as CEO of the Abram Wilson charity. I'd been in discussions with my trustees about it since 2019. But then COVID came along and put those discussions on hold. We picked them back up at the end of 2022 and after a strategic review meeting in April this year it finally felt like the right time for me to leave and make some space for new things to emerge.


You know when Forrest Gump goes on that really long run? He starts off on his own and then some people decide to run with him. Then some of those people leave and new ones join and Forrest Gump just keeps on running until one day he doesn't. He just stops, turns around and says, “I'm pretty tired. I think I'll go home now.” A long time ago, one of my founding trustees likened my journey to Forrest Gump’s run. She said people will join you, then some will leave and new people will come along. You're like Forrest, you just keep running. Until one day, like Forrest I decided to stop running. But unlike Forrest, I haven't felt quite as sanguine about it. Even though I've done everything I set out to do it still doesn't feel good enough.


The Abam Wilson charity has been successful. Its programmes have been effective. Its trustees are supportive and have the energy and passion to lead it through to its next chapter. It's financially stable. I’ve been listed in WISE100, a national index recognising the top women in social enterprise and have been a recipient of the WACL Talent Award. I’ve even published an autobiographical children’s book about my experiences called ‘Becoming Brave’.


So, what’s my problem?


It’s partly me wishing I could have left in a good year, but the truth is there's never a good time to do something big and bold that requires a bit of risk taking. There will always be something. This year we’re in the throes of a cost-of-living crisis, which is having a direct impact on fundraising. Last year, we were shaking ourselves off from COVID. 2020 and 2021 we were battling our way through the pandemic. I couldn't have left before 2020 because that would have been too soon. Next year it’ll be something else. Apparently, there’s never a good time to leave something you started!


Realising this I turned my attention to what I could control and with that information I weighed up the pros and cons and decided it was time to step down, but no matter how hard I tried to view the situation objectively it felt like failing to me. Making the decision to step down ate into all my old insecurities about not being good enough, letting people down, disappointing them and making them feel angry with me. To be clear, no one feels let down or angry. Some have been surprised but for the most part people have been happy and supportive that I’m moving on to do something else. Yet my feelings have not always aligned with what I know to be true on a cognitive or intellectual level: that this is the best decision for me and the organisation at this time with the information that I have available to me.


There's been so much written about failure over the years: ‘fail again, fail better’; ‘face your fears and do it anyway’; ‘what if I fail, but what if you fly?’. All great Instagrammable quotes, but no one really talks about how hard failing is. Why is it so hard? Because you have to let go. You have to be vulnerable. You have to face the possibility of being wrong or of things going wrong and who the hell wants to do that? But then I remind myself of something I went through about eight years ago and in the end, things turned out alright.


It was 2015 and I found myself standing precariously on the precipice of my life knowing I was going to need to take a big leap very soon. I needed to quit my part time job so that I could focus on the Abram Wilson charity full time. I knew that was risky. I'd have to give up a secure income and then what? What if I couldn't raise any money? My mind would go to worst case scenarios: I’d get kicked out of my place; I'd be homeless; I’d let everyone down. With these thoughts holding me back I teetered for too long and the next thing I knew someone pushed me off the cliff edge. It was my boss from my part time job. She'd generously solved my conundrum by effectively firing me on the spot, “Your services are no longer required. No need to work your notice period. Goodbye.”


I walked home in a daze without my work laptop. When I arrived, my housemates hadn't even left for work yet.


“Didn't you leave already?” They asked.


“Yeah…” I replied. “I think I just got fired.”


I sat in the silence of our shared kitchen wondering what to do. All I had was a very slow, very old MacBook which I’d inherited from Abram. I weighed up my options: start applying for another job; or figure out how to get a new laptop ASAP, focus on Abram Wilson and cross my fingers that the grant application I'd been working on for the last 12 months would be successful. The money would give me a total of six months to turn things around. I chose the latter and that was almost a decade ago.


At the time I didn't have the luxury to dwell on feeling like a failure. My ego was bruised for sure, but I could see that life had given me an opportunity; being fired was actually the very thing I needed because I’d been too scared to hand in my notice.


In the early days it was terrifying because the unknown isn’t easy. But I figured out ways of dealing with it so that I wasn't a ball of anxiety all day every day. Failing is tough but the risk of failing is even tougher. That’s where the real work lies: living with the risk of failure and being okay with that. Because when you fail, when things actually go wrong, when bad things really do happen and you get fired or your marriage ends or someone you love dies, you deal with it in the best way you can. But the anticipation of failing or of something going wrong is far worse and that’s what will hold you back.


When you finally get to the failing part, I’ve always found that new doors open up. Failing is really an opportunity in disguise to experience something you may not have even imagined yet. It's taken me eight years including four weeks of intensive clowning instruction by the most amazing teacher, Angela de Castro (and one of the inspirations for my book ‘Becoming Brave’) to really embody this lesson.


It's why, despite old stories coming back to haunt me about not being good enough, I have been able to be brave and make the decision to step down as CEO of my charity. I’ve given the Abram Wilson charity everything I have and I know in my bones that the time has come for me to stop running. To move on and do something else. To let someone else have a go. To take another leap of faith.


I've learned the hard way that life is not guaranteed to us. We only have one. Before Abram passed away, he said to me, “There's still so much I want to do.” He was 38 at the time, just getting started in his mind. But in actual fact, it turned out to be the end and he had no choice in the matter. When I look back on the last 11 years I know that I’ve done everything I could to continue some of the work that he didn't get to do and I think he'd be proud. I know he absolutely loved ‘Becoming Brave’. I can see his big, beautiful smile as I imagine his reaction, eyes lit up, “Jennie! This is awesome!”


Don't wait. If you want to do something but you're feeling a bit scared, then figure out a way of practicing being with your fear so you can do the thing that you know your heart is longing for. As Mark Twain once said, “There isn't time. So brief is life.”


Be brave. You'll be okay.



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