#278 Helen Hanison: Outgrowing the Career Everyone Else Envies — Part Two

Summary

Podcast Summary: Chief Change Officer Episode #278 – Helen Henderson: Outgrowing the Career Everyone Else Envies — Part Two

Introduction

In Episode #278 of Chief Change Officer, host Vince Chan welcomes career coach and former board-level PR executive Helen Henderson for the second installment of their two-part series, “Outgrowing the Career Everyone Else Envies.” This episode delves deeper into Helen’s transformative journey from corporate success to meaningful career redesign. Helen shares invaluable insights on aligning personal values, redesigning careers with agility, and mastering the mindset needed for enduring transformation.

Act 1: Alignment to Me (00:01:48 – 04:21)

Helen Henderson emphasizes the foundational importance of aligning one’s career with personal strengths, values, and purpose. She outlines a bespoke “career compass” composed of three components:

1. Strengths: Helen notes that while professionals often recognize their strengths through appraisals and feedback, it’s crucial to re-engage with these strengths, especially when feeling disconnected from one’s work. “For any career redesign to be robust, it needs to be strengths-based or else we’re in fantasy land” (04:21).

2. Values: Helen highlights that values are directional, guiding how we use our strengths to express what we stand for. She asks, “What do you want to stand for? What are the most important things drivers for you in life?” (04:21).

3. Purpose: Moving towards action, Helen defines purpose as the driving force behind living aligned with one’s values. It’s about what actions will make one feel purposeful and alive.

Act 2: Career Redesign (04:21 – 08:50)

Transitioning from alignment, Helen discusses career redesign as the actionable phase where self-awareness transforms into real-world applications. Key points include:

• Pilot Testing Multiple Designs: Helen advocates for exploring various career paths through pilot tests and conversations, dismantling the myth of a single true pathway. “There’s a number of ideas, and once you can start to see that, you can start collecting experiences or collecting conversations or both and just testing them” (07:50).

• Agility in Career Planning: She emphasizes an agile approach—continuously iterating and adapting based on new information and experiences. “That’s the fastest route to transformation” (07:50).

Act 3: Transformation (08:50 – 14:18)

Even the best career designs require mindset mastery to navigate obstacles and maintain resilience. Helen outlines:

• Mindset Mastery: Developing the ability to handle setbacks without derailing progress. “We need the mindset mastery to strive long enough to actually succeed” (08:50).

• Resilience Tools: Learning to interrupt negative self-talk and anticipating practical barriers to stay on track.

Hope Mapping: Anticipating and Navigating Obstacles (08:50 – 14:18)

A standout concept introduced by Helen is the “Hope Map,” a psychological tool adapted from William Schneider. It involves:

• Anticipating Worst-Case Scenarios: Thinking through potential obstacles and planning actionable responses. “Hope mapping helps you think about worst-case scenarios and then what would you do if” (09:28).

• Creating a Resilient Plan: By outlining responses to challenges, individuals can maintain hope and resilience when faced with actual setbacks. “You are that close. And the growth you actually want for yourself is just the other side of navigating this” (14:18).

Resilience and Support Systems (15:49 – 27:30)

Helen and Vince discuss the non-linear nature of career redesign, likening it to swimming where hitting a wall isn't an end but a push in a new direction. Key insights include:

• Embracing Non-Linearity: “I don’t think anybody’s career, or life for that matter, is linear. It’s more like zigzags” (16:44).

• Avoiding Common Pitfalls:

  1. Skipping Career Clarity: Not taking the time to understand strengths, values, and purpose (21:22).
  2. Being Married to One Idea: Helen warns against anchoring to a single career path, advocating for multiple viable options.
  3. Failing to Pilot Test Ideas: Testing and iterating career ideas before making significant moves.
  4. Lacking Support Systems: The importance of having coaches, mentors, and a trusted support network to provide guidance and fresh perspectives (21:22).

• Community and Support: Vince shares how conversations with guests reinforce his commitment to the podcast’s mission, underscoring the value of a strong support system. “Support systems are vital. That might mean hiring a coach… or simply having conversations with people who share your vision” (24:18).

Key Takeaways

1. Start with Alignment: Understanding your strengths, values, and purpose is essential before embarking on career redesign.

2. Adopt an Agile Approach: Be open to exploring multiple career paths and continuously adapt based on new experiences and information.

3. Use Tools Like Hope Mapping: Anticipate challenges and plan responses to maintain resilience and hope during transformations.

4. Build a Support Network: Engage with coaches, mentors, and like-minded individuals to provide guidance and encouragement.

5. Embrace Non-Linearity: Accept that career paths are often zigzagged, requiring flexibility and continual reassessment.

Conclusion

In this enlightening episode, Helen Henderson provides a comprehensive framework for transforming one’s career by aligning personal values, designing agile career paths, and mastering the mindset needed for lasting change. Her practical tools and profound insights offer listeners a roadmap to outgrowing their current selves and achieving fulfilling, purpose-driven careers.

Notable Quotes

• Helen Henderson on the importance of strengths: “For any career redesign to be robust, it needs to be strengths-based or else we’re in fantasy land” (04:21).

• Helen on career redesign agility: “We keep iterating, always moving through. And that’s the fastest route to transformation” (07:50).

• Vince Chen on resilience: “Failure isn't part of the manual because if we keep moving, learning, adapting, we don’t fail. We figure it out” (25:59).

Resources Mentioned

• Helen Henderson’s Website: helenhannison.com
• LinkedIn Profile: Helen Henderson on LinkedIn
• Book: A Smart Guide to a Purposeful Career – Includes a Hope Map quiz for listeners to discover their career type.

Join the Community

Become part of the 130,000+ followers outgrowing themselves with Chief Change Officer. Subscribe on LinkedIn, Apple Podcasts, Spotify, and YouTube @chiefchangeofficer.

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This summary captures the essence of Episode #278, providing a comprehensive overview of Helen Henderson’s insights on career transformation. Whether you’re feeling stuck or seeking purposeful change, this episode offers actionable wisdom to guide your journey.

Transcript

[Narrator]

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[Helen Henderson]

If.

[Narrator]

You'Ve been having your McDonald's sausage McMuffin.

[Vince Chen]

With an iced coffee from somewhere else.

[Narrator]

Now is a great time to reconsider. In the Pacific Northwest, it's never too cold for an iced coffee in the morning. Grab yourself a medium caramel, French vanilla or classic iced coffee for just $2.29. Beverage may cause craving for McMuffin or hash browns. Prices and participation may vary. Cannot be combined with any other offer or combo meal.

[Vince Chen]

Hi everyone. Welcome to our show. Chief Change Officer, I'm Vince Chen, your ambitious human host. Our show is a modernist community for change, progressives in organizational and human transformation from around the world. What happens when your shiny successful career starts to feel like a trap? Helen Henderson has the answer. She went from board level PR executive to career coach after realizing that the ladder she was climbing was leaning on the wrong wall. In this two part series, Helen shares how she hit pause, got unstuck, and built a career that actually fits. We'll talk about career detour, tough choices, and why midlife isn't a crisis is a chance to redesign. If your job looks great on paper but feels like sandpaper, this one is for you. Let's get into it. Let's dig into the boat. Now you structured into three Act 1 alignment, Act 2 career redesign and Act 3 transformation. First, why did you choose these three as the core structure? Why start with alignment? Why follow that with career redesigned and then end with transformation? And second, for each of these acts, what are the key takeaways or core messages you would want readers to walk away with?

[Helen Henderson]

Let's start with act one, the act of alignment to Me. The act of alignment is an important foundational step for everyone in career redesign. And I'm pretty insistent actually that we give this proper time and attention at the beginning of working with somebody. Because otherwise if we don't hesitate there on purpose and take inventory, what happens is I'm helping somebody kick the can down the road of what they think or assume the right problem solve is. Now, maybe I'm supporting them, but I'm just supporting their own thought process that they would have had without me. What I'm trying to do very deliberately here is say, let's go back to basics. We build a career compass. So very personal, highly bespoke, and it's made up of three components. One is strengths. And I find the professionals I work with tend to be pretty fluent at talking to their own strengths. They build careers on them, they've heard them in appraisals. They're aware of what other people get value to about them and their work. However, if you're feeling very disconnected from what you do, you might not be owning them as much as you used to, or you might feel very disconnected from them. You might be discounting them altogether, assuming everybody has them. So there's something there. And that's important because for any career redesigned to be robust, it needs to be strengths based or else we're in fantasy land, what we can do. So it's important, but it isn't as important as values. So we very quickly move on to the value of values because they're directional. We need to utilize our strengths in order to express our values. So values are less easy for people to access. They operate under the consciousness. But put very simply for time now, it's what do you want to stand for? What are the most important things drivers for you in life? Because that's what we need to your career to have synergy with. We need to have some kind of logic link between what you do and what you feel is most meaningful. And then we wrap it all up with a sense of purpose. So we start to get a bit more action oriented about living into those values, if you like. What is going to feel purposeful now? It's a verb. What are you doing to achieve that feeling, that alive and aligned feeling? Now Act 2 is really like the meat in the sandwich is career redesign. And it's a completely different gear again, it's all about action. How do we convert that radical self awareness, that incredible career clarity we've got in Act 1 into our real world now? And we translate that into a series of pilot tests, we start thinking about a number of different career designs that, that have merit, that feel resonant for you. So that starts to dispel the myth that there's one true pathway you should be on or used to be on or wish you were on. It's there's a number of ideas and once you can start to see that, you can start collecting experiences or collecting conversations or both and just testing the. I suppose it's like, can't say that today stress testing your own aviation because there's no risk that way. You've already put yourself in the environments in some way or given yourself exposure to different ideas to before you make any dramatic moves or big leaps. And so it's an agile career design is very agile. You keep attracting incoming information, you keep testing, you keep tweaking. And so you're always iterating, always moving though. And that's the fastest route to transformation, which is the third act. The act of transformation is really because even the best of career designs aren't enough all on their own. We need the mindset mastery to strive long enough to actually succeed, to understand how to encounter the inevitable obstacles and barriers and not get to own off the track. And that takes a certain amount of learning to interrupt our inner critics and anticipating practical barriers and obstacles and having the resilience and the tools to keep moving forwards. Anyway. Yeah, that's all three.

[Vince Chen]

Yes. For this podcast, I always say it's about walk the walk, talk to talk leadership. I like to talk to guests who have gone through real change themselves. Not just sharing advice, but lived experience. That's the kind of value I want to bring here. Now, when I skim through your book, one word really stood out, which is hope map. What is it? Can you walk us through the idea?

[Helen Henderson]

Yeah, sure. Hope mapping is in the act of transformation and it's an important part of protecting your plans. Because if we can anticipate obstacles and do the cognitive heavy lifting to decide how we would navigate them if they show up, it's not as hard when they do. Hope mapping is actually a psychology tool. I wish I could claim it as my own, but it's actually from a psychologist called William Schneider and there's seven steps to it and this is explained in depth and in fact, I think the QR code in that chapter leads through to your own hope map. So you really get the chance to use all the tools that my one to one clients get to use in coaching. Having had the explainer in the bit, what it does is really help you Think about worst case scenarios and then what would you do if. And make implementation plans. So the happens is you've got away literally on the map. It's a map of grids, if you like, when, Yes, I wish I could have I had one quick enough to hold up. But you'll see it. It's a map of grids. It's a bit like one of those complete your own stories where if something happens, you go to that box on the right and if the other thing happens, you go to the box on the left. What you don't do is stop. You don't need to get stuck. You have the answers already down. And I think that is really such an important part of getting into that final stage of action with career redesign. Because it is challenging, it is disruptive. Inevitably any change is. And if you get wobbled off as you go through, what you find is you'll lose track of where you are, you'll lose hope, you'll have doubts that settle in and start getting louder. And that might seem like a reasonable, valid signpost to abort mission. And it's the thing you can do. I think what I always say to people who are feeling at that point, the problems are coming at them, they're that close. But now there's this obstacle that threatens the entire thing. You are that close. And the growth you actually want for yourself and the hope that you've held close for yourself is just the other side of navigating this. So don't stop now. The only short way to fail is to give up trying. So that's why the hope map is so important. It's actually a very practical tool and psychology backed. You asked about protecting hope and I think that to me is actually all about the resilience involved. And that's a bit more self talk. It's understanding how to nurture yourself through what might become hard. And that can be about interrupting inner critics whose voice is almost indiscernible from your own thoughts about this plan isn't good enough. This is too risky. It's not responsible to keep trying. Whatever it is that comes up for you, it's important to acknowledge it. A lot of people want to avoid those thoughts and squash them, or they feel like they're actionable instructions to stop trying. And that is somehow valid. But what's important to know is those somewhat negative sort of dialogues that pop up for us probably stem from something that was valid in the past. We don't need to carry them. They're outdated stories for today. So it's about looking at them and thinking, so hang on, what's the anxiety here? If that's the message from my inner critic, fear of failure or fear of success sometimes, what can I do about that? How would I dilute that? So we're not ignoring or avoiding the message, we're actually embracing it and using it to spark some kind of action. So it's a bit like the hemp map, although that tends to be practical. But it's the same idea again. Let's embrace the things that threaten to hold us stuck again, albeit down the line, and do something actionable to make sure that doesn't happen and then call time. That's enough from the inner critics and that's enough doubt. So you back yourself, you've done the thinking by this point, really quite in depth thinking, and you deserve to carry that through to its eventuality.

[Vince Chen]

Yeah. As you were explaining, it reminded me of something a career coach asked me years ago. He said, vince, what would you do if you couldn't fail? I remember being younger and not really knowing how to answer that question, but it stuck with me. Change is always hard. It comes with risk, uncertainty, setbacks. And like you said, once you've made the decision, don't stop. Think ahead. Map out the possible risks. Anticipate the bombs. I study finance, so I tend to look at everything through that lens. In finance, we calculate risks, reprice them, we build models to manage them. But in life, most risks cannot be measured on a spreadsheet. So, yeah, sometimes you have to take a step forward, even when you are unsure. And if one path doesn't work out is not the end, you still got options. Hitting a wall doesn't mean full stop. That's one of the biggest takeaways I've gotten from our conversation today.

[Helen Henderson]

Yeah, no, I love that. Actually, it's not a full stop. It's a comma. I often say hitting, sometimes we need to hit the wall. If you think of a wall in terms of a swimming pool, you have swim lengths, you do hit the wall. But it also gives you the impetus and the momentum you need to push up again in a different direction. And I do think career redesign, it is not linear.

[Narrator]

If you've been having your McDonald's sausage.

[Helen Henderson]

McMuffin with an iced coffee from somewhere.

[Narrator]

Else, now is a great time to reconsider. In the Pacific Northwest, it's never too cold for an iced coffee in the morning. Grab yourself a medium caramel, French vanilla, or classic iced coffee for just $2.29 beverage may cause craving for McMuffin or hash browns. Prices and participation may vary. Cannot be combined with any other offer or combo meal.

[Helen Henderson]

I don't think anybody's career, or life for that matter, is linear. It's more like zigzags. And so long as we understand we keep we're motivated to keep on point because we know our why. We uncovered that in the value of values and unpacked our purpose. And I think if you have that motivation behind you, you never want to stop figuring it out. And maybe career redesign is the problem you never stop solving and never want to. It's an agile I think we're talking about career rigidity, and it's that agile mindset of thinking about your career as if it's a series of projects rather than one ladder or one linear journey that really helps people keep.

[Vince Chen]

I really like the swimming pool analogy because I enjoy swimming myself. I get it. Sometimes you just need to pause, catch your breath. You're tired and you need a break. But after the rest you get your energy back. You keep moving, you keep breathing. Even when your head underwater, there's a rhythm to it. We've overran a bit, but I have one or two more quick questions because they tied right into this idea of transformation. You mentioned earlier something that stuck with me, which is don't get stuck in the past or the present. Could you say more about what you mean by that?

[Helen Henderson]

So I think we've talked a little bit about inner critics. Getting stuck in the past really, to me means what stories are you telling yourself? What stories have you carried with you from your past? And it might not be your past career chapters, it might be way further back, but they are beliefs. They will appear as if they're beliefs you feel are as solid as truth. However, if you are stuck in work that's wrong and struggling, or overwhelmed and disconnected, then it's worth tracking what stories are holding you there? Is there a story of I can only do what I've always done? Is there a story of it would be such a waste to just look away from everything I've achieved. Is there a story of is too long, way down at this point, point of being successful to try something new? It's too late for me. What are the stories? Where have they come from? Are they social prescriptions? Are they things that your family brought you up on or maybe didn't mean to, but inadvertently that's what you saw? Model what are they? Because if you can make their origins, the origin story, visible, then you start to give yourself permission to unpack them and really question is that serving me to make my choices through the lens of these stories? So that's the past. The present is again, this idea of persevering. And if you think I'm feeling like I want to hold the book up again. But if you're that person in the circle, and you know, you're probably excellent at persevering in your profession, because we have been absolutely weaned on this idea that perseverance is a virtue, but it isn't if it's holding you stuck, violating your values and has you loathing what you do, even if it used to make sense. So it's again, just giving yourself permission to meet yourself where you are today, not where your past self put you, and just question what serves. What is actually going to get you closer to the hopes and vision that you hold for yourself? Because that isn't often the same as staying where you feel stuck. It's time. It's a call to action, isn't it? It's time to at least open up about what career redesign might mean for your next chapter.

[Vince Chen]

I really like the circle metaphor. I think that captures the main idea of your book as well. So this is really my last question for Interview. Your book is called A Smart Guide to a Purposeful Career. What are some of the unsmart things people tend to do when they feel stuck?

[Helen Henderson]

Yeah, easily. I think if I go through the apps, if I do it in order, then what I would say is the first thing that would not be smart would be not to take the time to get all that career clarity. Because really, I think for anyone, unless you can understand what you are strongest at, but also enjoy most, that lights you up and feels purposeful to you, then there is no career design that you know will be aligned with that you haven't taken the time to understand what it needs to align with if you're going to feel fulfilled. So that would be the first big red flag for me. The second one would be to have an idea that you're very married to. People who have a singular idea that they're very married to often find it very hard. In psychology, they call it anchoring. And you've probably heard of this through the financial sort of side of life. But it's the same in this lane. Whatever idea you come up with first, you're not ever so prepared or flexible about moving too far from. So that is why in career redesign, we start ideating and we come up with a minimum of three career life designs that you find attractive and appealing. You don't have to do them all. We've only one person, but we do have to come up with them and think about them and move into them in quite a bit of depth. So that would be the other unsmart thing to be married to one hope or idea. There's a sort of part two with that. One of not trying, not pilot testing the idea, not stress testing it, not understanding how you respond when you expose yourself to this idea that you've had for yourself. Because how can any of us know if we really going to love that environment or this nature of work or be able to access it? It's very risky, I think, to give anything up without having first diluted the risk and tested it robustly. And then I think the final thing would be to think that you've done everything it needs, having gone through the thought process of aligning but also redesigning. Because the truth is transformation takes more than that. It takes this resilience and knowing how you top yours up when it feels like the levels are getting dangerously low. And that I think that would be unsmart not to take account of and I will admit bias, but I also think it would be unsmart not to put support in place, whether that is a coach or important others. Mentors, people who you really trust, have your best interests at heart, but know you and understand what you hope for yourself. Not to abdicate responsibility for your ideas, but to have input and an influx of other ideas and fresh thinking on them that just provoke thought. Yeah, probably quite a lot. But that's four, I think.

[Vince Chen]

One last thing I want to say about community and support, whether it's a coach, a group of like minded people, or even just one person who gets matters so much. Actually, you probably don't know this. None of my guests do. Each of you is part of my support system. Every time I talk to a guest from somewhere in the world, it reminds me that I'm doing the right thing with the podcast. There are moments, many moments, when I doubt myself. Of course, we all do. But these conversations with real people who care about change, they ground me. They remind me this is real. This work matters. So yes, support systems are vital. That might mean hiring a coach, just like hiring a trainer when you go to the gym, or leaning on your family or siblings or friends, assuming they're all trustworthy and available, or simply having conversations with people who share your vision and feelings. That's how we stay afloat. That's how we keep going when things get messy or uncertain. And like you said, failure isn't part of the manual because if we keep moving, learning, adapting, we don't fail. We figure it out. That, to me, is the key.

[Helen Henderson]

Exactly. I couldn't have said it much better yourself. And it's a privilege actually to hear you saying that. These conversations help you something. And that's. That's very flattering. So thank you for saying that.

[Vince Chen]

No, I'm serious. Every single one of you, I mean it. Each week I get emails from different people saying, hey, I love to be on your show. Hey, I love to be on your show. And I talk to every one of them. For me, even it turns out they are not the right fit for the podcast. I still made a new connection and most of the time they've already checked out my work before reaching out. So we are already aligned on some level and that's how we keep the engine moving. Failure, not an option. Stopping, also not an option.

[Helen Henderson]

Nice. And that resilience will keep you in momentum, won't it? I think a lot of this is all. Is there a momentum game? Actually.

[Vince Chen]

Before we conclude, is there anything I haven't asked that you would like to share? Something on your mind or something you feel is important for our audience to listen?

[Helen Henderson]

I don't think I've got. We covered a lot and that's been. I agree it's been severally enjoyable, but really energizing. I don't think there's anything. I feel like that's a shame. I haven't been able to say that. I suppose it's the thing of where do people find me? So maybe the website is the obvious1. Helen hannison.com But LinkedIn, I think I feel much the same as you. Meaningful connections will always be important to me and that's the space I collect people. So that. That would be great. And I think to get the book, I would say let's pop a link in for that because I've just done or upgraded my sort of page about the book. There's a bunch of offers and opportunities in only in there. So it is the right way for people to have a glimpse in and see if it's for them and get it if they want. I suppose the only other thing that we haven't talked about, but I don't know if you think it's an A value add would be there's a quiz that people might like to do to discover their act type. So if you're feeling a bit stuck in hesitation about where to start and you're not sure what version of stuckness you're struggling with. You just have this sort of quite ambiguous feeling. The actual quiz is literally one minute. It's quite light, but it really does a good job of signposting whether you're stuck with the career clarity bit or you're stuck. You know exactly what you need to align with, but you don't know the idea or how to move from A to B. Or it's this mindset mastery that is about transformation. So the quiz would be a fun, quick way to have an entry point into never getting stuck again.

[Vince Chen]

And that ends our two part series with Helen Henderson. From breaking down limiting beliefs to mapping out purposeful action, Helen's approach flips the usual career advice on its head. Redesigning your work life isn't about powering through. It's about pausing, rethinking, and making moves that actually match who you are. Now, hopefully you're walking away with fresh clarity and maybe even your own hope map. Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, Leave us top rated reviews, check out our website and follow me on social media. I'm this Chen, your ambitious human host. Until next time, Take care.