How to Stop Self-Sabotage by Failing Ahead Of Time

We can’t reach our goals when we don’t know how to do it, right? Wrong!

In fact, that is one of the most detrimental beliefs that holds us back from making our goals a reality.


Because when you tell yourself you can’t get started when you don’t know how, you fail ahead of time.

You give up without ever putting in the effort. 

And you miss the opportunity to learn and grow along the way.

So what can you do instead?

How can you stop failing ahead of time?

That’s exactly what we’re talking about on the I’m Busy Being Awesome podcast this week.

So if you find yourself feeling stuck, confused, or lost when it comes to working toward your big goals, make sure you tune into episode 58.

You can listen to the episode below, or stream it on your favorite podcasting app here:

Prefer to read? No problem! Keep scrolling for the entire podcast transcript.



  • What failing ahead of time is and whether it shows up in your life
  • The top four beliefs that keep us stuck
  • How to take action and move forward rather than playing small



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Episode 58: How To Stop Self-Sabotage By Failing Ahead Of Time

Hey everybody. What’s happening? How are things going with you?

This podcast episode is coming out on the last day of August, which means September is upon us. And I often think about this time of year as almost another “new year.”  Of course, for many people, January 1st is the “new year new beginning.” But for me, September 1st marks a similar fresh start. And I think it’s because of September often marking the start of a new school year combined with all of my years as a teacher that this connection is so strong for me.

So every time September rolls around, I love to use it as a reminder to pause and think about where I am at in my life. I take some time to check in with how things are going and think about where I’ve moved forward. I like to reflect on where I’m at with my goals and my focus areas for the year. And I brainstorm what I might want to start doing more of or less of with the coming months ahead.

As I was doing this practice over the weekend, I thought I would share with you an approach that I’ve found especially effective in helping me uncover areas where I’ve unintentionally held myself back. And it’s really helped me shift my thinking and start taking action toward some of the things that I want most in my life.

Now, since I know so many of you also have big plans for yourself and your life, I wanted to share this strategy with you, too. That way you can also be on to yourself and catch where you might be unintentionally holding yourself back without even realizing you’re doing it.

Failing Ahead of Time

And the concept that I want to talk about today is failing ahead of time. So today we’re going to talk about what failing ahead of time even is, why we do it, why it could present a problem for us, and what we can do about it to start moving forward.

So failing ahead of time. What in the world is this? Honestly, it is just like it sounds. Failing ahead of time is giving up – or not even trying at all – when you have a goal or a dream or even a project on your to-do list. It is giving up or deciding not to try before you even put in any real effort.

And while you may be thinking, “Um, I think I’d know if I was giving up or failing ahead of time…”

The thing is, the way “failing ahead of time” presents itself is often quite sneaky. In fact, we usually don’t realize we’re doing it. Because we tell ourselves thoughts like, “I don’t know how to do it,” or “I don’t have time to do it,”  and because these thoughts feel true to us, we don’t even try.

I Don’t Know How

In fact, “I don’t know how” is probably one of the most common beliefs that leads to failing ahead of time. Because as I mentioned, that thought feels really true to us. Just think about a time when you said this in your life. Maybe you wanted to take on a new role at work, maybe you wanted to build a business, maybe you wanted to start a podcast, or sell your art on Etsy. If you ever wanted to work on something new, and you didn’t know the exact step by step process, chances are your brain offered you some version of the thought “I don’t know how to do this.”

And when we keep thinking to ourselves, “I don’t know how to do this,” not only do we believe it, but we also don’t do anything to change it. We don’t do anything to learn how to do it. So instead, we stay stuck. We don’t move forward. And we fail ahead of time.

For example, “I don’t know how” is actually a thought that held me back from starting this podcast much earlier than I did. I had this podcast on my mind for almost a year before I finally got started on it in 2019. But I kept telling myself, “I don’t know how to do it. I don’t know how to record a podcast. I don’t know how to edit a podcast, or get it online, or have it show up in iTunes or Stitcher. And I don’t know how to get it to potential listeners.” Blah, blah, blah.

Stuck In Confusion

And because I kept making excuses and telling myself different versions of “I don’t know how…” I just stayed in the same place. Because when I tell myself “I don’t know how,” I feel confused. I feel lost. I feel stuck. And when I feel that way, I do nothing to figure it out. I do nothing to lean into the confusion. I do nothing to learn how to do it. And since I don’t do anything to learn, I stay stuck and I fail ahead of time.

Fortunately, I finally caught that thought and recognized what I was doing. And after doing some coaching, I decided to start practicing the thought, “I’m figuring it out” instead.

Now, here’s the deal, both thoughts – I don’t know how. And I’m figuring it out. – felt true to me.  But one of them was actually going to get me somewhere. Because when I told myself, “I’m figuring it out,” then I started watching YouTube videos on how to start a podcast. I took a course. I started playing around with GarageBand. And eventually, I do, indeed, figure it out. I move forward. And again, this is because I decided to stop failing ahead of time by telling myself “I don’t know how.”

It Probably Won’t Work

Another super common thought that often trips us up and has us failing ahead of time is some version of, “it probably won’t work.” Again, it doesn’t matter what it is you’re working toward. As long as it’s something different, or unfamiliar, or potentially challenging, you’ve probably heard some version of the thought “it probably won’t work” pop up in your mind.

For example, I was talking with a friend of mine the other day. We were exploring how she can create a schedule for herself now that her kids are technically back in school but they’re distance learning on Zoom. And we came up with a schedule that allows time for her to get her own work done while also having space and flexibility to help her kids when they’re not on the actual Zoom call with their teacher.

Now, it’s a very different type of schedule than she’s used to. (It’s an approach that I use with some of my ADHD clients that works really well.) And it has her working within a relatively condensed block of time. In fact, she has about two hours of focused time where she does all of her most important projects for work. And then the rest of the day is reserved for the smaller, less concentration-intensive projects that she can do more “on the fly” with greater flexibility depending on what her kids need.

And again, this was entirely different from the schedule she’s used to, which is 8 hours of uninterrupted time. So her brain really wanted to resist it. She kept saying, “I just don’t think this will work.” Or “it probably won’t work because of XYZ.” 

If You Think It Won’t Work, You’re Right

But here’s the deal. If you tell yourself it’s not going to work, it probably won’t work. Because when you’re telling yourself it’s not going to work, you’re most likely going to feel discouraged, maybe skeptical, or maybe doubtful. And when you show up to your schedule for the day feeling doubtful or skeptical, you’re probably not going to go all-in on those big tasks that you want to complete during that focused time of work.

Instead, you’re probably going to treat your schedule like you do your more typical workday when you have eight hours to complete the thing. So maybe you probably get started on the project. But then you quickly check your email. Then you scroll through Facebook. And then you go back to the task. And you rinse and repeat until that focus time is over. Of course, when this happens, you prove to yourself that the schedule doesn’t work. That it’s not possible. That you can’t get it done by using this approach.

In other words, you fail ahead of time because you don’t even give yourself a shot. You don’t give yourself the opportunity to see what does work.

Try This

I mean, what if you practiced just the slightest shift in thought? What if, rather than telling yourself it won’t work, you instead think, “maybe this could work for me.” The second option feels so much lighter, doesn’t it? It feels open and curious. And when you feel that way, you probably go into the process willing to give it a try. And when you give it a try, you learn something. So even if it doesn’t quote-unquote “work” as you expected, you still learn something so that you can pivot and try something different going forward.

And honestly, chances of it not working at all whatsoever is pretty slim. Chances are, at least some of it will work. And if that’s the case, you can keep adjusting as necessary until you find what does work. But when you tell yourself that it won’t work, then you don’t even try, and you for sure won’t get there.

So if you hear your brain thinking some version of, “this probably won’t work,” or “I don’t think this will help,” or “this won’t work,” get curious. Because it’s possible that you’re missing an opportunity by failing ahead of time.

I Haven’t Been Able To Do It Before

Another common instance where I see this come up, and especially with my clients, is when we tell ourselves, “I haven’t been able to do it before.” So, I’ve never been able to stay organized for more than a week before. I’ve never been able to stick to a new habit for more than a couple of days before. I haven’t been able to use a calendar or a planner consistently before. I’ve never been able to stay focused for long stretches of time before. I’ve never been able to actually follow through and complete a goal before.

And when we practice this belief, it presents so many different challenges for us in terms of failing ahead of time. First of all, just like our other examples, when we tell ourselves that we’ve never been able to do it before – when we use the past as evidence that we won’t be able to do in the future – we 100% set ourselves up for failure.

Our Past Doesn’t Predict Our Future

And what’s so fascinating about this perspective is that it doesn’t actually make any sense. Why would we look to what we’ve done in the past to be able to tell us what we can do in the future? I think I’ve talked about this on the podcast before, but I love the example, so I’ll give it again. Think about a baby who is just learning to walk. It’s not like this little baby tried to walk once, fell down, and then thought to themselves, “well, that didn’t work. I guess I just need to be carried around for the rest of my life.” Of course not.

And what’s more, it is because that baby fell down and got back up over and over and over that she had enough strength in her legs to be able to walk. It’s necessary in order to get to the next stage.

Think About A New Driver

Or think about a 15 or 16-year-old who is just learning to drive. You know the first time that they got behind the wheel it was not perfect. You know the first 10 times they tried to parallel park they probably hit one of the practice cones. But just because they didn’t get it right in the past doesn’t mean that they stopped. They didn’t just give up and think to themselves, “well I’ve never been able to parallel park before. I guess I’ll never get my driver’s license.” Of course not.

But for some reason, so many of us – I think sometime in our early twenties – start believing that we need to have done it all before. All of a sudden we start looking to our past and believing that if we’ve failed in the past or haven’t had success in the past, that means we won’t in the future. And we completely forget the truth that the way we learn how to do things is by practicing and improving and getting better.

So What?

Here’s the real question. So what if you haven’t been able to use a calendar consistently before? So what if you have never been able to stick to a habit for more than a couple of days? What can we learn from that? What data can we pull from your past experiences, so we can learn from it and do better than next time? You don’t have to throw in the towel. You don’t have to fail ahead of time just because you haven’t been able to do it in the past.

And what’s more, those thoughts probably aren’t even true. If you believe that you have never stuck to a habit for more than a couple of days in a row, I’d like to challenge that. Because my guess is that you have brushed your teeth for more than a couple days in a row. Am I right? I thought so. Habit.

If you believe that you haven’t been able to use a calendar consistently before, I would like to challenge that. Have you adhered to a Monday through Sunday schedule? Have you gone to work Monday through Friday or whatever your work schedule is? If so, then you have used to calendar consistently. You might not have used a planner or calendar in a particular way that you have in mind, but don’t tell yourself you’ve never been able to use a calendar before. Don’t tell yourself that you’ve always failed at it before. Because it’s not true. 

I’ve Never Done It Before

And a related thought to “I haven’t been able to do it” that also creates problems for us is simply, “I’ve never done it before.” And this is another big thought that holds people back. I was working with a client several months ago who wanted to open up her own business and become an entrepreneur. But she kept holding back because she was telling herself, “I’ve never done it before.” And in fact, she combined several of these thoughts together. “I’ve never done it before. I don’t know how. So it probably won’t work.”

She had the trifecta of “failing ahead of time thoughts” looping around in her brain, which of course created her result. For years, she never put herself out there. And because she didn’t put herself out there, she never learned from her experiences. And because she didn’t learn what works and what doesn’t, she never built the business. That is, she never built her business until she challenged those thoughts and started thinking differently. Because once she did that, it changed everything.

Why We Fail Ahead Of Time

So, can you hear yourself in any of these situations? Have you ever noticed times when you have failed ahead of time? If you’re human, the answer is probably yes. We all do this at different times in our lives. So if it has happened to you, nothing has gone wrong. It simply means you’re human with a brain.

But why is it that we do this? Why is it that we often opt to fail ahead of time instead of actually trying and going all-in?

Well, as I’ve talked about in other podcasts, our brain is trying to do its job and keep us safe. And to our brain, something new or unfamiliar seems dangerous, and in turn, a legitimate reason not to try (or try again). Our brain has no interest in expending extra energy in order to get uncomfortable. It simply wants to conserve energy and survive.

So when our brain comes upon something new or different, it is going to start grasping at excuses. It’s going to offer you, “but I don’t know how to do this. Or it probably won’t work. Or it’s never worked in the past, I don’t see why it would work now.” Because when we fail ahead of time, we don’t have to put ourselves out there. We don’t have to do that scary thing. We don’t have to risk failing publicly.

When we fail ahead of time, we fail quietly. Nobody else knows. So on the surface, our brain likes that better. Because we don’t have to risk feeling uncomfortable, embarrassed, ashamed, frustrated, or whatever else might come up for you if you didn’t create the exact result you wanted the first or second or 30th time you tried.

Why This Is A Problem

And let me be the first to say that I get it. Believe me. I know it’s super uncomfortable to make mistakes in front of people. And if you decide to take that route, that’s absolutely okay! However, I think it’s important to be aware and intentional about that decision rather than just letting it happen to you. okay.

Now, with that being said. If you do want to try something new. If you do want to step outside of your comfort zone. Or if you do want to go after the new goal or establish a new habit, but you find yourself failing ahead of time, then it’s time to dig in. It’s time to get curious.

Because here’s the deal, whether it’s intentional or not, the reason why we fail ahead of time is so we don’t have to feel a negative emotion. If we fail ahead of time, we think it’s going to keep us from feeling uncomfortable, or embarrassed, or ashamed, or frustrated, or whatever else we might feel when we put ourselves out there. 

But the first thing I want to remind you is that you create those emotions. You create both your positive and negative emotions with your thoughts.

Opportunity For Growth

So if you decide to apply for a higher-level position in your job, and you don’t get the offer, you get to decide what you think about that circumstance. You get to decide whether you think to yourself, I knew I couldn’t do it, can’t believe I even tried. This was such a waste of time and I shouldn’t even be here. Or, “Interesting. what can I learn about this application experience? What did I learn during the interview? How can I grow and move forward from this experience? What can I try differently next time?”

That first line of thinking is probably going to create some pretty negative emotions. The first line of thinking is probably going to create feelings of frustration or discouragement or embarrassment. But if you think to yourself instead, “what can I learn here? How can I move forward from this experience?” Then you feel curiosity. You feel open. And you find ways that you can take steps forward without beating yourself up in the process. 

Negative Emotions Either Way

And here’s another important thing. Let’s say you want to open a business or go up for that promotion, but you fail ahead of time instead. You’re thinking to yourself, “it probably won’t work” or “It didn’t work last time,” so you decide not to give it a try because you don’t want to feel that discomfort.

Well, chances are good that you will still feel some kind of negative emotion. But the difference is that instead of your thoughts about putting yourself out there making you feel uncomfortable, you instead feeling frustrated or disappointed because you’re thinking “

what if?” What if I would have done that? Or I should have given that a try. So if you’re going to be uncomfortable at least some of the time in both situations, what would you prefer? Would you rather be uncomfortable while taking massive action as you grow and learn and make things happen? Or would you rather feel discomfort from your thoughts about being stuck or regret? For me, the answer is growth every time.

How To Fail Forward

So if you’ve heard yourself in any of these different scenarios I mentioned today. If your brain offers you thoughts like, “I don’t know how,” “it probably won’t work,” “I’ve never done it before,” “it’s never worked in the past.” I encourage you to get curious.

If you are telling yourself, I don’t know how. Ask yourself, but what if I did know? What if I did know what to do? Make yourself answer, and move forward from there.

If you’re telling yourself it probably won’t work. Ask yourself, but what if it did? How could this work? And take that step forward.

If you tell yourself I’ve never been able to do it before, start investigating. What can you learn from the last time you tried? Take that into account, adjust as necessary, and move forward.

Because I’m telling you, failing ahead of time – while it might feel easier in the short-term — is holding you back from those incredible things that you want to do. And believe me, I get it. I am working through these exact same thoughts that you are. So when I hear them come up, I remind myself that these thoughts are just my brain trying to play it safe. And I think to myself, “noted. Thanks, for your input, brain. But we’re going to move forward now. Because I’ve decided that I would rather feel the discomfort of growth than the discomfort of being stuck.

I invite each of you to do the same. 

And if you would like some help exploring these concepts. If you think you might be failing ahead of time in different areas of your life and you’re ready to break out of that pattern, let’s talk. Just head here and sign up for a consultation with me. We will talk about where you’re stuck, where you want to go, and we’ll do a little coaching. And then we’ll explore whether my coaching program is a great fit to help you move forward and reach that end goal.