Ep #51: How to Overcome Perfectionism with Failure

How to Overcome Perfectionism with Failure

I’m wondering, do you have something in the next chapter of life that you want to create, but you keep holding yourself back because you’re afraid that you’ll fail, that other people might judge you, or that you just won’t do it perfectly? If this sounds like you, maybe you identify as a perfectionist, like I used to.

Perfectionism has been something that I noticed as a pattern in my life long before I lost my husband. There was a time when I actually thought of it as a badge of honor. I considered myself someone who has high standards and who upheld them, producing high-quality work. But what I’ve learned lately is that I reached a point where this perfectionist pattern wasn’t actually serving the life that I want to live. It was holding me back. And the same might be true for you.

Join me on the podcast this week to discover where perfectionist thinking might be holding you back and how you can begin to overcome it, using failure as a tool. I’m sharing how perfectionism kept me from going after the life I really wanted to be living, and the incredible shifts that I have created since addressing my perfectionist tendencies.

Listen to the Full Episode:

If you like what you’ve been hearing on this podcast and want to create a future you can truly get excited about even after the loss of your spouse, I invite you to join my Mom Goes On coaching program. It’s small group coaching just for widowed moms like you where I’ll help you figure out what’s holding you back and give you the tools and support you need so you can move forward with confidence.

What You’ll Learn from this Episode:

  • The ways we justify our perfectionist tendencies to ourselves.
  • Why perfectionism isn’t serving you, even though it can feel like something to be proud of.
  • The ways that perfectionism has held me back in all areas of my life.
  • Why a different perspective of failure is such a useful tool in overcoming perfectionism.
  • The difference between a Worthy Fail and an Escape Fail.
  • How I’m using an impossible goal to overcome perfectionism while still creating a life I love.


Featured on the Show:

Full Episode Transcript:

Welcome to The Widowed Mom Podcast, episode 51, How to Overcome Perfectionism with Failure.

Welcome to The Widowed Mom Podcast, the only podcast that offers a proven process to help you work through your grief to grow, evolve, and create a future you can actually look forward to. Here’s your host, certified life coach, grief expert, widow, and mom, Krista St-Germain.

Hey there. Welcome to another episode of the podcast. So, we’re going to talk about failure and perfectionism. I’m wondering, do you have something in the next chapter of life that you want to create, but you keep holding yourself back because you’re afraid that you’ll fail, or you’re afraid that other people might judge you, or you’re afraid that you just won’t do it perfectly? Maybe you identify as a perfectionist, like I did.

Perfectionism has been something long before my husband died that I have noticed as a pattern in my life. At a certain point, I actually thought it was a badge of honor. I considered myself someone who has high standards and who upheld them and who produced high-quality work.

But what I’ve learned lately is that I reached a point with some of my perfectionist patterns that it wasn’t actually serving the life that I want to live. It was holding me back. And if it’s holding me back, it might be holding you back.

So, as always, I’m going to go first and I’m going to figure it out for myself. And then I’m going to tell you how you can do it for yourself and for your life. So, that’s what I’ve been up to lately. I’ve been working on a project where I fail on purpose. Not because I love failure. Not because it feels amazing. But because I know that getting comfortable with failure, welcoming the unwelcome is the way to change those perfectionist patterns.

So, in this episode of the podcast, I’m going to tell you all about my little project, what I’ve been doing, hat I learned, and how you can do it too. I know how much time and energy I have spent in perfecting things. I know how much time and energy I have spent in trying to avoid, heaven forbid, that someone might think badly of me.

I know how I have not set big goals for myself when I wasn’t absolutely convinced that I could accomplish them, because I wasn’t willing to risk failure. I know how I have been holding back from being vulnerable with other people because they might not like what they see.

And you know, and I know, more than a lot of people, that life is short. It is precious. And I want you to spend your energy in the most powerful way possible. I want you to create a life that you really love and I don’t want anything, including perfectionism, to get in the way of your life or mine. So, let’s jump into it.

As you know, I am a life coach certified through The Life Coach School. And one of the things that The Life Coach School has is a master coach program, a master coach training program. And I decided this year that I wanted to be considered a master coach candidate, and went in January, of all terrible places, to Grand Cayman, where we had our in-person master coach training event.

But the in-person training event was really only a small portion of the actual master coach process. So, after we got back form master coach training, sadly said goodbye to the beaches of Grand Cayman, we all had to do a project. And the project was really different depending on what the individual needed.

And lo and behold, my coaches who know me well know about my perfectionist patterns and helped me figure out a way to craft my master coach project with overcoming this pattern, changing this pattern in mind. So, what I set out to do was to fail 90 times in 90 days. And I would fail toward a goal that I believed was impossible.

Now, why would one do that? For the longest time, I asked myself that very question. In fact, my teacher Brooke Castillo has been teaching the impossible goal concept to my very stubborn brain for the last several years. And I think I had convinced myself that I embraced that tool. But honestly, I had not. So, what the heck is an impossible goal? Why would we even set one? These are the questions my brain had as well.

An impossible goal, as my teacher teaches it, is one in which you really don’t believe you can hit. It basically gives you the opportunity to set a goal so big, so brazen that when your brain says you can’t do it, when your brain says it will never happen, when your brain offers to you, “Who do you think you are?” that you even see it seems ridiculous.

And you can tell your brain, “I get it. It’s ridiculous. We’re never going to hit this goal. It’s fine.” We don’t really have to be serious about hitting this goal. We have nothing to lose. It’s impossible. But let’s go get it anyway. Let’s just try. What’s the worst that can happen? We don’t hit it? Yeah, we already believe that we’re not going to hit it, so that’s okay.

We just kind of take the argument that our brain always wants to offer us when we go to accomplish a goal, we take that argument off the table and we just acknowledge straight out of the gate that yes, the goal is impossible. It flies in the face of any sort of traditional goal setting that you’ve ever been taught.

We’re taught to set realistic goals, set smart goals. They’re specific and they’re measurable and they’re actionable and they’re realistic. They’re supposed to be things that our brain believes is possible. And in some ways and some places, I still believe there is a place for that.

But the impossible goal gives us permission to just dream big and not actually worry about whether we get there or not. The impossible goal gives us permission to go after something so big, not even because of the actual thing that we’re pursuing, but because of who we get to be as a result of pursuing it.

It’s a way for us to evolve, to grow, to become that next up-leveled, best, highest, most amazing version of ourselves. Because really, that’s what life on the planet is all about anyway, right? It doesn’t really matter if we make all the money. It doesn’t really matter if we get the amazing job. But it does matter that we like who we are. It does matter that we’re living our best life. It does matter that we choose consciously to create what we want and we don’t let self-imposed limitations hold us back.

That does matter and that’s what the impossible goal, which it took me a while to embrace, is really all about. Get the failure off the table. Who cares? Go for the big thing anyway because of who you get to become in the seeking of it, in the going toward it.

So, I set an impossible goal of making $150,000 in three months. And my brain was very clear in telling me that is ridiculous. So, it fits the criteria of an impossible goal. My brain doesn’t believe that it’s possible. So much more money than I have ever made that it felt laughable to me.

And that’s the point, because now I don’t need to argue with it. I don’t’ even really need to achieve it. but I get to think creatively, I get to show up differently, I get to fail on purpose. I get to stretch myself and grow and make myself uncomfortable and do all of the belief work required of me to create something like that, knowing full well that I won’t create it, but not really caring.

So, my master coach project was to create 90 fails, fail 90 times towards an impossible goal of creating $150,000 in the same three months. Now, failing and how we define it was really important to my project, and it’s really important if you decide to do this in your life.

What is a fail? A fail in this instance is where we try to create a result, we take the action that we think could create the result, but yet we miss the mark. We don’t actually create the result. But it isn’t because of lack of effort. It isn’t because we didn’t get muddy. It isn’t because we didn’t try hard and work hard. It’s because we just fell short, giving it our best effort, we still fell short.

And that’s what we call a worthy fail. I didn’t come up with this, my teacher Brooke did, so I’m not taking credit for it. But a worthy fail is one where we were in the ring, we showed up, we were brave, we took the action and it didn’t work out. But we tried. Versus what I have done many times before, which is an escape fail, where we say we’re going to do something, but then we don’t. We say we’re going to try the scary thing, and we make an excuse. We say we’re going to show up and meet the person, and feel nervous, and then we hide. That’s an escape fail.

So, those fails didn’t count towards my project. My 90 fails needed to be 90 things that I actually tried on and that didn’t produce the result that I wanted. Now, why would anybody want to do this in the first place?

Failure doesn’t feel good. Why would you want to fail on purpose? And the answer to that is because our primitive brain is wired. And you’ve heard me talk about this, if you’ve listened to the episode on widowhood and the motivational triad. And you might want to go back and have a listen to that episode if you’re not familiar to it because I explain this in much more detail.

But the Reader’s Digest version of this concept is that our primitive brain is designed to seek pleasure, avoid pain, and be efficient. It just wants to keep us safe and alive. It does not want us to do things that it perceives are scary. It associates fear with death.

And there was a time in this world when our survival depended on this part of our brain regularly. We literally lived in caves. We were killing animals. Animals were killing us. And we needed a part of our brain to make sure that we stayed safe.

But that part of our brain is still the way that it is, and the society that we live in has changed drastically. We don’t really need that same seek pleasure, avoid pain, be efficient pattern anymore. And, in fact, now that pattern can be what traps us in perfectionist patterns.

Because when we are trying to avoid pain – and by pain, in this instance, I mean emotion. When we’re trying to avoid rejection, when we’re trying to avoid judgment, when we’re trying to avoid discomfort, when we’re trying to avoid all the sharp corners that are out there in our emotional lives – that means we aren’t going to grow. That means we aren’t going to take risks. That means we’re just going to stay small.

And for me, that means my business isn’t going to grow, I’m not going to help more of you. Before this, that meant I wasn’t going to date again. It means I’m just going to keep doing what I’ve been doing because it’s comfortable, and if it ain’t broke, don’t fix it. That’s what our primitive brain would have us do.

So, why fail? Fail because every time you do, you get to face your own judgment. You get to get good at either feeling judgment and not worrying about it, or deciding to think differently about yourself.

Every time you fail, you get to experience rejection. Rejection, by the way, that is created by your own brain. We never experience the rejection that someone else might feel. We only experience our own rejection. Someone might tell us we didn’t do a good job, but honestly for me, that’s not even the worst part of it. For me, the worst part of it was my own thoughts inside my own head where I told myself I didn’t do a good job or I should have done a better job.

So, I wanted to try failure as a way to get good at going towards the uncomfortable, at welcoming the unwelcome, at leaning into the sharp points. Because if I can get good at that, knowing that that’s always what’s going to happen every time I go to grow, then I can iterate faster. Then I don’t have to spend so much time perfecting things.

My teacher also teaches a concept called B-minus work. Another thing, surprisingly enough, that perfectionists tend to recoil at, “I’ve always been an A student, what are you talking about, B-minus? That’s not acceptable. We don’t get B-minuses. We get As.”

And what she teaches is it’s not about the grade. It’s about what’s the work in the world that you’re here to do? And how much time do you spend pushing yourself past the point of diminishing return perfecting something in the name of the gold star, but in the process, losing your ability to impact the world, diminishing the amount of contribution you can make because you’re trying to make it perfect?

Sometimes, if we just say good enough is good enough and we recognize where that point is and we don’t go past the point of diminishing return, we just get our work out there, that’s when we make a difference.

Now, intellectually I knew this. I’ve been listening to my teacher for years. And I watched the impact that her work had on my life. And I knew that the reason she was able to impact my life so much is because she only held herself to the standard of B-minus. She did good work, but she didn’t waste her time perfecting that good work to make it great. She just got it out in the world in a way that I could read it, I could consume it, I could listen to it, I could learn from it.

But there was something just a little bit missing there. I saw it intellectually. I saw the concept of it. But I really didn’t want to feel the feelings of doing it myself. I really didn’t want to feel that uncomfortable feeling of putting out something in the world that wasn’t quite perfect.

Now, maybe it’s different for you. Maybe you don’t over-perfect on things like emails and podcasts. I don’t know what you over-perfect on. But if you relate to the perfectionist tendencies, there is something, probably many things, that you’re holding yourself back from.

So, maybe it’s the next step in the career. I just talked to a woman this week who is an attorney and she wants to hang her own shingle. She wants to go out on her own and break out of the firm that she’s working for and create her own law practice. And she’s stuck right now. She’s holding herself back. And what’s in the way is her unwillingness to fail, her unwillingness to feel those emotions.

Maybe you want to date again but you don’t want to feel the rejection. There’s some feelings that might happen as a part of dating again, as a part of putting yourself out there, and you don’t want to feel them. There’s nothing wrong with you. You’re human. This is the way that we are designed.

We are designed to seek pleasure, avoid pain, be efficient. So, naturally we’re steering clear of things, we’re not taking risks, we’re limiting our possibilities because we don’t want to feel the feelings that might be on the other side. That’s not a good or bad, right or wrong choice. But it does limit what’s possible for us.

And so, I wanted to seek failure because I wanted to free my brain to pursue discomfort on purpose because I know discomfort is the way to a bigger life and to the next best version of me. So, that’s what I did. First, I sat down and I brainstormed lots of different ways that I could fail towards making this impossible goal of 150K in 90 days.

And I just came up with a big list and I asked myself, what are the things that I know, the person that is earning that amount of money, what is she doing in her business? How is she putting herself out there that I’m not? Where am I holding myself back that she isn’t? An di just brainstormed all of those things.

And so, you can do this. What are those things that you would need to create, what are those results you would need to create, what are those actions you would need to take to create those results?

So, let’s say it’s the career and you want to start a new career. What would you have to do to make that happen? Do you have to go back to school? If so, you need to apply. Do you have to ask your boss for a different position? If so, maybe you need to schedule a meeting and ask. Is it a resume that hasn’t yet been updated? What is it? What are all of the things that you would need to do to create this new result that you want, that you could fail at?

If it’s a new relationship that you want to be in, what would you have to do to start dating again, to find that new relationship? Well, you might have to investigate online dating. You might have to create a profile. You might have to actually ask someone out. You might have to chat with someone. Of course you’re going to have to do these kinds of things. You’re going to have to put yourself out there.

So, you come up with the results that you want to create and you come up with the action steps that would get you there, and then you decide to do them even when they feel scary. And if you’re anything like me, you’re going to want to throw up. That’s fine. You’re going to feel very uncomfortable. That’s the idea.

If you want to throw up and you want to feel uncomfortable, you’re probably right on track. If bravery is required, it’s because fear is present. And if fear is present, growth is in the works. Green light.

So, here’s how this went for me after I planned my fails. Of course, my initial list of fails, honestly, wasn’t that exciting. And just about the time I started into my failure project, I actually started dating at the same time.

So, the first few weeks of the failing for me were quite productive, very uncomfortable, but quite productive. I did a lot of things and I did them faster than I normally would. One of the things I initially decided to do was to send out more honest vulnerable communication to people on my email list.

So, if you’re on my email list, you probably felt that switch happen. Before this project, I was really only sending a couple of emails a week and they were more transparent sometimes than others. But I would say, in general, they were a little guarded.

But I decided, “I’m going to be honest with people. I’m going to let them kind of walk with me through my life, and that’s uncomfortable for me.” What was also uncomfortable for me about that was to allow myself a time limit in which I could write those emails. Because perfectionist brain has me writing an email and spreading it out and editing it forever and overly perfecting it and getting upset when there’s a typo. That’s what perfectionist brain was doing for me.

So, I decided, not only am I going to be more honest and open about what’s going on in my life. I’m also going to limit the amount of time I spend doing it. And when the timer dings, the email is done.

So, I went from sending a couple of honest emails, but semi-guarded, to several a week that were very transparent and I dropped my guard and I was honest with what was going on in my life. I took people along on this dating journey that I’ve been on the last few months. I shared some of the vulnerable things that were coming up for me with my husband’s grief and I just really allowed myself to feel uncomfortable through all of it.

So, the first few weeks were good momentum. Then I actively started dating the boyfriend. And needless to say, he distracted my brain. Actually, he didn’t distract my brain. I let my thoughts distract me. And I enjoyed it, so no regrets. But definitely, my inspiration to fail got a little side-barred because I was pretty interested in spending time with him.

And, of course, at that same time a couple of weeks into our dating, COVID-19 started to happen and so the world just started to get a little bit weird. And in the middle of my 90 days, it just felt like kind of a lull. So, it started out with an enthusiastic uptick, and then in the middle kind of dropped into a lull. And then, somewhere toward the end of the middle, I really decided, “Okay, it’s time. We’ve got to get going.”

And I started doing the work to get myself motivated to fail and I started thinking more creatively about failing and I started failing more. And here’s what I learned in this whole process. By the way, I failed way more than 90 times; way more. So, I definitely hit the fail goal.

Of course, I didn’t hit the 150K, and that’s fine. Again, that wasn’t the point. But here’s what I learned. There’s three main things that I learned that I want to share with you. Because you’re going to be able to apply this to your life too, whatever it is that you’re trying to fail at.

The first thing I learned is that the more you fail, the easier it gets. And that’s a good thing. You start getting momentum. You start getting excited about it. You start seeing that failure actually, because it’s the plan, is a good thing in this way. And so, the momentum starts to build.

It’s like a ball rolling down a hill. It just kind of gathers momentum as it goes and it gets faster and faster and faster. And then, all of a sudden, you’re looking for ways to fail in pursuit of your goal and seeing how much more comfortable you’re getting as you go. And the little things that used to bother you start bothering you less. It’s the strangest thing.

The second thing that I learned – and this is probably what honestly tripped me out the most, is that sometimes even when you plan to fail, you don’t. There were so many times, especially in this last little bit here, where I was really stretching myself in my brain, I thought, to do things that felt beyond me, to make asks that I felt were bigger than me, that surely would be fails, things that I would request to people, they would absolutely say no.

So, for instance, podcast requests. There are a few podcasts and a few life coaches in particular who I just think the world of. They hung the moon in my eyes. They’re amazing people and they have amazing podcasts and there’s some grief podcasts that I just think are absolutely phenomenal. And in my mind, they feel above me. That’s how I have been thinking of them, that they are kind of out of my league.

So, surely, if I ask them to be on my podcast or if I asked to go on theirs, if I asked to collaborate in some way, I would get a polite, “Thanks, but no thanks.” Surely that will happen, right?

Not as much as I thought. So many times, when I thought, “For sure this is going to be a fail, but what the heck, I’ll make the ask,” the answer was yes. It’s the craziest thing. The answer was yes.

And then, here’s what I learned. All this time, I’ve been holding myself back from asking for the things that I thought were out of my league, that I thought were above me. And all of this time, I probably could have made those asks and I probably would have gotten yesses.

So, where are you holding yourself back because you’re telling yourself “It’s a definite fail? It’s a definite no. It’s never going to work out.” And so you don’t even pursue it because your brain can’t even contemplate that it could be possible.

I challenge you, what are those things? Because they are not the fails that you think they are. And that field that you think is full of failure, there’s a bunch of yesses. There were for me. And it’s the strangest thing because you make the request expecting the fail and you get a yes, and all of a sudden, you feel mixed. You feel like, “Dang it, I’m happy that I got the yes, but really I didn’t get the fail.” And it’s very peculiar. So, I would ask people for things and they would say yes and, holy cow, it’s amazing. So, sometimes even when you plan to fail, you don’t fail.

And the last thing that I learned is that truly, failure is what we make it. Yes, I hit my 90 fails. In fact, I far surpassed 90. No, I did not reach my impossible financial goal. So, did I fail? Yes, many times.

On a microscopic level, I failed many, many times. I tried things over and over and new things and they didn’t work. And I didn’t make the money I wanted to make. Many, many fails.

But on a macro level, if I step back, if I stop squinting so critically at the details of my fails and I step back and I look at the impact of those fails on my life, then did I fail? Of course not. Quite the opposite. I succeeded because I made friends with failure.

I let myself go to the place where rejection didn’t matter anymore, where fear didn’t matter anymore, where judgment didn’t matter anymore, where other people’s opinions are so much less important to me, where my own mean thoughts are so much more in check.

I can do something and miss the mark, but I can be nice to myself about it. Someone else can have an opinion about me for missing the mark, and I can be nice to myself about it. I don’t have to take their opinion on as my own. And you don’t either.

So, whatever it is that you want to do, whatever it is that you’ve been holding yourself back from, however you’ve been wasting your precious energy trying to make things perfect before you show them to the world, stop it. And I say this with love. And I say this as a person that has now lived almost – well, 44 years on the planet.

You don’t need to spend the kind of time that I spent perfecting things for fear that somebody else might have an opinion, for fear that you might judge yourself. You can just decide, “You know what, I’m always doing my best and I don’t have to make it perfect to make it valuable. I can go with B-minus. I can get my work out there because my work matters. My life matters. My contribution matters. And what I want to accomplish is so much more important than never feeling a negative emotion because I never risk putting anything out in the world that was less than perfect.”

See, like right there, I could go back and I could edit that part of the podcast out where I just screwed up a little bit, but I’m not going to do it because it would take time, and that’s not the best use of my life. But old me would have gone back and we would have edited that out. Heaven forbid you would hear me make a boo-boo and misspeak.

And so, that’s what I got out of failure. The more you fail, the easier it gets. Sometimes, even when you plan to fail, you don’t. And failure is what we make it.

So, if you are struggling with perfectionism, consider failure on purpose. Go set a big hairy scary goal that your brain absolutely believes there’s no possible way for you to accomplish, and say, “So what? I get it, brain. It doesn’t even matter. It’s not about the result. It’s about who I get to become in the pursuit of the goal.”

And then go fail your way to not worrying about the little stuff so much, go fail your way to a bigger life. I promise you that the only reason you don’t have the life you want yet is because you haven’t allowed yourself to feel the feelings that that life requires of you. And that’s possible for you.

And I just simply cannot stand it if you are telling yourself that you just have to settle for this mediocre new normal. It’s crap. I just can’t handle it. I just can’t handle it.

You deserve a life that you love. You are capable of anything that you want to create and that is what I want for you. And that is what failure can give you. And there’s no reason, there’s nothing any different about me than there is about you. If I can get good at failure, you can get good at failure.

So, go get good at failure. Go feel the feelings. Go put yourself in the ring. Thank you so much for listening. Remember, I love you, and you’ve got this. And I’ll see you next week. Take care.

Ready to start building a future you can actually look forward to? Get a free copy of Krista’s Love Your Life Again Game Plan, and learn her three-step process so you can stop feeling stuck and start creating your next great chapter. No matter what you’ve been through, your past does not have to define what’s possible in your future.

Text the word PLAN to 1-858-widows-1, or visit coachingwithkrista.com/plan and get Krista’s Love Your Life Again Game Plan delivered straight to your inbox. A future you love is still possible and you are worth it. Text the word PLAN to 1-858-widows-1, or visit coachingwithkrista.com/plan and get your free game plan today.

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About your coach

I created a new life using small, manageable steps and techniques that made sense. The changes I experienced were so profound I became a Master Certified Life Coach and created a group coaching program for widows like us called Mom Goes On. It’s now my mission to show widowed moms exactly how to do what I’ve done and create a future they can look forward to.

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