Five lessons for aspiring social entrepreneurs
Feather-ruffling, hustling and flying over the grass
As I make way for new leadership at Year Here after 9 years at the helm, I’m distilling the lessons I’ve learnt — the hard way.
This is a letter to my successor, to the entrepreneurs behind Year Here’s burgeoning venture portfolio and to anyone who finds themselves in position to start or scale a social business.
May your path be easier than, but just as awe-inspiring and fulfilling as, my own.
1/ Brace yourself for criticism cos if you’re not ruffling feathers, you’re not doing your job.
No meaningful change in this world has ever been uncontroversial. A sprinkle of criticism is part for the course. But when it’s your baby that’s being critiqued, it can hurt.
When I was just starting out with Year Here, I remember taking the idea to Columbia University’s Jackie Simmons who I’d done some work with at The Young Foundation. She asked lots of tough questions about the model and it seemed obvious to me that she wasn’t enamoured with Year Here. Jackie has since become a good friend and I’ve learnt that asking critical questions is her MO but, at the time, I remember feeling thrown and dejected. Does she think I’m a terrible human? Maybe I am. 😱
As a first time entrepreneur with lots of self-doubt, criticism of Year Here hit different to the more quotidian feedback I got in my day job.
My knee-jerk response was to flex the model to appease her critique. But aim to please everyone and you’ll end up pleasing no one. If you aren’t being criticised as a leader, you aren’t being bold enough. It’s part of the job.
Over the years, we’ve had a handful of critics alongside the many cheerleaders. We’ve even had one or two online trolls. I’ve learnt to use criticism to stress test my beliefs. Then, once tested, I stand by them — even if that means losing a few fans.
2/ The hustle is real
Being scrappy and brazen didn’t come naturally to me. In the early years of my career I was scared of picking up the phone, preferring email. Later on, I would still feel awkward about asking people for stuff — probably for fear of rejection. So becoming a salesman, as founding Year Here necessitated, was quite the challenge for me.
In 2015, we recruited a bumper cohort of Fellows. With our running costs steadily mounting, I had to sell 27 placements and 10 consulting projects in a matter of weeks. If my one-man-band sales effort failed, we could be in seriously hot water. There’s nothing like the fear of not being able to keep the lights on and the staff paid to push you through any childish foibles.
It’s not just sales. Securing press attention, raising investment, or landing a big partnership – all of it requires you to take a risk, be vulnerable and hope for the best. The first few times it feels like asking out the hottest guy in the room with everyone looking at you. But the more you do it, the less your face burns and the milder the inevitable rejections sting.
“It is forbidden to walk on the grass. It is not forbidden to fly over the grass.” Augosto Boal
Entrepreneurship is the most incredible lesson in flying over the grass. To get the job done you often have to take the unconventional route, to reject the received wisdom and have the imagination and courage to do things differently.
3/ Sometimes the best thing to ask is: does it actually work?
In my first few years working in charities, I was surrounded by managers who were interested in questions like “did you secure the funding?”, “have you completed the report for the board?” and “is this within budget?”. There were far fewer questions about whether the projects I was managing were having impact. Inevitably you start optimising for metrics like amount of money raised and extent of funder happiness, not impact. In the social sector, we seem to just assume that our work is effective.
But, of course, social impact is far from guaranteed. And striving for effectiveness starts with critical questioning: does it actually work? Whether we like it or not, the world doesn’t provide us with the incentives to shoot for quality and impact. We have to make that drive in-built.
4/ Whole-hearted execution makes a good idea into a great one.
The ‘does it actually work?’ question is all about strategy. When you’ve nailed a strategy, every decision that follows should be intentional — never arbitrary or random. Intentionality, flair and an eye for detail is what makes for whole-hearted execution. Without it strategy falls flat.
I learnt what it meant to really execute from people like Sophie Howarth, co-founder of The School of Life, who has an incredible ability to take a concept (like “a philosophy school for the masses”) and execute it fully, down to every last carefully-considered detail. Sandy Campbell’s strategy involved making his charity Workingrite look more like a construction company than a youth club so that its young apprentices felt like they’d started their adult careers, not another youth employability programme. Whether it was adopting the colours of black and yellow in the brand or hiring staff directly from the construction industry, Sandy knew that his strategy was nothing without unwavering execution.
5/ Being productive doesn’t always mean being productive.
As a leader, you will need to put your shoulder to the wheel everyday. You’ll want everything to be tip top and it will grate you if it isn’t. You’ll want to make progress through that list of million and one things to do, to build and to improve.
But you also have to be pragmatic. From time to time, you have to keep that antsyness in check and remember to be happy, healthy and whole (you are, of course, more than your job).
This lesson has been hardest for me to learn because graft, high standards and ambition are things I really value. They are good things in themselves but, now, I can see times when I’ve prized those qualities above all else — and my performance has slipped as a result.
“Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” Abraham Lincoln
Starting or running a small business demands such a jumble of skills. In a given week, you might find well yourself writing a press release, building some financial projections and drafting a legal contract. No one comes into entrepreneurship with all these skills down pat. Just like making time to rest and recover, you also have to make time for learning, for sharpening your axe, even as your to do list mounts.
Leadership is scary. There’s no one to hide behind and people around you that look like they’re doing, well, better. They look like they’re running faster, raising more money, getting more press, having a more joyous, glamorous time along the way. Always, resist the urge to compare your backstage with their frontstage.
“Life shrinks or expands in proportion to one’s courage” Anaïs Nin
Never feel like you’re not worthy, in whatever context you find yourself in. If you, like me, feel a rush of anxiety when you think you’re out of your depth, remember that imposter syndrome is fightable.
Breathe deeply and tell yourself that you have a right to lead.
Do this because because emanating a sense of inadequacy or desperation has never led to great opportunities — and do it because it’s true.
