How do you make such a big decision?
Do you ever get caught up with all the nuances and criteria that could play into a big decision?
Your head swimming by all the different things you could factor into your choice…the “what if this” and “what if that” questions?
I know I can, and that’s just what my client Henri* was facing just a few months ago.
When I first started coaching Henri, he was in the early stages of a major career transition. While he was looking forward to this next chapter, “The rollercoaster of excitement and defeating anxiety that comes with making a career transition wasn’t something I was experienced with or prepared to handle.”
Many of us can relate. Any career move can be overwhelming, but when the change you’re trying to make is particularly big, the whole thing can be quite daunting.
For Henri, “The sheer volume of feasible choices to consider in the tradespace quickly became overwhelming. Do I completely change industries? Am I willing to take a title and compensation step back to do so? Is travel and location more important than total compensation to me? How strongly should I consider the team I’ll be working with relative to the other considerations of the job?”
“I honestly changed my mind about these questions on a daily basis, so I knew I needed help to settle my anxious brain.”
Many of us can understand how Henri was feeling, when we’ve been making our own big, life-altering decisions. It’s easy to spin ourselves into a frenzy trying to optimize for every criteria, every decision.
Enter coaching
Realizing that his current approach to his career transition wasn’t serving him, Henri felt that bringing in a coach would help him more effectively get to his ultimate goal - a career move that would set him and his family up for their next chapter.
“When I approached coaching, I thought following a prescribed process would be an ideal way for my style of decision making. I was hoping that would keep things well defined and easy to follow the steps to reach an optimal outcome. I was looking for an easy process solution without knowing what the end-game target truly was.”
To help clarify Henri’s thinking, and to leverage his craving for structured process, we began with a series of exercises aimed at narrowing in on Henri’s goals and values, what aspects of a new role would support those goals, and how to position Henri’s experience and skills to align with that kind of role.
Clarifying focus
Those activities helped Henri gain clarity around what he really wanted and what he had to offer. But exercises alone weren’t going to help him unlock the results he craved. Henri needed to figure out how he wanted to show up to align his experience with the role he was seeking.
“Christina did an amazing job of starting me through some structured process to organize my thoughts and help establish targets for our success criteria, that was right up my alley! But, she didn’t let me off the hook that easily; she did an excellent job at gradually pushing us out of structured process discussions and into a mindset shift towards the perspectives on how to make a successful career transition.”
As we continued coaching, we began to focus on how Henri wanted to highlight his experience and skillset in a way that would best align with the opportunities he wanted to pursue. The more Henri positioned himself with intention, the more his confidence grew.
“Ultimately, our focus was on my personal values, how my career choice can support my value system, and how to keep a perspective on evaluating job options in light of these prioritized values. This approach gave me the confidence to step into all interviews & company conversations with a firm understanding of what I have to offer, what I am targeting for my life, and how the next career choice will be optimally beneficial for my future employer and my family.”
Throughout these conversations, Henri was able to refer back to the work we did in the initial exercises, using them as a map for himself to achieve his north star goal. Before an interview, or when deciding if an opportunity was one he wanted to pursue, Henri could review what he had written, allowing him to focus on the intersection between what he wanted and what he had to offer.
Making a decision
Henri’s hard work paid off.
“Ultimately, I had four strong options to consider. As a final step, I revisited the prioritized values that Christina and I had worked through in coaching and it helped me find clarity to make a final decision.”
Rather than spinning over all the possible competing criteria, like he had been when we first started working together, Henri was able to find clarity in what was most important, and how he wanted to evaluate the tradeoffs between the different options.
That clarity made all the difference.
“As a wonderfully satisfying end to this coaching engagement, Christina’s support helped me in my negotiating and decision making to reach a company, position, and life-fit that I’m absolutely thrilled with.”
What big decisions are you facing?
What would help the answers become clear?
Should we talk?
You’re here. You want to be there. 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?
* Shared with permission. Name and identifying details changed to honor client privacy.
August 21, 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.
