EP54: Four Reasons It’s So Hard to Find the Courage to Quit Corporate (and How to Do It Anyway)
If you’re still in your corporate job — serving someone else’s agenda, showing up for work that doesn’t fit who you are or what you believe in — this episode is for you.
n this short, punchy episode, I’m breaking down four reasons it takes so much courage to quit corporate — and how to move through each of them so you can make a confident, grounded exit into more meaningful work of your own.
Because if you’ve been scheming, dreaming, and planning your career change for months (or years) but somehow still haven’t made your move, there’s a reason for that. You’re not lazy, incapable, or confused — you’re human. And your fears are doing their job: trying to keep you safe.
We’ll unpack what’s really keeping you stuck — and what to do about it.
If you’re ready to stop planning and start acting, I can help you map your next steps.
Book your Courage to Quit session — a 90-minute deep dive to create a clear, personalised plan for your transition out of corporate and into your calling.
Listen here
Full Transcript
Alisa
If you are still in your corporate job, and if you've been thinking, scheming, and planning your way out for weeks, months, or maybe even years — but somehow you're still there, somehow you're still serving someone else's agenda, still inside of a system that you fundamentally don't fit within or maybe even agree with — then this episode is for you.
I am gonna keep it short and punchy today, and my goal here is to:
Help you understand specifically what it is that's keeping you stuck, and
Give you practical steps you can take to build your resilience, calm your nervous system, and create a personalized exit plan that gives you a clear and empowered path out.
This is From Corporate Into Calling, and it's time to find the courage to quit.
1. Money
Okay, I'm gonna walk you through four different reasons that it's so hard to find the courage to quit corporate.
And for each one, I'm going to give you a podcast episode of mine that you can go and listen to if you wanna go deeper into that topic. And I'm gonna give you a really practical suggestion for something that you can do this week to help quiet your fears and find that courage within you.
Let's start with a big one.
The first reason it's so hard to quit corporate is, of course, the money. And I'm not here to tell you that that isn't real. I won't tell you that you can easily replace your corporate salary quickly after you step into meaningful and regenerative work. But the money part does need a little prising open because it's so powerful — and that is absolutely deliberate.
It is the number one piece of leverage that corporate employers have over us, and it's not just about the amount of money that they might be offering you, but the way that they hand it out and all the lifestyle pieces that surround that.
Now, I have a lot of episodes that go into this and a lot of details, so I'm not gonna do that here. But if this is the big blocker for you, I really recommend taking a look at some of my earlier episodes. I have about four or five all around the topic of money — different ways that you can think of making money and supporting yourself as you move into regenerative work, how to tackle that fear, how to build yourself a financial plan. And I'll list all of those in the show notes as well.
The big takeaway that I want to offer you is that being inside a corporate organization can skew our perspective on money. I've worked with people who have had two years’ runway — savings enough to support their lifestyle for two years — and didn’t feel that that was enough. And I've worked with people who were very unhappy in their job, but were not willing to consider change until they had saved for both private school and college for each of their three children.
Now, I would argue that those are very privileged positions to be in and that they give you a lot of options, even if it doesn't feel that way. I'm not trying to minimize fear around money or the very real need for a safety net, particularly in countries that don't provide that safety net for their citizens — I’m looking at you, USA — but there are lots of different ways to approach this so that money doesn't become this immutable excuse not to even try.
You don't have to quit your corporate job and volunteer for the next five years and have no income. There are a lot of things you can do to ease the control corporate money has over you.
You can review your lifestyle and your spending. Identify costs that are actually specifically because you have a corporate job — like, let's say, wraparound childcare because you have to work such long hours, or maybe transport costs to get you to that job, or meal services and takeaways because you never have enough time to cook. All kinds of costs that are there specifically because you have that job.
You can think about your work flexibly. You can consider contracting even to your existing employer or reducing hours to give you some stability as you navigate the transition into meaningful work of your own.
If this is where you need to focus, have a listen to Episode 17: Regeneration and Money — A Financial Plan for Your Purpose-Led Career. In that episode, I will walk you through the different options and help you build out a solid financial plan that will ease your fear and open your possibilities.
The other really important thing to be aware of with money is that it almost always acts as a kind of cover — or, as I've said, an excuse — for deeper fears that are less tangible and actually much more difficult to tackle. I see this with my clients all the time.
We create that robust and flexible financial plan, and that allows them to see where the real resistance lies. And it might be in one of these next three areas that I'm gonna share with you.
2. Identity
The second reason that it's so hard to quit corporate is that your identity is deeply tied to your job.
Look, you have poured so much of your adult life into work. Starting right back during your education, you have worked for this. You've planned for this. You've achieved incredible things, and it has also demanded so much of you as well — real sacrifices in terms of your time, your peace, and your ability to enjoy real life and the things that really matter to you.
And the natural coping strategy for that is to go even deeper into your work, to the point that it becomes who you are.
I think of words that Kevin shared with me. Kevin was a highly experienced banker and he told me, “I knew my career was not serving me, but I could not imagine doing anything else. It took me over ten years of deep reflection to reacquaint myself with the person I am sufficiently to remember: I am not my job.”
Now happily, Kevin has made a very successful career transition and is doing work that he feels deeply fulfilled by in the regenerative space. But please do not let it take ten years for you.
This is where some inner work is required, and I wanna invite you to make time for reflection and ask yourself: What am I getting from my job and from my job title that I'm afraid I can't get elsewhere?
I strongly recommend writing down your answer — not judging yourself, just letting the words flow and seeing what comes up. Even just the act of doing this exercise will start to give you some distance and perspective, and you will see that yes, you can find those things elsewhere — that you are not reliant on your job to tell you who you are.
And here's my offer to you: send me what you write. I will read every word, and if you want me to, I'll offer my perspective and some specific insights that might help you. You can send that to me at alisa@regenerativeworklife.com.
Now, if you wanna go deeper on this topic, have a listen to last week's episode — that’s Episode 53: Who Are You Without Your Job Title? In that episode, I share stories of clients who have really struggled with this, as well as my own experience of discovering who I was beyond the CEO and Founder title that I enjoyed and really clung to for 15 years.
3. Self-Doubt
Okay, let's move to the next reason it's so hard to quit corporate — and it is self-doubt.
This third reason is one that I think a lot of high-achieving, very experienced and quote-unquote “successful” professionals find hard to admit, at least out loud. And I would say that self-doubt is almost always present to some degree, lurking under the surface of practical considerations like money, security, skills, or experience.
The fact is, no matter how good you are at what you do now, stepping out of the perceived security of a corporate setting and having the audacity to pursue meaningful, regenerative work of your own — whether that's as a consultant, a freelancer, taking a very different path in your employment, or even starting your own business — it's really quite scary.
I think I've told the story before on the podcast of a VC that I had worked with during my time in climate tech — partner level, very well known and respected in the industry. He had a change of circumstances with moving countries that meant he was still working for the same fund, but he needed to work with them as a contractor. And as part of that agreement, he had to find a certain amount of freelance work outside of his main employer.
And he called me and said, “Alisa, I need your advice. I need to understand how to do this. I have never worked for myself. You’ve always worked for yourself. How do you do that? I’m terrified of what it means to work for myself, to have to put myself out there. I'm worried about people rejecting me, and the idea of having to sell myself just makes me feel a little bit sick.”
And look — it is totally normal to feel this way. People at the highest level feel this way.
And here's a kind of hack you can do if you recognize that self-doubt is an issue for you: outsource your confidence.
Now, I'm really not one normally for shortcuts, but this one just makes so much sense and works really well and gives you that immediate kind of boost you need to finally get free of corporate. Surround yourself with people who have taken similar journeys — that could be following them on LinkedIn, reading interviews about them, volunteering in places where you can be around these kinds of entrepreneurs. Be really deliberate about who you spend time with during this period.
If you've got a bunch of friends who think you are absolutely unhinged to think about leaving your job — they can stay your friends, but don't give them airtime right now. Seek out the people who absolutely back you to do something incredible. Borrow that confidence, and soon your own self-confidence will start to catch up.
You can learn more about this in Episode 14: Three Fears Holding You Back from Purposeful, Regenerative Work, and one of those key fears is self-confidence.
And actually, if this is a topic that you'd like me to do a dedicated podcast episode on, just let me know by email. I think this could be a really interesting one to go even deeper in. I love getting feedback and suggestions for episodes — this podcast is for you, so please get in touch and let me know what you'd like to hear.
4. Your Nervous System Is Trying to Keep You Safe
Okay, the final reason — reason number four — that it is so hard to find the courage to quit corporate is that our nervous systems are trying to keep us safe.
Right now, there is probably a tricky kind of battle going on inside your body and your subconscious — which, to me, are all one and the same: the nervous system, your body, your subconscious.
You know viscerally what it's costing you to stay in work you do not want to be doing, and to serve an organization whose values you don't align with. You feel that in your bones or maybe in your belly. It's probably a weight that you are carrying around with you every day.
But at the same time, your subconscious is desperately trying to keep you safe. And as far as it's concerned, the safest place is where you are right now — what you already know — no matter how much you might hate it.
So you can put all of the practical pieces in place, but if you don't tend to your nervous system, you are in for a bumpy ride. And you might find that you never get past that planning stage into actually taking action and making a grounded, empowered exit from your corporate job.
So what can you do? It's simple, really. Be kind to yourself. Give yourself space. Go for walks. Take long baths. Be in nature — whatever works for you. Let those difficult feelings come up and remind yourself — out loud if you can — that you are safe, that you can do this. Breathe deeply. Shake your body out, and make sure you've given enough attention to all the incredible things that you will gain from making this transition. Keep bringing yourself back to that.
This nervous system work is one of the most important things I help my clients with, and it is so powerful when you bring together the practical outer work — like having a financial plan in place, creating a sensible timescale for change, reviewing flexible options — with the absolutely essential inner work of uncovering the deep fears and beliefs that might be sabotaging your efforts, and really working at this subconscious level to rewire your neural responses so that quitting doesn't equal fear, risk, and doubt, but freedom, possibility, and joy.
And I offer all of that inside a 90-minute coaching session. It's completely confidential — it's just you and me — and you will come out of that powerful session feeling resourced, ready, and with a personalized exit plan that you can feel really good about and act on right away.
Take a look at regenerativeworklife.com/courage — that link is also in the show notes. There you'll find all of the details about the Courage to Quit session: exactly what we'll cover, what you'll learn, who it's for (and not for), and a lot of frequently asked questions.
This is a really strategic investment you can make in yourself that will take you from trapped and anxious to clear, grounded, and free. That link again is regenerativeworklife.com/courage.
Recap
Okay, let's quickly wrap up what we have looked at today — the four reasons that it is so hard to find the courage to quit corporate:
Money
Identity
Self-Doubt
Your Nervous System Trying to Keep You Safe
For each of these, there are practical steps that you can put in place. Listen to the episode again — actually do the work. I promise you, the shift is so much closer than you think it might be.
Thank you for listening. I'll see you back here next week on From Corporate Into Calling.
