Is it possible to have a brain wired for entrepreneurship, but actually thrive best within traditional employment?

This insightful episode flips the script on the common narrative in both the ADHD and business worlds: that entrepreneurial traits automatically mean you should start your own business. 

Instead, host Diann Wingert explores the concept of intrapreneurship—bringing creativity, innovation, and entrepreneurial spirit into an existing organization—and how this path might be the most strategic decision for many ADHDers.

If you’re wrestling with the decision to go solo or stay employed, give this episode a listen. It just might give you permission to build a life—and career—that truly works for your brain.

Three key takeaways:

Entrepreneurial traits ≠ Entrepreneurial career: 

You can be creative, visionary, and disruptive without having to start your own business. Don’t fall for the myth that employment is “settling.”

Intrapreneurship unlocks impact & stability: 

Express your entrepreneurial strengths inside an organization. Lead without authority, innovate processes, and treat your role like you own it—while benefiting from structure, resources, and a steady paycheck.

Signs that traditional employment isn’t right for you:

Not everyone is meant to shine as an intrapreneur. If every manager is a nightmare, structure feels suffocating, or your best ideas die in committee, maybe going solo is your move. But it’s all about matching your brain and real life with the right path—not shame, not hustle-culture FOMO.

Workplace roles & cultures where ADHD-ish traits thrive:

Look for product development, business strategy, internal consulting, startups, project-based work, or innovation labs. Go where experimenters are rewarded, hierarchies are flatter, and outcomes matter more than bureaucracy.

Mic Drop Moment:

“Infrastructure isn't the enemy of innovation. Structure, when it's the right structure, is what lets your brain do what it does best without getting derailed by all the shit you hate doing."

Action Step:

Take 10 mins for honest self-reflection. Where do you really do your best work? What structure supports you? Then, make the choice that serves your life—not LinkedIn optics or anyone else’s expectations.

About the Host:

Diann Wingert is a seasoned business coach, consultant and speaker. Drawing from her many years of experience as a former psychotherapist, serial business owner, and someone who thinks "outside the box," ADHD-ish host, Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and the world of work.

Enjoyed the Episode?

Share your thoughts! Leave a review and let Diann know what resonated, challenged, or inspired you. Your feedback helps ADHD-ish reach more listeners who need to hear these honest conversations.  

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

Question, what if you have an entrepreneurial brain, but you shouldn't be an entrepreneur? Now, I know that sounds like a contradiction, but stay with me. I have met a number of people with every entrepreneurial trait you can think of, creative, innovative question everything. Hate following stupid rules and who are absolutely miserable when they try to run their own business. Maybe the problem isn't them. Maybe we've all been sold a story that entrepreneurial traits equal entrepreneurial success and that story is bullshit. So today I want to talk about intrapreneurship and why staying employed might be the most strategic decision you could make.

So I had a free consultation last week with someone who was absolutely convinced she was broke. She's got this incredible brain, comes up with solutions no one else can see. Questions every inefficient process, gets bored with routine in like 3.5 seconds and has a million and one brilliant business ideas. Classic entrepreneurial ADHD traits, right? She's been told her whole life she's too much for traditional employment. Too many ideas, too many questions, too much energy. So she quit her job, three times actually, and started three different businesses over a five-year period and here's the thing, she's fucking miserable every time. The admin buries her, the inconsistent income gives her panic attacks, the lack of structure means nothing gets finished.

And so she ends up crawling back to employment, feeling like a failure because she can't make the entrepreneurship thing work. And I'm sitting here thinking, what if you're not failing at entrepreneurship? What if entrepreneurship is failing you because here's what no one talks about. Having an entrepreneurial brain doesn't mean you have to have an entrepreneurial career. We've created this whole narrative in the ADHD space, hell, in the business world generally, that if you're creative, innovative, and hate following arbitrary rules, you're supposed to quit your job and start a business as if employment and entrepreneurship are the only two options and one is clearly superior to the other, that's garbage.

Today I want to talk about intrapreneurship. What it means, how to know if you're better suited to it than solo business ownership, and how to express all those entrepreneurial traits while keeping this stability of employment. Because some of you need to hear that staying employed isn't settling, it's strategic. So let's get into it, all right, what the hell is an intrapreneur? If you've never heard the term, it was coined back in the 70s, entrepreneur Gifford Pinchot wanted a word for people who act like entrepreneurs, but do it within an existing organization. These are the people who develop new products, create new divisions, solve problems that didn't have solutions.

Basically operating like they own the place even though someone else signs their paychecks, think about it. Someone at Google developed Gmail, someone at 3M invented post it notes because they were screwing around trying to solve a problem no one asked them to solve. These weren't CEOs or founders, they were employees with entrepreneurial brains who had the infrastructure, the resources, and this is key, the guardrails of an organization supporting them. Here's the distinction that matters, entrepreneurial traits are not the same thing as an entrepreneurial career path. You can have every single characteristic that we associate with entrepreneurs, creativity, vision, like this magical ability to see around corners, impatience with bureaucracy and the drive to build something but still function better, be happier, and do more impactful work within someone else's organization.

That is not a consolation prize, that is winning and self awareness. Because intrapreneurs have something that not all entrepreneurs have. They know that infrastructure isn't the enemy of innovation. Sometimes it's the thing that makes innovation possible. And let me say that again for the people in the back who've been made to feel like needing structure means you're not a quote unquote real entrepreneur. Infrastructure isn't the enemy of innovation, structure, when it's the right structure, is what lets your brain do what it does best without getting derailed by all the shit you hate doing.

So if you're sitting there thinking, I have all these ideas and I want to build things, but every time I try to do it on my own, it is a shit show, you might not be bad at business. You might be an intrapreneur in entrepreneur's clothing. Okay, so maybe you figured out, you know what I think I'm an entrepreneur. Now what? Now what? How do you scratch that entrepreneurial itch without the entrepreneurial risk? Well, first let's talk about the permission problem, most intrapreneurs wait to be asked. They wait for their boss to tap them on the shoulder and say, hey there, I've noticed you're quite brilliant and creative, would you like to redesign our entire client onboarding system? Honey, that ain't happening.

That is like waiting for someone to ask you to the prom when they don't even know you exist. Instead, you have to demonstrate value first, then advocate for the autonomy to keep doing it. What does that look like practically? Here's a few examples, propose new initiatives within your role, see a gap, fill it. Notice something broken, fix it. Have an idea for a better way, pilot it on a small scale and show the results. I'm not saying go rogue and reorganize the entire company, that's going to have a very different and undesirable effect. I am saying find the spaces where you can experiment within your sphere of influence to prove the concept.

Ready for more? Volunteer for the shit nobody else wants. Now, hold up, cross functional teams, innovation committees, the projects that don't have a clear playbook, these are intrapreneur playgrounds. Everyone else is avoiding them because they're ambiguous and messy but you're built for ambiguous and messy. Here's another, create internal systems or processes that don't currently exist. And this one is my absolute favorite because it is high impact and low risk. You're not asking for permission to change how the company works, you're just documenting what you're already doing in a way that other people can use. Then suddenly you're the person who solved a problem that nobody even realized was a problem.

Here's another, lead without authority. Now, you can't have too big an ego and do this, so ask yourself if that applies. But leading without authority is because influence is not the same thing as hierarchy. Some of the best intrapreneurs I know don't manage anyone officially, but everybody comes to them because they get shit done and they make things better. That, my friends, is true leadership. You can also decide to treat your role like you own it. Now, this is a mindset shift, but makes all the difference. You don't have to own the company to have an ownership mentality around your work. I mean, what would you do differently if this was your business? What would you change? What would you protect? That is how you operate as an intrapreneur.

And here's the thing, some companies will absolutely love this. They will promote you and give you more rope and let you run with your ideas. Other companies are going to have a panic attack because you're coloring outside the lines. Now, that is information, information that will help you figure out if you're in the right organization to be an intrapreneur, or if you need to find a company that actually wants what you have to offer. But here's what you can't do wait for permission to be entrepreneurial within your role. The best entrepreneurs don't ask, can I do this? They demonstrate value and occasionally ask for forgiveness later within reason, obviously. Don't burn the place down and claim you're being an innovator.

Now, what are some signs that you might actually need to go solo because here's the other side of the coin. I don't want to be the person who convinces someone to stay in a situation that's genuinely wrong for them. So here's what you need to know, intrapreneurship is a totally legitimate path, and so is entrepreneurship. The question is, which one is right for your brain and your life? Here are some signs that employment, even as an intrapreneur, isn't actually working and you might need to go out on your own. You are consistently butting heads with every manager at every organization and I don't mean you had one shitty boss, we've all had that.

I mean, you have a persistent pattern of conflict with authority across multiple jobs, multiple companies, multiple industries. At some point you have to ask yourself, is every manager I've ever had incompetent? I mean, what are the odds of that? Or do I genuinely struggle to function within hierarchical structures? Here's another, structure feels suffocating, not supportive. Hey, there's a difference between structure that enables you and structure that constrains you. If you feel like you're in a cage or a straitjacket, no matter how good the job is, that's important information. If you have a specific vision that requires total autonomy to execute, that's another clue you might need to be on your own. I mean, hey, some ideas can't be built within someone else's organization.

If you're carrying around a vision that needs complete control to bring to life, employment is going to feel like a huge ass compromise indefinitely. If you keep getting fired or quitting in patterns. If you've been let go from three jobs in a row for not being a team player or not following process, or some version of you're too much. You just might be an entrepreneur or you might be an asshole, possibly both but probably you're an entrepreneur. And here's an important one too, your best ideas die in committee and it makes you freakin homicidal. Now some of you are listening and thinking, yeah, but that's just corporate bureaucracy. Sure, but if you can't tolerate corporate bureaucracy without rage quitting, that's a sign you need a different path.

Here's the strategic question, is the problem the specific organization you're in or is it the very concept of being employed? Because sometimes the problem is the company. Maybe you are in a risk averse innovation, hostile death by committee culture and you would absolutely thrive somewhere else, maybe anywhere else. But sometimes the problem is deeper, sometimes you actually cannot function with anyone else calling the shots and that's fine. That is information about what you need. What matters pattern recognition, something those of us with ADHD tend to be really naturally good at. One bad job, that's a bad job. Five bad jobs against different industries that, my friend, is a pattern.

Now it's time for a reality check, the part where we stop romanticizing entrepreneurship and really get honest and strategic about whether you actually have what it takes to go solo. And I don't mean do you have what it takes in terms of courage or vision or any of that inspirational bullshit. I mean, does entrepreneurship match your actual life, your actual brain and your actual circumstances? Let's start with risk tolerance, do you have a financial runway like an actual runway? Not I'll figure it out along the way runway, that's not really a runway, by the way.

You know, most businesses take longer to become profitable than you think so can you cover your bills for 6 to 12 months with inconsistent or no income? What are your obligations? You got kids, you got a mortgage, aging parents that rely on you? Student loan debt, health conditions that require really good insurance? These aren't things to minimize, ignore or wish away. They're real factors that affect your capacity to take risks. And here's the ADHD specific piece, how do you handle uncertainty and instability? Some ADHD brains thrive on it, the adrenaline of not knowing where next month's money is coming from is actually kind of a turn on for them.

Other ADHD brains totally dysregulate under financial stress. The anxiety tanks their executive functioning and they literally cannot work at all. Neither is better or worse, it's just information about what kind of environment you and your brain need to function. Next question, can you handle the administrative burden of running a business? I'm talking taxes, invoicing, compliance, insurance, bookkeeping, contracts, payment processing. Booooring. You know, the detail oriented, deadline driven shit that has really nothing to do with your creative vision, but it's absofreakinglutely part of running a business.

If you have ADHD, this shit is probably painful. The question is, can you outsource it, automate it, or build systems around it? Or does even managing the systems overwhelm you? I'm not saying you have to love admin to be an entrepreneur. I'm saying you have to have a realistic plan for how it gets done without destroying you. And what's your relationship with self management? This is one I find most of us don't know to ask until we're in trouble. Do you need external structure to get things done? Are you motivated intrinsically or do you rely on other people's expectations to get you going. Can you set your own deadlines and actually have any hope of meeting them? Because here's the thing about employment yeah, your manager is an annoying fuck, but they're also providing external structure and accountability. They're deadlines that you didn't have to set yourself.

And that means motivation that doesn't require you to generate it from within yourself. When you're self-employed, all of that has to come from you or you have to pay someone to provide it, which cuts into your profit margins. And finally, how do you handle feast or famine income patterns? Every successful businesses have slow months and slow years, including mine, can you tolerate that psychologically and practically? Or does the inconsistency make you so freaking nervous that you cannot function on the revenue generating activities you need because you're spiraling about money?

Look, here's what I want you to hear, there is no moral superiority in entrepreneurship, choosing stability is not weak. Choosing a steady paycheck because you have people depending on you is not playing small. Recognizing that you simply do better work when someone else handles the boring shit is not a character flaw. This is a lifestyle design question, not a character one. So stop letting these Instagram entrepreneurs who started with trust funds or rich husbands make you feel shitty about choosing employment. They're solving a different problem than you are.

So let's say you've done the assessment, you're clear headed and realize entrepreneurship is my path. You want to use your entrepreneurial brain within someone else's organization. Awesome. Now you need to find the right organization because not all employment is created equal. I want to suggest the types of roles that generally leverage entrepreneurial traits. Ready? Product development or innovation roles. You are literally being paid to create new things. This is about as close to entrepreneurship as you can get while employed.

Another entire category that's great for intrapreneurs is strategy or business development positions. You are literally figuring out what's next, not managing what already exists. Your job is to see around corners and identify opportunities. Then there are internal consulting or change management roles. You come in, diagnose problems, design solutions, implement them and move the fuck on to the next challenge. It is project based which means it doesn't get boring.

Here's another one that's quite popular working in startups. Startups are a great place for folks who are intrapreneurial but for whatever the reason aren't going out on their own. The structure is still pretty loosey goosey. Everyone wears multiple hats and trust me there is plenty of room for you to define your contributions and your role. You may even get an equity upside without having to shoulder the risk. Then there are project based or contract roles with a fair amount of autonomy. You get brought in for your expertise, solve the problem and move on. There's lots and lots of variety without all the administrative burden of running your own company. And then there are entrepreneurial divisions within larger companies.

Now these are a little bit harder to find, but some big companies intentionally create entrepreneurial pods, innovation labs, new market divisions where you get the resources of the big company with the autonomy of a startup and they're well worth seeking out. Now, company culture also matters as much as the role. So if you are going the intrapreneurial route, here's what I want you to look for. Tolerance for experimentation and failure. Do they actually mean it when they say they want innovation? Or do they low key punish anyone who tries something that doesn't work?

Flatter hierarchies, not necessarily flat flat, because flat flat organizations have their own problems, but they're just flatter. What I'm talking about is flatter hierarchies where ideas can come from anywhere and you don't have to have 17 levels of approval in order to pilot something new. Company cultures that are results based, not process based will be a great fit for you. Are you measured on outcomes or on how well you followed the playbook? Because entrepreneurial brains will always break the playbook if it's not efficient. And companies that have a history of promoting from within based on initiative. Do people who solve problems and create value get rewarded or are they told to stay in their lane?

Then of course there are always the more obvious red flags you want to avoid. Like companies that say we want innovative thinkers, but then you have like 47 layers that you have to go through to get anything approved, that's innovation theater. They want to look innovative, they want to cosplay innovative, but they're not changing anything. Then the red flag of companies that talk about entrepreneurial culture, but they are micromanaging. We want you to think like an owner, but also CC me on every single email and get approval in advance before you do anything, oh hell no.

And finally, companies that have very rigid role definitions with no wiggle room or room for expansion. If you're a job description is set in stone and you're not allowed to evolve it based on your own strengths, you're going to be bored in six months tops. The right role in the right company can feel like entrepreneurship without the existential terror of payroll. You get to build, innovate, create impact, and go home at the end of the day without worrying about where your health insurance is coming from. That is not settling, I'll say it again, that's strategic.

All right, let's bring this home. If you take nothing else away from this episode, please take this, entrepreneurial traits are valuable in many, many contexts. Self employment is just one of them. The goal isn't freedom from structure, it's finding the right amount of structure for your brain. Some of you need to go solo, you know who you are. You've tried employment in every possible configuration and it just never works.

So go, build your thing, I support and encourage you to do that. But some of you need to stop forcing yourself into the entrepreneurship box because you think that's what you're supposed to want with these ADHD traits. You can be creative, innovative, visionary, and disruptive, all the things the business world claims to value, and still do your goddamn best work in someone else's organization. You are not broken. You are not scared. You are not settling. You're being strategic and intentional about creating the conditions where you can thrive.

So here's your action step, do the honest self assessment. Ask yourself, where do I actually do my best work? What environment brings out my strengths and supports my challenges? What do I need to be successful? And can I create that as a solo business owner, or do I need an organization to provide it? And then make the choice that serves your life, not the one that looks good on LinkedIn. Because at the end of the day, this is about building a life that works for your brain, not proving to someone else that you can do something who doesn't happen to pay your bills. You have permission to stay employed if that's where you thrive. You also have permission to go solo if that's what you need. Just make sure you're choosing based on self awareness and not shame.

All right, before we wrap up, if this episode helped you realize something about yourself, I have a favor to ask, leave a review for this podcast. Here's why it matters, reviews are how other entrepreneurial folks with ADHD-ish brains find this show. The algorithms love reviews and honestly, they are how people who need to hear this kind of content actually discover it exists. And look, I put a lot of effort and dollars into making every episode of this show. The research, the strategy, the recording, the editing.

If you've been getting value from it, a review is a pretty awesome way to say thank you and doesn't cost you a dime. So take two minutes, tell me what resonated, tell me what you disagree with. Tell me what changed how you think about your business or your brain. It helps more than you know and because you have ADHD too, do it now before you forget. There's a link in the show notes to make it easy.