EP25 When Your Career Doesn’t Go to Plan: Finding Clarity at a Crossroad

Are you standing at a career crossroad and wondering why it feels so messy, emotional, or overwhelming?

 In this episode of Career Advice That Gets Results, Christine Eliseev takes you inside the real experience of career transitions, and not the glossy reinvention stories you see online, but the human, honest, messy middle that most people never talk about.

Whether you’re navigating redundancy, burnout, stalled progression, or a quiet sense that you’ve outgrown your role, this episode helps you understand why crossroads feel so destabilising and why that doesn’t mean you’re behind.

Christine shares personal stories, real client examples, and a grounded advice for recognising the messy middle as a normal and necessary part of transformation. You’ll learn why fear shows up, how to name the roadblocks in your way, and why you don’t need the whole plan to take your next step.

If you’re feeling stuck, uncertain, or quietly questioning what comes next, this episode will help you breathe again, get perspective, and see your crossroads for what it truly is: the opportunity to be available and open for something great.

In this episode you’ll hear about:
• The reality of transformation vs the what it looks like from the outside
• What the “messy middle” really is and why it matters
• Why naming roadblocks is so important
• Why you’re not behind, even if it feels like others are moving ahead

This is your invitation to stop judging where you are and start seeing what’s possible from here.

Transcript

Welcome

Christine 0:00

Hey there. Today we're going to be talking about when you get to a point where you realize you're at a career crossroads. Maybe your career plan isn't, well, going to plan. And now you need to figure out what direction you're going to go. So actually this whole season we're going to be talking about crossroads and transformation. But today we're going to focus specifically on some bits that happen in the middle that are very messy, some ways to think about roadblocks that you might be thinking about or seeing come up, and also what does actually being at a crossroad mean? And the fact that it doesn't actually mean that you're behind.

Christine 0:51

So I hope you get a lot out of this. I would really like to hear from you. Drop me a note, either via email or DM, and tell me what you think of this episode.

Christine 1:04

Hi, and welcome to Career Advice That Gets Results. I'm your host, Christine Eliseev. This podcast was created to give you support, ideas, and clarity as you go through career and business transitions. Each episode offers grounded guidance, practical tools, and gentle encouragement to help you identify opportunities, understand your options, and map a way forward that truly fits you. I spent many years climbing the corporate ladder while raising a family and traveling the world. I had many wins and many lessons, but I've always come back stronger. In 2020, I was asked to help guide other professional women experiencing setbacks, and this podcast is part of that response. I'm glad you're here. We can get through this together. I suspect you're here with me today because you're approaching or at a transition point, some sort of crossroad, and you're working through what direction you need to head from here. And how do you know you're moving forward in a way that feels aligned to what's really important to you?

The Messy Middle

Christine 2:16

I'm Christine Eliseev. If this is the first time you and I are having this moment together, then welcome. And if you've been here with me before, welcome back. Today we're starting a new season and a new year with something that a lot of people are talking about right now. Career crossroads.

Christine 2:37

I'm not talking about the glossy I'm reinventing myself kind. I'm talking about the messy, confusing I didn't expect to be here kind. There are lots of ways to describe it, but no matter what you call it, it means change. Change for you, your identity, your family, and possibly your financial position.

Christine 3:05

If you're feeling stuck or like you've somehow fallen behind, or maybe even left behind, you're in the right place. This whole season is about figuring out which direction to go, and I'm honored that you've allowed me to help you work through this. Before we dive in, I want to take a moment with you.

Christine 3:23

I call this an opening moment, and I use it any time I sit down to talk to someone who's navigating something big. I would like you to take in a deep breath and hold it for a second. And now release it and let it carry out some of that tension that you're holding on to. Now, I want you to set aside everything else that you've been thinking about and free yourself to focus on just you. Okay, feel that, be aware of it. And if you find yourself getting distracted or stressed, you can get right back here with another deep breath and a reminder to yourself to set aside everything else so you can focus. Okay, let's get into this.

Christine 4:20

When you're at a crossroad, it's easy to imagine that everyone else handles it with confidence and clarity. But if you look closely at all these stories of people who have made big midlife shifts, you'll see something different. You'll see real humans standing in uncomfortable moments, making imperfect decisions, and slowly finding their way towards something that fits. I'd like to give you a couple of examples.

Christine 4:50

Take Joe Cribb. Today she's a consultant, an author, a TED speaker, and a vineyard owner. From the outside, it looks like she had a bold, curated reinvention, but the real story started with a health crisis that forced her to question everything. She didn't glide into her new life. She fought her way through fear, uncertainty, and a loss of an identity that she's held on to for years. The glossy part came later, the messy part came first.

Christine 5:22

Mish McCormick's story is a joyful and expansive one. She added becoming a wedding celebrant to her already thriving fitness career. But even that wasn't a whimsical pivot. It was a late night study and extra training and vulnerability of stepping into something completely new at fifty. She didn't abandon her old path, she simply widened it.

Christine 5:49

But even widening an existing path still takes courage, energy, and a willingness to become a beginner again. These stories are inspiring, but it's more important to remember that none of them felt glossy when they were happening. Crossroads rarely do. They're not the polished I'm reinventing myself type moments that we see on social media. They're messy. They're the I didn't expect to be here moments, the ones where your confidence wobbles and your identity feels shaky, and you can't really see the future. It's quite foggy. Transformation only looks shiny from the other side. In the middle it's uncomfortable, it's emotional and human, it's really messy, the messy middle.

Christine 6:36

And it's totally okay for you to feel a bit untethered. We're going to be working through that starting today.

Christine 6:44

My own crossroads was so, so messy. From the outside today, looking at this portfolio career that I have, it might look intentional and curated, but there were lots of times when it didn't feel that way to me. When I was fifty and climbing the corporate ladder, doing what I was good at and doing what was expected of me, I got to a point where I realized I wasn't actually moving at a pace that would get me to my goal. And that was heart wrenching. You know what? I'm here to tell you that it's okay to grieve for the loss of what you thought your future was going to look like. Take the time, acknowledge it. It's okay to grieve. Transitions just aren't tidy. Mine wasn't, and neither are those for the people that I work with. I tried and failed at several things, but I iterated and I tweaked what wasn't working, and it's that messy middle part that's what made the transformation possible. It's also quite liberating.

Christine 7:52

Once you understand and truly know that you're at a crossroad, your future is so filled with just so many more opportunities that you're now available to take. If you were still where you were three, six, or twelve months ago, you might dismiss the greatest opportunity to transform your life because you weren't ready and available to be open to it at that moment. You were still working towards a future that just isn't going to arrive like you dreamed. It's those kinds of opportunities that I was unexpectedly open to, that allowed me to build a career that now includes project delivery, advisory work, a business supporting new immigrants, and leadership mentoring. It's what gave me the freedom to be present for my family and for my community. My path isn't right for everyone, but it was right for me, and that's the point.

Christine 8:49

At a crossroads, there isn't one right direction. You might do best by keeping on the same road that you're on, but just in a healthier environment. How does the idea of turning into something completely new make you feel? Does the idea of going down more than one path pique your interest?

Christine 9:10

You have options in front of you, but the common thread between all of them is that you need to make a decision and take action to bring them into reality. The people who thrive aren't the ones who feel certainty. They're the ones who take the next step, even when the path is still forming under their feet.

Christine 9:33

So now that we've established that things get messy, and they always do, so the good news is that's nothing to be scared of, and it's not an indication that you're not making progress. In fact, I would argue that the messiness is proof that you're making progress. What if you aren't seeing the mess? Well, there's usually a few reasons why, and by a large margin, the biggest reason is fear. Change is scary. It's totally okay to be scared. Well, it's okay to be scared as long as you don't let it stop you from doing something.

Christine 10:08

I personally was so scared of so many kind of ridiculous things. I was scared of real things too, like the financial impacts any decision I made would have on my family. I've always been the breadwinner, and everything sits squarely on my shoulders. In fact, on my phone, the wallpaper is a quote by Maya Angelou that says, If you don't work, nothing else will. So yeah, how invested am I in this? I was terrified of messing up. Which brings me to another point. I'm also a bit of a perfectionist. Uh okay, truth be told, I'm a raging perfectionist, and it can really paralyze me if I let it. I work every day on being okay with good enough. I know it can be hard, but if you aren't trapped by that perfectionist mindset, I would love to know how you did it. Please let me know. I'm serious. I'd really, really like to know.

Christine 11:05

Another thing that may sound kind of silly, but really does scare me is being judged. Do you ever worry about what others think of you? What people you've worked with in the past might think of you if you go off and do something totally different? I've gotten better at this over the years, but still sometimes I worry about what others think. And you know what I do? I remind myself that they're not thinking about me actually at all. And if anyone from my past thinks less of me because of the road that I've chosen, then honestly that's their problem and not mine.

Christine 11:39

But I get you. I know you're scared, so go ahead and feel that, but take the next step anyway. Let's do a little something that I would do if I was sitting in the chair right next to you right now. What if I could guarantee you that no matter what path you decide on, that you will be wildly successful? Just kind of what if. You will find you're living your life in a way that has meaning and purpose and lifestyle that goes way beyond what you could get into in your current or most recent career. And the way that you got there was because all of the things that are stopping you are magically taken away. Let's say I'm your fairy godmother, and I can remove everything that's stopping you from getting to your goal with a swish of my wand. I'll make that happen for you. But to do that, you have to tell me what needs to be disappeared. What are those things? What are those things that are in your way, those roadblocks? I need you to specifically name them so that we can go out and smash them away. Just get rid of them. I want you to spend some time thinking about this question. Imagine me with my wand just waiting for you to tell me what needs to be done. Write it down in your notebook or put it on a sticky note on your computer or your bathroom mirror. What do you want to ask me to make go away?

Christine 13:14

It's really important that you can name these things. Fear is such a weird thing. It can lose its grip on us when we put a name to it. Just the name gives you a place to start from in dealing with whatever it is. And fear might not be your only roadblock, but this is true for roadblocks. If you can name that roadblock, the things that are in the way, including those fears, we can figure out a way around, over, or through it. We always can.

Christine 13:49

There's a speaker and author that you may have heard of named Marie Forleo. She wrote a book called Everything Is Figure-Outable. And truth be told, I still have that book in my Audible playlist and haven't finished listening to it, but that's on me, not her. But honestly, the title really says everything. It really is figure outable. And this has kind of been a mentality I've had throughout my life. I don't know why, but I've just never believed that anything was insurmountable. But it was really nice to see somebody put it so clearly into a book.

Christine 14:27

Now, yes, some things are harder to figure out than others, and a career crossroads that you're staring at is absolutely leaning on that hard side. But here's the thing, you don't have to figure it all out before you take a step.

The Benefit of Naming Roadblocks

Christine 14:41

In fact, you might get more clarity after you take that step or two or three more. Different opportunities and solutions may appear that you can't see right now while you're standing squarely at that intersection. I actually love this about solutions. The first one you come up with doesn't have to be the final one that you land on. You're allowed to modify as you go based on what you've learned along the way or what new opportunities showed up. There's no rule that says you can't change your mind. The one thing though I do advise people that I want you to keep in mind is that you may hear sometimes you have to take a step back to move forward. If you hear that, I want you to be really wary. I've heard it, especially when I was considering moving between firms, and I know you may have heard this as well. And honestly, I'm going to call BS on this. And you can quote me on that. It's totally different if you need a job and you're okay taking a lower ranking or lower payroll than the one that you've had in the past because you need to keep a roof over your head and feed your family. That's totally different. I'm talking about when you have more control over the situation and you have options. No, you don't have to take a step back to move forward.

Christine 16:04

By the way, the next episode in this series is all about the different types of crossroads you might find yourself at and kind of what approaches we take, depending on which crossroads you're finding yourself in. So that's the next episode in this season. Um, that would be episode 26 or episode two in season three. Um, but yeah, you might see it as uh listed as episode 26.

Christine 16:28

Okay, also I feel like I should clarify something at this point. Yes, this podcast is called Career Advice That Gets Results, but the results have almost nothing to do with me. The results are yours, and I tell the same thing to the people who have gone through one of the programs that I run called the Bounce Back Roadmap. And I'm just giving you some advice, a proven framework, and some solid tools to help you make decisions. I advise, but I won't tell you what to do. Slight nuance there, but I really am your supporter and you're the rock star. You've done a lot already. You have success under your belt, you also have lessons. All of that informs which path you decide to start going down.

Christine 17:14

My next point, and I want you to really hear this. Being at a crossroad does not mean you're behind. This is one I have to remind myself of every now and again. Remember how I said that I was worried about what people I used to work with would think about the changes that I was making? Part of that was because I had this muddled mix of jealousy and sadness and anger and frustration and maybe even a little betrayal that I'd spent so many years working towards a goal that I wasn't going to achieve. I was chasing a title that I really should have known earlier wasn't ever going to be mine. I had lots of blind spots, and I was angry with myself that I didn't pick up on them sooner. I didn't work the system as well as others, and I didn't have strong enough relationships with the right people. That's a story for another episode, and there's lots of ways I've I've recovered from that and actually moved moved beyond. Um, all of this angst, though, was coupled with the absolute joy and happiness that I had for many of my friends and colleagues that were getting the promotion and getting invited into the partnership and really doing amazing things. I'm still absolutely thrilled to see all of these people move up, even if I didn't. And I say that with all honesty. These two conflicting feelings can sit side by side. I was never once angry or upset with these people around me. But what it did instill in me was a sense of stagnation. That I went from being right with them, or in some cases, even in line ahead of them, to being left behind by my peers and my friends. Is this something that resonates with you?

Christine 19:02

There's probably been a time when you heard about someone's promotion and you wondered, wait a minute, why them or why them now? Even if you know they're fully qualified, you may have had a touch of jealousy intrude into your thoughts. And you have every right to feel that. Relationships, specifically work relationships, are complex. But here's the real deal. You're not behind. It's a false narrative that there's this linear path. Even if you are on similar paths, everyone starts on that path from a different place. Some have more privilege than others, even if they don't recognize it. You joined the path, carrying all your past wins and lessons that I mentioned before. But those were different wins and lessons than everybody else that's on that same path is carrying. It's natural to compare yourself to others.

Christine 19:55

That's ingrained in us through the whole concept of performance measurement and. Tying a person's performance and promotions into not much more than metrics or OKRs or KPIs. Sure, metrics tell us something. It's a standard that everyone can be measured against, but it is biased. But you're not metrics. You're not OKRs or KPIs, and you're so much more than what can actually be measured. Have you ever noticed that corporate performance metrics change almost every year? Even the metrics that are kind of fixed, the ones that you really have little control over. Think about what that means in practice.

You’re Not Behind

Christine 20:37

I want to tell you a story about a mid-level consultant that I'm working with who has been at the same level for five years, and don't worry, she gave me consent to share this. She was told back then, when she was moved up into this level, that she should expect to be there for about six years. So in her mind and in her planning, she should be preparing for promotion right about now. When she started in this role, her company told her that she had to bill at least 82% of her time to clients to be ranked as a top performer. This is called utilization at many places. Well, today, that same threshold to be ranked as a top performer is 93%. So an 11% increase over five years. She's being evaluated on lots of other things too, but this hours thing may tank everything else. And what's worse, she actually has very little control over how many hours she's allowed to bill, because that's sorted out long before she's ever even brought into projects. And for her role, the people who do the pricing and the sales side of things, they often budget for that role to bill either 80% of their time or less, and definitely never at 100% of the time. This is the crossroads that she has been standing in. And if she was still there, she would definitely not get promoted because she will not hit the mark. And honestly, it's no fault of her own. Does that mean she's behind? Of course not. She has the years, she has the experience, she has the knowledge and the skills. And she has now just as much skill and hours as the people who were promoted five years ago. But the goalpost shifted on her, so what was good then is not good enough now. Could you say the goalpost shifted for you? She sure did, and those were her exact words to me. As a side note, she has recently accepted a really good offer from another company. And remember how earlier I mentioned that if you could name a roadblock that you could figure out a way around, over or through? That's exactly what she did. She subsequently recognized that her initial focus on hours, factors that were beyond her direct control, was actually misplaced.

Christine 23:08

Upon reflection, she identified an alternative approach. By advocating for earlier involvement in the sales process, she would be able to influence planning and secure the adequate time allocation. Her previous perspective was shaped on the constraints of not being engaged in the sales process. So as soon as she was able to say, actually, if I get involved with the sales process, this problem can go away. That became a lesson that she would carry with her for life. Does it fix her problem at her current company? No, it doesn't, and it won't. So she decided to make a change. But just now she has a way to look at this going forward.

Christine 23:49

So here's my takeaway for you. You're not behind, you're not late, you're not off track, you're just standing at a crossroads. And that alone means that you're ready for something new. Your fears, your doubts, your grief, your frustration, all of that is part of the messy middle. And the messy middle is where the transformation actually begins. You don't need the whole plan right now. You just need the next step. And you're capable of taking it.

Christine 24:16

I want you to reframe some of the things that might be going through your head. If you're saying I should have figured this out by now, I want you to reframe that and try saying I'm allowed to be exactly where I am and I'm allowed to move forward one step at a time. By saying that you should have figured it out by now, all that does is create pressure. But giving yourself permission to take one step at a time creates possibility.

Christine 24:45

This week, I want you to name the things that are standing in your way. The roadblocks, the fears, the beliefs, the practical constraints. Write them down somewhere. Write them where you'll see them. Because once you can name what's in the way, you can start figuring out how to move around it, or over or through it.

Christine 25:06

Thank you for spending this time with me today. And remember, there are opportunities everywhere. You just need to be ready and open to meet them. See you next week.