Photo by Simon Edwards

10 Things No-one Ever Told You About Running Your Own Event (But Probably Should)

Laurence McCahill
Mar 13 · 8 min read

Since The Happy Startup School was born in 2012 we’ve hosted hundreds of events, from small meetups to retreats and festivals.

Over that time we’ve learnt a great deal about what it takes to create an impactful gathering — where attendees typically arrive a little apprehensive, but leave feeling fuller in every sense.

“These guys have mastered the art of igniting collective inspiration, support and trust, magically between strangers.” Nisha Bora, Social Entrepreneur, India

I put the success of our events down to one thing – we just love bringing people together.

We’re not alone — we each have an innate desire to connect with one another. It’s a fundamental human need and can even extend our life – the world’s happiest people are the most connected and live longer.

Through our work with entrepreneurs, leaders and changemakers the world over, we’re coming across more and more leaders like us, that are not only building companies but building communities.

After all, where there is a clear mission, there are believers.

Innovating how we gather

Naturally when you’ve found a group of people with a shared interest the obvious next step is to come together in person. However, be warned – what might start off with just a bunch of friends, or even an online community, can quickly swell into a something much bigger before you know it.

Our first event was a humble meetup above a pub in London (admittedly not very innovative). We’ve since raised the bar and had thousands of people attend our events from Barcelona to Bangalore. We’ve run ideas cafés, hijacked conferences, popped up at festivals, gone on bike rides, jumped off mountains and even hosted a death bed meditation.

We’ve enjoyed challenging the convention of what a business event looks like – we’ve found that the more memorable the experience, the greater the impact.

Sharing what we‘ve learnt

Given that we’ve developed a reputation for putting on a good show, we regularly get messages from people wanting to know how we do it. I’ve already laid out some of our approach here and there, but in this post I wanted to touch more on the soft skills – the stuff we don’t talk about.

Lots of people try to host events, but very few stick around for the long haul. It can be a hard slog if you don’t get it right and there sure are easier ways to live your life.

But if you get it right, there are few more rewarding things to be part of.

So buckle up, here are some things that you should know so you’re prepared for the rollercoaster ride ahead.

1. You need the mindset of an entrepreneur

Some people love rollercoasters, some people hate them — there’s ups and downs, uncertainty and fear (and maybe a bit of excitement too). Just like running a business or event it’s how you cope with the feeling that will determine whether you survive or thrive.

To succeed you’ll need to develop a growth mindset and get comfortable feeling uncomfortable. With any event something will go wrong along the way, it’s how you handle it that matters.

2. You’ll need to ask for help (and lots of it)

Running an event is like building a startup in super-quick time. You’re up against the odds – whether that’s time, budget or resource. You’ll need to get in the habit of asking for favours from those around you, particularly those with more experience than you. Any great event has a team of people in the background collaborating to bring a vision to life, even if it means relying on goodwill at the start. But the quality of your team will dictate the quality of your event. Which leads me on to…

3. You’ll need to get good at selling your vision, fast

Like any good visionary, you’ll have to spend time at the beginning sharing your ideas and painting a picture of the future that inspires others. You’ll need to sell the outcome of what you’re creating to collaborators, stakeholders and potential customers even if it’s not actually happened yet (and you’re still unsure yourself whether you can pull it off).

Just remember that the more convincing you are, the more belief and confidence others will have in you to bring this vision to life. Sure, the imposter syndrome will rear its ugly head, just don’t let it dominate you.

4. You’re the only who really cares at the beginning

With any new idea you’ll have a strong vision in your head, but everyone else will be too busy to listen (or won’t quite have the time to get it). The first few times you share this idea with others you’ll most likely get blank looks, or even worse no look. Sometimes even those you think are a dead cert, don’t show up. You’ll have to develop a thick skin and see this as a marathon not a sprint. But each step you make is a step forward.

If you care, they’ll care. It just might just take longer than you think.

So don’t worry about big numbers early on, find one believer, then two, then three…

5. It will be *way* more work than you think

When taking on a new project we can often look at things with rose-tinted glasses. We underestimate how long something will take and focus on the best, not worst, case scenario. But as you can’t have a clear picture of all the tasks that require your attention – or if like me are a stickler for detail – then chances are working on it will take double the amount of effort you think.

I’d recommend tallying up your hours – from sales and marketing, to logistics and delivery – to get a true picture of how long you’re spending on putting this thing on. While this may put you off doing it again, it will also create a transparent view of what the true cost is and help you make a better judgement call.

6. You can fake it before you make it

As one of our community members said recently “forget practice makes perfect, practice makes progress.”. Moving forward is the key thing with any creative pursuit. Procrastination can be a killer.

This is because too many people make the mistake of trying to get everything in place at the beginning. But as I mentioned, your job early on is to sell the vision to the world. And you can do this without too much work.

So thingify it – ie. create a landing page or a slide deck, use images, words and graphics that capture your vision (or if that’s not your bag bring in someone that can do it for you). Faking it before you make it will help you to lower the risk of putting on a show and allow you to pre-sell before making any big commitments. You can work out the details later.

7. You’ll learn things about yourself you didn’t know

Let’s be clear, you’ll push the limits of your comfort zone. And as a result learn things about yourself that you didn’t know, some good, some bad. But you’ll learn nonetheless so you can do things differently second time around. When we ran our first few events we had no clue what we were doing. But over time we built up our experience and confidence to the point that we could host bigger gatherings. Incremental changes lead to bigger changes before you know it.

8. It will consume you 24–7 (if you let it)

As much as you try to put it to the back of your mind, you’ll be thinking around the clock about the details, both big and small. Ideas will come when you least expect them. Some people will offer advice, others will question your motives. Over time you’ll learn how to detach yourself from the success of it, but deep down you know that as the buck stops with you, you’ll want to make it damn good and prove the doubters wrong.

9. There’s *always* one

My parents worked in the hospitality industry for many years and said to me before we hosted our first big event ‘don’t worry, there’s always one’. And they were right.

At almost every big event I’ve been part of, there’s been one person that can dominate your attention and make you feel like everything isn’t working. But as much as we try to do our utmost to ensure everyone has an amazing experience, we can’t always please everyone. When this has happened in the past, we’ve looked critically at what we could have done differently, and typically the answer has been not much.

Over time we’ve learnt not to let the experience of one person bring us down or limit our ability to put on a great show for everyone else. You have no idea what’s going on for people and have to let go. If it’s 2 or 3 then it’s a problem worth looking into. So don’t let the one negative spoil the plethora of positives.

10. It will be worth it, it will be worth it, it will be worth it

Credit: Dan Edwards

A lot of the most rewarding things in life don’t come easy – having children, running a business, training a dog and you can add hosting events to that mix.

But just because something is hard, it doesn’t mean it’s not worth doing.

Even though you might think otherwise when you’re in the thick of it, I can bet that after a few days of recovery you’ll want to do it all again. Human nature means we only remember the good bits (why else would people have more children…).

Sometimes ignorance is bliss — you don’t know what you don’t know at the beginning. But being aware of some of the roadblocks ahead can mentally prepare you for the highs and lows of bringing people together.

Good luck. 💪
(It will be worth it)

The Happy Startup School run transformational gatherings like Alptitude and Summercamp for purpose-driven entrepreneurs and leaders

The Happy Startup School

Build a life and business rich with purpose

Laurence McCahill

Written by

Co-founder The Happy Startup School. Building a global community of heart-shaped entrepreneurs and leaders, one event at a time.

The Happy Startup School

Build a life and business rich with purpose