“At the end of the day, when it comes time to make a decision, all you have to guide you are your values, and your vision, and the life experiences that make you who you are.”

–Michelle Obama

5 Strategies for Making Big Decisions – Stephanie Pellett CreativeWe all face tough choices in our lives and businesses. Should we partner with that company, or go back to school for that certificate, or take on that short-term contract in order to fund our next big product launch? I’ve written before about how to choose which business idea to start with, but what about if you’re struggling to decide whether you should do something at all? Often we end up at a crossroads, without a clear idea of how to move forward. Which path do we choose? What should we say no to? Is it even worth it? Will we regret not doing it?

Here’s the bad news: these are questions with no easy answers. Every single opportunity you face will be unique to you. As with most things in life, there’s no one-size-fits-all solution for figuring out the next right step to take. Those decisions depend on so many factors, most especially your own personal values system and goals.

That’s also the good news! Nobody can make your decisions for you, because nobody is you. Only you can ultimately know what’s right for you, your life and your business. Yes, this is occasionally annoying – for example, I can’t count how many times I have heard from clients OR said myself, “Can’t you just tell me what to do next!??!?!” But at the end of the day, it’s also freeing. You get to decide what’s right for you. You get to decide what aligns with your values & goals. You’re in charge, and that can be fun and exciting.

If you’re still at the point where making big decisions feels more overwhelming than freeing, I’m here to help. Here are five of my favourite tools and prompts for choosing well for you.

1. Make a weighted pros & cons list

We’ve all made a pros & cons list before, but for me they just don’t cut it. Regular pros & cons lists help you lay out important facts, but they don’t provide any context. They assume that all factors are created equal, when they most assuredly are not! One pro could easily be more convincing than four cons put together. And while we usually do a bit of this balancing intuitively, in our heads, a weighted list can bring even more clarity. By adding numbers, you’re bringing in tangible factors to what can often be a wishy-washy, amorphous process.

I find that this technique helps the most with situations that “look really good on paper.” Those kinds of decisions can be so tricky, because to others (and their values systems), an opportunity might seem like a no-brainer. It’s easy to get swept up in those opinions, or to be “seduced” by the shiny positive factors on the list. Maybe there are only a handful of cons, so they seem easy to brush aside. Not so fast!

5 Strategies for Making Big Decisions – Stephanie Pellett Creative

This process literally and figuratively allows you to add (your) values to the decision-making process. It forces you to reckon with the shiny things and the downsides based on what is right for you and only you. Maybe others wouldn’t see a one-hour commute as a huge con, but for you it would be a massive drain on your energy. Maybe others would feel excited about weekly paid staff lunches out a fancy restaurant, but you personally could care less. Assigning tangible, numerical values helps you see what is truly important to you, and what is not.

How To Do It:

Get a big pad of paper with lots of space, and draw a line down the middle. I prefer analog to digital for this! Set a timer for 10 minutes, and write down every pro and con you can think of in each column. Then, set a timer for 5 minutes, and go down each column and assign each item a value out of 5, with 5 being “This factor is very weighty and important!” and 1 being “This factor isn’t really that significant to me.” I find it helps me to put the cons values as negative numbers, where -5 is “really bad” and -1 is “not so bad”. At the end, tally up the columns and see which one wins. Of course, you don’t automatically have to make your decision based on this list! But it usually helps shed some light on the facts of the situation as it relates to your own personal values.

5 Strategies for Making Big Decisions – Stephanie Pellett Creative

2. Do a post-mortem, in advance

A post-mortem is the process of debriefing on a particular situation. Let’s say you recently ran an event with a small team. Your post-mortem would entail meeting as a group to discuss what went well, what was a disaster, and what could have been done differently. You’d make notes of all the changes that need to be made, find solutions to nagging problems, and come up with fun opportunities to add more joy and ease for next time. Post-mortems are a simple practice, but generally bring a HUGE amount of learning, growth and value. 

What’s cooler is that they can also be used ahead of time, as a prompt to anticipate problems or play out situations in advance. All you need is a bit of imagination and the right questions, and suddenly you have access to a whole wealth of information that can help you design a better situation for everyone involved. This process can also help us make decisions! By thinking through (in advance) all the things that could go right or wrong, we put ourselves in a clearer mindset. Doing a post-mortem ahead of time forces us to be realistic about what it will actually take to see something through, and that can help us decide if it’s something we can commit to.

How To Do It:

Close your eyes and imagine yourself at the “end” of the decision you’re considering: for example, a year after you’ve taken that job, or 6 months after you ran that event, or 3 months after you launched that new offering.

Ask yourself a few questions: What happened that made this situation the worst-ever for me? What are the factors that made it such a terrible experience? What did I do or not do that contributed to my unhappiness in that situation? Then, ask yourself the same questions in a positive sense: What happened that made this situation the best-ever for me? What are the factors that made it such a positive experience? What did I do or not do that contributed to my happiness in this situation?

Once you’ve written all this out, check in. Which situation feels more likely, based on the information you have now? How much control would you have over the factors that would improve or worsen it? How much control would others have over the factors that would directly affect you? Would the worst-case scenario still feel worth it, or does it sound like an absolute nightmare? Do you feel like you have the bandwidth to take the risk that the worst-case scenario could come to pass? Again, you needn’t feel like you have to make your decision based on what this process uncovers, but more often than not you’ll find more clarity to help you decide.

3. Listen to your body

We’ve all heard this one before, but it can be hard to know what it actually means. Especially since fear and excitement can feel so similar inside our bodies! They’re very close to the same vibration. That being said, our bodies contain so much wisdom that we can tap into in order to make decisions. Here are three concrete, practical strategies that I find helpful when a decision is weighing on me:

  • Notice how you sleep: I like the way Elise Cripe writes about sleeping on big decisions. “Are you tossing and turning over doing the thing? Are you tossing and turning over not doing the thing? There’s your answer. Go with the choice that will allow you to fall asleep faster tomorrow night.”
  • Feel it in your chest: Marie Forleo has some great tips about paying attention to your body’s signals about your inner knowing. Her major question is “Do I feel expansive or contracted?” I often notice this in my chest – do I have a feeling of wanting to retreat into myself? Or do I have a feeling of energy moving outwards from my chest? For more on this test, watch her video here.
  • Recognize your automatic actions: Sometimes our bodies are one step ahead of us, so it can help a lot to notice your behaviour. Maybe you’ve already found yourself researching exciting lunch places near that job you’re considering taking. Or perhaps you’ve already drafted a letter of resignation from your company! Or maybe you’ve been on that same checkout page seven times in the past week. What are you already doing and what can it tell you about what you really want to do?

4. Choose based on who you want to be

5 Strategies for Making Big Decisions – Stephanie Pellett Creative

If you’ve tried some of the above strategies, and still aren’t getting a clear answer, that’s actually great news! It means that neither choice will be disastrous for your life or business! It means that no matter what you choose, you’ll learn something valuable and helpful. Yes, you might have to wave to the ghost ship that didn’t carry you, but everything will still be more than okay. (Spoiler alert: MOST decisions are like this.)

In cases like these, I love to turn to Ruth Chang’s framework for making decisions. Her idea is that hard choices are hard precisely because both options have major upsides and downsides, making neither necessarily better than the other. She says: it is not that one of the two options is better and we are too stupid to know the difference. Instead, the two options cannot really be compared because hard decisions like these are driven by our personal values, not statistics or objective data.

Her recommendation is to see hard choices as a chance to create our own reasons for making a particular decision. We can use hard choices as an opportunity to express our personalities and become the people that we want to be. Her framework encourages us to make the choice based on the person we wish to become, and what we want more of in our lives. We can use choices as a way to express our values. As Gretchen Rubin says, we can “choose the bigger life.”

5. Toss a coin

I promise I’m not being facetious when I suggest this, it’s a technique that’s helped me make decisions many times in my own life! A few years ago, I was trying to decide whether I should move to Korea to teach English or stay in Toronto and try to get a job. I was watching YouTube videos about decision-making non-stop, until one of them suggested this technique. Find a coin, label heads as “yes” and tails as “no”, and throw it in the air, telling yourself that whatever side wins is the decision that you’ll go with.

The idea is that while the coin is in the air, you’ll find yourself hoping that it’ll land on one of the sides. Or you may also have a reaction when you first see which side is facing up. Are you relieved that it’s heads, or does that cause you dread? Do you feel excited that it landed on tails? That information might be all you need to know to make your final decision.

Another similar strategy is to pretend that you’re putting the decision into someone else’s hands. Send a loved one your pros & cons list and post-mortem, and ask them to tell you which decision you should make. Chances are you’ll have a reaction to their decision, which can help you point to what you really want for yourself. 


Just Decide

A caveat: try not to spend TOO much time on the decision-making process. Decision-making can be a dangerous form of procrastination! More often than not, the choice itself is not as pivotal as the commitment to that choice. Use all the tools in your arsenal to choose well, and then commit to whatever you decide. Marshal your energies behind it, give it everything you’ve got, and see it through until the end.

I’d love to know: What strategies do you use to make big decisions in your own life and business? What has helped you come to a solid conclusion in the past? What helps you find clarity when decisions feel murky and confusing? Let me know in the comments below or over on Instagram @stephpellett!

PS. Need some space to find clarity about the next step in your own business? Download my Dropping In Questionnaire below, which is designed to help you identify blind spots and opportunities for growth. And it’s free!

Dropping In to Your Business – Stephanie Pellett Creative