Why aren’t you wearing those shoes?
They seemed perfect when I bought them.
I was looking for new shoes. And I thought I had found them.
I loved the color. They had just the right amount of details. Interesting, without being distracting. The heel height was perfect. The price was great.
And yet…
Every time I went to wear them, something didn’t quite feel right.
At first, I thought it was the socks. Perhaps I wore a different pair when I tried them on in the store?
I tried thicker socks. That didn’t help. So I tried thinner socks. Still not right. I even bought new socks.
And yet, every time I went to wear them, something didn’t quite feel right.
And so I didn’t wear them.
Eventually, I had to acknowledge to myself that something that seemed perfect on the surface wasn’t actually the right choice.
Has this ever happened to you?
So often, we look for reasons to say yes (or no) to something, and we look hard. I wanted these shoes to work so much that I kept seeing all of their great attributes, ignoring the fact that they just didn’t fit.
The more advanced we get in our careers, the easier this becomes. We know what to look for, and we’re often surrounded by people who tell us what we want to hear. We can find ways to justify anything we want. We know what numbers are needed to make the case, who will tell us it’s the right decision, and how to share the story so others get on board.
By not seeing the full picture, by not taking all the data seriously, we can make suboptimal decisions, sometimes even bad ones.
It might be the job we take that seems like a great opportunity, despite the red flags.
It might be the relationship we stay in because it was good once, even though it isn’t anymore.
It might be continuing to pursue a product the market has rejected, keeping the employee who isn’t pulling their weight, or buying shoes that look good but don’t fit.
So what can we do?
The next time you have that feeling in the back of your mind that perhaps there’s more you should be considering, try these tips:
Consider your criteria
If you were to make the decision today (not knowing you had the option in front of you), what would your criteria be? Thinking about it in the abstract and then returning to the solution in front of you can open up new insights to help make a better choice.
Perhaps you’ve invested a lot in a new product. Consider what early signs you need from the market to continue investing in its ongoing development. Or maybe you’re facing a big repair on your car. Have you already decided when you want to consider buying a new one?
Argue the other side
Advocating for an opposing viewpoint can help us see things we’re missing when we’re invested in our current perspective.
Perhaps you’re noticing you’re a little over eager to hire the amazing candidate you just interviewed. What are the reasons you should say no? Or maybe you find yourself a little quick to say no to an invite to a dinner party. Why would going be a good choice?
Do a pre-mortem
Considering the future if you make your decision can be helpful. What are all the things that could go wrong with your decision?
Maybe you’re considering one of two big projects. Get the team together and consider: you’re a year into the future and the worst has happened. What caused things to go wrong? Or perhaps you and your partner are considering buying a new home. What could happen in the next 5 years for you to hate where you’re living?
We often unconsciously look for reasons to make the decisions we WANT to make, even when they’re not the decisions we NEED to make. Considering your decision criteria, advocating for the other side, and considering all that could go awry can help you make more solid decisions.
What decision do you want to more deeply consider today?
As you read this, are you finding yourself wanting a thought partner, someone who can support you in creating the life you want?
I help people get from here to there.
Let’s talk. Book time, and we’ll figure out how to get you unstuck and get going.
How will you iterate towards the person you’re becoming?
March 6, 2025
About the author:
Christina Von Stroh is a leadership coach who helps her clients become wildly successful by applying iterative software development practices to achieve their dreams. Want to work with Christina to help you iterate towards the person you’re becoming?
Book your free strategy session.
