4 slightly uncomfortable questions

So a few weeks ago I was on this flight to Malta (terrible plane food by the way) where I was speaking at the the “Ahead of the Game” Business Leaders conference and I found myself doing something I don’t often get time for:

Reflection.

As in, stare-out-the-window reflection.

What came to me was from VICE to YMU to the whole Sidemen journey, there've been these random recurring questions that have absolutely shifted my perspective (in a positive way) over the years.

Like, genuinely changed-the-entire-direction-of-my-business type questions.

So today I thought I'd dump the four biggest ones on you.

Perfect for a weekend :)

1/ "Are you playing the infinite game or the finite game?"

Stay with me.

Basically, are you playing to win a specific round or are you playing to stay in the game forever?

Most people are obsessed with the short-term stuff (daily sales, follower counts, etc) when the real opportunity is thinking way way beyond that.

I'm not saying short-term wins don't matter, of course they do.

I love a quick win as much as anyone.

But if that's ALL you care about, you end up making really bad decisions that sabotage your long-term success.

Like burning bridges for a quick deal, or cutting corners on quality to hit a target.

2/ "What am I avoiding looking at?"

This one's a little uncomfortable.

We're all avoiding something, right?

Sometimes the most important thing isn't what you're looking at, it's what you're deliberately NOT looking at.

The stuff you skip past in reports.

The conversations you keep putting off.

The metrics you conveniently forget to check.

And the crazy thing?

That stuff you're avoiding is probably the EXACT thing you need to focus on.

3/ "Who can solve this problem better than me?"

My biggest weakness as an entrepreneur for YEARS was thinking I needed to do everything myself.

Classic control freak behaviour, right?

I know I'm not the only one.

But here's the reality check: you're probably not the best person to solve most of your business problems.

Read that again.

There are people who can do specific things 10x better than you, in half the time, with less stress.

Finding these people and getting out of their way is possibly the most valuable skill in business.

This doesn't mean you're not good!

It means you're smart enough to know where your time creates the most value.

Your turn: 

What are you stubbornly doing yourself that someone else could absolutely crush?

Who's in your network with the exact skills you're struggling with?

4/ "What would make this worth doing even if it fails?"

This last one's a bit of a mind-bender.

Most of us judge projects solely on their outcomes:

Did it make money? Did it grow the audience? Did it hit the targets?

But there's this whole other way of thinking:

What if the process itself is valuable regardless of outcome?

• What will you learn?

• Who will you meet?

• What skills will you develop?

• How might it position you for something else?

When you identify what makes something worthwhile regardless of conventional success, you suddenly have this crazy freedom in how you approach it.

I've found this completely removes that paralysing fear of failure.

Because even if it "fails" by normal metrics, you've still won in ways that might actually matter more.

Your turn:

What project are you hesitant to start because you're afraid it might fail?

What would make it valuable even if it didn't succeed in the way you initially hoped?

Questions > Answers

Obviously I don't have all the answers.

Nobody does.

That's kind of the whole point.

But I've found that asking better questions has been 100x more valuable than hunting for perfect answers.

The right question at the right time can change your perspective, your decisions, your entire trajectory really.

Try sitting with one of these this weekend.

Just pick the one that stood out the most to you (you know the feeling).

And let me know how it goes!

I love hearing about these lightbulb moments.

Remember, the creator mindset is all you need to grow 🌱

Did someone forward this to you? Sign up here to get the next one straight to your inbox.

If this email landed in your spam or promotions folder, move it to your primary inbox so you never miss an update from me.