What I learnt from writing and performing comedy for the first time.

And what lessons are there for business.

I turn 57 this year. I’ve got four grown-up kids, two grandkids, a sourdough starter called Kevin, and a recent scrotal injury from over-enthusiastic African drumming in West Bridgford. Midlife is weird.

To process all of this, I did what anyone trying to cling to relevance as they take a route straight through what is known as “Mid Life” might do: I wrote and performed a stand-up set about it. It was meant to be a laugh — and it was (genuinely people I didn’t know and who had paid to be there laughed at my jokes) — but somewhere between the cold-water swimming, the tantric mishaps, and the frozen peas, it also taught me a few things about life. And, surprisingly, about business.

You can see an audience recording of my set here (it’s a bit sweary):

Here are five things I learned from writing the set, and seven lessons that comedy has to offer anyone trying to lead, build, or run something.

Five lessons from the comedy set itself

1. Reinvention is survival

In my 20s, a perfect morning involved tequila and regret. These days it’s breath work on Hampstead Heath, cold-water swimming, meditation and a healthy bowel routine.

Ageing isn’t decline — it’s just evolution, stepping into your authority and maybe accompanied by some rebranding. If you don’t adapt, you stall.

2. Lean into the ridiculous

There’s a fine line between a midlife awakening and a midlife crisis. I crossed it holding a djembe.

But embracing the surreal lets us talk about real: masculinity, vulnerability, and ageing, without needing a TED Talk voice.

Sometimes laughter is the only way to tell the truth. Remember, it was only ever the Fool who could tell truths to King Lear.

3. Small things matter most

After all the beneficial spiritual investigations, it was a Hob Nob and a cup of tea from my wife that felt like real love.

It’s a blend of the quiet gestures and the big speeches that build culture and trust.

4. We need spaces to unravel

The drumming circle I joined was full of middle-aged blokes howling half naked instead of going to therapy (to be fair it was actually a form of therapy too). It was mad. It was beautiful. It was necessary.

How do we go about creating spaces for people to be vulnerable, messy, uncertain, and human? I run a men’s group that begins to tackle these issues. Its free and open to all.

5. Everything takes time to ferment

My sourdough starter, Kevin, has more Instagram followers than I do. He’s also a metaphor:
Life gets richer with time and care. But it also leaks, explodes, and smells a bit odd. That’s okay. Growth is never neat. In a world of perfection, of “American teeth” the real beauty lies in the wonky.

So those are the main lessons from my set, but what about the process? As someone who has written books, including one on public-speaking, I learnt loads about presentation and more. Here are my takeaways.

Seven lessons for business from writing and performing comedy

1. Timing is everything

In comedy, half a second too early or late kills the laugh. Indeed, not leaving enough space kills a laugh. In business, mistimed messages, clumsy rollouts, or not leaving enough breathing space between things does the same. Think about the Greek Kairos time, the time that is right for you.

2. Test before you commit

Comedians workshop their material. Then they try it out on “friends” often the hardest to please of audiences. Then they try it in small rooms before moving to bigger stages. Stewart Lee tests his work-in-progress shows for 100 nights at the Soho Theatre before going on tour. It’s small, intimate, he can feel the response to lines and jokes and this allows modification and refinement. Business does do this, but not enough.

3. Specificity beats generality

I could have just said “an African drumming circle in town”, but being specific and saying “West Bridgford” is way funnier than “a town.” The better known the town for its stereotype the better the joke. “Frozen peas on my groin” is better than “I was sore.”
Vague language is forgettable. Be precise. Be human. It’s what people remember. The same applies to your marketing.

4. Failure is feedback

Bombing in public is brutal — but every comic needs to go down badly at least once. It sharpens your instincts.

Businesses need more of this attitude. If failure isn’t an option, neither is growth: you don’t get one without the other. No-one (and no business) would choose to fail but sometimes the darkest night of the soul brings the greatest illumination.

5. Be human or be ignored

Audiences can smell a fake. So can customers, staff, investors, and stakeholders.
Comedy demands honesty and vulnerability. Business needs to stop pretending it doesn’t. Vulnerability and empathy are strengths rather than weaknesses, embrace them. The modest boast on Linkedin is easily seen through; the mantra “it’s all about the team” when it’s clearly not, rings hollow; the removal of ESG/sustainability when it falls “out of fashion” is an indication of the type of business you are.

6. Don’t punch down.

Humour aimed at others, aimed at minorities, delivered with an edge of cruelty, isn’t humour. It’s bullying. A comedian shouldn’t bully or demean, shouldn’t victimise, and shouldn’t humiliate. At my end-of-course performance the owner of the business that organised the training (let’s call him John) delivered a misogynistic, body-shaming, and nasty “comedy” set. Worse, he had people planted in the audience to “heckle” so that he could put them down too.

How many businesses have you worked in where there is an undercurrent of bullying and humiliation? Did it ever produce the best performance? Did it ever attract and retain the best talent? Does it ever produce the best comedy show? The answer to all of these is a resounding no.

7. Trust the process and be open to learning.

John (see point 6) didn’t attend any of the training and hadn’t followed a process. If he had attended his numerous “isms” would have been called out on the way. There’s something here about hierarchy. Leaders need to be humble enough to go back to the shop floor, to go back to school and start learning again. We are all in this together.

These are my takeaways from the experience. I loved it. I will do another performance. I will still get nervous. I will continue to seek-out mid-life activities, otherwise I wouldn’t have any new content.

The comedy coach assigned to us was Anthony Williams and he (and his wife Dawn who is also a comedian) was wonderful, truly inspiring and able to meet each of us where we were. Sadly I can’t be as positive about the company that organised and promoted the training I’m afraid. If you want to learn comedy skills find a local comedy club and go there, they will undoubtedly hold courses. Or drop Anthony a line via http://rockcentral.co.uk/