64. How to Do Hard Things: 7 Strategies to Move You Forward
Episode 64
We all encounter moments where we have to face something difficult — whether it’s a challenging project, an overwhelming assignment, or something as mundane (yet daunting) as organizing our finances.
In this episode of the Learn and Work Smarter podcast, I’m breaking down seven practical strategies to help you tackle hard things head-on. We’re not just talking about forcing yourself through discomfort — we’re talking about real, actionable methods that make tough tasks feel more manageable.
By the end of this episode, you’ll know exactly how to break down intimidating tasks, push past resistance, and create momentum so that hard things become just things you know how to handle.
🎙️Other Episodes + Resources Mentioned
Episode 36: How to Stop Procrastinating
Episode 38: How to Be a Resourceful Person Who Can Figure Things Out
Episode 52: Episode 52: SOPs and Workflows
✏️Enroll in SchoolHabits University (Curious? Check it out!)
-
The following transcript was autogenerated and may contain some interesting and silly errors. But in the name of efficiency and productivity, I am choosing not to spend my time fixing them 😉
64 How to Do Hard Things: 7 Strategies===
[00:00:00] You know those moments when you sit down to start something that you know is going to be challenging. Maybe it is a project for work, a paper for school, or something personal, like organizing your finances for tax season, which is what I have to do, and you just freeze because we know it's gonna be hard suddenly anything else seems more appealing. You check your phone, you grab a snack, you rearrange your desk. Heck, even a sock drawer organization moment even sounds good. Anything to delay actually starting the one thing that we're supposed to be doing. You are not alone if this is a familiar scenario. It even happens to me.
All right? Our lizard brains are wired to avoid discomfort, and that is a lovely and adorable little survival mechanism that we came with. But the problem is that this means that we can perceive difficult tasks as painful even when they're not. Our physiological response to writing a difficult [00:01:00] report looks the same on the inside as our physiological response to anticipating a true painful stimulus like entering battle.
But here's the thing: being able to do hard things is one of the most important life skills we can develop. We only ever grow when we do hard things. These are the facts. And it's my guess that you already know this and you're like, okay, I, I get it. But how do I do hard things? That's the title of this episode, right?
How do I not let all of the hard things that I need to do take me out at the knees? How do I get started on these hard things when I know it's going to hurt?
These are great questions that we are of course going to cover today. We're gonna break down exactly how to do hard things with seven practical strategies that you can use, either independently from one another, or you can combine them for a nuclear option. Whether you're a student struggling with an overwhelming assignment, maybe a professional procrastinating on tackling a big work project, these [00:02:00] strategies are going to help you face the hard thing head on.
Now, speaking of procrastination, if your ears just perked up when I said that I have an entire episode about how to stop procrastinating. In that episode, I explain that one of the biggest reasons we procrastinate, there's several primary ones, but one of them is that something feels difficult, and that figuring out why something feels hard is the key to overcoming our aversion to that task.
If you haven't listened to that episode yet, it is episode 36 and everything that I link or anything that I mentioned today on the show is gonna be linked at learnandworksmarter.com/podcast/64. Alright- let's get started.
[00:03:00]
There is no reason to wait. So tip number one for how to do hard things is to acknowledge the difficulty.
Recognizing that something is hard can actually make it easier. This is a classic case of calling a duck a duck. If you didn't know me, that's one of my favorite expressions, and I probably use it too much, but I think that it is super relevant here.
It's when we go into a hard task with some expectation that we should be able to handle it. If you're listening to this on a podcast app and you're not watching on YouTube, I'm like, air quoting the should, right? That it should be easy. That other people can do it. So that means it should be simple for us.
Okay? That type of mentality gets us in trouble.
If you know you're about to engage in something hard, name it as something hard.
Engaging in a hard task, like having a difficult conversation with somebody that you've been meaning to have, or going back to school after taking 15 [00:04:00] years off, or maybe going for your third round of interviews at your dream job. These are all hard things, and telling ourselves otherwise can deliver a shock to the system when we actually sit down to do the thing. The mentality of "this is hard and" capital and "I've got it" can be really helpful here. "This interview is going to be one of the hardest things I've ever done and" capital and "I have good social skills and can communicate well, so I'll be fine." Okay. These are the healthy internal monologues that allow us to call a duck a duck and move forward anyway.
I want you to think of it this way. Imagine you signed up for a marathon because why not? You've never run one before, but you've run a 5K, so you think to yourself, Hey, like this, this marathon is not gonna be a problem. If you don't admit that the marathon is a hard task, then you're not gonna use the proper strategies to prepare yourself for it, and you probably won't train sufficiently, or maybe even not at all.
You may [00:05:00] not have an appropriate meal the morning of the race to sustain your effort for 26.2 miles. If you don't admit to yourself how hard a marathon really is, you may show up to the race with a pair of, you know, dingy sneakers with no tread. Okay. I know this is kind of an odd example, but it's meant to illustrate the point that facing the reality that we're about to do a hard thing allows us to prepare properly and to think about what strategies we might need to bring to the table.
All right, but again, if you show up to race day in denial that the race is gonna be hard, you are not going to show up with your strategies and you're not gonna make it to the finish line.
If you want a more practical example in the context of work, let's go back to that hypothetical round of interviews.
Okay. Let's say that you apply to your dream job and you've made it to the third round of interviews, and now you're interviewing with the, you know, the CMO, the chief Marketing Officer. Okay. This is going great. Well, that's probably gonna be a more challenging interview than the initial phone call [00:06:00] that you had with the HR department, right?
This is something that you need to prepare adequately for. You might be nervous, you might have fear, you might have self-doubt, and, and all of the feelings that come with doing hard things, but denying the difficulty of that interview sets you up for failure.
But the moment that you can say, okay, my interview is next Tuesday and it's going to be hard and I need to be ready, then you are entering the arena with the correct mindset that lets you think about how to change your approach, how to uplevel your interview game to think more broadly about how you can prepare for the interview, how to get creative about who you can ask to do a mock interview with.
Right. These are all great strategies to prepare for a hard interview, but none of which you would arrive, arrived at if you had denied the difficulty of the task in the first place. Does that make sense? So call a duck a duck.
Alright, tip number two, identify [00:07:00] exactly what's hard. When you're faced with a hard task, your brain is gonna try to convince you that the entire task is difficult.
But if we pause and we think, and we break it down, we usually realize that only certain parts of the task are really that hard.
For example, let's say that you are a college student and you have to write a semester long research paper. The entire thing feels impossible. Okay? But what if you stop and you ask yourself, all right, what part of this feels the hardest?
Maybe it's coming up with a thesis. Maybe it's finding sources. Maybe it's actually that you don't have total clarity about what the assignment is actually supposed to be. Okay.
Or if you're at work and you're struggling with a big presentation, what specifically feels overwhelming? The design? The research, the data that you have to collect and you don't even know where it is or how to get it? Speaking in front of people?
By identifying the exact sticking point or the exact part that feels hard to you, you can separate [00:08:00] what's actually hard from what's just uncomfortable. And once you do that, you can start tackling the problem piece by piece instead of letting it paralyze you.
The problem is that hard things can mess with our emotions, right?
So if we're facing a, everything messes with our emotions. So if you're facing a challenging task that maybe you have been avoiding for a while, the semester long research paper, the presentation at work, you know, whatever, and it's attached to a high stakes, you know, outcome, like your job performance or your grades in a class, you're going to have elevated feelings about it.
And when we have heightened emotions, we are more likely to catastrophize. So catastrophizing is a kind of cognitive distortion when we exaggerate something as worse than it really is. We say things like, this entire report is hard. I will never get this done. This whole thing is impossible.
[00:09:00] Catastrophizing is normal, but it's completely unhelpful when we're actually trying to do something.
So quick bonus tip here is that if you find yourself catastrophizing about something hard, see if you can achieve some emotional regulation before trying to figure out what exactly is hard. Remember, that's the tip here, right?
Trying to identify the exact thing that's hard, and we cannot do that when we are catastrophizing.
All right. Tip number three, break the task down. This tip is huge. It's also given a lot as advice for this kind of thing, and I don't want you to hear this advice of break the task down and be like, oh, well that doesn't work.
Like I've tried that. I challenge you, and I'm gonna walk through this tip and explain how it works in a second, but have you really truly tried to break a large task down into discrete units and attack one at a time? Have you actually done that or have you just sort of just lowkey thought about it and then determined that, you know, well, [00:10:00] that's too basic a strategy to work for me?
It works. Okay. Now, when something feels overwhelming, it's usually because we're looking at the entire task as one massive thing instead of seeing it as a whole bunch of smaller steps.
Like, let's take an example. I mean, examples make everything clear, right? So let's take an example from work. Everything's easier and clearer when we talk about examples, right? So take an example from work. Say that you've been asked to create a new, um, file organization system in your office. If we think about it as just one giant project, I have to completely overhaul this entire system.
Then that task is going to feel too hard, it's gonna feel too painful. We're gonna become paralyzed and probably catastrophize, right? And then, and then we don't get the thing done.
But if we break it down, it becomes much more doable. Something like step one, take inventory of all the current files. Step two, research different organization methods.
Step three, I'm kind of winging this on the spot, so there's probably a better way to do this, but test a [00:11:00] small, you know, um, subgroup of files before applying the system to everything, right? Now instead of an impossible task, we actually have clear specific actions, and this is something that you would write down.
It's not something you just sort of loosely design in your head and then see if you can remember what your plan is later. No, you actually write it down. For students. This applies to studying too. Instead of thinking I have to study for my final exam, like there is a lot to that, right? There's a lot to that, that it feels massive.
It feels vague. And to your brain, it's gonna feel painful. And of course we avoid painful things. So instead we break it into step first. Um, figure out what's on the test, right? Then second, organize and consolidate your notes. And then you're probably gonna wanna make a study plan and make some study materials.
And then you actually have to study those study materials.
Tackle one chapter at a time, one unit at a time. Each step that you complete moves us forward without feeling like we're [00:12:00] drowning. But here's where it gets a little tricky. Okay? When we're overwhelmed, our brains resist breaking things down.
We tend to think, oh my gosh, like even figuring out the steps here to break it down is too much work. And that's because overwhelm activates our stress response. And when our brains perceive a task as too big, it triggers avoidance. It is a protective mechanism. Not laziness. It's it's biology that's designed to protect us.
Actually not doing that. Right. A quick trick, I guess a hack strategy approach, whatever, to get past this. You just say to yourself, okay, what is the very first thing that I need to do if I had to start at gunpoint? I know that doesn't like decrease the stress of it, but like if you world was gonna end, if you didn't start now somewhere, what would your automatic response be?
Okay. If you're too overwhelmed by thinking, well, I'm gonna break down this whole thing and [00:13:00] map out my steps on a whiteboard, for some people that might be really helpful. Okay. But for some people, you just have to think to yourself, if I had to start right now without overthinking this, where would I start?
Start there. That tiny shift forces your brain into sort of a problem solving mode instead of avoidance mode. And then once we take the first step, momentum follows. We're gonna talk a little bit more about momentum and some of the other, um, uh, tips here. Okay.
Tip four, consultant resources. So often we struggle with hard things 'cause we assume that we have to figure them out alone.
Okay. But the truth is there are always resources available. We just have to find them and use them.
In fact, so many people reach their goals, not because they're geniuses, but because they're skilled at knowing what their resources are. Uh, they know where to find them, and then they know how to use them.
If you are stuck at something at work, ask yourself, what tools are available to me? Maybe a coworker has experience with this exact [00:14:00] problem. Maybe there's an online tutorial that walks you through it step by step.
I once had a friend call me in a complete panic. Well, it started as a text and then went to a phone call 'cause she had to create a pivot table in Excel for work. She reached out to me. She was all worked up asking me if I knew how to do it. I didn't. It had been so long since I had used Excel, so like I couldn't remember it, but I literally just Googled how to make it a pivot table in my phone.
I found a two minute video and sent it to her. That's all she needed. It was like step by step to make a pivot table do this. She could have done that herself. Okay. And saved so much emotional drama.
This goes back to tip one and even tip two a little bit, which is sometimes the hardest part isn't the task itself. It's, it's how we react to it. It's how we define it, right?
For students, the same principle applies. If you don't understand a concept. Have you asked your professor for help? Have you checked YouTube or Khan Academy?
If you don't know what resources to look for, ask [00:15:00] somebody. Ask someone that you trust. Say, what do you do when you need help with something like this? What do you do when you don't get the math? What do you do when you're stuck on writing? Do you go to the writing center? Do you use a tutor? What, like sometimes just knowing what other people are doing to get past the same problems that we are facing can change everything and one of the best ways to make sure that you have resources at your fingertips is to make your own. And this doesn't apply in every situation. I know that. But in episode 52, I talk about how to make SOPs, which are standard operating procedures, for yourself so that you don't have to reinvent the wheel every single time you face a challenge. If you've never thought about creating your own personal bank of resources, that episode's gonna walk you through it. I'll link it in the show notes along with episode 38, where I go even deeper into how to be resourceful when you're stuck.
But the bottom line here is that when we're facing hard tasks, we tend to think that we're the only ones who have ever been in that scenario, that we are the only ones who know how hard it is.
Listen, there are so few [00:16:00] tasks, I mean, obviously on the like frontier of Technology, there's brand new things that have never been done before, but for your typical run of the mill, like work tasks, school tasks, they've been done before.
Like it's old- what's the expression? Old hat. Old? I don't know. They've been done before. People have done them before. People are doing it all the time. There's videos on YouTube about how to do absolutely anything. Okay. Ask chat gPT how do you do this? Ask someone you know. It's when we think that we're the only ones who know what it's like to suffer in front of a challenging task, and there's nobody who knows how to do this, that's, that's when everything becomes worse.
You know what I'm saying? Okay.
Tip five, start with what you know. Our brains love momentum, and that's why starting is often the hardest part. When something feels overwhelming, our brain is gonna tell us that we don't know where to begin. But here's the thing, you don't have to start in the right place.
You just have to start somewhere. So let's say that you [00:17:00] need to prepare a business report that's like so vague, but like whatever, and you feel completely stuck. Instead of staring at a blank screen, start with something you do know. Maybe that's the background section. Maybe that's something as small as, I don't know, setting up the document format the way that it's supposed to be set up.
Once you take action, any action, literally any action, no matter how small you create this little seed of momentum and that momentum lowers the mental resistance to keep going.
For students, the same principle applies. If you're stuck on a math problem that seems impossible, solve the parts of the problem that you do understand first. Actually sit down and attempt the problem to figure out, okay, well this is where I get stuck.
I know steps 1, 2, 3, but I get stuck on 4, 5, 6. Right. If you're struggling to write an essay, start by jotting down bullet points, or even just retyping the [00:18:00] assignment prompt into Google Docs. The act of just getting words on the page, even if they aren't perfect, even, it's just, you know, the prompt that you copied and pasted whatever that breaks the inertia and that makes the task feel more manageable.
Let me give you an example from my own life of when I had, um, no idea how to start something or where to begin. No idea. So I just jumped right in with what I knew. I know I just said I didn't know anything and I didn't, but let me explain. And then I started with the most random thing, okay? I remember when I wanted to start a podcast, this one, I had absolutely no idea how. Nobody in my circle, none of my friends, none of my family had does podcasting, right? Like that's not, that's not my people, right? And I had no clue about any of it. So I asked somebody in a business group that I belong to, it's like, you know, a Facebook business group that I pay to [00:19:00] belong to.
And they said, oh, you know, you definitely wanna use this hosting company. This one's like a really good one. I use Buzzsprout. Shout out to Buzzsprout, but I didn't even know what that meant, like hosting company. Like I didn't even know what that meant, but I was like, oh, okay. Somebody that I trust said use this hosting company.
So I googled the hosting company and I bought like the most basic plan. So like that's where I started. I don't know if that was the first step, uh, that was like appropriate. That's what I should have done, but that's what I knew. And when I, when I bought that hosting or subscribed to that hosting company's subscription plan or whatever, then I was like, oh, I wonder if they have a Facebook group. So I joined that company's free Facebook group, and then I learned a few things about tech and equipment, and I so slowly started drafting some potential episodes and then the rest is history. But I have no idea if that was the correct order.
In fact, it most definitely [00:20:00] was not, but it got me moving. And it's the momentum that makes things feel less hard than they are.
If momentum is the thing that we need to get through the hard things, and we can only get momentum by taking action, that's the nature of momentum, right? Then that means we have to take action somewhere.
Action creates momentum, and then action creates motivation. Okay? The strategy here is to let go of the idea that there is one correct place to start that's false. And that belief can be paralyzing. There are many places to start. I could have started my podcast maybe by drafting my episodes. Okay. I could have started by, um, buying my mic.
I could have started by purchasing recording software. Okay. I just happened to start by going with a recommendation for a hosting company. Okay. That, that somebody had had said, that was the one thing I knew. Even though I didn't know it before, but like I felt confident when someone said, use Buzzsprout, I was like, oh, okay. And then that led me to the [00:21:00] Facebook group, and then that led me to more information. And here we are.
If I had this rigid belief that there was one correct step, I never would've taken any step at all. Okay. Hard things become less hard when we remain cognitively flexible. When we accept the reality that there's more than one way to skin a cat, so to speak.
There's the absolute worst expression there is. And I do have a cat in the corner under my recording table. As we speak, I'm sorry, Martin.
So I actually do speak about this in my resourcefulness episode. That part of being resourceful means adopting the mentality that we'll work with what we have, we'll work with what we know, that we'll dive in with whatever we've got at our disposal and figure it out from there.
Okay? If you can get yourself to start anywhere, you're gonna find that the hardest part is already behind you. Hard things are not the same as impossible things. And when we're faced with a difficult [00:22:00] task, our brains often trick us into blurring the two together. That feeling of this is too hard. It quickly spirals into, I can't do this.
When in reality what we should be telling ourselves is this is gonna take effort. Yeah, this is gonna take effort, right? The good things take effort. A great way to reality check this thought is to ask yourself, I already, I already mentioned this, but I'm gonna say it again. Has anyone ever done this before?
If the answer is yes, which I can almost guarantee you it is, yes, then it is possible. It might be frustrating.
It might take longer than you'd like,
and and it might stretch your skills, but it is not impossible.
Think about it. Learning a new language is hard. But people do it every single day. Public speaking is hard, but millions of people have gotten better at it. Writing a PhD dissertation incredibly hard, but students finish them all of the time and they don't die, right?
Hard doesn't mean can't, it just means effort required. But if we [00:23:00] treat hard as if it means impossible, then we let difficulty stop us before we're even started.
And here's the thing, again, sometimes the biggest obstacle isn't the task itself. It's our resistance to doing something that feels hard. Our brains like efficiency and they're going to default to avoiding effort whenever possible. But effort is not the enemy. Struggle doesn't mean you're failing. It just means that you're learning, you're adapting, and you're growing.
Now, quick mind. I feel like I'm doing a lot of mindset for this tip, but like this is what holds us back from doing hard things. So very rarely is it the skill, like a lack of skill that holds us back from doing the hard thing. 'cause you can just go out and get the skill. You can Google it, you can figure out the skill.
It's the mindset work that prevents us from even saying, oh, I could probably use some skill here. Right? So quick mindset shift here, instead of saying, this is hard, try saying this is figureoutable.
Okay? Because it is hard. Things don't mean stop. [00:24:00] They mean slow down, focus and take it one step at a time. If you approach hard things with that mentality, we're gonna be more likely to push through instead of tapping out at the first sign of struggle.
All right, the final and seventh tip, get clear on the end result.
One really big reason that things can feel difficult is because we don't actually know what done looks like.
If we don't actually know what the final product is expected to be, then the task itself can seem amorphous and unclear. And to our brains, that translates into impossible. At work, if you are tasked with launching a new product, but Project Pro product, I combine the two, whatever, a new product, whatever, and you don't know what the final deliverable should be, of course it's gonna feel impossible.
So that's why it is so important to get clear on the expectations. Ask yourself or your boss, or a colleague, whatever. What does success actually look like? [00:25:00] For students, if you're writing a research paper, make sure you understand exactly what the teacher's looking for. What is the criteria for success?
How will you know when you're done? So in teaching when I went to teaching school, so I have a master's in special education and and they teach us to, when we're teachers that we need to provide students with something called criteria criteria of success. A criteria for success, and it's basically like a document.
It's almost like a rubric. It's kind of like a rubric, but it's like a jacked up rubric where you've got the rubric. Okay? If you do all of these things that you've met, you've, you've met success and you've achieved what the objective. Okay. But also to provide examples, sample products of maybe prior work submitted by students, or maybe we make it up ourselves to show students something like, this is what I'm looking for.
If you match the picture, okay, you have [00:26:00] been successful. That doesn't happen in the workspace, okay? You don't have your boss saying, Hey, like I drew up a rubric for you and I have a, you know, a sample report, but to, you know, for you to try to match. But I'm sure your colleagues made a report. I'm sure some similar type of report is floating around the office somewhere that you could at least, at least, at least look at that you could try to maybe, um, break apart and, and dissect and scrutinize and say, okay, they did this on this report.
I could probably do that too. They did this. I might not need that section. They did this. I could probably do that too. Okay, so what happens is that in this type of scenario, when we aren't totally clear on what the final expectation is supposed to be like or what's really expected of us, another kind of cognitive distortion is at play, and it's called emotional reasoning. Emotional reasoning is when we create a false reality based on our feelings [00:27:00] and not based on facts. So if we are feeling
unclear about an assignment or a project or a hard thing we're doing, our brain is gonna do this silly little thing where it now tells us that the actual task is unclear. Okay? It's actually that our feelings are unclear. We don't know how we feel about it. We feel that it's scary. We feel that it's like unclear, but is the thing actually unclear?
Is it? Could you actually find the assignment? Dema details? Could you look at the syllabus? Could you read the directions again? Could you read your boss's email again? Mm-hmm. It's our feelings of ambiguity and murkiness that fool our brains into thinking that the thing itself is unclear and therefore hard.
Okay. I'll bet the thing itself has direction somewhere you're just not clear on where or what they are. These darn feelings have a way of getting the best of us, don't they? Ugh. To be a plant. Just kidding. When we know what we're working toward, [00:28:00] it is easy to, easier to map out how to get there.
Okay. Let's do a quick recap of the seven tips before I wrap us up.
Number one, acknowledge the difficulty we are going to start calling a duck a duck. The sooner we admit that something is hard, the sooner we can prepare for it properly. Denial only makes things harder.
Tip two, identify exactly what's hard.
Not everything about a task is difficult. Pinpoint the exact part that's holding you back so that you can address it directly. Tip three, break the task down. Overwhelm thrives on vagueness. Take the massive impossible task and break it into tiny doable steps. This will lower your resistance.
Tip four, consult your resources.
You do not have to figure out everything on your own. The most successful people aren't necessarily the smartest. They're just the best at finding and using resources.
Tip five, start with what you know. Action creates momentum. It doesn't [00:29:00] matter if you start in the right place because very rarely is there a right place.
Just start with what you know.
Tip six, separate hard from impossible. Hard means effort required. It doesn't mean impossibility if someone else has done it. You can figure it out too.
Tip seven, get clear on the end result. If a task feels impossible, ask yourself, do I even know what the final product should look like?
Clarity makes execution easier.
Here's the deal though. Doing hard things gets easier when we make a habit of it, the more we practice these strategies, the more capable we become, not just in school or work, but in every area of our lives. If you struggle with speaking up at meetings, challenge yourself to say one teeny tiny thing every time.
Studying the very vague, you know, verb to study. If that is overwhelming to you, start learning how [00:30:00] to create a study routine so it becomes second nature. Yes, I teach that in SchoolHabits University. I cannot not say that. If starting something feels impossible commit to just one small step. The more we expose ourselves to difficult things, the less they scare us.
Because we develop a track record of success every single time we do something that's hard and it doesn't kill us, we become, in a good way, jaded by that thing that was hard. And the next thing that we face that's hard. We're like, okay, it's hard, period, but I'm not having all the feelings about it. It is hard and I'm going to do it. Not, it is hard, and what if I can't do it and it's hard? And if I don't do it, then everyone's gonna think I'm gonna fail. Too many feelings here. Let me be clear. This is not at all about forcing yourself through burnout or ignoring your limits. Okay? It's a, it's more about recognizing that hard things don't have to feel like brick walls.
They're just steps, okay? Some bigger than [00:31:00] others, but they're just steps. Nonetheless, we do hard things by taking a step, and then another one and another one.
So the next time you find yourself staring at a difficult task to take a breath, work through the steps and remind yourself that you can do hard things.
If you found this episode helpful, please share it with someone who could use a little motivation. And if you want more strategies like this, don't forget to hit follow so you don't miss future episodes.
Thank you for listening, and as always, never stop learning.
