Re-Thinking

For Ambitious People (like you)

How do you make a good decision? How do you know if you’re making one? 

If you’re like me, you have a tendency to make decisions on the spot very quickly. On the other hand if you’re like my fiancĂ©, you tend to hold off on making decisions altogether. What’s the right way to do this? 

Well, it depends. 

If you’re in leadership at work, you’re charged with being the creative one. You need courage to lead your team in the right direction. For that to happen, you need to know what the right direction is. Courage is needed because you can never be sure, it’s just your best guess, or it’s based on something that happened in the past. 

I’ve been guilty of making plenty of mistakes with my team, trying something out and then having the rest of management force my hand to revert things back to the way they were. The amount of change I’ve had to manage over the years has been huge. But my team has had to work through more, because with every challenge, there is the easy way to do things, and then there is a riskier way to do something. The bet might pay off or it might get you unemployed. That’s why you need courage. The courage is what keeps you on the tightrope, making sure you get to the other side. You can’t lose your nerve. To have the confidence to take these risks, you need to think clearly.

Here’s an easy way to start: write down your thoughts on paper. 

The over simplicity of this action isn’t lost on me, but trust me - the difference between the complex and the simple is in the act of writing it down. It’s a well known thing in the literary world that writing well comes from re-writing. I argue that thinking clearly comes from re-thinking. The two are interlinked, so I’ll show you an example of how this works in practice for me. 

Whenever I’m unsure of something I write “I’m unsure about this because….” 

Whenever I need to make a tough decision “The right thing to do here would be to [fill in the blank] because…”

When I’ve got too much on my plate and I don’t know how to prioritise, I’d write “I need to do 1, 2, 3, 4, 5. The most important thing is [fill in the blank] because…”

Just start writing. Your mind will fill in the blank. The first try is just about writing down what’s on your mind. It doesn’t have to be clear. When you read it back to yourself, you’ll notice instantly that your thinking is now more directed. It’s more potent. Write, read, re-write, repeat. 

But what do I write? Write down the challenge you’re facing, and the key people involved that will be impacted by it. 

Next, brainstorm. Use the empty page to it’s potential. Write the possible solutions and ways to make it work. If you can’t think of any, involve your team and the key people that will be impacted. Don’t organise a meeting - instead, try talking to people 1 on 1 to bounce ideas and get their thoughts. 

Where do I write? There’s something different about writing with a pen and paper. I’ve heard some people like to type what they’re thinking, but for me, a pen and paper (or Remarkable tablet) feels more real. You’re not writing for anyone else, just for yourself. It doesn’t need to be perfect and your handwriting only needs to be readable to you. 

Just write.

Here are a few questions I ask myself regularly when I’m doing this exercise:

1. Where did this thought stem from originally? 

Try to find the heart of the issue that you’re trying to fix. Maybe someone missed a zero in the report. 

2. Will solving this problem lead to new challenges?

This is where you consult your crystal ball. If there is a possibility of further challenges from your solution then communicate them before you implement this to all your key stakeholders that are going to be impacted by this. This is the detail I’ve missed in the past, and it’s hurt. You don’t have to miss it. 

3. How do I feel right now? 

Am I angry, frustrated, confused? Am I overly happy and optimistic because your crypto portfolio went up 20% overnight? Note what you’re feeling when you’re making a big decision because your mood right now might be what influences your future for months (or years) to come. 

4. A variation of Peter Thiel’s quote - “If there was a gun to your head, how would you get this done in ______ instead of ______?” The original quote talks about getting your 10 year goal done in 6 months. (Credit to Tim Ferris for this one).

How long is this going to take? Longer than it used to take. But since the quality of your life is made up of the quality of decisions you make - it’s probably worth a few minutes of your time. I was having a coffee with a friend the other day and he told me he had a lot on his mind and he filled up 5 pages that morning! But he felt so much better after getting it out. You will too.

Over time, you’ll get faster and faster at thinking holistically. You’ll add more questions like the above to your arsenal. This is a good place to start. So start.

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