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Career decision tools (part 3): let go

This is part 3 of a 3-part series on career decision tools. Read part 1 here and part 2 here.

Stories are my wheelhouse. My coaching clients come to me to make sense of their story, or to figure out their next plot point. My professional / personal branding clients come to me to harness the power of their story, and find the angle and language that fits.

So, here’s a story for you (shared with permission) from a client we’ll call Jane. It’s about letting go.


Long before I met Jane, she was on track to create her ideal life and career, but she was terrified of making bad decisions. Specifically she wanted to invest her money wisely and live in a home she owned, so she thought of buying a condo, but she was scared it would end up being a bad decision.

Jane told her therapist this, and her therapist said this:

“So what? So what if it ends up being a bad decision?”

It seemed like a rhetorical question, and Jane was confused and frustrated. She never went back to therapy and she never bought a condo.


Years later, Jane came to me for career coaching. We’d been working together on and off for over a year, and she was considering whether to take a new position she had been offered. It was complicated, and once again she was worried that she would make a bad decision.

She had previously shared the condo story with me, and I brought it up during our session. First I jokingly asked her “so what? so what if it ends up being a bad decision?” (trust me, I am hilarious). Then I asked her how that response had landed with her, when her therapist said it years earlier.

Jane: “I just found it unhelpful, like, really unhelpful.”

Me: “And how about now, when you look back on it? What has changed?”

Jane: “I think she was trying to tell me that it doesn’t matter that much. And maybe that the idea of “good decisions” and “bad decisions” is oversimplified. Life is more complicated than that. I think she was trying to tell me that maybe any decision (even the one I thought might be “bad”) is better than the agony I was inflicting on myself by living in fear. I think she was saying a lot, just in a really ineffective way that I couldn’t see at the time.”

Me: “And what could she have said, that would have been more helpful?”

Jane: “I don’t know. Maybe she could have asked me what a “bad decision” meant. I would have told her that I was scared I would buy a lemon of a condo and it would disintegrate or experience an unrecoverable drop in value. I would have told her I wanted a partner to buy a home with, but that I felt disempowered waiting around for a partner when I could just do it on my own. I would have told her that I felt really unknowledgeable about condos, and that I wasn’t confident in my ability to learn about them. I would have told her that I wasn’t sure where to find people with integrity who could help me and would have my best interests in mind.”

Me: “…”

Jane: “And she could have asked me what would it would mean if I later decided the decision had been “bad”. I mean, what does that even mean? Maybe I would have felt like a total badass buying a condo on my own at 26, even if I had to sell it a few years later at a loss, or whatever… maybe that would have come with great lessons and I would have gone on to buy like 5 more condos because now I knew how to avoid some common traps.”

Me: “This “bad decision” label is fascinating. That was quite a smorgasbord of stories and emotions underneath it. And it was doing double-duty, because really you had two decisions underlying it: (1) Do I buy a condo now (vs waiting)? and (2) if yes, which condo do I buy? On the first question, you couldn’t predict the future, you could only accept the unknown. On the second question, you were identifying that you needed more education (knowledge) and support (trustworthy people). All very reasonable. And then there’s the outcomes. We take decisions based on the information available to date. We witness outcomes once time unfolds. If the condo building burns down, was buying the condo a bad decision? Not necessarily, right?

Jane: “I think I was definitely wrapping up the outcomes with the decision. But you’re right, you never know what’s going to happen. You can take an educated guess, but that’s all. I needed help to see how I could make a “good decision” – even if there were a few gaps. I needed to learn to have confidence in my ability to make “good decisions”.

Me: “And knowing what you know now, with the benefit of additional experience, how do you make a “good decision”?

Jane: “A good decision is one where I consider all the information available to me. A good decision is one where, if I feel I lack information, I get more input. That might be talking to an expert, or reading a book. A good decision is a decision I make (not one I wallow in forever).

Me: “And how could we apply that framework to the current decision, of whether to accept this new position you’re been offered?”

Jane: “I have all the information. I have done so much research. I am scared but I’m pretty sure I’ll regret not going for it. So I need to take it. Based on the possibilities it represents. And I’ll learn the outcomes as I go. I also need to make the decision and move on. A good decision is getting out of limbo.

Me: “And how does that feel saying that out loud?”

Jane: “so good! like I’m done thinking about it. I’m ready for something to happen. I’m not leading with fear, I’m ready. I’m going to tell them tomorrow.”

Me: “Awesome. And we want everything to be even better than you are expecting. And we hold space for that. And also, if things don’t end up being as great as you expected, if there are surprises around the corner (and there usually are a few), what happens then? How do we view this decision then?

Jane: “I can still know that I made a good decision. I thought it through and I took action. The outcomes are basically separate. Plus, I’ll get to influence those, and I’ll do my best to influence the outcomes all along the way.”

Me: “Right, because life and careers don’t unfold over decades with a handful of critical point-in-time decision moments. Of course some decisions matter more than others, but you make decisions every day. In the ways you show up. In the ways you work. In the ways you relate and seek impact.”

Jane: “Yes. This seems like a big decision right now, and it is, and it’s also just one decision in a long line of decisions. It’ll be fine. I feel so much better about it. I am letting go.”


And that, my friends, is the story of Jane, her cryptic therapist, the illogical way we label decisions “good” and “bad” when what we’re really labeling is unpredictable outcomes, and… ultimately… letting… go…

In the end, what keeps a lot of people stuck and / or hurting in their careers (and apparently their real estate lives), is judging past decisions and fearing future ones.

Major decisions are usually complex, nuanced, and fraught with future unknowns. Analyze them, feel your way along, then decide what a “good decision” means for you right now, and make one. Comment below or DM me over here to let me know how you’re doing with this.

I’m cheering you on.


Want to learn about coaching? Here’s a link to get on my calendar for a free intro session.

About Allison

Inspiring radical evolution in work and life.

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