People don’t like to fail. We don’t want to feel it or talk about it, and we fear it deeply and intensely. Our brains are designed to keep us safe and protect us, and they aim to seek pleasure, not failure. But when it comes to running a business, failure is essential.
All success is built on a pile of failures, and if you want to be more successful in your business, you have to be willing to fail. The more success you seek, the more failure you have to be willing to experience. So this week, I’m showing you how to start viewing failure differently, build failure resilience and stop allowing failure to hold you back from what you are capable of.
Listen in this week as I discuss the concept of failure, failing forward, and creating failure resistance. I share the importance of learning to fail and why you should be actively looking for opportunities in your business to do so, and I show you how to use failure to create the massive success in your business you know you are meant for.
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What You’ll Learn from this Episode:
- How our brain thinks and processes the possibility of failure.
- An example of a goal I had that I didn’t fully meet.
- The reason our minds need time to rejuvenate and rest.
- Why you don’t want to avoid failure and how to go towards it.
- How to see what worked, what didn’t, and what you’re going to shift, tweak and change the next time.
- Why you shouldn’t let your fear of failure stop you from helping your people.
Resources
- Send me an email!
- Connect with me on LinkedIn, Facebook, and Instagram!
- Join my Facebook group Savvy Money for Women in Business
- 33: How to Do a Useful Mid-Year Review
Read the full transcript now
You’re listening to the Mastering Money in Midlife podcast with Debbie Sassen Episode 34.
Welcome to Mastering Money in Midlife, a podcast for midlife women in business to overcome financial anxiety and make more money without burning out or sacrificing their families. Join Certified Life and Money Coach Debbie Sassen, as she shares practical business strategies and mindset shifts that help you dissolve the money blocks that keep you stuck in a cycle of under earning and under saving, sabotage the growth of your business and prevent you from building the wealth that you desire.
Hello, my friends. Welcome back to the podcast. How are you doing today?
We are having so much fun here in Israel. My parents have been in town for two and a half weeks. And, we are doing all the things: We’ve been to museums. We have baked cookies together. We went to the Israel Aquarium, where we have live sharks in the aquarium.
There is a part of the aquarium where you actually feel like you’re in the water, and the shark swims overhead. We went there on Sunday, with how many of my kids? I don’t even remember how many of my children were there, how many of my grandchildren were there.
But between the fish, and the butterflies, and the ice cream… We had to have ice cream. Everybody was so happy, thrilled. We were just this gorgeous group of four generations enjoying time together. It has been a brilliant visit.
If you’ve followed my podcast for any length of time, you may have heard me talk about my parents who were supposed to come back in December. Actually, they were supposed to be here in Israel one year ago, maybe even a little bit more. But because of COVID, and the numbers that were going up last summer, they delayed their visit. Then, canceled their visit.
Then, they scheduled again for December 1st, but that got shut down when Israel closed her borders. And then, we had a May 1st date, which was delayed again, because my dad and stepmom actually had COVID. And now, finally, here we are, at the end of June, and they have been spending such wonderful, delicious time with me and with the family.
We played MONOPOLY™ and just had a brilliant time together; everybody getting to know each other on a fun-loving and deep level. I hope that wherever you are in the world, that you are always having family time, scheduling that time together.
I know I talk about money on the podcast and building our businesses, but our business is here to serve our life. If you’re not spending time in your life, and using your money, and your time, and all of your resources to create those beautiful family connections, there’s a missing piece.
I hope that you can go and carve out some time for yourself and create those meaningful relationships with people in your life. So, that is what is going on in my world.
I will also say, for those of you who have listened to the last couple of episodes, I’ve mentioned my group program, Wired for Wealth; that launched in June. It was an accident that the launch actually happened at the same time that my parents were visiting. And, since we’re going to be talking about failure resilience today, launching while you’re having a very intense family visit is a big failure.
Now, of course it wasn’t planned that way. But I have written to a few of my friends and mentioned this is a hard ‘no’ for the future. Don’t ever plan two intense things at the same time. It is just a big, emotional stretch capacity, beyond what anybody needs to give.
One day, I’m going to record a podcast on the importance of rest in your business. How resting your body and resting your mind, and giving yourself luxurious time, is how you allow your physical body cells to repair themselves and rejuvenate.
You’ve probably heard me talk about weightlifting in the past, because I do that with my trainer a few times a week. And actually, it’s quite interesting because when you’re lifting weights, sometimes you go to failure. And that fits nicely in with the topic of the podcast today.
Just like the cells in your body and your muscles need to break down and then repair themselves to get stronger, also our mind needs time to rejuvenate; for neural pathways to be created and the old ones that we’re trying to deconstruct. To take that programming, that old programming, and dissolve it. That also needs time to dissipate and disappear. We need luxurious time so that all of our most brilliant ideas can bubble up to the surface.
But since I am still in the messy middle, where the launch is just about completed and my parents are still here, and I have not yet rested, I think we’re going to have to wait till July till we talk about the importance of resting in our business.
So, just for today, we’re going to talk about failure, failing forward and creating failure resistance. This is the perfect topic to follow what I spoke about last week. If you haven’t listened to last week’s podcast, it was all about creating a useful midterm review in your business.
By the time this podcast drops, it’s going to be the beginning of July; still the perfect time to do a midyear review in your business, and then plan your business going forward for the second half of 2022.
I want to encourage you to put yourself in places and situations where you can fail. And I know that might be like, “Oh, no, Debbie. I don’t want to fail. It feels horrible!” That’s exactly what we’re going to talk about today on the podcast, because people don’t like to fail. We don’t want to feel it. We don’t want to talk about it. We fear it deeply and intensely.
And in fact, if you could see me now, you would notice that I’m looking over at my whiteboard, and I have some notes from a recent session that I had with my client. My client has some capital that he wants to invest in his business. I will point out as an aside, yes, this is a he. You might think that I only work with women, but I work with women and men. This is one of my male clients.
Anyway, he has some capital that he wants to invest in his business. And, as he said to me, “I’m a bundle of nerves.” He has a fear of failure; what if he runs out of money before his business takes off? Yeah, that is a very normal feeling. It is a very normal thought to be having; as you’re launching a new business venture, as you’re launching a new business, as you’re doing something new that you have never done before.
Maybe it’s a podcast. Maybe it’s writing blogs. Maybe it’s a webinar that you want to offer, or a workshop live. Whatever you’re doing that’s new in your business, that you haven’t done before. Even things that you have done before, there is always the possibility for failure. And, we avoid it.
So often, we keep ourselves small, we’re not visible. We don’t make hard statements, which could be polarizing or could be misinterpreted by people. Because we’re afraid of all of the things that we’re going to feel, in our body, that are going to be very uncomfortable.
We don’t want people to judge us, reject us, shame us. And let’s be very, very frank, our brains have been wired… Our primitive brain has been wired to avoid failure. Our brain is designed to keep us safe, and protect us, and to seek pleasure.
Failure doesn’t feel very good. Failure is like, “Oh my gosh, I did something wrong. I didn’t manage to catch that wild animal. And now, that wild animal is going to attack me. It’s going to kill me. It’s going to eat me, and then I’m going to die.” That is how our brain thinks and processes the possibility of failure.
But when you’re growing a business, the most important thing you need to realize is, your road to success is paved with a pile of failures. And that means, that if you want to be more successful in your business, more successful than you already are today, however you want to measure that for yourself, you have to be willing to fail. And if you want more success, you have to be willing to fail more.
You have to be willing to experiment without any guarantee of the outcome. And you have to be open and willing, in the moment. Or, in the messy middle, before you see if things have worked out or not. You have to be open and willing to feel very uncomfortable.
That’s where resilience comes in. Because resilience is actually just stretching and growing your emotional capacity for doing the hard things, for feeling the uncomfortable feelings. The more you can be resilient in your body… That’s that strength, that emotional strength that you can create for yourself, the more resilience you can create. The more you can allow yourself to “fail,” and not make it mean anything about you as a person.
And, here’s where we often get sort of twisted up in our minds. There is the absolute failure of let’s say, losing money, not having money. That’s one way our brains react, like, “If I don’t have money, I’m not going to be able to eat, and then I’m going to die.” That’s one type of failure that we don’t want to feel.
Then, there’s what we make it mean about ourselves if we do fail. We think that we’re unworthy, we’re not enough. Maybe we feel like, “Oh, no. With my age, I’ll be 59 this month, in July, maybe I’m too old to grow a business. Maybe I’m too young; I’m too tall, I’m too short, I’m too fat, I’m too thin. I have too many freckles on my face. I don’t have enough freckles. I have the wrong color hair; the wrong color eyes, my hair is blond, or brown, or gray,” or whatever it is.
We make all of these external attributes, the things in our mind that make us unworthy, or we think that they’re making us unworthy, and because of that, we can’t grow a business. We’re afraid of failure.
That’s just the way our brains have been programmed, since we were little kids. Usually, kids on the playground, in school or nursery school, they weren’t very nice. And so many people, so many of my clients, have had stories of being out on the playground, and the girls laughing at them, or the boys laughing at them. Or, even stories in the classroom, where you didn’t know your ABC’s, you failed the spelling bee, or you failed your times tables.
One of my clients once told me that she had to stand up on a chair, and she had to recite her times tables. The teacher shamed her because she couldn’t remember. Whether it was a math test, or a history test, or geography test, whatever it was, if you didn’t do well, we have these stories in our mind that we’re not going to be successful.
Perhaps, even your parents said it. If you weren’t in the group of kids who got 90’s… I have to say that I was always an academic; I loved school, I loved learning, and I just soaked it all up. There’s a whole bunch of other people in the world who hated school, or didn’t do well in school, or their brains just didn’t process information the way teachers gave it, over in school.
They heard messages, either from their teachers or their parents, the principals, or all of the above, like, “You’re not going to amount to anything. You have to work harder. You’re not trying hard enough.” These stories are like tape recorders in your mind, replaying this message over and over and over again, that you’re not going to amount to anything.
That shows up in your business as this deep-seated fear of failing, and kind of like shriveling up and turning into nothing. But when you are in business, we have to learn to fail forward. That means lean into the failure. Look for opportunities to fail. And when it happens, not if it happens, but when it happens, we want to look at the results, and examine the results with a neutral mind.
Just like a scientist, we want to look at the numbers, look the data; it’s just information. We want to see what we can learn from that information. And let me talk about my own launch, a little bit. I’m going to record another podcast where I go into it more deeply.
My goal for Wired for Wealth, was to enroll ten women into the program. As of today, seven women have said ‘yes,’ and have enrolled in the program. Now, you might be looking at that and saying, “Wow, Debbie. Your first launch with Wired for Wealth, seven people said ‘yes,’ that’s a huge win.”
And yes, it is. It is a big win. I am very thankful, grateful for the women who said ‘yes;’ who have put their trust and faith in me, as a coach and as a leader, to guide them as they build their businesses. They’re going to do the work. I totally trust in their genius, that they have all of those gifts inside of them.
Back to my program. I also want to look at my not meeting my goal, as a failure. Not as like this failure where I have to be like, “Oh, woe is me,” and curl up, just hang out on my bed, eat chocolates and watch movies for the next three weeks. But I didn’t meet my goal. My job now, as a business owner, is to figure out why, if I had a sales goal, I didn’t meet my goal.
Can you imagine Apple®, when they launched their next iPhone®? They’re going to have sales estimates of how many iPhones they believe that they’re going to sell out in the first day, the first month, the first six months, the first year.
And, if they don’t meet their sales targets, you better believe that they’re going to go and analyze the data. They’re not going to beat themselves up. They’re not going to judge themselves harshly. They’ll look at their ads. They’ll look at their marketing. They’ll see if their messaging was on target.
They’re going to see if the people who, through their social media ads, through their print media ads, did those people actually see the ads? Were they price sensitive? Did people show up at the Apple stores? They will go through all of the numbers, and they’re going to really learn from the data.
They’re going to figure out what was working. Maybe they thought that certain states, in the United States, were going to have high sales. Or, certain countries were going to have high sales. And, for whatever reasons, those didn’t work out as planned. They’re just going to evaluate, and assess, and tweak their process for the next time.
That is how you fail forward. How you create failure resistance is, number one, you’re going to create that emotional capacity to fail. And the second thing is, you’re going to analyze the data. Figure out what worked, in whatever that new thing is.
Let’s say you want to run a webinar, and your goal is to have 100 people sign up and register for your webinar, but only 44 people registered. Okay, what worked? Forty-four people registered. You got your message out; people said ‘yes.’ They showed up. They didn’t show up.
What didn’t work? Well, my goal was 100. There were 56 people who I really believed were going to show up and sign up for my webinar, and they didn’t. Now, maybe it’s because you didn’t share more broadly. You didn’t have your messaging honed and refined, so that you were really speaking to your ideal clients. Whatever it is.
Or, you only showed once or twice, but you weren’t willing to go out there every single day, multiple times a day, and talk again and again and again about your webinar. So, people just didn’t hear. That would be something that you would want to tweak for the next time; double your efforts in your marketing and your sharing, in order to double your enrollments.
It’s always about what worked, what didn’t, and what you’re going to shift, and change, and tweak the next time. It’s not about shutting yourself down, or quitting your business, and finding all the evidence in the world to prove that you weren’t meant to be successful.
It’s also, by the way, not about you following somebody else’s seven-step roadmap to success. Because what worked for one person, with their unique personality and their temperament and their way that they like to do things, might not be the exact roadmap that works for you.
So, if you took somebody’s roadmap, let’s say for running webinars, and it didn’t work, it could be because you’re just a different kind of person. You don’t want to make it mean anything about you. Of course, your primitive brain is going to think that if you follow somebody else’s exact plan or blueprint, it has to work out. But that’s only because your brain is looking for that certainty and that safety, because it doesn’t want to fail; it doesn’t want to get eaten by that wild animal.
Again, we just want to notice what was going on. Maybe recognize that something felt off, like in your body or in your mind. That somebody else’s way of doing things, didn’t quite jive with you the right way, but you decided to follow their plan anyway.
Now, when you evaluate, you’re going to say to yourself, “I did that thing, but it didn’t feel comfortable for me. Did it not feel comfortable because I’m not used to it? Or, is it uncomfortable because it’s just not me?” That’s the kind of information that you’re looking for, when you are failing with the next thing that you’re trying in your business.
We don’t want to avoid failure, right? We want to fail forward; we want to go towards it. We want to try new things, and build up that pile of failures. Because by creating that pile of ‘no’s’ and failures and things that didn’t work, we’re going to create next to it, a pile of successes and ‘yeses’ and things that did work in our business.
That is how you’re going to create the massive success in your business, that you know you are here for in this world. Just imagine that there are people in this world who are waiting for you to show up. Let’s say that you’re a copywriter, and you have been divinely contracted to work with someone and help them in their business; to call in their clients, because you’re just like a word magician.
You know how to write their blogs, and their sales pages, their websites, their emails, and your people are waiting for you. But because of your fear of failure, of messing up, you’re not going to show up. You’re not going to serve your clients and help them grow their business.
Or, let’s say that you’re a coach. And there are people in the world who need healing, who want to shift the way they’re thinking about things, who have goals that they want to achieve. And, you’re not going to show up and help them because you’re afraid of your failure.
Or, you’re a photographer. You have a unique way of seeing the world through your lens; both the lens of your camera and the lenses that are in your eyes. You process light, and colors, and shadows, and perspective differently from other photographers. Your people are waiting for you, too. Are you going to stop them from receiving your services, because you’re afraid of failing? Because failure feels uncomfortable in your body?
Just think about them. They’re hungry for you. They’re waiting for you, and they want you to show up. Don’t let your fear of failure, and the discomfort that you feel in your body, stop you from helping your people.
I like to say, you’ve heard me say it before, that my clients are divinely contracted to work with me. Similarly, your clients are divinely contracted to work for you. Be willing to go the extra mile. Be willing to try new things. Be willing to fall flat on your face. And get up, brush yourself off and do it again.
Every success is built on a pile of failures. Your success; your massive wild, outrageous success in your business. And all the money that you would love to make in your business, is built on creating that pile of failures, day after day, month after month, year after year.
Don’t hold yourself back. Don’t let failure mean anything about you as a person. Because the only thing it could possibly mean about you as a person, is that you have grown more resilient. You have more emotional and energetic capacity. You have more knowledge, more information, more skills.
Just imagine that you are that weightlifter who’s lifting barbells and doing your push-ups and doing your sit-ups. Your muscles are honed and refined and they’re cut. All of your hard work on your physical muscles, on your emotional muscles, on showing up, and being resilient and failing, and learning from every single experiment that you’re going to do in your business, that can only mean that you are more, not less, of a person because you tried new things.
Some of them didn’t work out, and some of them worked out. So, that is my message for you today, my friends, is to fail. Fail frequently, fail forward and create resilience. Failure resilience is where it’s at, in your business.
Plan for the second half of 2022. Go back to last week’s podcast, if you haven’t listened to it yet, and evaluate your results for the first half of 2022: All the things that worked. All the things that didn’t. What you want to tweak going forward. Put your plan in place for the second half of 2022, and be willing to fail beautifully, massively and create massive success.
I look forward to seeing you next week on the podcast. If you haven’t left me a review yet, please go to Apple Podcasts or to iTunes. I would love it if you would leave me a five-star review, share some comments, and let the world know about the podcast so more people can hear how they can grow their business, make more money and serve more people.
Alright, my friends. Bye for now.
Thanks for listening to Mastering Money in Midlife. If you want more information on Debbie Sassen or the resources from the podcast visit MasteringMoneyinMidlife.com

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