From Setback to Comeback: Strategies for Dealing with Disappointment

A familiar scene, it's late at night, and you're staring at your screen watching yet another self imposed deadline rapidly approaching. Despite your best intentions, blocking out your entire day, setting reminders, promising yourself this time will be different, you got pulled into a vortex of I just need two tasks. And before you knew it, hours evaporated into things that felt urgent but weren't. That nod in your stomach, that wave of disappointment crashing over you. If you are nodding right now, you're not alone. And here's the thing, there are reasons why we experience disappointment so intensely and so often, and there's something we can do about it.

So let's start this off by understanding why running your own business with ADHD creates a perfect storm for disappointment. There are three key factors at play here, and understanding them is crucial for developing effective coping strategies. First, there's what I like to call the emotional amplifier effect. When you're self employed, there is no buffer between you and the consequences of missed deadlines or forgotten follow ups. Every setback plays at maximum volume in your head because you're both the CEO and the entire freaking workforce. This isn't just about feeling bad. It's how our ADHD brains process emotions more intensely than neurotypical brains. Let me break this down a bit further. In a neurotypical brain, disappointment might register as, I don't know, a six out of 10.

But for us, that same disappointment hits like a 12 or a 15 out of 10. It's not just disappointment, it's disappointment with a side of shame, a sprinkle of imposter syndrome, and a heavy dose of why can't I just get my shit together? The second factor is what I call the time blindness tax. Now traditional business advice tells us work on your business, not in it. But here's what really happens. You sit down to work on your business strategy, alright, but the next thing you know, it's three hours later, and you've gone down the research rabbit hole for the perfect project management system, created five different color-coded spreadsheets, and completely forgotten about a client meeting you were supposed to prepare for.

This is not simple, poor time management. It is how our ADHD brains perceive and process time differently. You've heard it said we experience time in a nonlinear way. I kind of think of it like living in the matrix, where the word timeline has no reference points. It's why we can hyperfocus for hours on creating the perfect email template, but struggle to estimate how long it will take to complete a simple client project. The third factor is what I call the intensity of interest paradox. This is where the ADHD gift of hyperfocus becomes our kryptonite. When everything feels equally urgent or interesting or not urgent and not interesting, prioritization becomes nearly impossible. One minute you're responding to an important client email, and the next you're redesigning your entire website because Squarespace just released a cool new feature.

Now let's break down the most common disappointment triggers in self employment because you have to be able to see yourself in these problems to find the motivation to do anything about them. I've identified three major categories that tend to trip us up most often. First, there is the project management paradox, and this shows up in several common ways. Taking on too many clients because the opportunity seemed exciting at the time, or you haven't learned how to say no. Underestimating how long tasks actually take because we're time blind or time optimistic, as I prefer to say. We get lost in perfecting details instead of focusing on completing deliverables. We start strong with new systems, but then struggle to maintain them. And we forget to document our processes because they seem so obvious in the moment, we just can't remember them later.

The second category is business development spirals. Now this includes things like, I don't know, forgetting to follow-up with warm leads because circling back or checking in feels either boring or annoying, creating elaborate marketing plans that we fall madly in love with, but then they never see the light of day, getting excited about going to networking events, but then failing to nurture any of the connections we make there. Starting multiple streams for passive income, but not finishing any of them. Or neglecting regular client communications because we're too busy hyper focusing on something else.

And finally, there is the financial focus set of challenges, which includes delaying sending out invoices even though we need the income, forgetting to track our actual expenses in real time, impulsively purchasing business tools that never actually get used, not charging for all of the hours you actually spent because you think someone else would have done it faster, and, and this is a painfully timely one, missing tax deadlines despite promises and effort to stay on top of your bookkeeping. Can we all breathe a collective sigh? Now I am guessing you might be starting to feel a bit called out here.

You might even be triggered into a shame or rejection sensitivity spiral, but pump the brakes. I wanna remind you that I experience all of these things, and so do many of my private coaching clients. These struggles are real. They are very common in those with ADHD brains. And they may not stop us from being successful, but they do slow us down and cause us a lot of stress and strain. That's why I think we should take them seriously even if we're used to functioning this way. Make no mistake, you could get further faster and feel a lot more fulfilled if you didn't have all these baked into your business sources of disappointment. Now here's where things get good. Now that you see yourself in the challenges I've described and been reminded that they're not character flaws, but facets of your ADHD brain, we can get to the strategies and solutions that actually make things easier. Are you ready? Okay.

First is the one I call the business systems scaffold. Kind of think of it like your business's exoskeleton, but not like the one that Matt Damon wore in Elysium. Your business system scaffold would be more like the one the US military created called the Hulc. Hulc, H U L C, stands for the Human Universal Load Carrier, which enables soldiers in the field to have more speed and more endurance while reducing injury. I so want that for you in your business. Now, what does it look like in practice? Templates, templates, templates for everything, kind of like, Oprah. And you get a car, and you get a car, and you get a car. Okay, you get a template for everything.

Now a lot of people resist templates because they think they're boring. Yeah, they're boring because they save time. And it's time we want to save for things like client communications at every stage from screening, onboarding, offboarding, serving. You can create templates for this, and then go in and add just enough customization so they don't look like templates. You also can use templates for project briefs and project proposals, social media posts and content calendars, email responses to common situations. I always say if it's happened once, it'll happen again.

Everything is not an exception. There are plenty of rules and things that happen again and again and again. Those are where we can absolutely save time and reduce the risk of disappointment by using templates. You can also use templates for meeting agendas, meeting follow ups, and project timelines with built in buffer time. And I will come back to that again later. In addition to templates, your business system scaffolding can also include two more things. Automation. It's not always possible, but it is possible in plenty of places that you may not be using it.

For example, invoice reminders and payment processing, email follow-up sequences. It's a very obvious place where we can use automation, social media scheduling, calendar booking and calendar reminders, task management notifications, and regular client check ins. We can absolutely systematize and automate all of that. So it's like having an assistant working with you in your business. You set it up once, and then it just continues to go. And last category of your business scaffolding is your visual management tools. Now some of the more visual type project managers and task managers and, client records management systems, ones like Trello, Monday, G-Queues, Sunsama, I will link those in the show notes.

They're visual, and I have found a number of my private coaching clients really like them because they're more ADHD friendly. Visual management tools include things like project boards with status indicators that are very clear, so you know exactly where you are in the project. And if you're working with others, you know where they are in the project as well. Time tracking with visual cues make it harder to forget or get lost in the project. Deadline calendars with color coding, progress bars for ongoing projects, and visual checklists for routine tasks. All of the systems, all the software programs I've just mentioned have these, and they really, really help our visually oriented brains.

Next, I wanna share with you the energy management portfolio. Now I also talked about energy management in episode 241. That was the one about stretching your time horizon. But if you are a new listener to ADHD-ish, welcome. Or you missed that one, I am linking to that in the show notes for reference as well. So creating your energy management portfolio comes by identifying and working with your natural rhythms instead of trying to force yourself into some productivity guru's proven system, which tends to last about two weeks tops. How you implement your own individually crafted and customized to you energy management portfolio is by understanding your peak hours.

And I would break it down further, peak hours for creativity, peak hours for focus, because those are two different modes, if you will. Track your natural energy patterns, identify your most productive times of the day and week, plan your high focus work for those periods, schedule your admin tasks for the lower energy times. I would also say schedule the tasks that are intrinsically rewarding to you, like maybe faffing around in Canva and creating some social media graphics. You do not need to do those things during your peak energy hours.

That is a huge waste of your brainpower. Schedule them for low energy times because they're pleasurable, and they do not require a lot of brainpower. And build in recovery periods after periods of intense focus. Far too many of us try to go from one deep work block of time right into another. No wonder we get so many of us get burned out. I also recommend and do myself creating task batches. Now it depends on the nature of your work, not everyone can do this, and you may not be able to do it for all the different types of tasks you have.

But most of us have at least one type of task that we can group similar activities together. We can also schedule theme days or time blocks. I use both, we wanna minimize context switching so that you're not going from a client meeting to crafting an email sequence to balancing your books. That's too much drain and strain on our brains, so minimize that. Also, plan for transition times. I'm a huge proponent of transition rituals. So we are literally signaling to our brain, okay, we're going into a different mode now and set realistic limits on daily meetings.

My calendar management system, TidyCal, I have set, a maximum number of each type of meeting that I will allow myself to book or I will allow others to book on my calendar because I know. I know if I overdo it, I'm not gonna have a good day the next day, and I'm probably not gonna be bringing my A game to whatever meeting that is, so nobody wins. Another thing I am a huge fan of is the minimum viable day plan. This is the plan for when you really are not feeling great and you would probably write the day off otherwise, but then feel like ass about it later. So a minimum viable day plan is identify the essential tasks, create simple success metrics. In other words, make it easy for you to feel successful.

Build in flexibility for fluctuations in your focus. You have a plan for days that are good and days that are not so good and celebrate small wins consistently. Too many of us, it's all or nothing. So we are either pedal to the metal or we are a complete jerk lying on the couch doing nothing. We all need minimum viable day plans and probably need them more often than we realize. Okay, you ready for one more? I think of this as the biggest flex. Because once we've started implementing some of these strategies to make it easier to recover from disappointments, we can actually build a disappointment prevention protocol.

Now, this doesn't mean we're never gonna make mistakes. That is wildly unrealistic for any entrepreneur, ADHD or not. It's about building resilience and recovery strategies, so that disappointments are shorter, and our bounce back ability keeps getting stronger. There are three of these. Three categories: time buffering strategies, boundary setting techniques, and recovery protocols. Here's how they look under the category of time buffering, and you're gonna hate me for this one, but you will thank me later, add 50% more time to all estimates.

If you think it's gonna take an hour, block an hour and a half. You will resist and you will thank me later. Other time buffering strategies build and review periods before deadlines. This one has saved my bacon more than once, create space for the unexpected, you know you need it. Plan for fluctuations in your energy, because you know they happen, and set internal deadlines before the ones you communicate to others. This has been a game changer for me and a number of my clients that I've encouraged to use it.

You may have an agreed upon deadline with a client, but you set an internal deadline prior to that. That also helps you create that space for reviewing beforehand. In the category of boundary setting techniques, and I think you can also think of these as burnout proofing techniques, clear communication about your working hours and your availability. Cannot stress this enough. And this is oftentimes one of the most challenging things that I work on with my clients, is how many of us think we need to be always available. And yet we're complaining about burning out at the same time. We not only have to set those limits and those boundaries, we have to clearly communicate them and be willing to defend them as needed. Structured response time expectations.

If we communicate when people can expect to hear from us after they send us an email, they're gonna be most of them will be much less needy and demanding. And those that are still needing and demanding, we go back to point number one, clear communication about hours and availability. We also need well defined parameters for the scope of our projects. So many consultants I've worked with complained about how they agreed to one scope, and they found scope creep happening almost from the first week. That's a hard stop and go back and amend the protocol. Because otherwise, we're gonna be taken advantage of and end up working a lot harder for a lot less than we should be getting. Regular client education about these processes, some clients get it right away, others you're gonna need to remind, remind, remind. And more consistent policies about rush work.

I see a lot of people with ADHD, especially my creatives, they almost get excited about a rush job. And then they're later furious because they ended up staying up all night. We should always be compensated for rush work, and we should really think about whether we even wanna do it and under what conditions before someone requests it. In my experience, usually when somebody says they want something on the rush and we don't already have a policy and a protocol in place, what we just blurred out in response to their request is not going to serve us. Trust me on that one.

Lastly, recovery protocols. Every business has things that go wrong. Sometimes things go really wrong and seemingly from out of nowhere. But even though we may not be able to anticipate what will go wrong, we should have a protocol for what action steps we will take when it happens, not if. Also, communication templates for delays. Man, there is nothing like having a communication template that says, dear client, and instead of starting, we're ever so sorry, thank you for your patience, and so on and so forth. Delays happen, sometimes we missed a deadline. Sometimes it was through no fault of our own. But generally speaking, if we don't have a communication template for when delays do happen, our default is over explaining and over apologizing and still feeling shitty after the fact.

Create the template, you'll thank me later. Support network activation plans. This is something I really resisted for a long time along with the last one, self compassion practices. I'm naturally hard on myself by nature, and you may be as well. But refusing to recognize that I actually need to build self compassion practices into my solo business, as well as activation plans for recognizing when I need to get support, those have come late in my entrepreneurial journey, but are absolute game changers.

Every disappointment in your business journey isn't a setback. It's data. Data that helps you identify where you need to build systems and supports that work with your unique brain wiring. The goal of everything I've shared in this episode is not to convince you that you can eliminate disappointment entirely. That's impossible. The goal is to build resilience so that you can bounce back faster and actually learn from all experience. Your ADHD might make running a business more challenging in some ways, but it also makes you uniquely suited to adapt, innovate, and persevere. And that, my friend, is what successful entrepreneurship is truly all about.

Hey boss! If you're ready to put some of these strategies into use in your business, or at least you don't want to forget about them when you're ready later, I want you to grab my free worksheet that combines disappointment prevention, energy management, and systems scaffolding strategies all in one place by clicking the link in the show notes.