At University, there was a point when I realized I didn’t want to get a job that had anything to do with what I was studying.

In an effort to figure out what I actually did want to do, I started to take an interest in entrepreneurship. I looked at what ‘extracurricular activities’ my University had to offer in this sphere so I could see if it was for me.

That’s how I stumbled across the Social Entrepreneurship Society. They were running various projects, each with a social cause.

Sounds good – I thought.

So I joined.

And it turns out I was quite good at it. I quickly got promoted to project leader, and the following year I got elected as President of the society.

I had never really thought of myself as a leader before.

Yet there I was, in a position where I had 80 sets of eyes staring at me and awaiting my direction.

It would turn out to be the biggest challenge I had undertaken in my life until that point.

It was the first time I got a taste of what it's like to be a leader.

I think its something you can never fully prepare for.

So, of course, I made a lot of mistakes.

I want to share some of them with you today.

Putting positivity ahead of candor

In any endeavor, I’ve always thought it’s important to celebrate the successes. And I still think it’s important. Because if we only ever look to solve the things that aren’t going well, it can be difficult to stay motivated and appreciate how far we’ve really come.

So that’s the mindset I went into my role with. I was going to focus on the positive and celebrate the successes.

But there was a problem.

We got off to a really rocky start.

Several projects struggled to get off the ground and a few project leaders nearly quit before we’d even started.

That wasn’t good, because projects were the bread and butter of our society. They were the main reason people joined – they wanted to get their hands dirty.

I knew I had to do something to keep members motivated.

So I decided to celebrate the things that were going well. Only, there weren’t that many to choose from.

I felt like I was scraping the barrel.

At the same time, people could sense that things weren’t going so well.

There was an elephant in the room.

My approach never helped us deal with the real issues we were experiencing. They were issues that would plague us until the very end of the year.

In hindsight, I now know I should have led with radical candor. I should have started with:

“Hey guys, things aren’t going so well and we need to up our game.”

I believe that would have helped us address the issues early on.

Being able to focus on the positive is a wonderful trait and one that I admire in people.

That said, positivity should never come at the expense of honesty.

Not being on the front line

I’ve already mentioned that projects were the backbone of our society.

However, as President, I didn’t think it was my job to get involved with the projects directly. My job was to manage the society as a whole, right?

Maybe, but here’s the problem:

Most people had no idea what a successful project looked like.

For many, it was their first year in the society. They didn’t even know what a ‘project’ was.

In contrast, I had been there for some time. I had seen and thought about many successful and unsuccessful projects.

I knew what we had to do.

But I wasn’t the one doing it. So I tried my best to communicate to project leaders what we’re trying to achieve.

But it’s different when you haven’t seen it before.

That’s why many of our projects struggled to get off the ground. And all because I was stuck in my ‘managerial’ duties. Which were far less important than actually running a successful project.

I should have put myself on the front line. I should have taken the lead in one of our projects.

Rather than telling people what success looks likes, I should have shown them.

Trying to please everyone

One of the most difficult things about running a society at University is that people usually have other priorities, like their actual degree.

For that reason, member retention is very difficult. We would usually start the year with around 80 members and end with 20–25.

It was something I wanted to try and improve on.

So I did that by trying to take everyone’s views into consideration. That’s the approach I took when setting meeting times, organising events and running training sessions.

I wanted to make everyone happy, so they would have no reason to leave.

But the problem with trying to please everyone is that you end up pleasing no one.

The truth is there was always going to be a proportion of people that would leave. Running a project is hard work and it takes time, and many people (including myself) often underestimate just how much time they’ll need to spend on their University degree.

Instead of trying to please everyone I should have focussed on pleasing the people that were really committed to the society. Because they were the ones that delivered the results.

Comparing myself to others

Our society was actually not unique to our University. It existed in a similar form in many other Universities across the country and internationally.

Once a year, we all came together to present our projects to a panel of judges who would determine which team made the biggest social impact.

Now, I’m used to being a high performer. So I was keen to do well in this competition. But as I mentioned before, we had some problems at the start of the year that proved difficult to overcome. That meant we probably weren’t going to make it too far.

Unsurprisingly, we didn’t.

Naturally, I started to compare myself to other leaders who had done better and made a greater impact.

“What was it that they were doing that I wasn’t?”

This kind of comparison can be helpful at times, but too much of it isn’t useful.

And I was doing it too much.

Looking back on it, I was at a very different point in my leadership journey to many others. There were some that had been leaders their whole lives – some had captained sports teams, others had been the head boy/girl of their school, some had even started their own businesses.

I simply didn’t have the same level of experience as them.

There were also different factors at each University that affected the success of their team. For example, some teams got sponsorships.

I also found out some teams had really exaggerated their impact in their presentations. So it was like trying to compare a photo of myself to a photo of someone else that had been heavily edited.

Instead of trying to compare myself to others, I should have focused on comparing only my current self to my former self.

Delegating things that were my responsibility

Don’t get me wrong, I’m a big fan of delegation. I actually think most people micromanage too much. But there is such a thing as over-delegation.

In the first few weeks of the year, it became clear that one of the members who was also in a position of responsibility was not putting in the necessary work.

Even though I knew they had a good reason, I also knew their position was important and I needed to have a conversation with them about whether or not we should find someone else for that position.

I knew it wouldn’t be an easy conversation. But luckily for me, someone else volunteered to have it.

And I let them.

At the time, I told myself that I didn’t know the person in question that well enough, so it was probably better if someone else spoke to them.

In hindsight, this was just an excuse I made to myself because I didn’t want to have the difficult conversation.

Long story short, it led to all sorts of tensions in the society and a mess that could have been avoided if I’d had the guts to step up and do the thing I didn’t want to do, but was actually my responsibility.

Pandering to outside influence

I mentioned already that our society was part of a wider group of societies from different Universities. This wider group had its own management, and, in a sense, each individual society had to ‘report’ to this management.

Now, that might have been alright, but there were several things we were required to do that didn’t seem to be in the best interest of our society. There were processes that we had to go through that seemed overly corporate. This was supposed to be about entrepreneurship, wasn’t it?

But we had to do these things to be part of the wider group.

I later found out why we had to do all these things that didn’t really make sense for our society.

It was because the whole thing was sponsored by a few large corporates, whose goal was to recruit the most talented graduates. And what better way to find them than through a so-called ‘Social Entrepreneurship Society.’

Now call me a cynic, but I believe it was never really about the projects we were doing or the impact we were making. Because if those were the goals we were really doing a bunch of things that didn’t make sense.

But if the real goal was to make it easier for the sponsor companies to recruit, all of a sudden everything we were doing did make sense.

Once I saw it, I couldn’t unsee it.

The question is what did I do about it?

Absolutely nothing.

That’s right, I continued to do, and to ask my team to do the things that didn’t really make sense for us.

All because I was afraid we wouldn’t get invited to the party.

There was an alternative.

I could have ‘disaffiliated’ the society from the bigger group.

It would have been a bold move. We would have been out on our own. It would have been uncomfortable.

But sometimes, the right decision is the one that’s most uncomfortable.

Not communicating goals and expectations upfront

I mentioned already that we didn’t get off to a great start to the year.

I often picture the situation as a team setting out on some kind of running challenge. We all turned up to the starting blocks, seemingly ready to go the distance together.

We awaited the starting signal.

*BANG*

And off we were.

I sprinted ahead at full speed. But there was a problem. I looked around and none of my teammates were with me.

I looked back at the starting blocks, and they’re all looking at each other. Wondering what’s going on. Questioning if they’d missed something.

Before we started the year, it was very clear to me what we needed to do. I had been thinking about it for a long time.

I made the mistake of assuming it was clear to everyone else as well.

But it couldn’t have been, because I’d never actually communicated it to them.

No wonder they felt a bit lost.

Over-stretching myself

Here’s a list of all the other things I was doing while trying to run the society:

• My University degree
• Teaching salsa lessons
• Working part-time
• Trying to start a business
• Studying for a citizenship test
• Volunteering
• Trying to have a social life

It was too much.

I’m not really a believer in the idea that you should focus on just one thing, but I had taken that mentality a little too far and spread myself too thinly.

As a result, I probably didn’t dedicate the time that I should have to the society, and the time that I did dedicate I had other things on my mind, so I was constantly distracted.

That’s not a good recipe for leading a team.

Some final thoughts

There’s certainly no shortage of success stories on the internet. I believe one day I’ll be able to tell mine too.

But I also believe it’s important to talk about the full journey.

The above was one of my ‘not-so-success’ stories.

But I still don’t see it as a failure.

Even though I made a lot of mistakes, I don’t judge myself for them. I’ve learned from them, and the next time I’m in a position like this I’ll hopefully make 8 mistakes less.

Nobody’s perfect after all.