Starting Strong with ADHD: Overcoming Procrastination & Task Avoidance to Get the Ball Rolling

You know that feeling when you have a brilliant business idea but somehow six months later, you're still getting ready to start? Or when you get so excited about something that you jump in completely unprepared and realize halfway through you have no clue what you're doing? Well, if you're nodding along, you've got what I call the ADHD starting paradox. And today we're going to fix it.

Hey boss, I'm Diann Wingert and this is ADHD-ish, where we talk about building businesses with brains that work a little differently. Today I'm kicking off a three-part series on what I call the unholy trinity of ADHD business struggles. What am I talking about? None other than starting, stopping and switching gears. And by the end of this three-episode series, you'll have a complete system for managing all three. But first, let's talk about getting your ass in gear.

Hey, here's what nobody but me will tell you about ADHD entrepreneurs. We don't have just one starting problem. We actually have two completely opposite starting problems. And we ping pong between the two of them like we're in some kind of productivity hell. On one side, there's analysis paralysis. You spend three weeks researching the perfect email marketing platform before you've written a single email. You create 17 different versions of your business plan. You know everything about your industry except how it feels to actually show up and do the freaking work.

On the other side, there's what I call cannonball starting, where you get so excited about your new idea that you launch yourself into the deep end without checking if there's even water in the pool. You announce your new program before you've built it. You start a podcast without thinking about how you will consistently create that content. You jump in with both feet and wonder why you keep on face planting. Both of these feel productive in the moment, and that's why this is so hard for people who don't have ADHD to understand what we are up to.

Planning feels responsible. Jumping in feels brave. But they're both just different flavors of the same underlying problem. We're either waiting for the perfect conditions or completely ignoring the conditions altogether. And here's the kicker, both approaches set us up for failure, but in different ways. Over planning creates an impossible standard where nothing is ever ready enough to start. Under planning creates chaos that makes us want to quit when things inevitably get messy. Sound familiar? Yeah, I thought so.

So let's talk about Renee. Renee is brilliant at what she does. She's a marketing consultant who gets incredible results for her clients. But for eight long months, she's been, quote unquote, getting ready to launch a course. Renee has researched every course platform. She's written detailed outlines. She's even created a spreadsheet that compares 17 different ways to structure the course content. You want to know the one thing she hasn't done? Recorded a single lesson because, and I'll quote her, I want to make sure I have everything figured out first.

Meanwhile, there's Mark. Mark gets excited about starting a membership site and announces it to his email list before he's even decided what would be included in the membership each month. He sold founding memberships and then spent the next three months in panic mode trying to figure out what the hell he was actually going to give the people he's made promises to. Both Renee and Mark are dealing with the same core fear, they're just expressing it differently. Both of them are terrified they're not going to be able to sustain whatever they do manage to start. Renee thinks if she plans enough, she can outsmart that fear. And Mark thinks if he just jumps in fast enough, he can outrun it.

Spoiler alert, friends, neither of these strategies actually work. Let's dig in a little deeper to the analysis paralysis problem. When we over plan, we're usually trying to control something that just can't be controlled. The future. We think if we just research enough, plan enough, prepare enough, somehow will guarantee success but here's what really happens. First, we start confusing planning with progress. Spending three hours researching project management software feels productive, but it's not actually moving you toward your goal.

It's actually an elaboration of procrastination, wearing a productivity suit. I know that hurts. Secondly, we set ourselves up for impossible standards with this kind of strategy. When you've spent months planning something, it better be fucking perfect when you launch it. Well, guess what, friend? Nothing ever is. The pressure becomes so intense that nothing ever feels good enough to actually put it out there. So it's just a big old trap and third, and this is a big one, we're unconsciously protecting ourself from the possibility of failure or so we think. As long as it's still in planning mode, it can't fail, right? But it's Schrodinger's business idea. Simultaneously brilliant and terrible. Until you actually open the box and find out which one it is.

Now let's talk about the problem of the impulsive launch. Jumping in unprepared has its own set of problems. When we cannonball start, we're usually running on excitement and adrenaline and chasing dopamine. It may feel like clarity, friend, but it's not the same. ADHD brains are really good at hyper focusing on research and thinking we've planned when actually we've just gone down a series of rabbit holes. Spending six hours researching your target market and thinking you've done market research. Have you actually talked to a single potential customer? If not, then not. Or you get so excited about the solution you're creating that you forget to think about the most basic stuff, like how people will actually find out about it, or whether you even have the skills to deliver what you're promising.

Or how about what you're going to do when the initial excitement wears off, because you know it will. The worst part, impulsive starts often lead to what I call stopping problems, something we're going to cover in the next episode. When you realize halfway through that you didn't think it through, you lose confidence. It's inevitable. Then you fall into a research spiral, trying to figure out what you should have planned and in the first place. And that isn't going to solve the problem either. And can we talk about the elephant in the room? The sustainability fear. What is underneath both of these approaches is actually the very same fear. What if I can't keep this up?

Now this fear is completely rational, by the way. ADHD brains struggle with consistency and we know this about ourselves. We have started things before and not finished them, am I right? We've been excited about projects that turned into abandoned browser bookmarks, and most of us feel really shitty about this. So we either try to plan our way into guaranteed sustainability, which, by the way, is impossible, or we try to outrun the fear by moving so freaking fast, we just don't take the time to think about it, which usually just delays the inevitable reckoning. You know, the real problem is not that we can't sustain things. I mean, I have ADHD, and I've never missed a single week of releasing an episode of this podcast in over five years.

The real problem with sustainability is that we're often trying to sustain the wrong things. We're trying to sustain our perfect motivation, the perfect conditions, and our perfect, perfect plans. None of those are actually sustainable. What we need instead is to sustain imperfect action and that requires a completely different approach, one I call the messy start method. So here's where we get to the point in the episode where we fix this this with the messy start method. And it's built around one core principle. The goal isn't perfect preparation or pure impulse. It's informed action with built in course correction. The formula is 2% + 20%.

Let me break it down, instead of planning 100% all the way through or jumping in with 0% preparation, we aim for 2% effort and 20% planning. That's the 2% plus 20% formula. Let me explain what it actually looks like. 2% effort means starting with the smallest possible version of your brilliant idea. Not the beta version, not the minimum viable product version. The absolutely teeniest, tiniest thing that you could do that moves you in the right direction. And if you say, well, that's so small, why even do it? It doesn't matter.

Let me tell you something. One of the biggest things I've learned over time is that everything counts. So if you want to try this, let me give you some specific examples. Let's say you want to start a podcast. Two percent effort is recording a two-minute voice memo where you talk about your idea. It does not mean buying professional equipment and booking a recording studio. If you want to launch a course. 2% effort is teaching the concept to one person in a single 15 minute conversation, not creating a full curriculum with workbooks and bonus materials.

Let's say you want to start a newsletter, 2% effort is writing one email to your existing audience about something you learned this week, not setting up an email sequence and designing the templates to go with it. The point is to get into motion with something so small that it would feel completely silly and stupid not to do it. Now 20% planning means doing just enough research to avoid the most obvious pitfalls without falling into planning purgatory. It's not comprehensive market research. It's a quick gut check to make sure you're not missing something huge. I'm going to add something else to your planning toolkit. The five-minute blind spot check.

Five questions that take five minutes to answer. And don't tell me you don't have five minutes because if we have time to half-ass it or ruin it from the beginning, we have time to pump the brakes and do these five questions in five minutes. And to keep yourself honest and set good boundaries, I recommend using a timer. Are you ready? Here is the five minute blind spot check. First question what is the actual outcome I want? And don't tell yourself success, you need to be specific. I want to get five people signed up for my program or I want to test if people will pay for this new service I'm thinking of or even I want to see if I can consistently create content. Vague goals create vague action.

Now for the next question, what's the biggest thing that could go wrong and can I live with it? This is not the same thing as catastrophizing, we all have done enough of that. This is a realistic risk assessment. If you launch a program and only two people sign up, is that going to destroy your business or just bruise you around the ego? If you start a podcast and only your mom listens, is that failure or market research? Question number three, what do I need that I don't currently have? Skills, tools, people, time, money? Be honest about your gaps. You do not need to fill all of them before you start, but you really do need to know what they are. Some gaps you can work around, some you need to address and some of them just might be project killers.

Your fourth question, who is my first customer, user or audience for this? If you can't name a real person who would want what you're creating, you are not ready to start. This does not have to be a formal customer avatar. How many of those have you done already? It can be my friend Jenny who's always asking me about this, or people like me six months ago, but it does have to be specific. And number five, how will I know if it's working? You need to know what you're going to measure ahead of time to know if it's working. How many people need to respond to you for you to feel good about continuing? What does working look like after a week, a month, three months. Without this, trust me, you're going to keep on going forever or quit too early. That's it. Five questions, five minutes. Done.

If you can't answer all five quickly, you are either overthinking or you're not ready to start yet. All right, now we're going to talk about some starting systems that do not depend on feeling it otherwise being in the right mood. Now, here's the part that separates this from generic productivity advice, because haven't we all had enough of that? We need systems that work when we don't feel like it, because here's the truth about ADHD brains. We are simply not going to feel motivated most of the time. Motivation is unreliable and inspiration is fickle as fuck. If you are waiting until you're in the mood to get started, you're going to be waiting a good long time. Instead, we need to build starting systems that work for us regardless of your emotional weather report.

First, choose your starting signal, this is an external cue that triggers action mode regardless of how you feel. Your starting signal could be a specific time of day, a particular location, a playlist, or a physical ritual. The key is that it's consistent and completely divorced from your emotional state. Here's an example, I have a client who only starts new projects while sitting in her car in a specific parking lot of a specific coffee shop. A little weird. I don't know, maybe, effective? Abso-freaking-lutely. She does not sit around waiting for inspiration. She's driving to that specific coffee shop.

Okay, now second, I want you to set what I call a pathetically small first step. So small that you would feel ridiculous not doing it. If your project is creating a course, for example, your first step is not outline the entire freaking curriculum. Your pathetically small first step is to write one sentence about the problem this course solves. If you're starting a consulting practice, it's not create a business plan, it's text one person about what you're thinking of doing. The goal here is to remove all friction from the starting process. You are not committing to finishing, you're committing to beginning. Third, use the two-minute rule. Commit to working on your project for exactly two minutes, then give yourself permission to stop.

Now I'm going to tell you what usually happens is you keep going. Because actually starting was the hard part. And by two minutes, you're beyond the starting point. But even if you stop after two minutes, you've maintained momentum for two minutes and proven to yourself that you can show up over time, you can lengthen it. And fourth, have your next smallest step ready. Don't wait until you're in the middle of your two-minute session to figure out what comes next, that's too late. Know what your second step is before you take the first one. This prevents decision fatigue from killing your momentum. And if you're telling yourself a two-minute momentum doesn't count, that's only because you haven't tried it yet. You got to trust me on this.

Now here's where we start talking about building course correction into your starting point. And here's where the messy start method really does differ from just saying, just taking perfect action. We're not just starting messy, we're starting with built in ways to get back on track when things go sideways, because you and I both know they will. So before you start anything, decide when you're going to check in with yourself. Not if. When. Is it after a week? Two weeks? A month? Maybe it's three days, but mark it on your calendar now.

At that check in, you're going to ask yourself three questions. Is this working the way I thought it would? Not is this perfect but is it moving me toward my goal? Yes or no? 2. What have I learned that I didn't know when I started? This isn't about analyzing what went wrong, it's about highlighting new information that might just change your approach. And three what needs to adjust based on what you've learned? What would you do differently if you were starting today? And believe it or not, even if you're checking in with yourself after just a week, two weeks, a month, asking yourself these three questions, is this working the way I thought it would? What have I learned that I didn't know when I started? And what do I need to adjust is a game changer, and it's beyond easy to do it now.

This is not about judging your progress, by the way. It's about staying responsive to reality instead of stuck on your original plan. We also need to talk about what happens when you're stuck and build in some emergency protocols. You know you need to start something right? You've done your five minute planning, but you're still frozen. It happens. Here are some emergency protocols. When you're overthinking everything, set a 25-minute timer and start with whatever you have right now. Do not gather more information, do not do more research, and please, for the love of all things holy, do not wait for a better moment to start. Use what you know today and start. Give yourself permission to suck for the first draft, the first attempt the first version. Because remember this, motion is what creates clarity, not the other way around.

Now, when you want to jump in completely unprepared, this is your emergency protocol. Stop, take a breath. Do the five minute blind spot check now before you do anything else. And ask one more person what they think you might be missing. This is not about permission, but perspective. If your idea involves spending money or signing contracts, I want you to sleep on it. The excitement will still be there tomorrow, and if it isn't, that's a problem. But you know what else will be there? Better judgment. Now let's talk about the elephant in the room, the sustainability fear.

Let's be frank, you're probably afraid you're not going to be able to keep it up. And honestly, even though I told you earlier about my podcast being going for five years straight without a hitch, I also did not launch this podcast for two full years because of my unacknowledged fear that I wasn't going to be able to keep it up. The fear is real, and it's often based on real experience because we tend to be better starters than we are sustainers and finishers. But here's what you need to understand. You're not trying to sustain your motivation.

You're not trying to sustain perfect consistency. And you're also not trying to sustain the feeling that you have right now. What you're trying to sustain is the practice of showing up imperfectly and course correcting as you go along. That is not only completely different, I know for a fact that's something you can do. Now some days you're going to show up at 2% energy. Some days you're going to show up at 80% energy but both count. In fact, I want you to make this your new mantra, everything counts. The goal is not to maintain your peak performance. It is to make contact with your project even when you don't feel like it. It's kind of like a long-term relationship, whether that's a romantic partnership or even owning a pet.

You show up every day, day after day, whether your heart is in it or not. And over time, it works out. Because here's the secret the more you practice starting small and adjusting as you go, the more sustainable, quite literally everything becomes. Because you're not depending on the perfect conditions, or the perfect mindset, or the perfect motivation. You're depending on real systems that work even when you're tired, distracted or overwhelmed. Now let's talk about some real world applications and concrete examples of how these things look across different business scenarios. Here's one I hear about a lot so many people want to launch an online course.

Well, instead of spending three months creating a full course before you even know if anyone wants it, try this. Identify one core problem that you can solve for a group of people. Teach that solution to three people individually via Zoom, phone call, whatever. Charge them a small amount for your time. Notice what questions they ask, what parts of the course are confusing, and what they tell you they find most valuable. Then create a simple group version for the next three people. You're not building a course, you're testing demand and refining your approach in real time. And it's a lot less scary to do this way. Or let's say you want to start a marketing campaign.

Instead of creating a complete content calendar and designing all your graphics before you post a single thing, try this. Choose one platform, it could be TikTok, Facebook, LinkedIn, you name it. One platform. Write one post about one thing that you learned recently. Include one way that people can work with you and then post it, see what happens. Then write another one. Maybe tomorrow, maybe the next day. You're not launching a campaign, you're starting a conversation. Or how about beginning a new service offering? Instead of developing a comprehensive service package with pricing tiers and detailed contracts, you could try this, offer to solve one specific problem for one specific person. Do the work. Document what you did and how long it took. Use that data to inform your service offering.

You're not building a business line. You're testing your assumptions against reality. Or maybe you want to start a podcast. Instead of buying the equipment, designing the artwork, and planning 20 episodes before you record a single thing, you could try this. Record yourself talking about your area of expertise for 10 minutes using your phone. You heard me. And then listen to it. Do it again tomorrow or the next day on a different topic. After you've done this five times, you will know more about podcasting than you would from a month of research. I promise you, you will.

Now, here's the pattern. It's always the same, have you noticed? Start with the smallest possible test, learn from real feedback, and adjust based on what you discover. We also need to troubleshoot some common points of resistance. I imagine you might be thinking, but what if it's not good enough? Well, guess what? It won't be. That's the point.

Version 1 is supposed to suck. The job isn't to be perfect. The job is to teach yourself what version two should look like. Or how about this one? Oh, but what if people judge me, they might. Some of them will for sure, most won't care. But the ones who matter are going to appreciate your honesty about being a work in progress. Plus, you have already judged yourself more harshly than anyone else ever will, and you know I'm right about that.

Or you might be thinking, yeah, but what if I just waste time on the wrong thing? You'll waste more time planning the right thing than you will ever waste testing the wrong one. And there's no such thing as wasted time if you're learning from it. Or coming back to the elephant in the room, but what if I really can't sustain it? Well, you can't sustain perfection, and neither can I. But you can sustain small, consistent actions with built in course correction. You can focus on the sustainability of your effort, not the sustainability of your outcomes.

So here's what we covered today. Starting is not about perfect preparation or pure impulse. It's about informed action with course correction built in. We talked about the 2% plus 20% formula. Tiny action, minimal planning, and don't forget to do the five-minute blind spot check. Create mood independent starting systems, build in regular check ins. And remember, you're not trying to sustain your motivation. Good luck with that. You're trying to sustain a practice of showing up and adjusting as you go. Now, here's the thing about starting strong. It also sets you up for the next challenge, which is knowing when you've gone far enough.

Because ADHD entrepreneurs don't just struggle with starting, we also struggle with stopping. We get caught in perfectionistic loops. We avoid launching because of the fear of rejection sensitivity. Or we realize halfway through we are completely lost and dig deeper instead of changing direction. Well, I've got good news for you. That's what we're covering in the next episode, which I'm calling Stopping Smart. How to know when you're done, how to launch imperfectly, and what to do when you realize you're in over your head. But before you go, I need your help.

Now, I'm creating a comprehensive toolkit to go along with this three-part series and I need to know that it actually solves your biggest starting challenges. So will you let me help you by helping me? I need you to take 30 seconds and tell me what is the number one thing that stops you from getting started on important projects? Is it perfectionist planning? It is the fear of not being able to sustain it. Is it jumping in unprepared? Or maybe it's something else entirely that I've completely missed. There's a link in the show notes to a quick survey. Your input is literally shaping what I'm building for you. Because the best advice isn't generic. It's based on real challenges from real people building real businesses like me and like you. Thank you for joining me for this episode of ADHD-ish. And if these strategies help, do me a solid and share it with one other entrepreneur who's stuck in starting mode. And I'll see you again next week for Stopping Smart.