Ever launched a program, course, or membership that once set your heart on fire, only to find yourself completely over it just as it starts running like a well-oiled machine? If you’re an entrepreneur with ADHD, this scenario is all too familiar. 

In this straight-talking solo episode, Diann Wingert unpacks why boredom hits hardest when your business finally starts working—and what to do about it. 

7 Things You’ll Learn From This Episode:

The Real Reason You Get Bored: Learn the neuroscience of ADHD boredom and why your brain craves novelty (hint: it’s about dopamine, not discipline).

The “PROOF” Framework:

A practical tool to help you decide if it’s time to renew or release your business offers.

How To Build Boredom-Proof Systems: Discover strategies to rotate, redesign, and reinvent your business model so you stay engaged long term.

Strategic Delegation & Role Redesign: Find out how letting go of the dull stuff (or handing it off!) can reignite your passion—and even grow your business.

Permission to Evolve: Why shifting your focus is not failure, but good business and good self-care.

Want your entrepreneurial journey to last? Build boredom-proofing in from day one.

• Alternate focus areas each quarter.
• Design offers so they evolve or rotate naturally.
• Proactively plan breaks, new challenges, or learning cycles.

And, most importantly, give yourself grace when you need to pivot, change, or retire offers. Evolution isn’t failure; it’s strategic adaptation.

Fun Fact from This Episode:

Did you know that constraints—NOT unlimited freedom—are actually better for the ADHD brain? Giving yourself playful “rules” can boost creative energy and bring the spark back to your work.

If you’re ready to stop burning down perfectly good projects just because they aren’t as shiny, then tune in for some science-backed wisdom and real-life strategies from someone who gets it.

Next Steps: 

Download the FREE cheat sheet and put the PROOF framework to work today. 

Re-listen to Ep #277_ “The Soulmate Phenomenon: How ADHD Fuels Idea Infatuation In Your Business”  It’s the other side of the same coin! 

Mentioned in this episode: 

Episode # 288 “ADHD is Not Just in Your Head: Exploring Embodied Neuroscience” with Dr Miguel Toribio-Mateas 

About the Host

Diann Wingert is a seasoned psychotherapist-turned-business coach who blends neuroscience, entrepreneurial strategy, and real-life ADHD experience. Her specialty? Helping entrepreneurs design businesses around their brains, instead of fighting them. She’s the creator of The Boss Up Breakthrough coaching framework, where she brings actionable wisdom to entrepreneurs with ADHD who want a stand-out, sought-after, profitable business built on their unique brilliance, without burning out.  

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

You launched something, a program, a course, a membership. And when you created it, you were on fire, you couldn't wait to deliver it. Fast forward six months, maybe a year and now you'd rather organize your junk drawer than show up for it one more time. Here's the thing, it's successful, people love it. So why can't you just be grateful and keep doing the thing that works? Well, if you listen to episode 277 about the soulmate phenomenon, you know, I talked about how easy it is for brains like ours to fall in love with new ideas. This is the flip side, what do we do when something we've already got running has completely lost its shine? Because ADHD brains don't just fall in love with new ideas. We also fall out of love with existing ones, and sometimes spectacularly so. So today we're talking about boredom proofing your business. How to know whether something has genuinely run its course and can be released, or whether you need to find a way to make it interesting again. I'm Diann Wingert, and this is ADHD-ish.

Okay, so let's just say the quiet part out loud. Entrepreneurs with ADHD are really, really good at starting things, and we really suck at staying interested in them over time. And I want to be clear about what we're talking about today, because this is different from the soulmate phenomenon that I covered in episode 277. That episode was about falling in love with new ideas. You know when something shiny shows up and you're convinced, oh my God, it's the one and you're ready to pivot your entire business around it and maybe did. This episode is about the other side of the same problem.

You're already in it. You built it, you launched it, maybe it's even really successful. But now you're bored out of your mind and this isn't about whether to chase a new opportunity. It is, but that's not the whole thing. It's also about whether to keep or kill an existing one. And here's what makes this particularly brutal, we're often bored of the thing right when it's starting to actually work. Kind of perverse, right? I mean, right when the systems are finally running smoothly and we figured out all the kinks, when it could almost run itself and print money on demand, that.

That is when we're most likely to feel a burning desire to shut it down and start something else entirely different. I had a client recently, she had built a truly incredible course. Took her a year to create it, it was selling consistently, her students loved it. And she shows up to our call one day and says, I think I need to blow this up and create something new. I was not shocked or surprised. All my clients have ADHD and so do I. But when I asked why she couldn't give me a strategic reason for doing so, she said the obvious, it's boring. She said everything she needed to say. She taught it five times, so she was done. And here's the thing sometimes boredom is strategic information. Sometimes something has run its course, sometimes you've outgrown it, or the market has shifted, or it's genuinely time to move on.

But sometimes, and this is the uncomfortable truth, the problem isn't the thing. The problem is that you have an ADHD brain that is literally wired to crave novelty, including in the things you're already doing that are working well. So if you don't know the difference between this is boring because I'm complete with it and this is boring because I've done it five times and my brain needs a new source of stimulation, you're probably going to spend your entire working life burning shit down that could have been profitable, sustainable and genuinely enjoyable if only you knew how to boredom proof them. So that, my friend, is what we're doing today. We're getting hella strategic about boredom in your existing business, not just about shiny new things that are trying to seduce you.

So first we need to talk about why this happens. Because not everybody is a major nerd about neuroscience the way I am. And if you're the kind of person who needs to understand why you are the way you are, this is genuinely going to help. And I'm going to keep it as non academic as possible, because not everybody wants a neuroscience lecture. But you do need to understand what's happening in your brain okay. So here's the thing, ADHD brains have what researchers call dopamine dysregulation. And if you heard my recent interview with Miguel Toribio-Mateas, you know there's more going on upstairs than dopamine. But when we're talking about dopamine and we don't essentially produce enough or process it right, we don't distribute it well.

That neurotransmitter is the one that's tied to motivation, reward and pleasure in the same way that it is in neurotypical brains. But here's what it means practically, we need more stimulation to feel the same level of interest and engagement that other people can feel with less new things, novel experiences. The quintessential shiny object syndrome, those first few times you do something, pretty much anything and everything. Your brain gets a big ass dopamine hit. You're interested, you're motivated, you're engaged, it's go time. But once something becomes a little bit routine, once you've done it a handful of times and the novelty wears off, the shine is no longer shiny, the dopamine drops, and suddenly that thing that was not so very long ago exciting AF is now about as appealing as watching paint dry.

And this is why we are so damn good at starting businesses and often really shitty at running them. The startup phase is all about novelty, every day is different. You're figuring shit out, you're creating, you're problem solving. It is stimulating yourself. But running an established business, that's routine, that's repetition. That's showing up and doing the same thing you did last week and the week before and the one after that. And for brains like ours, routine can feel like fucking kryptonite. So here's where this gets tricky, we start to interpret boredom as proof that we are on the wrong path.

We think, well, if I was doing the right thing, I'd be excited about it on the regular. We think passion is supposed to be constant. We think if something feels boring, that means it's not what we're supposed to be doing and that is bullshit. Boredom is not a sign that you're on the wrong path. Boredom is a sign that you're human and specifically a human with an ADHD brain that needs a lot more stimulation than most. You can think about it this way. A neurotypical entrepreneur might get excited about optimizing their systems or refining a process. They might genuinely enjoy the predictability of a well oiled machine. You, you'd rather set yourself on fire.

That's not a character flaw. It's not a lack of discipline, it's not a lack of commitment. It's not a lack of gratitude. It's your fucking neurobiology and this is important because it's neurobiology it means you can't really negotiate with it. But you know what else it means? You're not helpless. It does not mean that you just need to give up every time you feel like it because you can't push through. It means you need to design your business differently than someone whose brain doesn't work like yours. You can't out discipline your dopamine system, but you can design around it. Which brings us to the question, how do you know whether something has genuinely run its course and it's time to bless and release, or whether you need to find a way to make it interesting to your ADHD brain again.

Well, I want to introduce a new framework I just created and you know I love me some frameworks. This one I'm calling the Renew or Release. All right, here's where the strategy comes in. When you start to feel that familiar itch to blow shit up, abandon a project, or completely pivot your business, I want you to run it through the Proof framework. Proof, P R O O F. It stands for profitability, relevance, operation, opportunity, cost, and fresh eyes. Let me break it down for you. P is for profitability, is this program, product, service, offer, business model still making money? Or could it with a couple of tweaks?

Here's the cold hard business question. Because you are, after all, in business to make money and to turn a profit. Strip away your feelings for a second and look objectively, is this thing that I'm thinking about blowing up profitable? Is it bringing in revenue? Is it contributing to my bottom line? If it is, then your boredom is expensive. Now that doesn't mean you have to keep doing it, but it does mean you need to be honest with yourself about what you're willing to sacrifice to the boredom gods. Now, if it's not profitable, but it could be with some adjustments, maybe better marketing, price increase, a slight shift in positioning, then the question becomes, is it worth the effort to make those tweaks or would that energy be better spent elsewhere?

Now, if it's actively losing money or breaking even with a shit ton of your energy and effort, that's useful information because maybe it has run its course. Are you ready for R? R is for relevance. The question here is, does it still align with where you are now headed? The truth is, if you are an entrepreneurial person with ADHD, you are constantly evolving. You're not the same person or the same business owner you were when you started this thing. So ask yourself, does this still fit with the direction I'm moving in? I had a client who had built a very successful online course teaching basic business setup for newbie entrepreneurs. It made decent money, but she'd evolved.

She was working with more established business owners now doing higher level strategic work. The course was still relevant to someone, just not to the business that she was now building and the clients she was now serving. That's very different from, well, I'm just bored of it, but it totally fits my brand and my audience, see the difference? So be honest, are you bored because you've outgrown it, or are you bored because it's Tuesday and your brain wants something shiny. O is for operation. Is the boredom about the task or about the outcome? And this is one of my favorite parts of this framework, because it's sneaky.

Sometimes we think we're bored with the thing, but what we're actually bored with is how we're delivering it. Let me give you an example, I worked with someone a couple years ago who was so ready to completely kill her group program. She was done with a capital D, but when we dug into it, she didn't hate the program. You know what she hated? Being on Zoom calls three times a week at the same time. The structure was what was killing her, not the program. So we redesigned it. We went asynchronous with occasional life calls, and guess what happened? She fell in love with her program all over again.

The surprising thing is, same content, same people, same program, really, but a different way of delivering it, different operations. So ask yourself, am I bored with the what or am I bored with the how? Because if it's the how, that, my friend, is fixable. That is something you can redesign that does not require blowing the whole thing up. You ready for O? Okay, O is for opportunity cost. What are you not doing because you're doing this? Now you know this, every time you say yes to something, you're saying no to something else. And with brains like ours, you're probably saying no to a whole lot of other things because you're constantly coming up with new ideas. Your time and energy are finite, even though we like to pretend they're not.

So, what are you not doing because you're still running this thing that you're feeling bored with? Are you not creating that new offer that you're genuinely excited about? Are you not taking on higher level clients that challenge and stimulate you? Are you not spending time on the parts of your business that actually light you up? If the opportunity cost is high, if this boring thing is blocking you from something that is genuinely and objectively better, then release it. Life's too short. But if you're vaguely thinking, well, I could be doing something else, that's not strategic. That's just your ADHD brain being like, well, what if there's something more fun over here? So be specific about what you're trading this for. F is for fresh eyes, dan someone else run it? Or can you redesign your role?

Now, most entrepreneurial folks and small business owners don't think about this because our identity is so wrapped up in our small business. It's the option that most people don't consider, not because they can't, it just doesn't occur to them. But ask yourself this, what if I didn't have to do the boring parts? What if someone else delivered this program for me? What if you hired someone to handle the operations? What if you licensed it to someone else? I'm actually working with one of my current clients on this as we speak. Or what if you automated more of it? You know, before you kill something profitable and functional, hit the pause button, pump the brakes and ask yourself, can I change my relationship to it? I know a coach who was bored witless with her membership. It was going great, but she wanted to shut it down.

So we examined her options and instead of shutting it down, she brought in a community manager. And now instead of having to be in the membership multiple times a week and resenting every freaking minute, she shows up once a month to deliver a high quality live training. Everybody's happy, it still makes money and she got her energy back for other projects. Fresh eyes can mean delegating, automating, or completely redefining what your role and relationship is with this thing. And with this one because it's the option most people don't consider and it can be hard to wrap your mind around. If this is something you're considering doing, you might need to spend a little time with a coach, strategist or consultant to figure out the how.

So here's how you use proof, when you're done being familiar with that oh, I'm so over this feeling, and you don't want to be destructive, sit down and answer these five questions. Write them out and I mean old school longhand pen and paper. It really does work better for this type of strategic thinking and problem solving. If the thing scores low across most of the categories, let it go. With love, with gratitude, and with zero freaking guilt. It served its purpose and now it needs to move on. If it scores high, if it's still profitable, still relevant, and you might be able to redesign or delegate some parts of it. Please don't kill it out of boredom. Renew it. Reinvigorate it. Reanimate it. Breathe new life into it. Trust me when I tell you, you won't regret this.

Now, let's talk about some boredom proofing strategies in addition to the proof framework. So let's say you've run something through proof and decided, okay, all right, fuck me, I admit it. It's worth keeping. Okay, you made your point or maybe you're starting something new and you want to redesign it so it stays Interesting. Even after the honeymoon phase wears off, because you're still going to be ADHD in the future, trust me on that one, too. So here are my strategies for boredom proofing your business. Build rotation into your business model from the jump. Instead of doing the same thing week after week, build in some natural variation. For example, if you have a group program and you run it three times a year with a break in between to market and launch, maybe you alternate between client work and content creation every quarter.

Maybe you have different seasons in your business where you focus on different things. I have a very good friend who's been doing this for years and swears to buy it with her ADHD brain. The key is, don't build your business in such a way that it requires you to do the exact same thing every single week indefinitely because you're not going to do it. You're going to burn it down. You're going to burn out, or you're going to get bored and start to blow shit up, even really good shit that's working. So design rotation in from the beginning. You know what else you can do? Create variety within consistency.

Now hear me out, you can have consistent offers without having monotonous delivery. Same program, different cohort, different guests, different examples, different challenges, same service, different clients, different problems. The framework can stay the same, that's actually helpful for your ADHD brain because you reduce decision fatigue. But the content, the people, the applications you use can vary. I do a lot of this in my business. I want you to think of it like jazz. The structure is consistent, but there's always room for improvisation. You can also use constraints as a creativity tool. Now, I know that sounds counterintuitive, if not crazy, but constraints actually make things more interesting for ADHD brains.

Let's be honest, when we have total freedom, we still get bored. But if we have a constraint like I can only use three colors for this sales page, or I have to teach this concept using, I don't know, movie analogies, or every month I'm going to interview someone for my podcast from a completely different background. Suddenly it's game on, it's a challenge, and it's interesting all over again. Constraints give your brain something to work with. Total freedom is actually boring and we don't do well with it. I want you to think of strategic delegation as your friend and listen, I'm going to be blunt. If you're bored with the logistics, the admin, the scheduling, the operational bullshit, if you want to stay in business, you need to delegate it.

Now you may not delegate all of it, but you certainly don't need to be doing all of it either and you probably shouldn't be. Figure out which parts that you genuinely need to do. Not because of your control issues and perfectionism, but because you have the will and the skill to do them, as well as the capacity. The parts that require your brain, your expertise, your specific brilliance, your magic. And then find ways to hand off, delegate, or automate the rest. Because boredom often comes from doing too much of what I call low stimulation work. So please give yourself permission to focus on the parts that keep you engaged and get someone else to do the other stuff, because there are people who love it, they're just not you.

We also need to accept the reality that some things are simply going to be boring at least at times. Real talk, not everything in your business can be thrilling all the time, some stuff is just kind of boring. Some weeks you're just going to have to show up and do the thing even though you're not excited. This is when we need to pull our big girl panties or our big boy boxers all the way up and maybe even snap on some suspenders because they're going to want to fall back down. And you know what, that's okay. The goal here is not to make everything exciting. That's pretty impossible. The goal is to design a business where enough of it is interesting, enough of the time that you can tolerate the boring parts. Think of it like, I don't know, like a balanced meal.

You're not going to love every single bite, but if enough of it tastes good, you'll probably finish the plate. Your business needs to have enough built in interest, enough variety and enough stimulation that the boring parts don't make you want to quit. One last thing, sometimes the most boring proof thing you can do is give yourself permission to change. Now hear me out, I'm not saying blow everything up and start over every six months, that's chaos. But giving yourself permission to evolve your offers, shift your focus, try new things, let some old things go that doesn't mean you're failing or lack the ability to commit. That's having a responsive, strategic business that grows and changes over time. We're not looking for the one perfect thing that we can do forever. I covered that in the soulmate phenomenon. The goal is to build a business that's flexible enough to grow with the ever evolving person you are.

Okay, let's bring this home. If you are an entrepreneur with ADHD, you are going to get bored. That's not a bug it's how your brain works. The question isn't, oh my God, how do I stop getting bored? The question is, how do I design a business that works with my brain? When something starts to feel stale, run it through proof. Is it still profitable? Is it still relevant? Is the operation the problem or the outcome? What is the opportunity cost and can I get some fresh eyes on it? And when you're building something new, boredom proof it from the start. Build in rotation, create variety within consistency. Use constraints to keep it interesting, delegate strategically and accept that some boredom is just part of the deal.

Now here's your action step for this week. Pick one thing in your business that you're feeling meh about and run it through the proof framework and I actually want you to write down your answers then decide. Renew or release. Either decision can be the right one. Just make it strategically, not because you're bored and it happens to be a Tuesday. I created a cheat sheet to support you in using the proof framework. You can grab it at the link in the show notes and it might be a good idea to re listen or listen for the first time to episode #277. It really is the other side of the same coin. Thanks for listening to ADHD-ish. If this episode resonated, I hope you'll share it with another entrepreneur with ADHD who might just need to hear it and I'll see you next week.