Jennifer Selby Long is no stranger to messy transformations. With three decades of experience in executive coaching, digital change, and tech leadership, she helps seasoned professionals navigate the personal minefield that comes with professional change. In this second installment, Jennifer dives deep into neuroscience-backed insights on why we sabotage ourselves—and how to stop. She breaks down how our brains are wired for fear, how to spot the voice of the “judge,” and how misplaced loyalty to bad bosses or toxic companies keeps people stuck. But she doesn’t stop at analysis—she arms Gen Xers with tactical empathy, reframing techniques, and political savvy to make their next move smarter. Because in a world where everyone’s changing, the winners aren’t the loudest—they’re the most self-aware.The Science of Self-Sabotage“Those negative voices? They’re not you. They’re old neural pathways—and you don’t have to obey them.”Jennifer explains how childhood-formed saboteurs derail adult decision-making—and what to do about it.How Judgment Blocks Reinvention“If you’re judging yourself or others, the judge neural network is in charge—and it’s contagious.”Learn how to spot the “inner judge” sabotaging your growth and weaken its grip before it wrecks your next chapter.Escape the Bad Boss Loop“Most people don’t leave bad bosses—they recreate them.”Jennifer outlines five traps professionals fall into when trying to escape toxic leadership—and how to break the cycle for good.Office Politics Without Selling Your Soul“You’re not imagining it—some power games are real. But empathy is your best defense.”From defensive email habits to managing power dynamics with grace, Jennifer offers non-sleazy tactics for Gen X leaders navigating messy org charts.Redefining What ‘Winning’ Looks Like“Change that sticks often doesn’t look like the win you planned—but it’s the win you needed.”A fresh lens on how to reframe wins, even if they come in smaller, slower, or stranger packages than you expected._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What insights on self-sabotage does Jennifer share?
When I started this business, which is actually my second business, a few years after it started, we hit the dot-com bust. And the business sank, right? And really struggled. And then again, we got hit in 2008 when the economy collapsed in the United States. And it is so easy to fall into the self-sabotage. The reason, though, is really interesting.
Thank you.
the AD, C-H-A-M-I-N-E, Shirzad Shamim. And he writes a great deal about the neuroscience of this because that self-sabotage is something that develops in very early childhood. It is almost entirely wired into our brains by the time we're five years old. Now, why is that in there?
those saboteurs as he calls them are neural networks that very tiny children develop to ensure their survival if a little tiny kid recognized that their parents were not infallible which is actually true It would be terrifying because they cannot care for themselves, right? So these neural networks form as a vital part of early childhood. They're just part of that survival mechanism.
However, in adulthood, we don't need those anymore. But at that point, they're really strong. They've been there for decades, right? Getting stronger and stronger, and they're just lurking in there.
and i want to really convey the important message that when you start to feel yourself self-sabotage that's not you that's the saboteur neural networks in your mind firing up that's all that is and they're sitting in there and they jump out when they get a signal that indicates that there's a threat to survival.
Of course, if you go after a contract in your new business and you work really hard on it, you put all this time into it. When you were an employee, if that contract didn't close, you still got your paycheck. But now all of a sudden, you're looking at, can I pay my rent? Can I make my mortgage? So that, of course, your brain fires that up as risk to survival. And so the saboteurs jump in there.
The universal saboteur is called the judge. Every single one of us has this. And the judge has snuck in there and is getting in your way when you feel a negative feeling and you are judging either yourself or
or someone else or the situation that is a sign that your judge is in there your judge is going to tell you you need me i am good for you but you don't need that judge to be talking and the judge is not good for you so the way that you can recognize that again you feel a negative feeling You're feeling stress, frustration, anxiety.
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Chapter 2: How can we identify and weaken our inner judge?
who was having a highly unpopular initiative and frankly wasn't doing it in a very effective way and was triggering people all around him. And my client really, truly put himself in that person's shoes. In one meeting, I even had him speak as that individual to me so that he was completely in that guy's shoes and he was able to make his case
and build his argument in a way that was compassionate, right? That was not competitive. That wasn't even about this other guy. The end result was that my client was much happier day in and day out. He was much more successful.
Not only was he able to fend off this drive to cut costs, he was able to get the several million dollars additional funding that he needed to do that, the higher level headcount that he needed to add. He was able to slow his attrition
a great deal and get that under control and this is not something that would have come for him so quickly with such success he becomes the guy who has the boss's ear where he becomes the guy whose organization is turning around and performing how did he not really face that judge and that talk with saboteur and weaken them by calling them out
And then in this case, calling forth his empathy for someone who was, in his mind, incompetent. And to really deeply have empathy so that he's not trying to compete against this guy, but to just get the right thing done.
Through all these years, you've worked with so many different people, each with their own unique characters and situations. I'm curious, looking back, can you recall any cases where you feel you didn't succeed in helping a client navigate or take charge of a change? By failure, I don't necessarily mean they disengaged with you, but rather the impact you aimed to create.
didn't work out as well as expected. Could you share one of those experiences? More importantly, what did you learn from it? Why do you think it was so challenging in that specific situation?
Oh, absolutely. Absolutely. And we've had a couple of those. One that comes to mind had such a surprising conclusion in that what I came to recognize was that this leader fundamentally did not want to change and grow. And as a result, we would make a few steps forward and then a few steps back. Interestingly, that particular leader was very strong in some other areas.
And the individual that person reported to, I guess you could say, was my core client. actually concluded that he needed to go find a better opportunity for this guy. Because this guy was absolutely not going to change in his own style to what was needed there. And he wasn't going to change in his fundamental beliefs about what the strategy should be of that division.
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Chapter 3: What are the common traps professionals face with bad bosses?
to make this change successful, we probably wouldn't have started down that path or we wouldn't have brought in some different people to lead them. So it is so vital to understand that change management is about hitting the target, right? Implementing the change on time, within budget, to a set standard.
But this can actually be much more profound for others than we recognize because they can come out of it with a new identity. Think of, for example, my clients who are financial analysts. Today, even just as recently as three years ago, the technology didn't really exist for them to spend the bulk of their time Truly advising senior business leaders on what they should be doing in the business.
They had very little time to say things like, hey, here's a market force that I see going on in Japan. And I think we need to focus 40% more of our sales effort there on this product line. No way. They were too busy being Excel jockeys, right? Today, that technology has come a very long way.
But what happens to someone who for 10 years has been spending most of their time, maybe not real happily, but spending most of their time just getting those numbers accurate? And now suddenly you are telling them that within a matter of months, those leaders are going to be able to press a button and see the data that you used to have put together for them.
And they are now going to turn to you and say, what should I do? Or what happens when the leader doesn't turn to them and say, what should I do? Now, suddenly it's a new identity and they're recognizing they have to earn it. They have to earn that credibility as something more than a master Excel jockey.
that is terrifying that's terrifying that's a whole new set of skills they're going to have to learn how to convert that data into a story they're going to have to learn how to influence they're going to have to learn how to read that person and speak in their language it's terrifying it's terrifying and so really recognizing that people are going to come out of this change with a new identity helps you as a leader
to have that empathy on the path and to be able to really encourage and support them and put in place what they need to get there that you otherwise might not have recognized, whether it's training and develop, mentoring, coaching, whatever it may be that they're going to need.
I'm really glad you brought up the freeze, unfreeze, freeze model, because that new identity in the last stage is the single most important part of that model.
Would you say that if someone gets stuck in the freeze phase but eventually manages to unfreeze themselves, it's a win? How would you personally define a successful change or a win when it comes to going through transformation?
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Chapter 4: How can empathy help in navigating office politics?
right they're being wise what it goes back to that personal vision what does that success mean to you individually not just the company right but for you as an individual what's the alignment there people will move mountains for you if they really understand how this large-scale change is connected to something more than a bump up in the stock price
or a decrease in operational overhead, but to them, their personal big whys.
So far, throughout our interview, we've focused a lot on how you help leaders drive, lead, and manage change within the teams and organizations. Many of our listeners might be change leaders or change managers in their own spaces or organizations. Yet, the other group of people listening might be experiencing changes themselves. They could be considering making a change.
or they may be forced to make a change because they've left their previous employer. You mentioned to me before that a situation often arises when people make a big career leap, sometimes wanting to escape workplace politics or ineffective boss. They might land a new job with similar terms, only to find themselves working for another ineffective boss.
The goal, the real goal, is to make a change for the better. But these people end up jumping from one lousy situation to another. I know you got some really good insights about that, about how people should try to manage the situation differently. Even if they eventually decide to change jobs, they could and they should aim for a truly better outcome.
Could you share with us some common mistakes people make when dealing with ineffective boss and how they might better handle the situation in order to set themselves up for more positive change.
I'm so glad you asked about this because I've had this conversation with so many people over the years and I was having this conversation with someone whose boss was a micromanager and it was driving him nuts. And I sat down and said, this would be a great blog post. And this was when people were blogging on LinkedIn, that LinkedIn post. garnered 45,000 views and counting.
It was shared out on the main thread through that weekend. I have never, I'm a coach. I'm not a famous person. I have never had so many views on a LinkedIn post or a blog in my life. And I recognize this is a really big deal. Everyone faces this, right? Everyone faces this.
at some time and you know what happens when we exit a situation because our boss is ineffective we're running from something versus running to something but of course making a change because you're running away from something usually doesn't pan out as well as when you're running towards something.
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Chapter 5: What does winning look like in personal transformation?
So when you find yourself thinking about your boss in these kind of sweeping terms, and again, you feel your judge coming on...
you're recognized that you're only feeding the intensely negative energy that's there and it does nothing to help you and does nothing to help your teammates the people around you so instead there are really five things that i think you can try to view the situation from a different perspective
and then handle it in a way that's going to work well for you, whether that's staying in it or making that leap toward another job or toward starting your own business. The first one, step back from that situation and first size up the degree to which his or her incompetence is truly affecting you.
It's disappointing when your boss routinely lets you down, but maybe slowing down your professional growth for a few months because they're new to the role and they're not good at it yet. That's one thing. But that's not in the same league as your entire bonus being on the line or even worse, your personal reputation being put in jeopardy with people you respect because the boss is ineffective.
So size it up. It's a reflective exercise. It's subjective. It looks different for you from someone else.
and even for you in different situations at different times in your life but it helps you calibrate that situation a little bit quiet down those nasty saboteurs so that you're calibrating it to your unique needs right is it short term and you just want to let it stop bothering you before you make a big change
or is this something that's really added up and you need to go and you just need to do that secondly assess if you're in a politically messy situation oh i hate this tip but if you do think you're in a politically messy situation you do have to begin some basic defensive action right employees have lost their jobs due to ineffective managers who failed to protect them
right so if you sense that level of risk and you feel it's important to keep your job oh it pains me but you got to start documenting conversations agreements you got to document open items and follow up emails after conversations Try to have more group conversations.
Oh, God, I just want to gag when I say this, but look, if you objectively size it up as politically messy, start doing those basic defensive actions. And no matter what, you must maintain your composure in a politically messy situation, no matter how absurd it becomes. The most absurd one to date is one that happened to a client about 24 years ago.
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Chapter 6: How do past experiences shape our current decisions?
So he just maintained his composure, told her that the objectives she was covering were for the other man's projects. He also made sure he paid more attention to having accurate data about his performance in writing, which did prove to be helpful later. And please don't become ultra paranoid. Please don't stop trying to build a positive working relationship, even in this situation.
It is still good to try to build a positive working relationship. A couple more, consider multiple ways to deal with the situation, right? Is the ineffectiveness entrenched? Or is the boss just having a bumpy transition? Look at options like going out of your way to ensure that the team achieves its goals while the boss gets up to speed on new responsibilities.
Or if there's something that you recognize the boss is always going to be ineffective at this part. offer to help out in an area that your boss doesn't enjoy and doesn't do well. I had one client who's great at team building, initiated team building outing. This boss just isn't good at that.
I had another one who is great, has an eagle eye on a project plan, just offer to validate that project plan because she could see she's always going to be better at it than the boss. And then
honestly this one's a little touchy but honestly ask yourself is it that the boss is completely ineffective or are you resisting adapting to a change that the boss is implementing so gosh it's painful to admit right that it might be that the strategy is sound but you hate it or you just don't buy into the direction
And if that's the case, at least you're recognizing you're resisting adapting to this change. You don't want to go along with it. And so in that situation, you have a choice. You can either say, you know what, I'm going to voice my concerns and I'm going to commit to making it successful for as long as I'm here because that's my job. That's what I'm here to do, right?
Or you're going to decide from a healthier, more grounded place, this change just isn't for you and you are going to leave. And maybe that's when you are going to go to build that business, but you're going to do it in a way that is very positive and constructive for those people around you and for yourself.
Because you'll have made a more intentional, informed choice rather than a choice that's driven by unexamined and unconscious feelings. That's when you wind up just working for a different flavor of a bad boss. Does that help?
Yes, absolutely. There's still so much to unpack. And not just when it comes to dealing with a boss, but also navigating office politics. These dynamics aren't just about one-on-one relationships. There are other players involved too. Interestingly, some people avoid using the term politics when discussing office environments.
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Chapter 7: What lessons can we learn from failure in leadership?
You mentioned how some of your clients, including senior leaders, face power struggles or have to navigate complex stakeholder relationships. Power dynamics come into play, and as they think about leaving a job or dealing with ineffective boss, they also have to consider the bigger political picture they're in.
I feel like this is an element often overlooked in the discussion of change management and leadership. Could you share your thoughts or experiences in helping clients manage these risks? How do you support them in balancing personal and organizational change? while surviving navigating the politics that comes with it.
Absolutely. Politics can exist for a couple of different reasons. And I think it's important to recognize which of those situations you're in. So politics can exist for extremely unhealthy reasons in all seriousness, because you have a leader at the top, who quite literally has a personality disorder.
Now, people who suffer from that problem often aren't aware that they're suffering from it, but also do not respond to coaching. And the politics that they drive are from a whole different place. And it is going to be extremely difficult in that environment to manage your way through the politics and to drive change. And that is one whole animal that is
It is just beyond the scope, I think, of what we could cover in this particular episode of the podcast. But the other driver, which I find much, much more common, is that politics exists because people have different needs and because people have different skill levels. And so someone who is particularly good at recognizing the needs of the people who wield the most power
is going to be better at figuring out how to get those people on board with the change, right? And so it becomes, so again, it's so funny that politics triggers our saboteurs make us want to defend ourselves, right? They are all about survival. But in fact, we circle right back to empathy because being able to understand
and empathize the competing needs of the many stakeholders involved in a change is the path forward. It is the path forward. You cannot move through the creative process that you need to have to construct that change in such a way that it meets multiple needs. You will not, without empathy, be able to bring together leaders who need to come together and who don't especially want to.
So, that, again, is the foundation. Above and beyond that, multiple steps, and maybe that's the subject for another podcast, but you will want to defend yourself against politics, but...
Opening yourself up to really putting yourself in the shoes of all of these people who seem to have power that perhaps you think they don't deserve is the foundation to understanding what's going on and to being able to navigate or, as I like to think of it, surf your way through those political waves and those choppy waters.
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