That was a choice: making difficult decisions

  • What do you want for dinner tonight?
  • What are you going to wear to the wedding?
  • Where do you want to go on your next vacation?
  • Are you going to the gym today?
  • What is your five year plan?
  • Which of these career paths is more lucrative?
  • Do you want that iced or hot?

We are faced with decisions and choices every damn day.

And as someone who doesn't even have a consistent coffee order, why is it so hard some times to make a decision? Or pick between a limited number of choices?

How do you weigh your options from something as simple as `what colour do you want your manicure today?` all the way to `do you want to have kids?'

Let's get into the juicy parts of decision-making 🍋 I am far from an expert in this area, and especially as someone who gravitates towards the Enneagram Type 2, I think more with my heart than my head. But I can say, as someone who has made a series of difficult decisions more recently, and watched friends go through the process of making difficult choices, I can confidently say that it is more of an art than a science 🧪 There are formulas and experiments you can run, millions of business books on how to make difficult decisions, but ultimately, you hold the paint brush, and no matter the strategy you're using today, it's up to you how you craft your moves.

Here's some tools I've used to paint some recent decisions 🎨

Be hyper aware of all the factors at play.

Similar to the process of seeking a meditative state, you need to be aware of every single component of your surroundings to lock into your zen state. From the white noise, to the pillow under your tushy, to the stress of your day, everything plays into what brought you there and how you can get where you're trying to go.

Are you making this decision out of fear?

Are you running away from something or running towards something else? You want to be running towards something — a lifestyle change, a passion, anything that will keep you moving on the trajectory you want. You can get there by thinking about why you're running away if that's your gut instinct initiating the decision. What would you need to see in your next choice that aligns more with what you want?

Are you making a decision out of necessity?

If you are experiencing limited options, think about why that's the case. Have you exhausted every other option and resource in your toolbox? Are you on a time limit? What can you expand and contract here that paints the masterpiece you're really trying to conjure?

Or maybe you're experiencing a limitation of yourself—physically or mental health related. Think about all the factors at play, and understand that sometimes the hardest decisions come down to your most basic needs not being met.

Are you making a decision with as many known pieces as possible?

This is when you put on your detective hat, and before you can shout that it was colonel mustard in the kitchen with the knife, you have to ensure you've knocked out every other piece of evidence and opportunity you may have missed on your first pass.

Who haven't you consulted that you should? What other view points on your decision are you missing?


Stand your ground.

This goes back to the people-pleasers and heartthrobs out there—when you share your decision, if you choose to, do not let other people's opinions of your decisions falter or alter the choice you ultimately decided.

When I was leaving Shopify, a few folks told me:

  • "You'll be back"
  • "They've been so good to you, it doesn't make sense to leave"

A huge part of how I managed this comes back to a book I recently read, the four agreements, and the first two agreements in particular:

  1. Be impeccable with your word
  2. Don't take anything personally 

You can only control your actions, everyone else's reactions to whatever you decide or choose are on them, and don't take it personally.

You don't have a sixth sense to know what they're going through or where they're coming from, you're also not their therapist and it's not your responsibility to justify anything you do with your life to anyone else around you.

As I'm typing this, I realize this is easier said than done.

"Just don't take it personally"

But we are all out here performing and trying our best to juggle the expectations of others with just the kind of person we want to be.

In the words of the infamous Brene Brown, be your true authentic self.

Quiet the noise, meditate without opinion, when you have all of the options in front of you, which is the path you want to go down?


It is OK for a decision you made to not work out the way you planned.

This roots so heavily in failure, and this 'anti-failure' culture that we are honestly toxically swimming in. There are communities like Fuckup Nights, and other cultural spaces where we can 'talk about failure' but we are definitely still rooted in that narrative, 'oh, that was a failure, try something different'

We have to acknowledge, everything changes. I think a global pandemic, climate crisis, abortion rights under attack and an illegal war in Ukraine (just to start) can all teach us that nothing is certain and everything can change with or without your influence.

You made the best decision for yourself with the best information you had at the time.

People are entitled to change their fucking mind. There are many people in my life I wish would change their mind on heated emotional topics, so I will never hold you accountable to a decision or thought-process you had at one point in time.

I am entitled to change my mind whenever I want and for whatever reason I have for myself, and I don't need to give you a reason for why I changed my mind.

What did you learn from this decision?

Give yourself time to reflect. Think about what lead you to the decision you made in the first place, and why you're now at a point where you need to make another decision?

  • What lead you to the choice you made originally?
  • What did you learn from that decision you made?
  • What has changed for you that has lead you to make a new decision?

This is scary. Change is scary even if it's for the better. Making 'wrong' decisions is scary.

No decision you ever make is a 'wrong' decision. You learn from every choice you make. It may lead you down a path you never thought for yourself, but when you find yourself there, just look back at the street signs, find yourself again if you've lost yourself.

Never forget

  • Decision making is an art, not a science.
  • Do not take anything personally.
  • There is never a wrong decision.

When it comes to art, someone once told me:

If no one hates it, no one really loves it either.


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