Have you ever thought, “Maybe I should just work for myself”?
Maybe it came after another difficult interaction with your boss.
Or after leaving a workplace that had become unbearable.
Maybe you were exhausted from constantly managing triggers, personalities, expectations, office politics, and trying to hold yourself together while still doing your job.
Maybe you lost a job and couldn’t imagine putting yourself through another workplace like the one you’d just left.
And somewhere in all of that, entrepreneurship started to look like an answer.
If I work for myself, I can control my environment.
I can choose who I work with.
I can set my own schedule.
I won’t have a boss triggering me.
I can finally do things my way.
That possibility can hold a tremendous amount of hope.
And maybe some relief, too.
But there’s something I don’t think we talk about nearly enough:
We may leave the workplace. But we don’t leave our nervous system, our history, or the survival strategies we developed there behind.
A quick introduction, if we haven’t met
If we haven’t met yet, I’m Cyndi Bennett, a trauma-informed career coach and founder of the Resilient Career Academy. You’re reading or listening to The Resilient Career Academy Newsletter #9, where we explore how the after-effects of complex trauma can show up in our careers and what becomes possible when we begin recognizing and removing the obstacles they can create.
Today, I’m starting a new conversation about something we haven’t talked about nearly enough: what happens when trauma survivors become entrepreneurs.
Leaving a difficult workplace and building something of our own can change a lot about our working environment. We may have more control over our time, the people we work with, the work we choose to do, and even the conditions under which we do it.
But becoming an entrepreneur doesn’t give us a clean slate.
We bring ourselves with us.
Our experience. Our strengths. Our resourcefulness. Our hopes for what this business might make possible.
And we may also bring some of the adaptations we developed long before we ever thought about starting a business.
Over the next several months, I want to explore what that can look like, not because there is one universal experience of entrepreneurship as a trauma survivor, but because I think there are conversations we need to start having.
And today, I want to start with a simple question:
What happens when the survival strategies that helped us get this far become part of how we build a business?
We Don't Start Our Businesses From a Blank Slate
When we start a business, we bring decades of experience with us.
We bring the skills we’ve developed throughout our careers, the things we’ve learned about people, the problems we know how to solve, and the experiences that have shaped what matters to us.
For trauma survivors, some of those experiences may have helped us develop strengths that serve us incredibly well as entrepreneurs.
We may be resourceful because we’ve spent much of our lives figuring things out. We may notice things other people miss because we’ve learned to pay close attention to what’s happening around us. We may understand people deeply, anticipate needs, adapt quickly when circumstances change, and keep going when things don’t go according to plan.
Those things come with us.
But so do the strategies we developed to protect ourselves.
And here’s where entrepreneurship gets interesting.
Some of the very same adaptations that helped us navigate difficult circumstances can look remarkably useful when we’re building a business.
Self-reliance can look like independence.
Hypervigilance can look like being exceptionally prepared.
People-pleasing can look like outstanding customer service.
Perfectionism can look like having incredibly high standards.
Over-functioning can look like the work ethic entrepreneurship supposedly requires.
Sometimes the things that helped us survive can also help us succeed.
Until they don’t.
That’s what makes these patterns so difficult to recognize. They don’t necessarily show up in our businesses looking like trauma responses. They may look like the qualities of a really committed entrepreneur.
And that’s what I want us to start becoming curious about.
I Thought the Triggers Would Go Away
One of the things I didn’t expect when I started my own business was that the things that triggered me would change.
In my corporate career, I had become pretty familiar with the situations that could knock me off-center. I understood what it felt like to navigate difficult workplace relationships, authority dynamics, conflict, feedback, and the unpredictability of working inside a large organization.
Entrepreneurship gave me more control over many of those things. I could decide what kind of work I wanted to do, who I wanted to work with, how I spent my time, and what I wanted to create.
And yet, I discovered that having more control over my working environment didn’t mean I stopped getting triggered.
The triggers were just different.
Suddenly, I was navigating things I hadn’t encountered in quite the same way as an employee.
I had to put a price on my own work.
I had to talk publicly about what I could offer.
I had to make decisions without knowing whether they would work.
I had to invest time and money without any guarantee of a return.
I could create something I believed deeply in and have nobody buy it.
And because I didn’t initially recognize some of those experiences as triggers, I didn’t necessarily recognize my responses to them as protection strategies either.
I just thought I was trying to figure out how to be an entrepreneur.
When Survival Strategies Put on Entrepreneurial Clothes
The tricky thing about survival strategies in entrepreneurship is that they don’t always look like survival strategies.
They can look like working hard. Being committed to our clients. Doing our research. Caring deeply about the quality of our work. Being careful with money. Wanting to make the right decision. Trying to build something we’re proud of.
And sometimes, that’s exactly what they are.
But sometimes there may be something else happening underneath.
We might spend months perfecting an offer because putting something into the world before we’re certain it’s good enough feels incredibly vulnerable.
We might give clients far more than we promised because the thought of disappointing them is difficult to tolerate.
We might keep our prices low, not because the market won’t support more, but because asking someone to pay us more brings up something we weren’t expecting.
We might research a decision endlessly, ask multiple people what they think, or sign up for another program because making a decision without knowing how it will turn out feels uncomfortable.
We might spend weeks figuring out something ourselves because asking for help doesn’t even occur to us until we’re already overwhelmed.
And we might work far beyond our capacity because no one is standing there telling us to stop.
That’s part of what makes this so complicated.
Entrepreneurship can actually reward some of these behaviors, at least for a while.
The over-functioner gets a lot done.
The perfectionist produces exceptional work.
The people-pleaser has happy clients.
The hyper-independent entrepreneur becomes incredibly resourceful.
Until the very thing that helps us build the business starts making it harder to sustain.
And if we don’t recognize what’s happening, we may assume we simply need a better business strategy.
Maybe sometimes we do.
But sometimes the business problem and the protection pattern are sitting right next to each other.
The Same Strategies May Also Be Some of Our Greatest Strengths
One of the things I want to be careful about in this conversation is turning every behavior we developed because of trauma into something we need to fix.
Because I don’t believe that’s true.
Some of the adaptations we developed to survive difficult circumstances may have also helped us develop qualities that serve us incredibly well as entrepreneurs.
We may be resourceful, adaptable, persistent, and deeply attuned to the people around us. Our lived experiences may help us see problems other people overlook or understand the people we serve in ways that can’t be learned from a business textbook.
Those strengths are part of what we bring to our businesses, too.
Our experiences may have given us tremendous empathy for the people we serve. They may have helped us recognize a problem that other people weren’t seeing. For some of us, they may even be part of the reason we started the business in the first place.
I don’t want us to lose any of that.
The question isn’t whether a particular trait is good or bad. Maybe the more useful question is:
Is this helping me build the business I want to build, or is it helping me feel safe while quietly getting in the way of what I want?
And sometimes, the answer may be both.
The self-reliance that makes us resourceful can also make it difficult to ask for help.
The empathy that helps us understand our clients can make boundaries more complicated.
The ability to anticipate problems can help us prepare, but it can also keep us preparing long after we’re ready to act.
That’s why awareness matters.
We don’t have to reject the parts of ourselves that helped us get here. But we can begin noticing when they’re serving the business we’re trying to build and when an old protection strategy may be making decisions for us.
And once we can see the difference, we have more choice about what happens next.
What Could Change If We Started Noticing?
I think one of the most powerful things we can do as trauma-survivor entrepreneurs is begin noticing what we’re bringing into our businesses without immediately deciding that something is wrong with us or that we need to change it.
We can become curious about why we work the way we do. Why certain parts of entrepreneurship feel relatively easy while others feel disproportionately hard. Why we keep getting stuck in the same places, even after we’ve learned the strategy, taken the course, or been told what we’re “supposed” to do.
Maybe the question isn’t always, What am I doing wrong?
Maybe sometimes it’s, What’s happening here?
What happens inside me when I need to make a decision without knowing how it will turn out?
What happens when I need help?
What happens when someone says no?
What happens when I have to put a price on my work?
What happens when something I created doesn’t sell?
What happens when the business starts growing, and more people can see me?
We don’t have to have answers to those questions right away.
Awareness gives us somewhere to begin.
Because when we can recognize that an old protection strategy may be showing up in a new entrepreneurial situation, we have an opportunity to decide whether it’s what we need now.
And that creates choice.
I Want to Hear What Entrepreneurship Has Been Like for You
This is a conversation I want to keep having.
I’ve spent a lot of time thinking, writing, and talking about how complex trauma can show up in our careers. But entrepreneurship creates an entirely different working environment, and I’m becoming increasingly interested in what happens when trauma survivors begin building businesses of our own.
I have my experience. I know the patterns I’ve encountered and the things that have surprised me along the way. But I don’t want to assume that my experience is your experience.
So, over the next several months, I’m going to be exploring Entrepreneurship as a Trauma Survivor here in The Resilient Career Academy Newsletter, and I’d love for you to be part of that conversation.
If you’re a trauma survivor who has started a business, is building one now, or has tried entrepreneurship in the past, I’d love to hear from you:
What made you decide to become an entrepreneur?
What has been harder than you expected?
And what has surprised you about yourself along the way?
You don’t need to know whether any of those experiences are connected to trauma. In fact, I’m most interested in hearing what you’ve experienced before we try to explain why.
You can share as much or as little as feels comfortable. Your experiences will help me understand this intersection more deeply and inform our conversations going forward.
Cyndi, this is such an important distinction. When we label these patterns as flaws, we can miss the fact that they may have once been adaptive and protective. Understanding the “why” behind a behavior can open the door to much more meaningful and sustainable change.
“When Survival Strategies Put on Entrepreneurial Clothes” - what a great way to put it! I agree with you, the link between trauma and throwing off traditional careers is powerful, especially when you reach a point where you just can’t keep pretending anymore in traditional corporate environments