“I want to know it will all work out.”
I was making the leap and had accepted a new role.
I knew it was a “towards” decision - I was moving towards work and a team that inspired me. I also knew that I couldn’t go back. I was closing the door on a chapter of my career.
Even so, I was struggling through the transition. Did I make the right choice? How was it all going to work out? Would I regret stepping away from my old role? Could I “hack it” in the new one?
And so I kept saying “I want to know it will all work out.”
Do you ever feel this way?
A version of this question has come up a lot in my coaching conversations recently.
“I want to make this change, but I’m not sure how it will go.”
“I’m ready to do something different, but what if I’m not any good at it.”
“I’m in this new role, and it’s feeling really messy. When will it get better?”
We all want certainty, but we never know what the future holds. And when we’re stuck on wanting that certainty, it’s easy for our thoughts to spiral around how bad things might become.
I’m going to fail. I won’t make enough money. I will let down those around me. I’m going to embarrass myself. It’s ridiculous to give up a sure thing for an unknown.
Next time you find yourself focusing on all the bad things that might come, try this exercise:
Envision the worst case scenario
This one is usually easy, our spiraling has often taken us there already. So lean in. What happens in the worst case scenario? What’s the impact? What would you do if that happened?
Say you can’t hack it at the new job. What happens? Do you get fired? Have to find a new job? Will you be out of work, burning through savings, have to sell your house?
Envision the best case scenario
Next, consider the best case scenario. The one where things go even better than your wildest dreams.
Will you be promoted in record time? Be able to retire early to sail the world? Make an incredible impact for your customers and your team?
Envision the most likely scenario
Most of the time, the odds are pretty slim that the worst case or best case scenario will actually come true. What’s the most likely outcome?
Will the road be a bit bumpy for a while, but you’ll figure it out? Will you need to rely on others longer than you’d like, but it’s still reasonable? Need to cut back in a few areas until your business picks up steam?
Now, consider the probability of each scenario. How does the future look now? Are you seeing any actions that could help reduce the likelihood of the worst case scenario, and improve the odds things will go well?
When we actually give ourselves a moment to consider multiple possibilities and the likelihood of each, we can often see more paths forward.
What future is in store for you?
Will you send me a message and share what you learn from this thought exercise?
November 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?
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