"The only real failure is when you give up on yourself" (Debbie Millman bonus episode)

0:00Radim Malinic:Hey, welcome to this bonus episode of the Daring Creativity Podcast. This is where I revisit the interview published earlier in the week, providing me with the opportunity to zoom in on a few stand-down moments for extra value and meaning. I've taken time to digest the goodness my guests share with me every single week. And this week I was chatting with Debbie Millman about her transformative journey from a pivotal class with Milton Glaser to becoming one of the most influential voices in creative conversations. She revealed the power of writing your future, choosing your courage over confidence, and redefining the meaning of failure as simply giving up on yourself.

0:41Radim Malinic:For that reason, I've chosen these topics as ones to highlight in this bonus episode. Confidence.

0:48Debbie Millman:I hear over and over again in my classes, I'll do that when I feel more confident. I'm going to do that when I feel more secure. And I ask them when they think that's going to be. Like, how are you going to get that way? You can't go into a supermarket and buy a box of confidence. It's not going to work that way. Confidence, my definition of confidence, is the successful repetition of any endeavor. That you have confidence based on previous experience, keywords, previous experience, That the last time you did that thing, you didn't fall on your face. That whatever it was, a podcast, a marathon, a meal that you were making, that somehow you created something that wasn't a failure.

1:44Debbie Millman:And it could be something that you've done many times, or it could also be something that because you've been so successful at other things, you feel like you can have that success follow you into something else. But the key here is understanding that you've built a foundation of confidence based on the successful repetition of any endeavor.

2:07Radim Malinic:I feel lucky that during the writing of my book, Daring Creativity, Daring Forever, I can speak to people like Debbie and gently get into topics that I want to know about more into the conversation and seeing what other people think about it what experience they have and couldn't have chosen anyone more knowledgeable and wiser than debbie to share with me her insights in a way and her way of seeing confidence is fascinating because the way she dismantles the most common excuse for creative paralysis is to be confident before starting how many people want to write a book and as soon as they open the editor they freeze how many people try to do a masterpiece or how many times even yourself have started on something new only to find yourself staring at a fish tank thinking yeah that needs cleaning before i could do any of this because in debbie's answer in debbie's way she reveals that confidence is something you cannot acquire beforehand because it requires the very experience you're avoiding confidence emerges only after a successful repetition, which only means your first attempt will always happen without any confidence.

3:22Radim Malinic:And this reframe matters because it removes an impossible prerequisite. You cannot feel confident about something you've never done before. The sequence must be attempt first, survive the uncertainty, gather evidence for experience, and then build confidence from that foundation think about learning anything fundamental like walking or speaking and Debbie I have to really tip my heart to Debbie because she's about pooping for the first time any guest use the word pooping that was quite exciting when Thiago Maia said the word George Foreman grill

3:55Debbie Millman:but we never had pooping yet so yeah that was pretty impressive because we're talking about

4:02Radim Malinic:creatives we're talking about confidence and facing the blank pages or career pivers understanding of confidence and the way it works is liberating because we can stop waiting for the readiness that can only come after actions start with courage instead knowing that confidence will follow once you have the results to reference the second standout moment follows from the same answer about courage. When you initiated the journey and what provoked you to do that, what motivated you

4:39Debbie Millman:to do that, what gave you the sense that you could do that? Two things, courage and hope. Courage and hope. And so you needed the courage to step into that certainty. I'm sorry, You needed that courage to step into that opportunity, that endeavor, before you knew what the result would be. The confidence only comes after the result. It never comes before. And so you need to be able to have some faith in your own courage to buoy that courage up, to take that first step. And if you think back to all the things we learn how to do, eating, talking, pooping, these all take time. We can't even go to the bathroom without potty training.

5:40Debbie Millman:Why would we think that anything else, any more complicated than that, would be something we could just do successfully out of the gate? We can't. And that's the first part of this. The second part is that we as humans hate uncertainty. The reason we hate uncertainty is because our brains started as reptilian brains and have evolved over time to have three parts, which are reptilian, mammalian, and the neocortex. and the neocortex is the part that we're all very familiar with. We use it to our awareness, will, creativity, all of that is controlled in that part of our brain. The mammalian brain is what makes us want to be connected and social and take care of each other.

6:29Debbie Millman:The reptilian brain is all involuntary action. It controls our metabolism and our heartbeat and our eye blinking, things that we don't think about. They just happen in our bodies.

6:40Radim Malinic:These two words are the fuel for creative action. Courage paired with hope in yourself. Or courage paired with faith in yourself. While confidence relies on the past evidence, courage operates in the absence of guarantees. It acknowledges uncertainty honestly while choosing to proceed anyway. This distinction transforms how you approach new work. The quote means That vulnerable feeling before starting is not evidence you are unprepared. It is the natural state of attempting something without previous successful repetitions to reference. Courage means recognises discomfort as normal rather than warning signs to stop.

7:27Radim Malinic:Debbie's own story demonstrated this principle. When she took Milton Glaser's class at 45, she had no confidence her ambitious goals would manifest. She needed courage to ride him down anyway, to show up despite feeling she had reached a plateau. Thirteen years later, everything came true, but only because courage initiated the journey when confidence was impossible. Our third moment focused on the meaning of failure.

7:55Debbie Millman:I think that failure, the only real failure is when you give up on yourself. Everything else is losing, and losing or rejection. And that's fine. We can't win every race. We can't win anything all the time. It's just not the way the world works, unfortunately. Wouldn't it be great if it did? I think the only failure is giving up on yourself. And there's a difference even between understanding that you might need to do something different. But if you just give up and defeat, maybe you just needed a little bit more time I think it was a great football coach since we're talking about sports that said I never lost a game I think he was the coach of the Green Bay Packers years and years and years ago and I can't remember his name but I can remember the quote he said I never lost a game I just ran out of time and I I loved that because that's a mindset that's a mindset that's a mindset of if i had more time i'd have done it i would have prevailed

9:04Radim Malinic:and i think that's really beautiful i've initiated the topic of failure based on my favorite quote from a cycling coach called charlie bergillias who manages team ef education easy post and he's got this quote which i mentioned in the story about the fact that on the way to winning you're going to do a lot of losing because losing is a way of trying to win but there's a difference between losing and failing and in his way he says failure is not doing what you want to do in the way that you want to do it so i've managed to squeeze that in in our conversation and it steered our chat about definition of failure and i love that in debbie's way she said that the only real of failures when you give up on yourself and that probably means to think it's the internet or we see people that say um i've got fear of failure i've got fear of failure and in a way debbie's definition of giving up on yourself as the only failure made me think that there's no such meme as i've got fear of giving up i've got fear of giving up on myself because ultimately we get disheartened with the lack of progress but we don't always give up we don't worry about that and i just love that moment happen the distinction between losing and failing reframes every setback you will encounter in creative work losing happens constantly because external factors beyond your control determine outcomes and if you interpret every loss as a failure you will quit before achieving anything meaningful debbie mentioned her own sports quote which was about a coach who said i never lost a game i've only run out of time because failure only happens when you internalize losses so deeply that you stop trying entirely the coach who said maybe i just needed a little bit more time acknowledges that success often requires persistence through longer on ways than expected.

11:22Radim Malinic:And Debbie's own 10-year plan took 13 years to fully manifest. If she had interpreted setbacks as failures rather than temporary losses, she would have quit before her goals materialized. In the last standout moment from this episode, I wanted to ask Debbie about the differences of our decades and how we perceive things.

11:45Debbie Millman:Our 20s are very much about establishing who we are, experimenting, playing, searching, longing. And then we move into our 30s. And I think we start to get a little bit more serious about our careers. Some of us get married, we start to think about a family, we start to accrue the more mature aspects of adulthood. And I think by 40s, you have achieved a lot of what you'd hoped for in your 20s, if you're lucky. And you begin to consider other things. You start to consider time in a different way. At that point, you know, your life is probably halfway over, unless you're really lucky and live a little bit longer into your 90s or 100s.

12:41Debbie Millman:And so things become slightly more both tangible, but also amorphous. You want more, but you're not quite sure how to go about it. And by the time you're in your 40s, it's a little bit harder to experiment. One of the things that I've learned as I've gotten older and wrote about in my last book was, as I've gotten older, I find it a lot more difficult and vulnerable making to do things that I'm not good at. I don't want to be humiliated. I don't want to be embarrassed. I don't want to seem less than. And so it's harder to start new things because I don't want to feel silly or look silly. And so when we're in our 40s, I think we're on the one hand trying to reach mastery, but also trying to consider other possibilities.

13:32Radim Malinic:I wanted to know from Debbie how she perceives the decades of our lives that change our perception of failure, confidence, courage. And honestly, how mortality awareness transform across decades and fundamentally shapes creative risk taking. mentions that in your 20s or let's say in our 20s we perceive time as unlimited it gives us time to experiment with no urgency we can afford to fail in public or in quiet restart explore different paths because we have decades stretched ahead when we get to our 40s we accomplish some goals and begin to question what comes next. Feeling sometimes that time is compressed, but still maintaining some hope for reinvention, for pivot, for future plans.

14:32Radim Malinic:But when we get into our 60s, time's finite nature becomes undeniable. The question shifts from someday to, if not now, when? And this awareness can either paralyze you with fear of failure or fear of future or fear of mortality or liberate you because you finally can attempt postponed dreams the whole concept of daring creativity is the fact that in every decade of our lives we very much should be continuing to evolve our work which is driven by urgency rather than being defeated by it because debbie says if not now when and i say now versus how like it doesn't matter how much you know about certain things and you just need to do that first step because it matters my conversation with debbie is full of beautiful incredible wisdom knowledge and insights and just human experience of someone who has been at the forefront of the creative industry for the last 40 years if not longer showing us the way how we can think, how we can carry ourselves, how we can invent new opportunities and ultimately gain influence in our industry by just being simply human.

15:57Radim Malinic:If you haven't checked out the full episode, I very much encourage you to do that. And I will see you on the next episode.