Making Difficult Decisions

There comes a point in most of our lives where we find ourselves at a crossroads.

Where we have to choose one path over another. 

The decision we make will influence the shape of the rest of our lives. 

I’ve recently been faced with one of these choices. 

In September, I started a Masters conversion degree in Psychology and have been running The Weekend University at the same time. 

Doing both simultaneously has led me to feeling unfocused; like my attention and energy are split in multiple different directions, and I’m not getting very far in any. 

Being home for Christmas gave me a lot of time to think the situation over, and it became clear that I actually had a choice between two paths. 

The first is to continue doing both, and the second was to stop doing the masters, and focus fully on growing The Weekend University.

I’ve never struggled with a decision more in my life. 

Whatever path I chose, was going to profoundly influence how my future turns out – the type of work I’ll be doing, where I’ll be doing it, and who I’ll be doing it with.

In the process of making the decision, some insights helped me gain some clarity. If you ever find yourself at a crossroads, and aren’t sure which path to take, they might be useful to consider.


#1 – Essentialism

I read Greg McKeown’s Essentialism a few years ago, and it left a lasting impression on me. 

One diagram in particular stuck in my mind: 

The circle on the left represents a non-essentialist approach to life. The diagram on the right represents an essentialist. 

We all know someone on the left side – who ‘has their finger in many pies’. 

This person seems to be a superhero. They’re master multi-taskers and doing loads of different things simultaneously. But as we can see from the diagram, their energy is going in many different directions, and they aren’t going very far in any. 

This is how I felt during the first semester of my Masters.

Essentialists, represented by the circle on the right, choose a different way to live. They decide to say no to a lot of different things, and pour themselves fully into the one or two activities that matter most.

As a result of having the discipline to say no to the many, they can go ‘all in’ and make significant progress in the few.

Simply being aware of Essentialism can help you make difficult choices in life. 

It can help you realise that time is a finite resource, and choosing to say ‘yes’ to one thing, invariably means saying ‘no’ to something else. 

By saying ‘yes’ to everything, we say ‘no’ to making significant progress in anything. 


#2 – The Sunk Cost Bias

Our brains come pre-wired with a set of biases. 

These are unconscious mechanisms that affect our decision making and behaviour. 

We’ll often do something because of an unconscious bias, and then invent a ‘rational’ reason why we did it after the fact. 

One of the most powerful of these biases is known as the ‘sunk cost’ bias. 

This theory states that the more we’ve invested in something, the more difficult we find to let it go. For example, imagine that you have £10,000 in savings, and you have just spent the past nine years investing £1,000 per year in a new business (Company A), making your total investment £9,000.

However, it has now become clear that Company A is very unlikely to succeed, and it’s probable that you will lose all £9,000 – even if you invest your final £1,000 in an effort to save it.

Now imagine another opportunity comes along to invest your final £1,000 in a different company (company B) that has a much greater chance of success. 

What do you think you’d be likely to do? 

The rational thing would be to invest your final £1,000 in Company B.

But if you’re like most of us, you’ll think: ‘Well, I’ve already invested 90% of my money in Company A, it would be such a shame for me to stop now.’

This example shows how when we’re already heavily invested in something (whether with effort, money, time or emotions), it distorts our reasoning and affects our ability to make good decisions. 

We value things more that we’re already heavily invested in. 

Therefore, it can help  to temporarily separate ourselves from our emotions and give ourselves some distance from the ‘sunk cost’ bias.

One of the most effective ways to do this is the ‘Knowing what I now know’ question. 

Simply put, this involves doing some time travel in your head, and going back to the time before you made your initial investment.

Then you ask yourself: ‘Knowing what I now know about how this is going to be, would I start it again?’ 

In my case, I took myself back to before I began my Masters, and asked myself the question. 


#3 – Excitement Goals vs ‘Should’ Goals

I have never see-sawed on a decision as much as this one. 

One day I was convinced that I should continue doing both the Masters and The Weekend University. The next, focusing on the business seemed like the best option.

After weeks of going back and forth, I finally made up my mind and decided to focus on the business. 

I contacted my course mates, course leader, and everyone else that needed to know.

But in the days that followed, I kept getting this nagging, guilty feeling that I had made the wrong move. 

I would wake up and think: ‘What have I done!?’ 

The feeling was so bad one morning, that I actually emailed my course leader and told him that I had ‘had a change of heart’ and would be coming back to do the degree. 

But now, I felt even worse.

Later that day, I told two different people about my ‘change of heart’, and what I had decided to do, and they both had almost the exact same reaction. 

They told me: ‘Great – but you don’t look happy. You look like you’ve forced yourself into something.’

And that’s exactly how it felt. 

When it really came down to it, I was excited as hell about going ‘all in’ on my business and where that could lead. But I was anxious about it too. It was a very uncertain path, and there were no guarantees it would work out.

The degree on the other hand, felt more like something I ‘should’ do. It was a more certain path that would give me more options in the future. 

But I felt heavy when I thought about doing it; restricted, limited, confined. 

So really the choice was between excitement (with uncertainty), and safety (with certainty). 

Which did I want more?


#4 – Explore All of the Options

I thought it over some more, and decided to call my course leader and ask for his thoughts. 

Luckily, he made me aware of another option I hadn’t even considered. 

It would be possible for me to take a ‘leave of absence’ from the degree, and recontinue (exactly where I left off) 1 year from now, or 2 years from now – if that’s what I wanted to do. 

This meant that I could throw myself fully at growing The Weekend University, and if I really had the desire to go back and do a Masters 1 year or 2 years down the line, then I could. 

So that’s what I decided to do.

It’s tempting to think that when we make a decision it’s an ‘either or’ scenario.

However, often there are other, better options we just haven’t considered yet – because we’ve been so focused on our choice. Therefore, if you’re struggling to decide between two alternatives, it can help to ask: ‘Is there another option here that I haven’t considered yet?’


We are our choices.

Jean Paul Sartre

The choices we make profoundly influence the life we’re going to lead. 

When we choose to say ‘yes’ to one potential future, it means saying ‘no’ to another.

And this can be quite a scary thing. 

Therefore, it can help to have some decision making tools at hand during these times to give ourselves the best chance of making the right move. 

Otherwise, we could end up doing something we might regret in later years.

Essentialism, the ‘knowing what I now know’ question, ‘should goals vs excitement goals’ and exploring all of the available options are four tools I found helpful in my case. 

Do you have any decision making tools that help you make the big choices in life?

If so, leave a comment below and let me know.