Which path will you take?
That day, I had a decision to make.
Will I keep doing what I’ve always done, or try something different?
There’s a lake on the other side of the ridge by my house. There’s a short loop close to the lake that takes 30 minutes, door-to-door. There are a couple of other longer options, taking me through the open space nearby, looping around a collection of athletic fields.
When I go for a walk, I have few decisions to make - one loop or more, short loop or long. It’s pretty easy, comfortable. I know what I’m getting into. Some days there’s even interesting wildlife (like the Canada geese that make their winter home in the area).
But that particular day, as I approached a parking lot by the far side of the lake, I noticed it.
There was another path! I could head south, across the street, and down the hill.
I had no idea what was over there, other than a bunch of houses. But for some reason I felt a pull.
Should I check it out?
Should I keep doing what I’ve always done, or try something different?
Has this ever happened to you?
This question comes up often in my coaching conversations with clients.
Should I stay with the company I work for now, or look for something different?
Should I continue down an individual contributor path, or make the move to a leadership role?
Should we stick with our current staff meeting agenda, or mix it up?
Should I look for a new job in the industry I’ve been in for years, or switch to one that aligns with my passions?
Should I continue in the domain where I have experience, or try a different role?
We’ve all been there. Sometimes something happens that makes the current trajectory of things no longer appealing - challenges we no longer want to tolerate, obstacles we’re tired of facing, or exhaustion from the feeling of constantly pushing the boulder uphill. Other times, we encounter a new path we’ve never considered before, or something shifts to make us reconsider a direction we had previously rejected.
And then we find ourselves asking the question…
Should I keep doing what I’ve always done, or try something different?
If you find yourself considering this kind of dilemma, consider these questions to help you make your decision:
Is this a reversible choice?
Sometimes trying something new can be a simple experiment where you can return to the familiar if things don’t pan out. Other times, opening one door means we have to close another. Which is true for the decision at hand, and can you influence the stakes?
Perhaps you’re considering taking on a stretch project at work. Once it’s done, can you return to your current responsibilities? Maybe you’re considering a dramatic new hairstyle - can you use AI or try a wig to see how the new style compliments your face shape before sitting in the stylist’s chair?
What will I gain or lose with each option?
Thinking about the tradeoffs - the pros and cons of each option, can often help make the path clear. This often allows you to consider how you value the attributes of the option, rather than the options themselves.
Maybe you’re considering leaving your current job for a new opportunity. How does the growth opportunity for the new role compare to effectiveness you have now because of your experience in your current position? Perhaps you’re thinking about buying a new home. How does the new location stack up against your current finished basement?
How can I get the information I need to make my decision?
As you dig into these questions, you often come up with new criteria you want to explore. Which questions really need to be answered, and how can you get those answers?
Perhaps you’re offered a new role at your existing company. How can you get a better sense of the people you’ll be working with? Or maybe you’re thinking about taking a class to learn a new hobby. Can you find reviews of the curriculum and the instructor?
We’re often faced with the decision - should I keep doing what I’ve always done, or try something different? Finding ways to make our choices more reversible, understanding how we value the attributes of the choices we’re considering, and getting the information we need to make our choice can help make the path clear.
What path should you be on?
What big decision are you facing right now?
Would a thought partner help? Someone to help you make sense of your choices to help make your path forward clear?
You’re here. You want to be there. Let’s talk. I can help.
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 20, 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.
