Welcome to a milestone episode of ADHD-ish! In episode 300, host Diann Wingert invites listeners into a raw, unfiltered conversation about the realities of entrepreneurship with ADHD.

Rather than a feel-good celebration, this episode delivers the hard truths that other neurodivergent entrepreneurs need to hear—no sugar-coating, no apologies, just authentic wisdom earned through real-world experience.

If you’re ready for tangible insight (and a few uncomfortable truths), this is your episode.

Here are the 3 Hard Truths Every Entrepreneur with ADHD Needs to Hear:

Your self-doubt isn’t wisdom—it’s unaddressed trauma.

That overthinking, need for certainty, and analysis paralysis? It’s not you being “strategic”—it’s the residue of years spent feeling “not enough.” The real challenge is rebuilding self-trust so you can act boldly, even if you’re terrified of being wrong.

There’s no magic pill or “perfect” system.

Stop believing the next planner, project management tool, or “ADHD-friendly” hack will make entrepreneurship comfortable. Success means tolerating discomfort, not shopping for something to eliminate it.

ADHD is not your get-out-of-jail-free card.

Acceptance isn’t hiding behind your diagnosis—it's doing the tough, creative work to adapt and grow. “I have ADHD, so I need to figure out how to do this differently” is where real progress begins.

Zero F*cks Given:

To “fulfilling my potential” (an ever-moving target designed to keep you feeling not enough).

To being “too niched” (connection and impact mean more than pleasing the masses).

to ADHD diagnosis gatekeeping (if this content helps and you see yourself here, you belong).

What I WON’T apologize for:

1. Being unmasked and openly ADHD.
2. Holding ADHD coaches to real standards.
3. Being selective about coaching clients (it’s about the right fit—not the right paycheck).

The bottom line? Consistency doesn’t come from trying to “fix” yourself—it comes from radical self-acceptance, messy action, and getting honest about what really stops you.

If you’ve been waiting for the “right” moment, the perfect plan, or permission, the only way to get clarity is to take action.

About the Host

Diann Wingert brings decades of experience as a psychotherapist and now a sought-after coach to entrepreneurs with ADHD traits. Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the neurodivergent experience.

Known for her candor and her refusal to compromise on what matters, Diann Wingert is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship.

If this episode inspired or challenged you, Diann wants to hear about it! Links to several ways to let her know are right here:

Leave a review and let Diann know what resonated, challenged, or inspired you.

Send Diann an email, DM her on LInkedIn or leave a voice message on her website. Diann responds personally to everyone.

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Hey, boss, it's Diann and this is episode 300 of ADHDish. Yeah, you heard that right, that's 300 weeks of showing up through my mistakes, my pivots, my what the hell was I thinking? Moments I've forgotten to hit record. I've re-recorded episodes that sounded like ass. I've dumped the ones that sounded great in my head, but not so much in the real world. I have definitely had moments where I wanted to quit, but I didn't and that matters.

Here's what also matters, over the five plus years it has taken to record and release these 300 episodes, I've had hundreds of conversations with other neurodivergent entrepreneurs. I've seen the patterns and I've learned some things that need to be said out loud. So this is not a best of episode, this is not a warm and fuzzy celebration. This is the stuff that I've been sitting on that just needs to come out. So if you're looking for some gentle encouragement today, this might not be the time to listen to this episode. But if you're ready for some truth that might sting a little, but could actually set you free, buckle up.

I'm calling this one, 3 hard truths 0 fucks given and 0 apologies and I mean all of it. Let's start with the hard truths. Okay, friend, hard truth number one. You, your self. Doubt isn't wisdom, it's trauma. Here's what I see all the freaking time. Smart, capable entrepreneurs with ADHD who are totally paralyzed by their overthinking. They need to see every possible outcome before they can make a move. They're waiting for guarantees. They're analyzing everything to death. And when I ask them what, why they're stuck, they tell me they're being strategic. They're being realistic. They're being responsible.

And I'm going to tell you something you might not want to hear, your overthinking isn't wisdom. Your need for certainty isn't strategic planning. Your analysis paralysis isn't you being thorough. It's trauma. It's what happens when you spend an entire lifetime being told that your difference is a problem that needs to be fixed. Think about it, if you grew up neurodivergent, you grew up knowing you were different. And different was almost never celebrated, it was corrected. You learned early that the way you naturally think, feel and act needed to be managed, controlled, or worse, hidden. You got feedback constantly that you were doing it wrong.

You were too much, too loud, too scattered, too intense, not focused enough, not organized. Enough, simply not enough like everyone else. So you learned not to trust yourself because every time you did, every time you followed your instincts, it seemed to blow up in your face. Over time, that lack of self trust becomes the most insidious obstacle to success as an entrepreneur. But here's the thing about entrepreneurship. It requires you to act on hunches. It requires you to take risks with incomplete information. It requires you to make intuitive guesses, follow your curiosity and course, correct along the way when you get it wrong. But when you don't trust yourself, you can't do any of that.

So instead you overthink. You seek external validation. You look for guarantees that just don't exist. You wait for permission that's never coming. And here's what really kills me the things you're doing to try to avoid mistakes. The perfectionism, the procrastination, the endless research and planning. Those things are actually more dangerous than the mistakes you're trying to avoid because they slow you down, they suppress your gifts, they kill your momentum. And whatever you do manage to accomplish ends up being so watered down, so safe that it's nowhere near as innovative or exceptional as what you're actually capable of.

So the hard truth is this, your self doubt isn't protecting you. The safety you're creating through all that overthinking and seeking guarantees, it is more dangerous than any mistake you could actually make. What you need to do instead is rebuild self trust and that means accepting that there are worse things than mistakes. I mean, making a mistake and learning from it, that's just a regular Tuesday in entrepreneurship. But never taking the shot because you're terrified of being wrong again, that is the real tragedy.

Hard truth number two, stop searching for the magic pill. This one's going to hurt because I know how seductive this pattern is. You keep searching for the magic pill. And by the way, I am not talking about ADHD medication here. Although sometimes people have unrealistic expectations about that too. I'm talking about the planner that's finally going to work. The project management system that's going to make everything easy. The morning routine that's simply going to change your life. The proven process, the step-by-step system, the coaching framework that's going to eliminate all the discomfort of running your own business.

You keep buying these things, you keep trying these things and, and when they don't work, you don't think, well, maybe there is no magic pill. You think, I just haven't found the right one yet. And here's the truth, you really don't want to hear. You're not actually looking for something that works. You're looking for something that will let you avoid discomfort. You're looking for a tool or a system or a coach that will make you comfortable doing the uncomfortable things that running a business requires and it doesn't exist.

No planner is going to make you enjoy bookkeeping. If you hate bookkeeping. No project management software is going to make you good at follow up if you suck at following up. No morning routine is going to automagically give you discipline in areas where, where you simply have none. No framework, including mine, is going to eliminate the uncertainty and discomfort that comes with entrepreneurship. What you're actually doing is shopping for solutions instead of building capacity.

You're trying to find a workaround for growth when you could just be growing. And the ADHD world makes this worse because we're constantly being sold the idea that we just need to find the quote unquote ADHD friendly version of everything. The ADHD friendly planner, the ADHD friendly productivity system, the ADHD friendly business model. But here's what nobody wants to tell you. Running a business requires doing shit you don't want to do. It requires discomfort. It requires growth. And no amount of color coded planners or Notion templates is going to change that fundamental fact.

The work is not finding the perfect system. The work is expanding your capacity to tolerate discomfort. The work is building your ability to do hard things even when they feel really hard. That's it. That's the whole game. So start shop, stop shopping, stop. So stop shopping and start building discomfort is the price of admission to entrepreneurship, not a bug that needs to be fixed? If you're still here, I'm going to lay down hard truth number three. Your ADHD is not a get out of jail free card. And this one's probably going to piss some people off the most. Some of you have been thinking that your ADHD diagnosis is a get out of jail free card. It's like a pre-approved reason to quit when the going gets hard. You might even be calling that acceptance.

Here's what it looks like. You have big dreams, I know you do. You pursue big goals. You're willing to work hard. But when the going gets tough, whether that's boredom or burnout, because it always gets tough in entrepreneurship, whether you're neurodivergent or neurotypical. By the way, you can pull out that card. Well, you know I have ADHD, so maybe this is just too hard for me. Maybe I need to reevaluate. Maybe I need to lower My expectations. Or maybe I'm just not wired for this and everyone nods sympathetically. No one questions it. I mean, you get understanding, not accountability.

Of course you had to step back. You have ADHD. That's self care. But you know what's really happening? You're not being realistic about your limitations. You're using your ADHD as a safety valve, or worse, an exit strategy. You're bailing before you've actually hit a real limit because ADHD gives you a socially acceptable reason to quit. And the really insidious part, you think you've accepted your ADHD. You think you're being self aware. You think you're being responsible by knowing your limits. But what you're actually doing is hiding behind your diagnosis. You're choosing a more socially acceptable version of victimhood and calling it acceptance.

Now, let me be very clear. ADHD is real, the challenges are real. I am not saying you should just push through or that ADHD doesn't matter. What I'm saying is that there's a difference between ADHD explains this challenge and ADHD. Excuses me from figuring this out when you say, I have ADHD, so I can't do this, that's where the conversation ends. You've absolved yourself of responsibility. But when you say, I have ADHD, so I need to figure out how to do this differently, that, my friend, is where the real work begins. That's actual acceptance.

Accepting that you're going to have to work with your brain. And that might require creativity and problem solving and, yes, discomfort. Your relationship to your ADHD matters so much more than the ADHD itself. I mean, two people can have exactly identical presentations of ADHD and yet have completely different outcomes based on whether they see it as a limitation or something they're learning to work with. So the hard truth is you need to decide if ADHD is the reason for everything that's wrong in your business and your life or that it's one facet of who you are that requires some accommodation and creativity. Because the story you tell yourself about what your ADHD means will determine your ceiling more than symptoms or impairment ever will.

Okay,tThose are the three hard truths. Now, I did warn you, this is not going to be gentle. Now let me tell you what I've stopped giving a fuck about. Because part of getting to 300 episodes, did I mention it's 300 episodes. Part of building a business that works, part of becoming someone who can tell you these hard truths, because I've had to learn them the hard way, has been learning what actually doesn't matter. So I want to share three things that I used to care about so much, and I just don't anymore. I never thought I'd find myself saying that indifference is a goal. But wait till you hear what it looks like now that I'm here. All right, you ready for the first one? Here we go.

Zero fucks given for fulfilling my potential. Now, if you grew up neurodivergent, you know exactly what I'm talking about. You're not living up to your potential was probably on every report card, every parent teacher conference, every performance review you ever got. It's the neurodivergent kid's burden. This constant sense that you're capable of so much more, that you should be doing better. You're just chronically disappointing everyone, including yourself. And here's what I finally realized, nobody actually knows what your potential is.

Not your teachers, not your parents, not your boss, not even you. It's completely made up. It's a moving target specifically designed to keep you feeling inadequate. I mean, think about it. When has anyone ever said, congratulations, you have officially fulfilled your potential. So you can sit back and relax now, like never because potential is infinite. It's unfalsifiable. You can always be doing more. You can always be achieving more. You could always be being more, which means you can never actually win this game. So I stopped playing. I'm building a life I actually enjoy with work, and that actually matters. And I decide that that's enough. If that's not fulfilling my potential according to someone else's rubric, I genuinely don't care, zero fucks given.

Number two, being too niched. Hey, I focus on working with entrepreneurs with ADHD traits. I now that is a tiny fraction of the people who have ADHD. Since most people with ADHD have jobs, not businesses, just like most neurotypicals. I have been told so many times that I'm limiting myself, that I could serve a bigger market, that more people should know about me. I could make more money if I expanded my focus. And you know what? It's probably true. I absolutely could water down my message and appeal to more people. I could play it safer. I could be more generic, cast a wider net.

But you know what? I don't want to. I'd rather be essential to the right people than somewhat helpful to everyone else. I would rather have deep, meaningful, lasting impact with a smaller group than surface level impact with the masses. And you know, want to know what's funny? You've probably heard the expression the riches really are in the niches, well, it's true. Even when people tell you your niche is too small. The clients I work with now, the listeners who've been with me for years, maybe even all 300 episodes, they're here because I'm not trying to be all things to all people. They're here because I speak directly to their experience. So if being too niched means that I'm building something meaningful instead of something massive, I can live with it.

Next up, zero fucks given number three ADHD diagnosis. Gatekeeping. I give zero fucks about gatekeeping ADHD diagnosis. Now, I think you know what I'm talking about. This whole are you officially or self diagnosed question. The implication that if you don't have paperwork from a psychiatrist means you're not legit, like you're somehow faking it or jumping on a trend. This pisses me off for so many reasons. And by the way, I was a licensed psychotherapist who had a legal obligation and privilege to diagnose people for over 20 years. First of all, wait lists to get evaluated right now are frickin insane.

In many places it takes months or even years to see someone who can diagnose you with ADHD. The dramatic increase in adult ADHD diagnosis has completely overwhelmed the supply demand ratio. So telling someone they're not legit because they haven't been officially diagnosed is basically telling them they're not legitimate because they don't have access to health care. Secondly, there are people who are employed in occupations where having ADHD on their permanent medical record could cause them real problems. Folks in the military, law enforcement, certain clearance levels. These are real constraints. For some people, getting an official diagnosis simply isn't worth the professional risk.

And third, some people cannot take medication or have a history of addiction, not uncommon with this condition. And they don't want to take stimulants. If the main benefit of diagnosis is access to medication that you can't or won't take, what is the point of jumping through the hoops and getting the official paperwork? And honestly, there are countless other legitimate reasons someone might not pursue an official diagnosis. Financial barriers, insurance issues, bad experiences with the mental health system, or living somewhere without access to qualified evaluators, just to name a few.

None of that makes them any less deserving of help. None of that makes their struggles any less real. ADHD is not some exclusive club that needs gatekeeping. If the content resonates, if the strategies help, if you recognize yourself in these conversations, you're welcome here. Period. This is one of the main reasons I rebranded this podcast or over a year ago and never looked back. Okay, so those are the three things I've stopped caring about. And now I'd like to tell you what I will no longer apologize for. They may sound like the same thing, but I think there's a difference between not giving a fuck and refusing to apologize.

Here's how I see it, not giving a fuck is, I don't know, passive. It's just not caring, but refusing to apologize. That's active. It's knowing people want you to apologize and saying nope. It's the distinction between something you no longer care about and something you will go ten toes down defending. So here are the things I will no longer apologize for. Number one, being openly and unmasked as a professional with ADHD. I am not going to apologize for who I am in my professional life. I spent years, really, honestly, decades, masking. And by the way, if you don't know what masking is, it's when neurodivergent people pretend to be neurotypical in order to make other people more comfortable.

In my previous career as a psychotherapist, oh, I was so good at this, and I was proud of it at the time. I was polished, poised, professional, and oh, so controlled. Nobody would have known I had ADHD if I didn't tell them and I wasn't telling. You know what else was fucking exhausting? Performing all day, every day is, I don't know, like holding your breath underwater. You can do it for a while, but eventually you gotta come up for air. So when I closed my therapy practice and pivoted into coaching, I made a very conscious decision. I'm gonna stop performing. I'm going to learn how to show up as myself, ADHD traits and all. And I was going to talk openly about it, my struggles, my process, and be as honest as I possibly could, even if I was scared.

Now, I'm pretty sweary in my personal life. So when I launched this podcast five and a half years ago, I did so with an explicit rating so my guests and I could express ourselves however we wished. Now, some people hear ADHD coach and think you can't possibly be reliable or professional. They make assumptions. They decide I'm not for them before they ever hear what I have to say. Others see my explicit rating and write me off immediately because of it. And you know what? Those aren't my people. The relationships I have now, the clients I have the privilege of working with, the listeners who show up for this podcast week after week. These are real relationships because I am myself and people know exactly who they're getting. There's no bait and switch.

There's no disappointment when they realize I'm not the polished, perfect version I was pretending to be. Multiple clients have told me that watching me be unapologetically myself, watching me mentor and I guess be a role model for what it looks like when you accept yourself without making it your whole personality, but no longer hiding it has been just as valuable as the rest of my coaching. Because acceptance is not about being loved or even liked by everyone. It's about being yourself and attracting people who value that.

So I will not apologize for being openly ADHD. Masking to make other people comfortable is in my rear view mirror and I am not pulling a U turn. All right, zero apologies. Number two, I will no longer apologize for holding ADHD coaches to actual standards and this one is guaranteed to make some people mad. But I'm going to say it anyway, there are way too many people who stumble and fumble their way into an ADHD diagnosis, think they're having a light bulb moment and the next thing you know they're launching an ADHD coaching business because they somehow think that having ADHD means they can help other people who have it too.

The I got diagnosed six weeks ago and now I'm an ADHD coach pipeline is all too real and I believe it's doing real harm. Now let me be clear, I am all for more ADHD coaches. More adults are realizing they have ADHD and can benefit from ADHD coaching. We need more people in this space, but we need competent people in this space. Having ADHD does not automatically make you qualified to help other people with ADHD. Good intentions do not replace real training. They don't replace experience with. They don't replace the humility to know what you don't know. I have seen the harm that gets done by very well intentioned and well meaning folks who overestimate their ability to help.

I've had clients come to me after working with other ADHD coaches who not only gave them terrible advice and over identified and projected their own struggles onto them, but far too many who simply took their money without delivering any real value. And when I call this out, when I say, hey, maybe you should get some actual training before you start charging people money to help them. People get defensive. They say I'm gatekeeping. They say I'm being elitist. They say everyone's an expert to the person who's two steps behind them. And I say if you are only two steps ahead of the people you are charging to help. You need to do better. Standards aren't gatekeeping. They're responsibility and their leadership and I will not apologize for saying that out loud.

All right, you ready for number three? 0 apologies for being selective about who I work with. I have a screening process if someone wants to work with me because I only work one on one with a limited number of people at a time. Some people are put off by this, they think I should just take anyone who wants to pay me. But I don't and here's why. I know who I am. I know how I am. I'm direct. I'm strategic. I occasionally swear when it helps me make a point, and I don't soften hard truths. I'm not going to hold your hand and tell you everything's going to be okay if I don't think it is.

That being said, I was a therapist for a very long time and a good one, I think. So I know how to be the cross between a kick in the butt and a warm hug. I am well aware that some people are intimidated by directness. Some people are uncomfortable when others are insightful. Some people are frankly turned off by my swearing, even though it's never directed at another person. Some people want a coach who's going to hold their hand and fluff their pillows and make them feel safe and that's not me. What you hear on this podcast is exactly how I show up in my coaching calls, and it's also exactly how I show up with friends and family.

What you see in here is very much what you get. And I also know that people with ADHD can be impulsive. We can engage in wishful thinking. We can have wildly unrealistic expectations of ourself and others. And that includes being impulsive about hiring coaches when we're not actually ready to work with them. So yes, I have a screening process, I have a conversation before I am willing to take someone's money. And I've been doing this long enough to know who's going to have an excellent outcome working with me and who just won't. Maybe their expectations are unrealistic. Maybe they're not ready to do the work. Maybe my style isn't what they need right now. Whatever the reason, if I don't think we're a fit, I say so.

And because I actually give a shit about other people, I will tell them what I think they should do instead of working with me at this point in my career and in my life, I'm really only interested in co creating excellent outcomes. I want to work with people who are ready, who are willing and actually can make use of what I have to offer. So if that makes me selective, good. I'm not apologizing for it. Okay, that's it, 300 episodes, three hard truths, zero fucks given, and zero apologies. Because here's what I've learned after five and a half years of showing up with ADHD for this podcast. Consistency doesn't come from fixing yourself. It comes from three things.

One, get brutally honest about what's actually stopping you. Not the story you're telling yourself, not the excuse that feels safe. The real thing, because once you name it, you can actually do something about it. Two, stop spending time and energy on shit that doesn't move you forward. Those planners. You're never going to use the research you're doing instead of taking action. All the time spent looking for the perfect system or coach. That's not preparation, that's avoidance, pretending to be productivity. And three, work with who you actually are, not who you think you should be.

I did not get to 300 episodes by trying to become less ADHD. I got here by accepting that I'm going to forget to hit record sometimes. Some episodes are going to go in the trash and that my process is never going to look exactly like anyone else. And then I show up anyway. You want to know the real secret to being consistent with ADHD? It's not discipline. It's deciding that imperfect action beats perfect planning every single time. It's showing up messy and doing it anyway. 300 episodes means I've been wrong a lot. I've changed my mind, I've course corrected and I kept going. That's not special. That's just what happens when you stop trying to think your way into action and just start acting your way into clarity.

So whatever, whatever you're waiting to be ready for, whatever you're overthinking, whatever you're using your ADHD as a reason not to do, just fucking start. I want to thank you for 300 episodes worth of showing up with me and here's to however many more we get. If this episode was exactly what you needed to get you going, I so want to hear from you. There's a whole handful of ways that can happen and links to do so in the show notes and hey, I'm Diann Wingert, this is Adhd-ish and I'll be back with you next week.